Organic electroluminescent devices and electronic apparatus

Abstract

The present invention provides an organic electroluminescent device and an electronic apparatus. The organic electroluminescent device comprises a cathode, an anode, and an organic layer, the organic layer comprising an organic light-emitting layer, the organic light-emitting layer comprising a first compound and a second compound, the first compound being selected from compounds represented by formula 1, and the second compound being selected from compounds represented by formula 2. JPEG2026520522000195.jpg51112

Description

Technical Field

[0001] This application claims the priority of the Chinese patent application with the application number CN202311635189.7 filed on December 1, 2023, and the entire content of the above Chinese patent application is hereby incorporated by reference and made a part of this application.

[0002] This application relates to the field of organic electroluminescence, and in particular, to organic electroluminescence devices and electronic devices.

Background Art

[0003] In recent years, due to characteristics such as self-luminescence, wide viewing angle, short response time, high efficiency, and wide color gamut, organic electroluminescence devices (OLEDs) have become very popular emerging flat display products both at home and abroad.

[0004] An organic electroluminescence device (OLED) usually includes an anode, a cathode, and an organic layer formed between these two electrodes. This organic layer may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an organic light-emitting layer (including a host and a dopant material), a hole blocking layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied to the organic electroluminescence device, holes and electrons are respectively injected from the anode and the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. The excitons release energy to the outside in an excited state, causing the light-emitting layer to emit light to the outside.

[0005] Currently, in the process of using organic electroluminescence devices, there are still problems such as poor performance, for example, the driving voltage is too high, the light-emitting efficiency is too low, or the lifespan is too short, etc. All of these affect the application fields of organic electroluminescence devices, so it is necessary to further study this field to improve the performance of organic electroluminescence devices.

Summary of the Invention

[0006] To achieve the objective of the above invention, this application adopts the following technical solution.

[0007] A first aspect of this application is an organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the cathode and the anode are arranged opposite each other, the organic layer is located between the cathode and the anode, and the organic layer comprises an organic light-emitting layer. The organic light-emitting layer comprises a first compound and a second compound, The first compound is a compound represented by formula 1, JPEG2026520522000002.jpg4040 formula 1 However, Ar1 and Ar2 may be the same or different, and each may be independently selected from substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, or substituted or unsubstituted dibenzothienyl groups having 6 to 30 carbon atoms. L, L1, and L2 are the same or different, and each is independently selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms. Ar3 is a penta-deuterated phenyl group, a biphenyl group, or a terphenyl group. The substituents in L, L1, L2, Ar1, and Ar2 are the same or different and each is independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C6-C20 aryl group, a C6-C20 deuterated aryl group, a C6-C20 halogenated aryl group, or a C3-C10 cycloalkyl group. The second compound is a compound represented by formula 2, JPEG2026520522000003.jpg2643 formula 2 L4 and L5 are the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms. Ar4 and Ar5 are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and each may be independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C6-C20 aryl group, a C6-C20 deuterated aryl group, a C6-C20 halogenated aryl group, or a C3-C10 cycloalkyl group, providing an organic electroluminescent device.

[0008] A second aspect of this application provides an electronic device including the organic electroluminescent device described in the first aspect.

[0009] This application provides an organic electroluminescent device in which the organic layer includes an organic light-emitting layer, the organic light-emitting layer includes a first compound having strong electronic properties and a second compound having strong hole properties, and by using the first compound and the second compound in combination as host materials for the organic electroluminescent layer, the balance between holes and electrons is adjusted, generating many excitons from the organic light-emitting layer and improving the performance of the organic electroluminescent device.

[0010] Other features and advantages of this application will be described in detail in subsequent specific embodiments. [Brief explanation of the drawing]

[0011] The drawings are provided to provide a further understanding of this application, constitute part of the specification, and are used in conjunction with the following specific embodiments to interpret this application, but do not constitute any limitation to this application. [Figure 1] This is a schematic diagram of the structure of the organic electroluminescent device of this application. [Figure 2]This is a schematic diagram of the structure of the electronic device of this application. Explanation of reference numerals: 100 Anode, 200 Cathode, 300 Organic layer, 310 Hole injection layer, 320 Hole transport layer, 330 Light emission auxiliary layer, 340 Organic light emission layer, 350 Electron transport layer, 360 Electron injection layer, 400 First electronic device [Modes for carrying out the invention]

[0012] The exemplary embodiments described herein will be described in detail below with reference to the drawings. However, the exemplary embodiments can be carried out in various forms and should not be understood as being limited to the examples described herein. On the contrary, by providing these embodiments, the application becomes more comprehensive and complete and fully conveys the concept of the exemplary embodiments to those skilled in the art. The described features, structures or characteristics can be combined in one or more embodiments in any suitable manner. The following description provides many specific details in order to fully understand the embodiments of this application.

[0013] In the drawings, the thickness of areas and layers may be exaggerated for clarity. In the drawings, the same reference numerals represent the same or similar structures; therefore, detailed explanations of these are omitted.

[0014] The described features, structures, or properties can be combined in one or more embodiments in any suitable manner. The following description provides many specific details to fully understand the embodiments of this application. However, those skilled in the art will recognize that the technical applications of this application can be implemented without one or more of the aforementioned specific details, or that other methods, components, materials, etc., can be used. In other cases, known structures, materials, or operations are not illustrated or described in detail to avoid obscuring the main technical ideas of this application.

[0015] According to a first aspect of this application, the application relates to an organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the cathode and the anode are arranged opposite each other, the organic layer is located between the cathode and the anode, and the organic layer comprises an organic light-emitting layer. The organic light-emitting layer comprises a first compound and a second compound, The first compound is a compound represented by formula 1, JPEG2026520522000004.jpg4040 formula 1 However, Ar1 and Ar2 may be the same or different, and each may be independently selected from substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, or substituted or unsubstituted dibenzothienyl groups having 6 to 30 carbon atoms. L, L1, and L2 are the same or different, and each is independently selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms. Ar3 is a penta-deuterated phenyl group, a biphenyl group, or a terphenyl group. The substituents in L, L1, L2, Ar1, and Ar2 are the same or different and each is independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C6-C20 aryl group, a C6-C20 deuterated aryl group, a C6-C20 halogenated aryl group, or a C3-C10 cycloalkyl group. The second compound is a compound represented by formula 2, JPEG2026520522000005.jpg2643 formula 2 L4 and L5 are the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms. Ar4 and Ar5 are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. The substituents in L4, L5, Ar4, and Ar5 are the same or different and each independently is deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, and an organic electroluminescence device is provided.

[0016] In the present application, the description methods “each... is independently”, “… are each independently” and “each of... is independently” are interchangeable and should all be understood in a broad sense, and in different groups, it may refer to the fact that the specific options represented between the same symbols do not affect each other, and in the same group, it may also refer to the fact that the specific options represented between the same symbols do not affect each other. For example, in “ JPEG2026520522000006.jpg2646”, each q is independently 0, 1, 2, or 3, each R” is independently selected from hydrogen, deuterium, fluorine, and chlorine, and its meaning is that formula Q-1 represents that there are q substituents R” on the benzene ring, each R” may be the same or different, and the options of each R” do not affect each other, formula Q-2 represents that there are q substituents R” on each benzene ring of biphenyl, the number q of R” substituents on the two benzene rings may be the same or different, each R” may be the same or different, and the options of each R” do not affect each other.

[0017] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of explanation, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl group" means an aryl group having a substituent Rc or an unsubstituted aryl group. The above substituent, that is, Rc, may be, for example, deuterium, a cyano group, a halogen group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, an aryl group, a deuterated aryl group, a halogenated aryl group, a cycloalkyl group, etc. The number of substitutions may be one or more.

[0018] In the present application, "a plurality" means two or more, for example, two, three, four, five, six, etc.

[0019] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, when L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and its substituent is 12.

[0020] In this application, an aryl group refers to any functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., a phenyl group) or a polycyclic aryl group. In other words, the aryl group may be a monocyclic aryl group, a fused aryl group, two or more monocyclic aryl groups conjugated via carbon-carbon bonds, monocyclic aryl groups and fused aryl groups conjugated via carbon-carbon bonds, or two or more fused aryl groups conjugated via carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated via carbon-carbon bonds can also be considered aryl groups in this application. Here, fused aryl groups may include, for example, bicyclic fused aryl groups (e.g., naphthyl groups) and tricyclic fused aryl groups (e.g., phenanthryl groups, fluorenyl groups, anthryl groups). The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group ( JPEG2026520522000007.jpg1720), perilenyl group, benzo[9,10]phenanthryl group, pyrenyl group, benzofluoranteyl group, chrysenyl group, spirobifluorenyl group ( This may include, but is not limited to, JPEG2026520522000008.jpg1719). In this application, such arylene group refers to a divalent group formed when an aryl group loses one more hydrogen atom.

[0021] In this application, the terphenyl group is, JPEG2026520522000009.jpg1231 and Includes JPEG2026520522000010.jpg1725.

[0022] In this application, the carbon number of a substituted aryl group refers to the total carbon number of the aryl group and its substituents. For example, a substituted aryl group with 18 carbon atoms means that the aryl group and its substituents have a total carbon number of 18.

[0023] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 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 20 carbon atoms; and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0024] In this application, the aryl groups as substituents on L, L1, L2, L4, L5, Ar1, Ar2, Ar4, and Ar5 are, for example, phenyl groups, naphthyl groups, etc., but are not limited to these.

[0025] In this application, a heteroaryl group 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 group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group; in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems conjugated via carbon-carbon bonds, and any of the aromatic ring systems may be one aromatic monoring or one aromatic fused ring. Examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridadinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, and indoquinyl. The group may also contain, but is not limited to, a lyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothienyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, etc.

[0026] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0027] In this application, a substituted heteroaryl group may have one or more hydrogen atoms in the heteroaryl group substituted with groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, and alkyl halides. It should be understood that the carbon number of the substituted heteroaryl group refers to the total carbon number of the heteroaryl group and the substituents in the heteroaryl group.

[0028] In this application, the alkyl group having 1 to 10 carbon atoms may include linear alkyl groups having 1 to 10 carbon atoms and branched alkyl groups 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. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl groups.

[0029] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0030] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl groups.

[0031] In this application, specific examples of deuterated alkyl groups include, but are not limited to, methyl trideuterated groups.

[0032] In this application, a deuterated aryl group means an aryl group containing at least one deuterium substituent, and specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl groups and pentadeuterated biphenyl groups.

[0033] In this application, the number of carbon atoms in a cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl groups.

[0034] In this application, a single bond extending from a ring system relating to a non-fixed position bond " The image "JPEG2026520522000011.jpg912" indicates that one end of the bond can be connected to any position in the ring system through which the bond passes, and the other end can be connected to the rest of the compound molecule. For example, as shown in formula (f) below, the naphthyl group represented by formula (f) is connected to other positions on the molecule via two position-independent bonds that pass through the double ring, meaning that any of the possible connection methods shown in formulas (f-1) to (f-10) are included. JPEG2026520522000012.jpg21125 JPEG2026520522000013.jpg20123

[0035] To give another example, as shown in formula (X') below, the dibenzofuranyl group represented by formula (X') is linked to other positions on the molecule via position-free bonds extending from the middle of one benzene ring, meaning that any of the possible linkages represented by formulas (X'-1) to (X'-4) are included. JPEG2026520522000014.jpg18115

[0036] In some embodiments of this application, the first compound is selected from compounds represented by formula 1-1, formula 1-2, formula 1-3, or formula 1-4. JPEG2026520522000015.jpg102150

[0037] In a preferred embodiment of this application, the first compound is selected from the compounds represented by formula 1-1.

[0038] The first compound is selectively chosen from compounds represented by formulas A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P. JPEG2026520522000016.jpg177113

[0039] In some preferred embodiments of this application, the first compound is selected from compounds represented by formula A, formula B, formula C, or formula D.

[0040] In some embodiments of this application, L, L1, and L2 are the same or different and each is independently selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.

[0041] Selectively, the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, C1-C5 alkyl groups, phenyl groups, or penta-deuterated phenyl groups.

[0042] In some other embodiments of this application, L, L1 and L2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

[0043] Selectively, L, L1, and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group.

[0044] Furthermore, L, L1, and L2 can be selected, either the same or different, and independently, from the group consisting of single bonds or the following groups. JPEG2026520522000017.jpg26150

[0045] Specifically, L, L1, and L2 are selected, either the same or different, and independently from the group consisting of single bonds or the following groups. JPEG2026520522000018.jpg55167

[0046] In some embodiments of this application, Ar1 and Ar2 are the same or different and each is independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

[0047] Selectively, the substituents in Ar1 and Ar2 are the same or different, and each is independently chosen from deuterium, halogen groups, cyano groups, C1-C5 alkyl groups, phenyl groups, or penta-deuterated phenyl groups.

[0048] In some other embodiments of this application, Ar1 and Ar2 are the same or different and each 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 phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

[0049] Selectively, the substituents in Ar1 and Ar2 are the same or different, and each is independently chosen from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group.

[0050] In some other embodiments of this application, Ar1 and Ar2 are the same or different and each is independently selected from substituted or unsubstituted groups W, the unsubstituted groups W being selected from the group consisting of the following groups. JPEG2026520522000019.jpg36167 However, JPEG2026520522000020.jpg913 represents a chemical bond, where the substituted group W has one or more substituents, each substituent independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group, and if the number of substituents on group W is greater than 1, each substituent is either the same or different.

[0051] Selectively, Ar1 and Ar2 are chosen from the following group of groups, which may be the same or different and which may be independent of each other. JPEG2026520522000021.jpg40168

[0052] Specifically, Ar1 and Ar2 are selected, either the same or different, and independently from the following group of groups: JPEG2026520522000022.jpg99165

[0053] In some embodiments of this application, JPEG2026520522000023.jpg827 and Each element in JPEG2026520522000024.jpg827 is independently selected from the following group of elements. JPEG2026520522000025.jpg46163

[0054] in particular, JPEG2026520522000026.jpg827 and Each element in JPEG2026520522000027.jpg827 is independently selected from the following group of elements. JPEG2026520522000028.jpg97166

[0055] In some embodiments of this application, in formula 1, JPEG2026520522000029.jpg2526 is selected from the group consisting of the following elements. JPEG2026520522000030.jpg128168

[0056] Specifically, in Equation 1, JPEG2026520522000031.jpg2528 is selected from the group consisting of the following elements. JPEG2026520522000032.jpg187167 JPEG2026520522000033.jpg205167

[0057] In some embodiments of this application, in formula 1, Ar3 is selected from the group consisting of the following groups. JPEG2026520522000034.jpg26150

[0058] Specifically, in Equation 1, Ar3 is selected from the group consisting of the following groups. JPEG2026520522000035.jpg64150

[0059] In some preferred embodiments of this application, in formula 1, Ar3 is Selected from JPEG2026520522000036.jpg1817.

[0060] In some embodiments of this application, the first compound is selected from the group consisting of the following compounds. JPEG2026520522000037.jpg245170JPEG2026520522000038.jpg233168 JPEG2026520522000039.jpg197169 JPEG2026520522000040.jpg197166 JPEG2026520522000041.jpg197169 JPEG2026520522000042.jpg202169 JPEG2026520522000043.jpg174168 JPEG2026520522000044.jpg169169 JPEG2026520522000045.jpg172167 JPEG2026520522000046.jpg177167 JPEG2026520522000047.jpg180167 JPEG2026520522000048.jpg197168 JPEG2026520522000049.jpg154169 JPEG2026520522000050.jpg186169 JPEG2026520522000051.jpg182167 JPEG2026520522000052.jpg182168 JPEG2026520522000053.jpg202168 JPEG2026520522000054.jpg207166 JPEG2026520522000055.jpg223169 JPEG2026520522000056.jpg228169 JPEG2026520522000057.jpg223166 JPEG2026520522000058.jpg186167 JPEG2026520522000059.jpg223169 JPEG2026520522000060.jpg202167 JPEG2026520522000061.jpg197169 JPEG2026520522000062.jpg179168 JPEG2026520522000063.jpg188169 JPEG2026520522000064.jpg214167 JPEG2026520522000065.jpg202166 JPEG2026520522000066.jpg178167 JPEG2026520522000067.jpg198169 JPEG2026520522000068.jpg207168 JPEG2026520522000069.jpg191168 JPEG2026520522000070.jpg181168 JPEG2026520522000071.jpg191165 JPEG2026520522000072.jpg176166 JPEG2026520522000073.jpg212168 JPEG2026520522000074.jpg196165 JPEG2026520522000075.jpg223167 JPEG2026520522000076.jpg193169 JPEG2026520522000077.jpg202169 JPEG2026520522000078.jpg46166

[0061] In some embodiments of this application, in formula 2, L4 and L5 are the same or different and independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0062] Selectively, the substituents at L4 and L5 are the same or different, and each is independently chosen from deuterium, fluorine, a cyano group, a C1-C5 alkyl group, or a phenyl group.

[0063] In some embodiments of this application, in formula 2, L4 and L5 are the same or different and 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 carbazoylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.

[0064] Selectively, the substituents at L4 and L5 are the same or different, and each is independently chosen from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, or phenyl group.

[0065] In some embodiments of this application, in Formula 2, L4 and L5 are the same or different and are selected from the group consisting of a single bond or the following groups. JPEG2026520522000079.jpg25168

[0066] Specifically, in Equation 2, L4 and L5 are either the same or different, and each is independently selected from the group consisting of a single bond or the following groups. JPEG2026520522000080.jpg46166

[0067] In some embodiments of this application, in Formula 2, Ar4 and Ar5 are the same or different and independently selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0068] Selectively, the substituents in Ar4 and Ar5 are the same or different, and each is independently chosen from deuterium, fluorine, a cyano group, a C1-C5 alkyl group, a phenyl group, or a penta-deuterated phenyl group.

[0069] In some other embodiments of this application, in Formula 2, Ar4 and Ar5 are the same or different and each 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 phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quarterphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.

[0070] Selectively, the substituents in Ar4 and Ar5 are the same or different, and each is independently chosen from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group.

[0071] In some embodiments of this application, in formula 2, Ar4 and Ar5 are the same or different and are each selected from the group consisting of the following groups. JPEG2026520522000081.jpg59170

[0072] Specifically, in Equation 2, Ar4 and Ar5 are either the same or different, and each is independently selected from the following group of groups. JPEG2026520522000082.jpg112168

[0073] In some embodiments of this application, in formula 2, JPEG2026520522000083.jpg827 and Each element in JPEG2026520522000084.jpg827 is independently selected from the following group of elements. JPEG2026520522000085.jpg88166

[0074] Specifically, in Equation 2, JPEG2026520522000086.jpg827 and Each element in JPEG2026520522000087.jpg827 is independently selected from the following group of elements. JPEG2026520522000088.jpg234166 JPEG2026520522000089.jpg148169

[0075] In some embodiments of this application, the second compound is selected from the group consisting of the following compounds. JPEG2026520522000090.jpg227166 JPEG2026520522000091.jpg209169 JPEG2026520522000092.jpg177169 JPEG2026520522000093.jpg172168 JPEG2026520522000094.jpg221168 JPEG2026520522000095.jpg180165 JPEG2026520522000096.jpg191166 JPEG2026520522000097.jpg198168 JPEG2026520522000098.jpg219169 JPEG2026520522000099.jpg75168

[0076] In some embodiments of this application, a host material and a guest material can be deposited in common by a multi-source deposition process, and the host material and guest material can be uniformly dispersed in an organic light-emitting layer. The doping ratio can be adjusted by controlling the deposition rate of the guest material during the deposition process, or by controlling the deposition rate ratio of the host material and the guest material.

[0077] Selectively, a multi-source co-evaporation method can be employed for the deposition of the organic light-emitting layer to form an organic light-emitting layer containing a host material and a guest material. The doping ratio can be adjusted by controlling the deposition rate of the guest material during the deposition process, or by controlling the deposition rate ratio of the host material and the guest material.

[0078] The relative content of the first compound and the second compound in the organic light-emitting layer of the organic electroluminescent device of this application is not particularly limited and can be selected according to the specific application of the organic electroluminescent device. Typically, the deposition rate ratio (%) of the first compound and the second compound may be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0079] In some preferred embodiments of this application, the deposition rate ratio (%) of the first compound to the second compound is 40:60, 45:65, 50:50, 55:45, or 60:40.

[0080] In some other embodiments of this application, a host material mixture can be formed by uniformly mixing a first compound and a second compound by mechanical stirring, and an organic light-emitting layer can be formed by depositing an organic light-emitting layer on the formed host material mixture and guest material using a multi-source co-deposition method, and the dope ratio can be adjusted during the deposition process by controlling the deposition rate of the guest material, or by controlling the deposition rate ratio of the host material mixture and the guest material.

[0081] Here, the first compound and the second compound in the host material mixture may be mixed in mass percentage. This application does not particularly limit the relative content of the two compounds in the host material mixture, and can be selected according to the specific application of the organic electroluminescent device. Typically, the mass percentage of the first compound may be 1% to 99% and the mass percentage of the second compound may be 1% to 99% based on the total weight of the host material mixture. For example, the mass ratio (%) of the first compound to the second compound in the host material mixture may be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0082] In one embodiment of this application, the organic electroluminescent device is a phosphorescent device.

[0083] In one specific embodiment of this application, the organic electroluminescent device is a green phosphorescent organic electroluminescent device.

[0084] In some embodiments of this application, the organic electroluminescent device includes, in order, an anode (ITO substrate), a hole transport layer, an emission modulating layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic coating layer.

[0085] In one specific embodiment of the present application, as shown in Figure 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one organic layer 300 interposed between the anode layer and the cathode layer, the organic layer 300 including a hole injection layer 310, a hole transport layer 320, an emission adjustment layer 330, an organic light emission layer 340, an electron transport layer 350, and an electron injection layer 360.

[0086] Optionally, the anode 100 includes an anode material, preferably a material having a large work function that contributes to hole injection into the organic layer. Specific examples of anode materials 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); 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 are not limited to these. Preferably, the anode includes a transparent electrode containing indium tin oxide (indium tin oxide) (ITO).

[0087] The hole transport layer 320 may optionally comprise one or more hole transport materials, which may be selected from carbazole polymers, carbazole-bound triarylamine compounds, or other types of compounds, and are not particularly limited in this application. For example, in some embodiments of this application, the hole transport layer 320 is composed of HT-1.

[0088] Optionally, the luminescence auxiliary layer 330 (also called the luminescence adjustment layer, hole adjustment layer, electron blocking layer, hole auxiliary layer, hole buffer layer, luminescence adjustment layer, or second hole transport layer) may contain one or more types of hole transport materials, the hole transport materials may be selected from carbazole polymers, carbazole-bound triarylamine compounds, or other types of compounds, and are not particularly limited in this application. For example, in some embodiments of this application, the luminescence auxiliary layer 330 is composed of HT-2.

[0089] Optionally, the organic light-emitting layer 340 may consist of a single light-emitting material or may include a host material and a guest material. Optionally, the organic light-emitting layer 340 may consist of a host material and a guest material, where holes and electrons injected into the organic light-emitting layer 330 recombine in the organic light-emitting layer 340 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, causing the guest material to emit light.

[0090] The guest material of the organic light-emitting layer 340 may be a compound or derivative thereof having a condensed aryl ring, a compound or derivative thereof having a heteroaryl ring, an aromatic amine derivative, or other material, and is not particularly limited in this application.

[0091] In some embodiments of this application, the green organic electroluminescent device comprises an organic light-emitting layer 340 containing the first compound, the second compound, and a guest material GD-01.

[0092] The electron transport layer 350 may have a single-layer structure or a multilayer structure, and may contain one or more electron transport materials, the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and are not particularly limited in this application. For example, in some embodiments of this application, the electron transport layer 350 may consist of ET-1 and LiQ.

[0093] Selectively, the cathode 200 includes a cathode material such as a material with a small work function that contributes to electron injection into the organic layer. Specific examples of cathode materials include 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, but are not limited to these. Preferably, the cathode includes a metal electrode containing silver and magnesium.

[0094] Optionally, a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 320 to enhance the hole injection capacity into the hole transport layer 320. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and is not particularly limited in this application. In some embodiments of this application, the hole injection layer 310 may consist of PD and HT-1.

[0095] Optionally, an electron injection layer 360 may be further provided between the cathode 200 and the electron transport layer 350 to enhance the electron injection capability into the electron transport layer 350. The electron injection layer 360 may contain inorganic materials such as alkali metal sulfides and alkali metal halides, or it may contain complexes of alkali metals and organic substances. In some embodiments of this application, the electron injection layer 360 may contain ytterbium (Yb).

[0096] A second aspect of this application further provides an electronic device including the organic electroluminescent device described in this application.

[0097] For example, as shown in Figure 2, the electronic device provided in this application is a first electronic device 400, which includes any of the organic electroluminescent devices described in the embodiments of the organic electroluminescent device described above. The electronic device may be a display device, a lighting device, an optical communication device, or any other type of electronic device, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, etc. Since the first electronic device 400 has the organic electroluminescent device described above, it has the same beneficial effects and is not mentioned again in this application.

[0098] The present application will be described in detail below with reference to examples, but the following description is for interpretation purposes only and does not limit the scope of the present application in any way.

[0099] Synthesis of the first compound Synthesis of the intermediate IM-a-no: Under the protection of nitrogen gas, 2,3-dichloronitrobenzene (20.0 g, 104.2 mmol), d5-phenylboronic acid pinacol ester (47.9 g, 229.2 mmol), tetrakis(triphenylphosphine)palladium (4.8 g, 4.2 mmol), potassium carbonate (57.6 g, 416.7 mmol), tetrabutylammonium bromide (13.4 g, 41.2 mmol), toluene (320 mL), ethanol (80 mL), and deionized water (80 mL) were added to a round-bottom flask. The mixture was heated to 75°C to 80°C and stirred for 72 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain the colorless oily intermediate IM-a-no (17.7 g, yield: 60%). Referring to the synthesis method for intermediate IM-a-no, the intermediates shown in Table 1 below were synthesized by substituting 2,3-dichloronitrobenzene in reactant A. Table 1 JPEG2026520522000101.jpg98167

[0100] Synthesis of the intermediate IM-a-nh: Under the protection of nitrogen gas, intermediate IM-a-no (16.0 g, 56.1 mmol), triphenylphosphine (36.8 g, 140.2 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask. The mixture was stirred and the temperature was raised to 175°C to 180°C, and the reaction was allowed to proceed for 36 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure. The resulting crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain the white solid intermediate IM-a-nh (9.2 g, yield: 65%). Referring to the synthesis method for intermediate IM-a-nh, the intermediates shown in Table 2 below were synthesized by substituting reactant B for intermediate IM-a-no. Table 2 JPEG2026520522000103.jpg114170

[0101] Synthesis of compound A20: Under the protection of nitrogen gas, intermediate IM-a-nh (5.0 g, 19.8 mmol), compound sub1 (12.9 g, 29.7 mmol, CAS: 217088-83-7), and N,N-dimethylformamide (50 mL) were added to a round-bottom flask. The mixture was stirred and cooled to -5°C to 0°C. Sodium hydride (0.6 g, 23.7 mmol) was added, and the reaction was stirred at -5°C to 0°C for 1 hour. The temperature was then raised to 20°C to 25°C and the reaction was continued for 24 hours. The reaction was stopped, the reaction mixture was washed with water, and then separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the eluent, and then recrystallized using a toluene / n-heptane mixed solvent as the mobile phase to obtain compound A20 (7.9 g, yield: 61%), which is a white solid. Referring to the synthesis method for compound A20, the compounds shown in Table 3 below were synthesized by substituting intermediate IM-a-nh with reactant C and compound sub1 with reactant D. Table 3 JPEG2026520522000105.jpg239168 JPEG2026520522000106.jpg107169

[0102] Synthesis of compound A46: Under the protection of nitrogen gas, intermediate IM-a-nh (5.0 g, 19.8 mmol), compound sub2 (8.7 g, 20.8 mmol, CAS: 191061-39-00), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g, 0.4 mmol), sodium tert-butoxide (2.9 g, 29.7 mmol), and xylene (50 mL) were added to a round-bottom flask, and the mixture was stirred and reacted at 135°C to 140°C for 16 hours. After cooling to room temperature, the reaction mixture was washed with water and then separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the eluent, and then the product was recrystallized and purified using a toluene / n-heptane solvent system to obtain compound A46 (9.8 g, yield: 78%), which is a white solid. Referring to the synthesis method for compound A46, the compounds shown in Table 4 below were synthesized by using reactant E in place of intermediate IM-a-nh and reactant F in place of compound sub2. Table 4 JPEG2026520522000108.jpg200168 JPEG2026520522000109.jpg208168 JPEG2026520522000110.jpg201165 JPEG2026520522000111.jpg195168 JPEG2026520522000112.jpg214168 JPEG2026520522000113.jpg109167

[0103] Synthesis of reactant F-89 used in compound B89 Under the protection of nitrogen gas, 2-chloro-4,6-bis(phenyl-2,3,4,5,6-D5)-1,3,5-triazine (20.0 g, 72.0 mmol), 3'-chlorobiphenyl-4-boronic acid (17.6 g, 75.6 mmol), tetrakis(triphenylphosphine)palladium (0.8 g, 0.7 mmol), potassium carbonate (19.9 g, 144.0 mmol), tetrabutylammonium bromide (0.2 g, 0.7 mmol), toluene (200 mL), ethanol (80 mL), and deionized water (40 mL) were added to a round-bottom flask. The reaction mixture was heated to 75°C to 80°C and stirred for 5 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain the white solid intermediate F-89 (24.8 g, yield: 80%).

[0104] Synthesis of intermediate sub a1: Under the protection of nitrogen gas, compound sub 3 (20.0 g, 74.7 mmol, CAS: 3842-55-5), 3-fluoro-4-biphenylboronic acid (16.9 g, 78.4 mmol), tetrakis(triphenylphosphine)palladium (0.9 g, 0.7 mmol), potassium carbonate (20.6 g, 149.4 mmol), tetrabutylammonium bromide (0.2 g, 0.7 mmol), toluene (200 mL), ethanol (80 mL), and deionized water (40 mL) were added to a round-bottom flask. The reaction mixture was heated to 75°C to 80°C and stirred for 10 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain the white solid intermediate sub a1 (21.7 g, yield: 72%). Referring to the synthesis method for intermediate sub a1, the intermediates shown in Table 5 below were synthesized by substituting 3-fluoro-4-biphenylboronic acid with reactant G. Table 5 JPEG2026520522000116.jpg36129

[0105] Synthesis of compound B73 Under the protection of nitrogen gas, compound IM-b-nh (22.5 g, 89.2 mmol), compound sub a1 (20 g, 49.6 mmol), tripotassium phosphate (52.6 g, 247.8 mmol), and N-methylpyrrolidone (200 mL) were added to a round-bottom flask. The reaction mixture was heated to 195°C and stirred for 12 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent to obtain solid product B73 (18.3 g, yield: 58%). Referring to the synthesis method for compound B73, compound sub a1 was substituted with reactant H to synthesize the compounds shown in Table 6 below. Table 6 JPEG2026520522000118.jpg114170

[0106] Synthesis of intermediate ai: Under the protection of nitrogen gas, 2,3-dichloronitrobenzene (20.0 g, 104.2 mmol), D5-phenylboronic acid pinacol ester (21.8 g, 104.2 mmol), tetrakis(triphenylphosphine)palladium (2.4 g, 2.1 mmol), potassium carbonate (28.8 g, 208.3 mmol), tetrabutylammonium bromide (6.7 g, 20.8 mmol), toluene (160 mL), ethanol (40 mL), and deionized water (40 mL) were added to a round-bottom flask. The reaction mixture was heated to 75°C to 80°C and stirred for 48 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain the white solid intermediate ai (18.8 g, yield: 76%).

[0107] Synthesis of intermediate aii: Under the protection of nitrogen gas, intermediate ai (18.0 g, 75.4 mmol), triphenylphosphine (49.5 g, 188.5 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask. The mixture was stirred and the temperature was raised to 175°C to 180°C, and the reaction was allowed to proceed for 36 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure. The resulting crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent to obtain the white solid intermediate aii (11.1 g, yield: 72%).

[0108] Synthesis of intermediate SL1: JPEG2026520522000121.jpg35138 Intermediate aii (10.0 g, 48.6 mmol), 4-biphenylboronic acid (10.1 g, 51.1 mmol), palladium acetate (0.1 g, 0.5 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.5 g, 1.0 mmol), cesium carbonate (23.8 g, 72.9 mmol), toluene (80 mL), ethanol (20 mL), and deionized water (20 mL) were added to a round-bottom flask protected by nitrogen gas. The mixture was heated to 75°C to 80°C and stirred and reacted for 48 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent to obtain the white solid intermediate SL1 (12.1 g, yield: 77%).

[0109] Synthesis of compound AA21: Under the protection of nitrogen gas, intermediate SL1 (5.0 g, 15.5 mmol), intermediate sub4 (6.5 g, 15.5 mmol, CAS: 1443049-84-0), tris(dibenzylideneacetone)dipalladium (0.1 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g, 0.3 mmol), sodium tert-butoxide (2.2 g, 23.2 mmol), and xylene (50 mL) were added to a round-bottom flask, and the mixture was stirred and reacted at 135°C to 140°C for 7 hours. After cooling to room temperature, the reaction mixture was washed with water and separated, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the eluent. The product was then recrystallized using a toluene / n-heptane mixed solvent to obtain compound AA21 (7.6 g, yield: 70%), which is a white solid.

[0110] The mass spectral data for the first compound is shown in Table 7 below. Table 7 JPEG2026520522000123.jpg144150

[0111] Synthesis of the second compound Synthesis of compound a3: Under the protection of nitrogen gas, starting materials a-1 (20.0 g, 48.9 mmol, CAS: 2071630-78-7), starting material b-1 (15.1 g, 48.9 mmol, CAS: 1762-84-1), tris(dibenzylideneacetone)dipalladium (0.4 g, 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol), sodium tert-butoxide (7.0 g, 73.4 mmol), and xylene (200 mL) were added to a round-bottom flask, and the mixture was stirred and reacted at 140°C for 6 hours. After cooling to room temperature, the reaction solution was washed with water and separated, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the eluent. The product was then recrystallized using a toluene / n-heptane mixed solvent to obtain compound a3-1 (23.1 g, yield: 74%), which is a white solid. A solution was prepared by adding trifluoromethanesulfonic acid anhydride (86.8 g, 307.8 mmol) and heavy water (30.8 g, 1538.9 mmol) at 60°C and stirring for 5 hours. Compound a3-1 (20 g, 31.4 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and the mixture was stirred. Next, the prepared mixture of trifluoromethanesulfonic acid anhydride and heavy water was gradually added dropwise to the mixed solution of compound a3-1 and 1,2,4-trichlorobenzene, and the mixture was stirred while heating to 140°C, after which the temperature was maintained. After reacting for 14 hours, the reaction mixture was cooled to room temperature and the organic layer and aqueous layer were separated. The organic layer was then neutralized with aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound a3 (10.97 g, yield: 54%). Referring to the synthesis method for compound a3, the compounds shown in Table 8 below were synthesized by using reactant a in place of compound a-1 and reactant b in place of compound b-1. Table 8 JPEG2026520522000126.jpg179165 JPEG2026520522000127.jpg226167 JPEG2026520522000128.jpg82169

[0112] The mass spectral data for the second compound is shown in Table 9 below. Table 9 JPEG2026520522000129.jpg54149

[0113] Fabrication of organic electroluminescent devices Example 1: Fabrication of a green organic electroluminescent device The device was fabricated using the following process. On an experimental substrate with an ITO / Ag / ITO thickness of 100 Å / 1000 Å / 100 Å, surface treatment can be performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate can be cleaned with an organic solvent to remove impurities and oil stains from the surface of the experimental substrate. Compound HT-1 and PD were co-deposited onto an experimental substrate at a deposition rate ratio of 97%:3% to form a 100 Å thick hole injection layer. Then, compound HT-1 was deposited on the hole injection layer to form a 1050 Å thick hole transport layer. Compound HT-2 was deposited on the hole transport layer to form a 470 Å thick luminescence auxiliary layer. Compound a3 (second compound), compound A2 (first compound), and GD-01 (dopant guest) were co-deposited onto the luminescence auxiliary layer at a deposition rate ratio of 60%:40%:10% to form an organic luminescence layer with a thickness of 320 Å. A 330 Å thick electron transport layer was formed by co-depositing the compound ET-1 and LiQ on an organic light-emitting layer at a 50%:50% deposition rate ratio. Yb was deposited on an electron transport layer to form an electron injection layer with a thickness of 15 Å. Subsequently, magnesium (Mg) and silver (Ag) were co-deposited on the electron injection layer at a deposition rate ratio of 10%:90% to form a cathode with a thickness of 125 Å. Compound CP-1 was deposited onto the cathode to form a 630 Å thick organic coating layer, thereby completing the fabrication of a green organic electroluminescent device.

[0114] Examples 2 to 40: An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the deposition rate ratios of the first compound, the second compound, and the first compound to the second compound in Example 1 were replaced with those of the first compound, the second compound, and the deposition rate ratio of the first compound to the second compound in Table 10.

[0115] Comparative Example 1 to Comparative Example 2: An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the deposition rate ratios of the first compound, the second compound, and the first compound to the second compound in Example 1 were replaced with those of the first compound, the second compound, and the deposition rate ratio of the first compound to the second compound in Table 10.

[0116] The compounds used to fabricate the devices in each example and comparative example are listed below. JPEG2026520522000130.jpg131170

[0117] Performance measurements were performed on the green organic electroluminescent devices prepared in Examples 1 to 40 and Comparative Examples 1 to 2. Specifically, the measured performance was 15 mA / cm². 2 The IVL performance of the device was measured under the following conditions: 20 mA / cm² 2 The lifetime of the T95 device was measured under these conditions. The measurement results are shown in Table 10 below. Table 10 JPEG2026520522000131.jpg232170

[0118] As can be seen from the table above, Examples 1 to 40 showed at least an 8.9% improvement in device current efficiency and at least a 33.5% improvement in T95 lifetime compared to Comparative Examples 1 to 2.

[0119] The organic light-emitting layer of the organic electroluminescent device of this application comprises a first compound and a second compound. The core structure of the first compound is such that a phenylcarbazole is linked to a triazine group via a nitrogen atom, and one benzene ring in the carbazole ring is completely deuterated, while an aryl group is linked to the other benzene ring. By substituted an aryl group on one side of the carbazole group, the aromatic conjugation range of the molecular structure is expanded and molecular symmetry is reduced, allowing the material to have better energy transfer properties and reduced crystallinity. The special asymmetric deuteration of the carbazole group can effectively improve the stability of the molecular structure and further reduce molecular symmetry, significantly improving the photoelectric stability and film-forming properties of the material. The first compound of this application has good carrier transport properties, energy transfer properties and photoelectric stability, and is suitable for use as a host material for the light-emitting layer in an organic electroluminescent device. An organic electroluminescent device using it as a host material maintains a low driving voltage and high luminous efficiency, and has clearly improved lifetime characteristics. The second compound of this application significantly improves the stability of the compound by selecting an indrocarbazole compound of a specific condensation type and completely deuterating the parent nucleus of the compound. The combination of these two groups of deuterated compounds has a balanced and high carrier mobility, and by using the above two materials as a mixed host material for a green organic electroluminescent device, the operating voltage of the organic electroluminescent device can be reduced, and the luminescence efficiency and lifetime can be improved. In particular, if the aryl group on the carbazole side of the first compound is a penta-deuterated phenyl group, the device performance is even better when combined with the second compound.

[0120] Specifically, compared to Comparative Example 1, the device fabricated in this application clearly reduces the driving voltage and improves the luminous efficiency. Upon investigating the cause, the following can be considered: By using the first compound of this application in combination with a second compound that has strong hole properties due to deuteration at a specific position in the phenylcarbazole core structure, the service life of the organic electroluminescent can be significantly improved.

[0121] Compared to Comparative Example 2, the device fabricated in this application showed a significantly improved service life. Upon investigating the cause, the following can be considered: The first compound of this application is deuterated at a specific position of the carbazole group, and the triazine and carbazole are linked by a single bond or an arylene group. When used with the second compound, which has strong hole properties, the photoelectric stability of the device can be significantly improved.

[0122] Although some embodiments of this application have been described in detail above with reference to the drawings, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical proposal of this application, and all of these simple modifications fall within the scope of protection of this application.

Claims

1. An organic electroluminescent device comprising a cathode, an anode, and an organic layer, wherein the cathode and the anode are arranged opposite each other, the organic layer is located between the cathode and the anode, and the organic layer includes an organic light-emitting layer, The organic light-emitting layer comprises a first compound and a second compound, The first compound is a compound represented by formula 1, Formula 1 However, Ar 1 and Ar 2 These are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothienyl groups. L, L 1 and L 2 These are the same or different, and each is independently selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms. Ar 3 These are penta-deuterated phenyl groups, biphenyl groups, or terphenyl groups. L, L 1 , L 2 , Ar 1 and Ar 2 The substituents in are the same or different and each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, The second compound is a compound represented by formula 2, Formula 2 L 4 and L 5 These are the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms. Ar 4 and Ar 5 These are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. L 4 , L 5 Ar 4 and Ar 5 An organic electroluminescent device characterized in that the substituents in are the same or different and each is independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C6-C20 aryl group, a C6-C20 deuterated aryl group, a C6-C20 halogenated aryl group, or a C3-C10 cycloalkyl group.

2. In Equation 1, L, L 1 and L 2 These are the same or different, and each is independently selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 12 carbon atoms. Available in sizes L and L 1 and L 2 The organic electroluminescent device according to claim 1, characterized in that the substituents in are the same or different and each is independently selected from deuterium, a halogen group, a cyano group, a C1-C5 alkyl group, a phenyl group, or a penta-deuterated phenyl group.

3. In Equation 1, L, L 1 and L 2 These are the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, and substituted or unsubstituted biphenylene groups. Available in sizes L and L 1 and L 2 The organic electroluminescent device according to claim 1, characterized in that the members are the same or different and each is independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group.

4. In Equation 1, Ar 1 and Ar 2 These are the same or different, and each is independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothienyl groups. Selectable, Ar 1 and Ar 2 The organic electroluminescent device according to claim 1, characterized in that the substituents in are the same or different and each is independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group.

5. In Equation 1, and The organic electroluminescent device according to claim 1, characterized in that each of the groups is independently selected from the group consisting of the following groups.

6. In Equation 1, The organic electroluminescent device according to claim 1, characterized in that the group is selected from the group consisting of the following groups.

7. In Equation 1, Ar 3 The organic electroluminescent device according to claim 1, characterized in that the group is selected from the group consisting of the following groups.

8. The organic electroluminescent device according to claim 1, characterized in that the first compound is selected from the group consisting of the following compounds.

9. In Equation 2, L 4 and L 5 These are the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, substituted or unsubstituted biphenylene groups, substituted or unsubstituted carbazoylene groups, substituted or unsubstituted dibenzofuranylene groups, and substituted or unsubstituted dibenzothiophenylene groups. Selectable, L 4 and L 5 The organic electroluminescent device according to claim 1, characterized in that the substituents in are the same or different and each is independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, or phenyl group.

10. In equation 2, Ar 4 and Ar 5 These are the same or different, and each is independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted quarterphenyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothienyl groups, and substituted or unsubstituted carbazolyl groups. Selectable, Ar 4 and Ar 5 The organic electroluminescent device according to claim 1, characterized in that the substituents in are the same or different and each is independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, phenyl group, or penta-deuterated phenyl group.

11. In Equation 2, and The organic electroluminescent device according to claim 1, characterized in that the groups are the same or different and each is independently selected from the group consisting of the following groups.

12. The organic electroluminescent device according to claim 1, characterized in that the second compound is selected from the group consisting of the following compounds.

13. The organic electroluminescent device according to claim 1, characterized in that the organic layer further comprises a hole injection layer, a hole transport layer, a light emission auxiliary layer, an electron transport layer, and an electron injection layer.

14. An electronic device comprising an organic electroluminescent device according to any one of claims 1 to 13.

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