Organic electroluminescent device and electronic device

Abstract

The invention provides an organic electroluminescent device and an electronic device. The organic electroluminescent device comprises a cathode, an anode and an organic layer. The organic layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a first compound and a second compound; the first compound has a structure as shown in a formula 1, and the second compound is selected from a structure as shown in a formula 2, a formula 3, a formula 4 or a formula 5. # imgabs0 #

Description

Technical Field

[0001] The present application relates to the field of organic electroluminescence, and in particular to an organic electroluminescent device and an electronic apparatus. Background Art

[0002] In recent years, organic electroluminescent devices (OLEDs) have become a very popular emerging flat-panel display product both at home and abroad. This is because OLED displays have the characteristics of self-luminescence, wide viewing angle, short response time, high efficiency, and wide color gamut.

[0003] An organic electroluminescent device (OLED) generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a luminescence adjustment layer, an organic light-emitting layer (containing a host and a dopant material), a hole blocking layer, an electron transport layer, an electron injection layer, etc. If a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light-emitting layer by the anode and the cathode, respectively. Then, in the organic light-emitting layer, the injected holes and electrons recombine to form excitons. The excitons are in an excited state and release energy outward, thereby causing the light-emitting layer to emit light outward.

[0004] At present, there are still problems of poor performance in the use of organic electroluminescent devices, such as excessively high driving voltage, low luminous efficiency or short life, which all affect the use field of organic electroluminescent devices. Therefore, it is still necessary to conduct further research in this field to improve the performance of organic electroluminescent devices.

[0005] It should be noted that the information disclosed in the above background technology section is only used to enhance the understanding of the background of the present application, and therefore may include information that does not constitute the prior art known to ordinary technicians in the field. Summary of the invention

[0006] The present application provides an organic electroluminescent device and an electronic apparatus, which are used to solve the device problems of low luminous efficiency and short life in the prior art.

[0007] In order to achieve the above invention objectives, this application adopts the following technical solutions:

[0008] According to a first aspect of the present application, the present application provides an organic electroluminescent device, comprising a cathode, an anode and an organic layer; the cathode and the anode are arranged opposite to each other; the organic layer is located between the cathode and the anode; the organic layer comprises an organic light-emitting layer;

[0009] Wherein, the organic light-emitting layer includes a first compound and a second compound;

[0010] The first compound has a structure shown in Formula 1:

[0011]

[0012] wherein Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups;

[0013] L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

[0014]

[0015] The substituents in 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, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms;

[0016] The second compound is selected from the structure shown in Formula 2, Formula 3, Formula 4 or Formula 5:

[0017]

[0018] In Formula 2, X is selected from O, S or N(Ar);

[0019] Ar is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms;

[0020] R1 is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms;

[0021] One of R2 and R3 is hydrogen, deuterium, cyano, a halogen group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and the other is a group represented by formula 2-1;

[0022] L3, L4 and L5 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0023] Ar4 and Ar5 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0024] The substituents in R1, R2, R3, L3, L4, L5, Ar, Ar4 and Ar5 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and a deuterated alkyl group having 1 to 10 carbon atoms;

[0025]

[0026] In formula 3, ring A is a naphthalene ring;

[0027] L6, L7 and L8 are the same or different and are 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 30 carbon atoms;

[0028] Ar8 is selected from the group shown in formula 3-1;

[0029]

[0030] T is selected from O or S;

[0031] Ar7 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms;

[0032] The substituents in L6, L7, L8 and Ar7 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;

[0033] each R4, each R5 and each R6 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms;

[0034] n4 is selected from 0, 1, 2, 3 or 4; n5 is selected from 0, 1, 2, 3, 4, 5 or 6; n6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0035]

[0036] In formula 4, L 10 , L 11 and L 12 are the same or different and are 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 30 carbon atoms;

[0037] Ar 11 and Ar 12 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0038] Each R7, each R8, each R9, each R 10 and each R 11 are the same or different and are independently selected from deuterium, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl having 3 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and deuterated alkyl having 1 to 10 carbon atoms;

[0039] n7 and n 11 are independently selected from 0, 1, 2, 3 or 4;

[0040] n8, n9 and n 10 are independently selected from 0, 1 or 2;

[0041] L 10 , L 11 , L 12 ,Ar 11 and Ar 12 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl having 3 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and deuterated alkyl having 1 to 10 carbon atoms;

[0042]

[0043] In Formula 5, one of M and Y is the other is O or S;

[0044] L 13 , L 14 and L 15 are the same or different and are 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 30 carbon atoms;

[0045] Ar 13 ,Ar 14 and Ar 15 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0046] L 13 , L 14 , L 15 ,Ar 13 ,Ar 14 and Ar 15 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, and cycloalkyl groups having 3 to 10 carbon atoms;

[0047] Each R 12 , each R 13 and each R 14 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms;

[0048] n 12 and n 13 are independently selected from 0, 1 or 2; n 14 Selected from 0, 1, 2, 3, 4, 5 or 6.

[0049] According to a second aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the first aspect.

[0050] The present application provides an organic electroluminescent device, wherein the organic layer in the organic electroluminescent device includes an organic light-emitting layer, and the organic light-emitting layer includes a first compound with strong electronic properties and a second compound with strong hole properties, wherein the core structure of the first compound is phenylcarbazole connected to a triazine group through a nitrogen atom, and one of the benzene rings on the carbazole ring is fully deuterated, and the other benzene ring is connected to a penta-deuterated phenyl group. The second compound is an aromatic amine compound with a large conjugated area. The first compound and the second compound are used together as the main material of the organic electroluminescent layer, which can adjust the balance between holes and electrons, so that the organic light-emitting layer generates more excitons, thereby improving the performance of the organic electroluminescent device.

[0051] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0052] 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.

[0053] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0054] Figure 2 It is a structural schematic diagram of an electronic device of the present application.

[0055] Reference numerals

[0056] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0057] 320, hole transport layer 330, luminescence adjustment layer 340, organic light emitting layer 350, electron transport layer

[0058] 360, electron injection layer 400, first electronic device DETAILED DESCRIPTION

[0059] Example embodiments will now be described more fully with reference to the accompanying drawings. However, example 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 example 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.

[0060] In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus their detailed description will be omitted.

[0061] The described features, structures or characteristics may be combined in one or more embodiments in any suitable manner. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application. However, those skilled in the art will appreciate that the technical scheme of the present application may be put into practice without one or more of the specific details, or other methods, components, materials, etc. may be adopted. In other cases, known structures, materials or operations are not shown or described in detail to avoid blurring the main technical creativity of the present application.

[0062] According to a first aspect of the present application, the present application provides an organic electroluminescent device, comprising a cathode, an anode and an organic layer; the cathode and the anode are arranged opposite to each other; the organic layer is located between the cathode and the anode; the organic layer comprises an organic light-emitting layer;

[0063] Wherein, the organic light-emitting layer includes a first compound and a second compound;

[0064] The first compound has a structure shown in Formula 1:

[0065]

[0066] wherein Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups;

[0067] L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

[0068] Ar3 is

[0069] The substituents in 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, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms;

[0070] The second compound is selected from the structure shown in Formula 2, Formula 3, Formula 4 or Formula 5:

[0071]

[0072] In Formula 2, X is selected from O, S or N(Ar);

[0073] Ar is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms;

[0074] R1 is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms;

[0075] One of R2 and R3 is hydrogen, deuterium, cyano, a halogen group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and the other is a group represented by formula 2-1;

[0076] L3, L4 and L5 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0077] Ar4 and Ar5 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0078] The substituents in R1, R2, R3, L3, L4, L5, Ar, Ar4 and Ar5 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and a deuterated alkyl group having 1 to 10 carbon atoms;

[0079]

[0080] In formula 3, ring A is a naphthalene ring;

[0081] L6, L7 and L8 are the same or different and are 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 30 carbon atoms;

[0082] Ar8 is selected from the group shown in formula 3-1;

[0083]

[0084] T is selected from O or S;

[0085] Ar7 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms;

[0086] The substituents in L6, L7, L8 and Ar7 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;

[0087] each R4, each R5 and each R6 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms;

[0088] n4 is selected from 0, 1, 2, 3 or 4; n5 is selected from 0, 1, 2, 3, 4, 5 or 6; n6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0089]

[0090] In formula 4, L 10 , L 11 and L 12 are the same or different and are 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 30 carbon atoms;

[0091] Ar 11 and Ar 12 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0092] Each R7, each R8, each R9, each R 10 and each R 11 are the same or different and are independently selected from deuterium, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl having 3 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and deuterated alkyl having 1 to 10 carbon atoms;

[0093] n7 and n 11 are independently selected from 0, 1, 2, 3 or 4;

[0094] n8, n9 and n 10 are independently selected from 0, 1 or 2;

[0095] L 10 , L 11 , L 12 ,Ar 11 and Ar 12 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl having 3 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and deuterated alkyl having 1 to 10 carbon atoms;

[0096]

[0097] In Formula 5, one of M and Y is the other is O or S;

[0098] L 13 , L 14 and L 15 are the same or different and are 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 30 carbon atoms;

[0099] Ar 13 ,Ar 14 and Ar 15 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0100] L 13 , L 14 , L 15 ,Ar 13 ,Ar 14 and Ar 15 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, and cycloalkyl groups having 3 to 10 carbon atoms;

[0101] Each R 12 , each R 13 and each R 14 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms;

[0102] n 12 and n 13 are independently selected from 0, 1 or 2; n 14 Selected from 0, 1, 2, 3, 4, 5 or 6.

[0103] 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.

[0104] 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 group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, cyano, halogen group, alkyl, haloalkyl, deuterated alkyl, aryl, deuterated aryl, haloaryl, cycloalkyl, etc. The number of substitutions can be 1 or more.

[0105] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0106] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0107] 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 may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0108] In the present application, terphenyl includes

[0109] In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents is 18.

[0110] In the present application, the carbon number of 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.

[0111] In this application, L, L1, L2, L3, L4, L5, L6, L7, L8, L 10 , L 11 , L 12 , L 13 , L 14 , L 15 , Ar1, Ar2, Ar4, Ar5, Ar7, Ar 11 ,Ar 12 ,Ar 13 ,Ar14 ,Ar 15 The aryl substituents are exemplified, but not limited to, phenyl, naphthyl, and the like.

[0112] 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.

[0113] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can 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.

[0114] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0115] 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 of 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.

[0116] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0117] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0118] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0119] In the present application, a deuterated aryl group refers to an aryl group containing at least one deuterium substituent. Specific examples of the deuterated aryl group include, but are not limited to, pentadeuterated phenyl and pentadeuterated biphenyl.

[0120] 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.

[0121] 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, and the meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10).

[0122]

[0123] 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 its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0124]

[0125] In some embodiments of the present application, the first compound represented by Formula 1 is selected from the structure represented by Formula 1-1, Formula 1-2, Formula 1-3 or Formula 1-4:

[0126]

[0127] In some embodiments of the present application, in the first compound represented by Formula 1, L, L1 and L2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0128] Optionally, the substituents in L, L1 and L2 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0129] In some other embodiments of the present application, in the first compound represented by Formula 1, L, L1 and L2 are the same or different, and are 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.

[0130] Optionally, L, L1 and L2 are the same or different, and the substituents independently selected from are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0131] Further optionally, in the first compound shown in Formula 1, L, L1 and L2 are the same or different, and are independently selected from the group consisting of a single bond or the following groups:

[0132]

[0133] Specifically, in the first compound represented by Formula 1, L, L1 and L2 are the same or different and are independently selected from a single bond or the following groups:

[0134]

[0135]

[0136] In some embodiments of the present application, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophenyl groups.

[0137] Optionally, the substituents in Ar1 and Ar2 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a pentadeuterated phenyl group.

[0138] In some other embodiments of the present application, in the first compound shown in Formula 1, Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0139] Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0140] In some embodiments of the present application, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0141]

[0142] Specifically, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0143]

[0144]

[0145] In some embodiments of the present application, in the first compound represented by Formula 1, are independently selected from the following groups:

[0146]

[0147] Specifically, in the first compound represented by Formula 1, are independently selected from the group consisting of:

[0148]

[0149] Optionally, in the first compound represented by Formula 1, Selected from the group consisting of:

[0150]

[0151]

[0152] In some embodiments of the present application, in the second compound represented by Formula 2, L3 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0153] In some embodiments of the present application, in the second compound represented by Formula 2, L4 and L5 are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0154] Optionally, the substituents in L3, L4 and L5 are the same or different, and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0155] In some embodiments of the present application, in the second compound represented by Formula 2, L3 is selected from a single bond, an unsubstituted phenylene group, an unsubstituted naphthylene group or an unsubstituted biphenylene group.

[0156] In some embodiments of the present application, in the second compound shown in Formula 2, L4 and L5 are the same or different, and are 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 carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.

[0157] Optionally, the substituents in L4 and L5 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0158] In some embodiments of the present application, in the second compound shown in Formula 2, L3 is selected from a single bond or the following groups:

[0159]

[0160] In some embodiments of the present application, in the second compound represented by Formula 2, L4 and L5 are the same or different and are independently selected from a single bond or the following groups:

[0161]

[0162] In some embodiments of the present application, in the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

[0163] Optionally, the substituents in Ar4 and Ar5 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0164] In some other embodiments of the present application, in the second compound shown in Formula 2, Ar4 and Ar5 are the same or different, and are independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted phenanthrenyl.

[0165] Optionally, the substituents in Ar4 and Ar5 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0166] In some embodiments of the present application, in the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are independently selected from the group consisting of the following groups:

[0167]

[0168] Specifically, in the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are independently selected from the group consisting of the following groups:

[0169]

[0170] In some embodiments of the present application, in the second compound represented by Formula 2, Ar is selected from substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms.

[0171] Optionally, the substituents in Ar are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a tert-butyl group or a phenyl group.

[0172] In some other embodiments of the present application, in the second compound represented by Formula 2, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl.

[0173] Optionally, the substituents in Ar are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0174] In some embodiments of the present application, in the second compound represented by Formula 2, Ar is selected from the group consisting of the following groups:

[0175]

[0176] In some embodiments of the present application, in the compound represented by Formula 2, R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl.

[0177] Optionally, the substituents in R1 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0178] In some embodiments of the present application, in the second compound represented by Formula 2, R1 is selected from the group consisting of the following groups:

[0179]

[0180] In some embodiments of the present application, in the second compound represented by Formula 2, one of R2 and R3 is hydrogen, and the other is selected from the group represented by Formula 2-1.

[0181] In some embodiments of the present application, the second compound shown in Formula 3 is selected from the structure shown in Formula 3-1, 3-2 or Formula 3-3:

[0182]

[0183] In some embodiments, in the second compound represented by Formula 3, L6, L7 and L8 are 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, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0184] In some embodiments of the present application, in the second compound represented by Formula 3, L6, L7 and L8 are independently selected from substituted or unsubstituted arylene groups having 6 to 12 single-bond carbon atoms and substituted or unsubstituted heteroarylene groups having 12 to 18 carbon atoms.

[0185] Optionally, the substituents in L6, L7 and L8 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0186] In some embodiments, in the second compound shown in Formula 3, L6, L7 and L8 are the same or different, and are 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 carbazolylene, a substituted or unsubstituted dibenzothiophenylene, and a substituted or unsubstituted dibenzofuranylene.

[0187] Optionally, the substituents in L6, L7 and L8 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0188] In some embodiments, in the second compound represented by Formula 3, L6 and L8 are independently selected from a single bond or the following groups:

[0189] In some embodiments, in the second compound represented by Formula 3, L7 is selected from a single bond or the following groups:

[0190]

[0191] In some embodiments, in the second compound shown in Formula 3, Ar7 is 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, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0192] In some embodiments of the present application, in the second compound represented by Formula 3, Ar7 is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0193] Optionally, the substituents in Ar7 are the same or different, and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0194] In some embodiments, in the second compound shown in Formula 3, Ar7 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrenyl.

[0195] Optionally, the substituents in Ar7 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0196] In some embodiments, in the second compound represented by Formula 3, Ar7 is selected from the group consisting of the following groups:

[0197]

[0198] In some embodiments, in the second compound represented by Formula 3, Ar7 is selected from the group consisting of the following groups:

[0199]

[0200] In some embodiments of the present application, in the second compound represented by Formula 3, Ar8 is selected from the group consisting of the following groups:

[0201]

[0202] Specifically, in the second compound shown in Formula 3, Ar8 is selected from the group consisting of the following groups:

[0203]

[0204] In some embodiments, in the second compound represented by Formula 3, each R4 and each R5 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0205] In some embodiments of the present application, in the second compound represented by Formula 3, n4 and n5 are both 0.

[0206] In some embodiments, in the second compound represented by Formula 4, L 10 , L11 and L 12 the same or different, each independently selected from a single bond, a substituted or unsubstituted arylene group 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 a substituted or unsubstituted heteroarylene group having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0207] In some embodiments of the present application, in the second compound shown in Formula 4, L 10 , L 11 and L 12 are the same or different and are 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;

[0208] Optionally, L 10 , L 11 and L 12 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0209] In some embodiments of the present application, in the second compound shown in Formula 4, L 10 , L 11 and L 12 are the same or different and are 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 carbazolylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted dibenzofuranyl group.

[0210] Optionally, L 10 , L 11 and L 12 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0211] In some embodiments of the present application, in the second compound shown in Formula 4, L 10 , L 11 and L 12 are the same or different, and are independently selected from a single bond or the following groups:

[0212]

[0213] Specifically, in the second compound represented by Formula 4, L10 , L 11 and L 12 are the same or different, and are independently selected from a single bond or the following groups:

[0214]

[0215] In some embodiments, in the second compound represented by Formula 4, Ar 11 and Ar 12 the same or different, and 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 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0216] In some embodiments of the present application, in the second compound shown in Formula 4, Ar 11 and Ar 12 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0217] Optionally, Ar 11 and Ar 12 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0218] In some other embodiments of the present application, in the second compound shown in Formula 4, Ar 11 and Ar 12 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted phenanthrenyl.

[0219] Optionally, Ar 11 and Ar 12 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0220] In some embodiments of the present application, in the second compound shown in Formula 4, Ar 11 and Ar 12 The same or different, each independently selected from the group consisting of the following groups:

[0221]

[0222] Specifically, in the second compound shown in Formula 4, Ar 11 and Ar 12 The same or different, each independently selected from the group consisting of the following groups:

[0223]

[0224] In some embodiments of the present application, in the second compound shown in Formula 4, each R7, each R8, each R9, each R 10 and each R 11 are the same or different and are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0225] In some embodiments of the present application, in the second compound shown in Formula 4, n7, n8, n9, n 10 and n 11 Both are 0.

[0226] In some embodiments of the present application, in the second compound represented by Formula 5, L 13 , L 14 and L 15 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 or 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0227] In some embodiments of the present application, in the second compound represented by Formula 5, L 13 , L 14 and L 15 are the same or different and are each 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.

[0228] Optionally, L 13 , L 14 and L 15 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0229] In some other embodiments of the present application, in the second compound represented by Formula 5, L 13 , L 14 and L 15are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted carbazolylene group.

[0230] Optionally, L 13 , L 14 and L 15 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0231] In some embodiments of the present application, in the second compound represented by Formula 5, L 13 , L 14 and L 15 are the same or different and are independently selected from a single bond or the following groups:

[0232]

[0233] Specifically, in the second compound represented by Formula 5, L 13 , L 14 and L 15 are the same or different and are independently selected from a single bond or the following groups:

[0234]

[0235] In some embodiments of the present application, in the second compound shown in Formula 5, Ar 13 ,Ar 14 and Ar 15 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.

[0236] In some embodiments, in the second compound represented by Formula 5, Ar 13 ,Ar 14 and Ar 15 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0237] Optionally, Ar 13 ,Ar 14 and Ar 15The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0238] In some embodiments of the present application, in the second compound shown in Formula 5, Ar 13 ,Ar 14 and Ar 15 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0239] Optionally, Ar 13 ,Ar 14 and Ar 15 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0240] In some embodiments of the present application, in the second compound shown in Formula 5, Ar 13 ,Ar 14 and Ar 15 The same or different, and are independently selected from the following groups:

[0241]

[0242]

[0243] Specifically, in the second compound represented by Formula 5, Ar 13 ,Ar 14 and Ar 15 The same or different, and are independently selected from the following groups:

[0244]

[0245] In some embodiments of the present application, in the second compound represented by Formula 5, each R 12 , each R 13 and each R 14 are the same or different and are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0246] In some embodiments of the present application, in the second compound represented by Formula 5, n 12 、n 13 and n 14 Both are 0.

[0247] In some embodiments of the present application, the first compound represented by Formula 1 is selected from the compounds represented by A1 to A222 in claim 10.

[0248] In some embodiments of the present application, the second compound represented by Formula 2 is selected from the compounds represented by E1 to E77 in claim 10.

[0249] In some embodiments, the second compound represented by Formula 3 is selected from the compounds represented by B1 to B62 in claim 10.

[0250] In some embodiments, the second compound represented by Formula 4 is selected from the compounds represented by D1 to D51 in claim 10.

[0251] In some embodiments, the second compound represented by Formula 5 is selected from the compounds represented by C1 to C49 in claim 10.

[0252] Optionally, the mass ratio of the first compound to the second compound in the composition is 1:99 to 99:1, preferably 10:90 to 90:10, further preferably 30:70 to 70:30, and more preferably 40:60 to 60:40.

[0253] In some embodiments, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound of Formula 2) in the composition is 30:70 to 70:30.

[0254] In one embodiment of the present application, the organic electroluminescent device is a phosphorescent device.

[0255] In a specific embodiment of the present application, the organic electroluminescent device is a red phosphorescent organic electroluminescent device.

[0256] In some embodiments of the present application, the organic electroluminescent device includes an anode (ITO substrate), a hole transport layer, a luminescence adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture) and an organic covering layer in sequence.

[0257] In a specific embodiment of the present application, Figure 1 As shown, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer, and the functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a luminescence adjustment layer 330, an organic light-emitting layer 340, an electron transport layer 350 and an electron injection layer 360.

[0258] Optionally, the anode 100 includes the following anode materials, which are preferably materials 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 comprising indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0259] Optionally, the hole transport layer 320 may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in the present application. For example, in some embodiments of the present application, the hole transport layer 320 is composed of HT-1.

[0260] Optionally, the luminescence adjustment layer 330 (the luminescence adjustment layer is also called a hole adjustment layer, an electron blocking layer, a hole auxiliary layer, a hole buffer layer, a luminescence auxiliary layer or a second hole transport layer) may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and the present application does not make any special restrictions on this. For example, in some embodiments of the present application, the luminescence adjustment layer 330 is composed of HT-2.

[0261] Optionally, the organic light-emitting layer 340 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 340 is composed of a host material and a guest material, and holes and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 340 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.

[0262] The guest material of the organic light-emitting layer 340 may 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 particular limitation thereto.

[0263] In some embodiments of the present application, in a red organic electroluminescent device, the organic light-emitting layer 340 comprises the first compound, the second compound and the guest material RD-01 of the present application.

[0264] The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions on this. For example, in some embodiments of the present application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0265] Optionally, cathode 200 includes the following 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: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode comprising silver and magnesium is included as the cathode.

[0266] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. 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 restrictions on this. In some embodiments of the present application, the hole injection layer 310 may be composed of PD-1 and HT-1.

[0267] Optionally, an electron injection layer 360 may be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 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 some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0268] A fourth aspect of the present application also provides an electronic device, which includes the organic electroluminescent device described in the present application.

[0269] For example, Figure 2 As shown, the electronic device provided in the present application is a first electronic device 400, and the first electronic device 400 includes any one of the organic electroluminescent devices described in the above organic electroluminescent device embodiments. The electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices, for example, it can include but is not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc. Since the first electronic device 400 has the above organic electroluminescent device, it has the same beneficial effects, and the present application will not repeat them here.

[0270] The present application will be described in detail below in conjunction with embodiments; however, the following description is used to explain the present application rather than to limit the scope of the present application in any way.

[0271] Synthesis of the first compound

[0272] Synthesis of intermediate Sub-a1

[0273]

[0274] Under nitrogen protection, 2,3-dichloronitrobenzene (20.00 g; 104.2 mmol), d5-phenylboronic acid pinacol ester (47.90 g; 229.2 mmol), tetrakistriphenylphosphine 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, heated to 75°C to 80°C, and stirred for 72 hours. The reaction solution was cooled to room temperature, deionized water was added, and the liquid was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent to obtain a colorless oil Sub-a1 (17.70 g; yield: 60%)

[0275] Referring to the synthesis method of the intermediate Sub-a1, reactant A is used to replace 2,3-dichloronitrobenzene to synthesize the intermediates shown in Table 1 below:

[0276] Table 1 Synthesis of intermediates Sub-a2 to Sub-a4

[0277]

[0278] Synthesis of intermediate Sub-b1:

[0279]

[0280] Under nitrogen protection, Sub-a1 (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, heated to 175°C-180°C under stirring, and reacted for 36 hours; the reaction solution was cooled to room temperature, deionized water was added, the liquid was separated, the organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure; the obtained crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid Sub-b1 (9.2 g; yield: 65%).

[0281] The same method as intermediate Sub-b1 was used, and reactant B was used to replace intermediate Sub-a1 to synthesize the intermediates shown in Table 2 below:

[0282] Table 2 Synthesis of intermediates Sub-b2 to Sub-b4

[0283]

[0284]

[0285] Synthesis of intermediate Sub-c1:

[0286]

[0287] Under nitrogen protection, 2-chloro-4,6-di(naphthalene-2-yl)-1,3,5-triazine (18.40 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL) and deionized water (35 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 with 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-c1 (18.42 g, yield: 83%).

[0288] Referring to the synthesis method of intermediate Sub-c1, reactant C shown in Table 3 was used to replace 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, and reactant D was used to replace 4-chlorophenylboronic acid to synthesize intermediates Sub-c2 to Sub-c32.

[0289] Table 3 Synthesis of intermediates Sub-c2 to Sub-c32

[0290]

[0291]

[0292]

[0293]

[0294]

[0295] Synthesis of compound A2:

[0296]

[0297] Under nitrogen atmosphere, Sub-b1 (6.31 g, 25 mmol), Sub-c1 (12.20 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.46 g, 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 0.41 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol) and xylene (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 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 n-heptane as the mobile phase to obtain a white solid compound A2 (12.86 g, yield: 78%, m / z = 660.31 [M+H] + ).

[0298] Referring to the synthesis method of compound A2, reactant E shown in Table 4 was used to replace Sub-b1, and reactant F was used to replace Sub-c1 to synthesize the first compound shown in Table 4.

[0299] Table 4

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306] Synthesis of the second compound

[0307] Synthesis of intermediate Sub-d1:

[0308]

[0309] Under nitrogen protection, RM-1 (16.20 g, 50 mmol), 4-chloro-2-formaldehyde phenylboronic acid (10.14 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (160 mL), anhydrous ethanol (40 mL) and deionized water (40 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 with 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-d1 (10.94 g, yield: 57%).

[0310] Referring to the synthesis method of intermediate Sub-d1, reactant G in Table 5 was used to replace 4-chloro-2-formylphenylboronic acid to synthesize intermediate Sub-d2.

[0311] Table 5

[0312]

[0313] Synthesis of intermediate Sub-e1:

[0314]

[0315] Under nitrogen protection, add Sub-d1 (49.90g, 130mmol), (methoxymethyl) triphenylphosphonium chloride (74.38g, 217mmol) and anhydrous tetrahydrofuran (500mL) to a 1000mL three-necked flask in sequence, and cool the system to 0°C with an ice-water bath; then slowly drop a solution of potassium tert-butoxide in anhydrous tetrahydrofuran (1M, 220mL) to the system; after the addition is complete, let the system slowly warm up to room temperature and continue to stir the reaction for 6h. Pour the reaction solution into 1000ml deionized water, extract with ethyl acetate (250mL×3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation to obtain a crude product. Purify the crude product by silica gel column chromatography using n-heptane as the mobile phase to obtain a red solid Sub-e1 (39.10g, yield: 73%).

[0316] Referring to the synthesis method of intermediate Sub-e1, reactant H in Table 6 was used to replace Sub-d1 to synthesize intermediate Sub-e2.

[0317] Table 6

[0318]

[0319] Synthesis of intermediate Sub-f1:

[0320]

[0321] Under nitrogen protection, add Sub-e1 (49.00 g, 119 mmol), Eaton's reagent (4.5 mL) and chlorobenzene (500 mL) to a 1000 mL three-necked flask in sequence, heat to reflux and continue stirring to react 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. Use dichloromethane / n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain solid Sub-f1 (21.70 g, yield: 48%).

[0322] Referring to the synthesis method of intermediate Sub-f1, reactant J shown in Table 7 was used to replace Sub-e1 to synthesize intermediate Sub-f2.

[0323] Table 7

[0324]

[0325] Synthesis of intermediate Sub-g1:

[0326]

[0327] Under nitrogen protection, RM-2 (18.56 g, 50 mmol), 2,5-dibromonitrobenzene (15.45 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 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 16 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 yellow solid Sub-g1 (14.92 g, yield: 67%).

[0328] Synthesis of intermediate Sub-h1:

[0329]

[0330] Under nitrogen protection, add Sub-g1 (22.26 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol) and o-dichlorobenzene (220 mL) to a 500 mL three-necked flask, start stirring and heating, and raise the temperature to reflux reaction for 16 hours. After the system is cooled to room temperature, the solvent is removed by vacuum distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid Sub-h1 (15.10 g, yield 73%).

[0331] Synthesis of intermediate Sub-j 1:

[0332]

[0333] Under nitrogen protection, Sub-h3 (20.66 g, 50 mmol), iodobenzene (12.24 g, 60 mmol), cuprous iodide (1.90 g, 10 mmol), 18-crown ether-6 (1.32 g, 5 mmol), 1,10-phenanthroline (3.96 g, 20 mmol), potassium carbonate (15.20 g, 110 mmol) and N, N-dimethylformamide (210 mL) were added to a 500 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, the reaction solution was poured into 500 mL of deionized water, filtered and the filtered solid was taken; the filtered solid was extracted and dissolved with dichloromethane and dried over anhydrous sodium 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 n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-j1 (15.17 g; yield: 62%).

[0334] Synthesis of intermediate Sub-k1:

[0335]

[0336] Under nitrogen protection, RM-3 (13.76 g, 50 mmol) and dichloromethane (130 mL) were added to a 250 mL three-necked flask in sequence, the system was cooled to 0 ° C, N-bromosuccinimide (9.35 g, 52.5 mmol) was added in batches, and the system was allowed to slowly warm to room temperature after the reaction was kept warm for 6 hours; the reaction solution was poured into 250 mL of saturated sodium thiosulfate aqueous solution and stirred for 30 minutes; extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and distilled under reduced pressure to remove the solvent 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-k1 (14.00 g; yield: 79%).

[0337] Synthesis of intermediate Sub-m1:

[0338]

[0339] Under nitrogen protection, add Sub-k1 (17.71 g, 50 mmol), 4-chloro-2-fluorophenylboric acid (9.59 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL) and deionized water (45 mL) to a 500 mL three-necked flask in sequence, start stirring and heating, and heat to reflux for 16 h. After the system is cooled to room temperature, extract with dichloromethane (100 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation to obtain a crude product. Purify the crude product by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a yellow solid Sub-m1 (11.31 g, yield: 56%).

[0340] Synthesis of intermediate Sub-n1:

[0341]

[0342] Under nitrogen protection, Sub-m1 (27.25 g, 67.50 mmol) and dry dichloromethane (280 mL) were added to a 500 mL three-necked flask, the system was cooled to 0±5°C, and a dichloromethane solution of boron tribromide (135 mL, 1 M) was added dropwise using a constant pressure dropping funnel. The temperature was strictly controlled within the range of 0±5°C during the addition process; after the addition was completed, the temperature was kept at 0±5°C for 2 h, and then the system was allowed to warm up to room temperature naturally and stirred overnight; the system was cooled to -78°C again, and methanol (11 mL) was slowly added dropwise using a constant pressure dropping funnel to quench the reaction; after the system was heated to room temperature, the reaction solution was extracted with dichloromethane (100 mL×3 times), the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed 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 product Sub-n1 (17.63 g, yield: 67%).

[0343] Synthesis of intermediate Sub-o1:

[0344]

[0345] Under nitrogen protection, add Sub-n1 (19.49 g, 50 mmol), cesium carbonate (32.58 g, 100 mmol) and DMSO (200 mL) to a 500 mL three-necked flask, start stirring and heating, and heat to 80 ° C for 4 hours. After the system is cooled to room temperature, extract with dichloromethane (100 mL × 3 times), combine the organic phases and dry them with anhydrous magnesium sulfate, filter and remove the solvent by reduced pressure distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid Sub-o1 (16.27 g, yield: 88%).

[0346] Synthesis of intermediate Sub-p1:

[0347]

[0348] Under nitrogen protection, RM-4 (13.41 g, 50 mmol), 1-bromo-5-iodonaphthalene (16.64 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous sodium carbonate (10.6 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL) and deionized water (35 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 16 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 with anhydrous magnesium sulfate, filtered and then distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (14.17 g, yield: 66%).

[0349] Referring to the synthesis method of the intermediate Sub-p1, the reactant K shown in Table 8 was used to replace 1-bromo-5-iodonaphthalene to synthesize the intermediate Sub-p2.

[0350] Table 8 Synthesis of intermediate Sub-p2

[0351]

[0352] Synthesis of intermediate Sub-q1:

[0353]

[0354] Under nitrogen protection, Sub-p1 (21.47 g, 50 mmol), tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution, 150 mL) and deionized water (150 mL) were added to a 500 mL three-necked flask in sequence, and the mixture was stirred at room temperature for 2 hours; extracted with dichloromethane (50 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and then distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (16.10 g; yield: 90%).

[0355] Referring to the synthesis method of intermediate Sub-q1, the reactant L shown in Table 9 was used to replace Sub-p1 to synthesize intermediate Sub-q2.

[0356] Table 9 Synthesis of intermediate Sub-q2

[0357]

[0358] Synthesis of intermediate Sub-r1:

[0359]

[0360] Under nitrogen protection, Sub-q1 (17.86 g, 50 mmol), platinum dichloride (0.916 g, 0.66 g, 2.5 mmol) and toluene (180 mL) were added to a 500 mL three-necked flask in sequence, the temperature was raised to reflux, and the reaction was stirred for 24 hours; 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 n-heptane as the mobile phase to obtain a white solid (12.68 g; yield: 71%).

[0361] Referring to the synthesis method of intermediate Sub-r1, the reactant M shown in Table 10 was used to replace Sub-q1 to synthesize intermediate Sub-r2.

[0362] Table 10 Synthesis of intermediate Sub-r2

[0363]

[0364] Synthesis of intermediate Sub-s1:

[0365]

[0366] Under nitrogen protection, RM-5 (18.62 g, 50 mmol), 3-aminodibenzofuran (9.16 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2', 4', 6'triisopropylbiphenyl) (XPhos, 0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and toluene (180 mL) were added to a 500 mL three-necked flask in sequence, the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, the reaction solution was poured into 250 mL of deionized water, stirred thoroughly for 30 min, filtered, and the filter cake was rinsed with deionized water until neutral, and then rinsed with anhydrous ethanol (100 mL); the filter cake was recrystallized from toluene to obtain a gray-green solid (19.70 g; yield: 83%).

[0367] Referring to the synthesis method of the intermediate Sub-s1, the reactant N shown in Table 11 was used to replace RM-5, and the reactant O was used to replace 3-aminodibenzofuran to synthesize the intermediates Sub-s2 to Sub-s18.

[0368] Table 11 Synthesis of intermediates Sub-s2 to Sub-s18

[0369]

[0370]

[0371]

[0372] Synthesis of compound B8:

[0373]

[0374] Under nitrogen protection, Sub-s1 (11.86 g, 25 mmol), 1-(4-bromophenyl)naphthalene (7.78 g, 27.5 mmol), tri(dibenzylideneacetone)dipalladium (0.46 g, 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 0.41 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol) and xylene (xylene, 120 mL) were added to a 250 mL three-necked flask in sequence, 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 magnesium sulfate, filtered and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid compound (13.20 g, yield: 78%, m / z = 677.26 [M+H] + ).

[0375] Referring to the synthesis method of compound B8, reactant P shown in Table 12 was used to replace Sub-s1, and reactant Q was used to replace 1-(4-bromophenyl)naphthalene to synthesize the second compound shown in Table 12.

[0376] Table 12

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383] The NMR data of some compounds and intermediates are shown in Table 13 below:

[0384] Table 13

[0385]

[0386] Preparation of organic electroluminescent devices

[0387] Example 1: Preparation of red organic electroluminescent device

[0388] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0389] PD-1:HT-1 was co-evaporated on the experimental substrate (anode) at an evaporation rate ratio of 3%:97% to form a film with a thickness of A hole injection layer (HIL) is formed by vacuum evaporating compound HT-1 on the hole injection layer to form a layer with a thickness of hole transport layer.

[0390] Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of Glow adjustment layer.

[0391] On the luminescence adjustment layer, the compound A2 is used as the first host, the compound D15 is used as the second host, and RD-01 is used as the dopant, and the organic luminescent layer is prepared by a co-evaporation method. The first host: the second host is mixed in a mass ratio of 60:40 to obtain a composition; the composition of the host material: RD-01 is simultaneously evaporated at an evaporation rate ratio of 98%:2% to form a thickness of of an organic light-emitting layer (EML).

[0392] On the organic light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form a layer with a thickness of The electron transport layer (ETL)

[0393] Yb is evaporated 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.

[0394] In addition, compound CP-1 is vacuum-evaporated on the cathode to form a layer with a thickness of An organic covering layer is formed, thereby completing the manufacture of a red organic electroluminescent device.

[0395] Embodiments 2 to 33

[0396] An organic electroluminescent device was prepared by the same method as in Example 1, except that the organic light-emitting layer combination in Table 14 below was used instead of the compound combination in Example 1 when preparing the organic light-emitting layer.

[0397] Comparative Examples 1 to 3

[0398] An organic electroluminescent device was prepared by the same method as in Example 1, except that the organic light-emitting layer host combinations shown in Table 14 were used to replace the combination of compounds A2 and D15 in Example 1.

[0399] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:

[0400]

[0401] The performance of the red organic electroluminescent devices prepared in Examples 1 to 33 and Comparative Examples 1 to 3 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 14.

[0402] Table 14

[0403]

[0404]

[0405]

[0406] Referring to Table 13 above, it can be seen that compared with Comparative Examples 1 to 3, the device current efficiency of Examples 1 to 33 is increased by at least 10.5%, and the life span is increased by at least 12.5%.

[0407] The organic light-emitting layer of the organic electroluminescent device of the present application comprises a first compound and a second compound, wherein one of the benzene rings on the carbazole ring in the first compound used in the present application is fully deuterated, and a deuterated phenyl group is connected to the other benzene ring as a substituent, so that the molecular symmetry is reduced while the range of aromatic conjugation of the molecular structure is expanded, so that the material has better energy transfer characteristics. In addition, the special asymmetric deuteration of the carbazole group can effectively improve the stability of the molecular structure, and can further reduce the molecular symmetry, thereby significantly improving the photoelectric stability and film-forming properties of the material. Secondly, the second compound used in the present application has a large conjugated area, which can improve the hole mobility of the second compound. Therefore, when the first compound and the second compound of the present application are combined as the light-emitting main material of the red organic electroluminescent device, the carrier balance in the light-emitting layer can be significantly improved, the stability of the film can be improved, and the luminous efficiency and life of the device can be improved.

[0408] Part of the embodiments of the present application are described in detail above in conjunction with the accompanying drawings; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the protection scope of the present application.

Claims

1. An organic electroluminescent device, comprising a cathode, an anode and an organic layer; the cathode and the anode are arranged opposite to each other; the organic layer is located between the cathode and the anode; the organic layer comprises an organic light-emitting layer; It is characterized in that The organic light-emitting layer includes a first compound and a second compound; The first compound has a structure shown in Formula 1: wherein Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups; L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Ar3 is The substituents in 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, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; The second compound is selected from the structure shown in Formula 2, Formula 3, Formula 4 or Formula 5: In Formula 2, X is selected from O, S or N(Ar); Ar is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms; R1 is selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; One of R2 and R3 is hydrogen, deuterium, cyano, a halogen group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and the other is a group represented by formula 2-1; L3, L4 and L5 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar4 and Ar5 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in R1, R2, R3, L3, L4, L5, Ar, Ar4 and Ar5 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and a deuterated alkyl group having 1 to 10 carbon atoms; In formula 3, ring A is a naphthalene ring; L6, L7 and L8 are the same or different and are 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 30 carbon atoms; Ar8 is selected from the group shown in formula 3-1; T is selected from O or S; Ar7 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms; The substituents in L6, L7, L8 and Ar7 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms; each R4, each R5 and each R6 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, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms; n4 is selected from 0, 1, 2, 3 or 4; n5 is selected from 0, 1, 2, 3, 4, 5 or 6; n6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; In formula 4, L 10 , L 11 and L 12 are the same or different and are 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 30 carbon atoms; Ar 11 and Ar 12 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Each R7, each R8, each R9, each R 10 and each R 11 are the same or different and are independently selected from deuterium, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl having 3 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and deuterated alkyl having 1 to 10 carbon atoms; n7 and n 11 are independently selected from 0, 1, 2, 3 or 4; n8, n9 and n 10 are independently selected from 0, 1 or 2; L 10 , L 11 , L 12 ,Ar 11 and Ar 12 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, cycloalkyl having 3 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and deuterated alkyl having 1 to 10 carbon atoms; In Formula 5, one of M and Y is -N=, and the other is O or S; L 13 , L 14 and L 15 are the same or different and are 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 30 carbon atoms; Ar 13 ,Ar 14 and Ar 15 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; L 13 , L 14 , L 15 ,Ar 13 ,Ar 14 and Ar 15 The substituents in are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, and cycloalkyl groups having 3 to 10 carbon atoms; Each R 12 , each R 13 and each R 14 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms; n 12 and n 13 are independently selected from 0, 1 or 2; n 14 Selected from 0, 1, 2, 3, 4, 5 or 6.

2. The organic electroluminescent device according to claim 1, characterized in that: In the first compound represented by Formula 1, L, L1 and L2 are the same or different and are 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; Optionally, the substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

3. The organic electroluminescent device according to claim 1, characterized in that: In the first compound represented by Formula 1, The same or different, each independently selected from the group consisting of the following groups:

4. The organic electroluminescent device according to claim 1, characterized in that: In the second compound represented by Formula 2, L3 is selected from a single bond, an unsubstituted phenylene group, an unsubstituted naphthylene group or an unsubstituted biphenylene group; L4 and L5 are the same or different and are 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 carbazolylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenylene group; Ar4 and Ar5 are the same or different and are independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthryl; Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; Optionally, the substituents in L4, L5, Ar, Ar4 and Ar5 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

5. The organic electroluminescent device according to claim 1, characterized in that: In the second compound represented by Formula 2, R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; Optionally, the substituents in R1 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; One of R2 and R3 is hydrogen, and the other is selected from the group represented by Formula 2-1.

6. The organic electroluminescent device according to claim 1, characterized in that: In the second compound represented by Formula 3, L6, L7 and L8 are the same or different and are 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 carbazolylene group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group; Optionally, the substituents in L6, L7 and L8 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Ar7 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrenyl; Optionally, the substituents in Ar7 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

7. The organic electroluminescent device according to claim 1, characterized in that: In the second compound shown in Formula 3, Ar7 is selected from the group consisting of the following groups: Ar8 is selected from the group consisting of:

8. The organic electroluminescent device according to claim 1, characterized in that: In the second compound represented by Formula 4, L 10 , L 11 and L 12 are the same or different and are 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 carbazolylene group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted dibenzofuranyl group; Ar 11 and Ar 12 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl; Optionally, L 10 , L 11 , L 12 ,Ar 11 and Ar 12 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

9. The organic electroluminescent device according to claim 1, characterized in that: In the second compound represented by Formula 5, L 13 , L 14 and L 15 are the same or different and are 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 dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group; Ar 13 ,Ar 14 and Ar 15 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; Optionally, L 13 , L 14 , L 15 ,Ar 13 ,Ar 14 and Ar 15 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

10. The organic electroluminescent device according to claim 1, characterized in that: The first compound represented by Formula 1 is selected from the group consisting of the following compounds: The second compound represented by Formula 2 is selected from the group consisting of the following compounds: The second compound represented by Formula 3 is selected from the group consisting of the following compounds: The second compound represented by Formula 4 is selected from the group consisting of the following compounds: The second compound represented by Formula 5 is selected from the group consisting of the following compounds:

11. The organic electroluminescent device according to claim 1, characterized in that: The organic layer further includes a hole injection layer, a hole transport layer, a luminescence adjustment layer, an electron transport layer and an electron injection layer.

12. An electronic device, characterized in that The organic electroluminescent device comprises any one of claims 1 to 11.

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