Organic electroluminescent apparatus and electronic device

Abstract

Provided are an organic electroluminescent apparatus and an electronic device. The organic electroluminescent apparatus comprises a cathode, an anode and an organic layer, wherein 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 is selected from a compound as represented by formula 1; and the second compound is selected from a compound as represented by formula 2.

Description

Organic electroluminescent devices and electronic devices

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202311635189.7 filed on December 1, 2023. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field

[0003] The present application relates to the field of organic electroluminescence, and in particular to an organic electroluminescent device and an electronic apparatus. Background Art

[0004] 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.

[0005] An organic electroluminescent device (OLED) typically includes an anode, a cathode, and an organic layer formed between the two electrodes. These organic layers may include a hole injection layer, a hole transport layer, a luminescence-assisting layer, an organic light-emitting layer (containing a host and dopant materials), a hole blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light-emitting layer by the anode and cathode, respectively. In the light-emitting layer, the injected holes and electrons then recombine to form excitons. The excitons, in an excited state, release energy, causing the light-emitting layer to emit light.

[0006] At present, organic electroluminescent devices still have poor performance problems during use, such as excessively high driving voltage, low luminous efficiency or short life. These problems have affected the application areas of organic electroluminescent devices. Therefore, further research in this field is still necessary to improve the performance of organic electroluminescent devices.

[0007] Summary of the Invention

[0008] To achieve the above-mentioned invention objectives, this application adopts the following technical solutions:

[0009] The first aspect of 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;

[0010] Wherein, the organic light-emitting layer includes a first compound and a second compound;

[0011] The first compound is a compound represented by Formula 1:

[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, and 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] Ar3 is pentadeuterated phenyl, biphenyl or terphenyl;

[0015] The substituents in L, L1, L2, Ar1 and Ar2 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, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, haloaryl having 6 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms;

[0016] The second compound is a compound represented by Formula 2:

[0017] 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;

[0018] 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;

[0019] The substituents in L4, L5, Ar4 and Ar5 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, halogenated alkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, halogenated aryl group with 6 to 20 carbon atoms or cycloalkyl group with 3 to 10 carbon atoms.

[0020] A second aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the first aspect.

[0021] The present application provides an organic electroluminescent device, wherein the organic layer in the organic electroluminescent device includes an organic light-emitting layer, which includes a first compound with strong electronic properties and a second compound with strong hole properties. The first compound and the second compound are used together as the main materials 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.

[0022] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] 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.

[0024] FIG1 is a schematic structural diagram of an organic electroluminescent device of the present application.

[0025] FIG2 is a schematic structural diagram of an electronic device of the present application.

[0026] Reference numerals

[0027] 100, anode 200, cathode 300, organic layer 310, hole injection layer

[0028] 320, hole transport layer 330, light-emitting auxiliary layer 340, organic light-emitting layer 350, electron transport layer

[0029] 360, electron injection layer 400, first electronic device DETAILED DESCRIPTION

[0030] Example embodiments will now be described more fully with reference to the accompanying drawings. However, the example embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these examples are provided so that this application will be more comprehensive and complete and will fully convey the concepts of the example embodiments 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, numerous specific details are provided to provide a thorough understanding of the embodiments of the present application.

[0031] 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.

[0032] Described feature, structure or characteristic can be combined in one or more embodiments in any suitable manner.In the following description, many specific details are provided so as to provide a full understanding of the embodiments of the present application. However, it will be appreciated by those skilled in the art that the technical scheme of the present application can be put into practice without one or more of the specific details, or other methods, components, materials, etc. can 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 application.

[0033] 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;

[0034] Wherein, the organic light-emitting layer includes a first compound and a second compound;

[0035] The first compound is a compound represented by Formula 1:

[0036] 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, and substituted or unsubstituted dibenzothiophenyl groups;

[0037] 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;

[0038] Ar3 is pentadeuterated phenyl, biphenyl or terphenyl;

[0039] The substituents in L, L1, L2, Ar1 and Ar2 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, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, haloaryl having 6 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms;

[0040] The second compound is a compound represented by Formula 2:

[0041] 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;

[0042] 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;

[0043] The substituents in L4, L5, Ar4 and Ar5 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, halogenated alkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, halogenated aryl group with 6 to 20 carbon atoms or cycloalkyl group with 3 to 10 carbon atoms.

[0044] In this application, the descriptions “each independently is”, “each independently is” and “each independently is” 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. The meaning is: Formula Q-1 represents 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 represents 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.

[0045] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease 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 substituent Rc can be, for example, deuterium, a cyano group, a halogen group, an alkyl group, a haloalkyl group, a deuterated alkyl group, an aryl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be one or more.

[0046] In this application, "plurality" refers to two or more, for example, 2, 3, 4, 5, 6, etc.

[0047] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.

[0048] 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 (such as 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 conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon conjugation, two or more condensed ring aryl groups connected by carbon-carbon conjugation. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon conjugation can also be considered as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene Peryl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl, spirobifluorenyl In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0049] In this application, terphenyl includes

[0050] 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 being 18.

[0051] In the present application, the number of carbon atoms 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.

[0052] In the present application, examples of aryl groups as substituents of L, L1, L2, L4, L5, Ar1, Ar2, Ar4, and Ar5 include, but are not limited to, phenyl, naphthyl, and the like.

[0053] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. For 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 triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a 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 silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0054] 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.

[0055] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, 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.

[0056] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. 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.

[0057] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0058] In the present application, specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

[0059] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0060] 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.

[0061] In the present application, the number of carbon atoms in 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.

[0062] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. This means that one end of the link can be connected to any position in the ring system that the link 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 via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10).

[0063] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions in the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0064] In some embodiments of the present application, the first compound is selected from the compounds represented by Formula 1-1, Formula 1-2, Formula 1-3 or Formula 1-4:

[0065] In a preferred embodiment of the present application, the first compound is selected from the compound represented by Formula 1-1.

[0066] Optionally, the first compound is selected from the compounds represented by Formula A, Formula B, Formula C, Formula D, Formula E, Formula F, Formula G, Formula H, Formula I, Formula J, Formula K, Formula L, Formula M, Formula N, Formula O or Formula P:

[0067] In some preferred embodiments of the present application, the first compound is selected from the compound represented by Formula A, Formula B, Formula C or Formula D.

[0068] In some embodiments of the present application, 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.

[0069] 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, a phenyl group or a pentadeuterated phenyl group.

[0070] In other embodiments of the present application, 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, or a substituted or unsubstituted biphenylene group.

[0071] Optionally, L, L1 and L2 are the same or different and are independently selected from the substituents in which are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0072] Further optionally, 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:

[0073] Specifically, 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:

[0074] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0075] 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.

[0076] In other embodiments of the present application, 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.

[0077] 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.

[0078] In other embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

[0079] in, represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

[0080] Optionally, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0081] Specifically, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0082] In some embodiments of the present application, are independently selected from the group consisting of:

[0083] Specifically, are independently selected from the group consisting of:

[0084] In some embodiments of the present application, in Formula 1 Selected from the group consisting of:

[0085] Specifically, in Equation 1 Selected from the group consisting of:

[0086] In some embodiments of the present application, in Formula 1, Ar3 is selected from the group consisting of the following groups:

[0087] Specifically, in Formula 1, Ar3 is selected from the group consisting of the following groups:

[0088] In some preferred embodiments of the present application, in Formula 1, Ar3 is selected from In some embodiments of the present application, the first compound is selected from the group consisting of the following compounds:

[0089] In some embodiments of the present application, in Formula 2, 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 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0090] Optionally, the substituents in 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.

[0091] In some embodiments of the present application, 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, or a substituted or unsubstituted dibenzothiophenylene group.

[0092] 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.

[0093] In some embodiments of the present application, in Formula 2, L4 and L5 are the same or different and are independently selected from a single bond or the following groups:

[0094] Specifically, in Formula 2, L4 and L5 are the same or different and are independently selected from a single bond or the following groups:

[0095] In some embodiments of the present application, in Formula 2, Ar4 and Ar5 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 24 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0096] Optionally, the substituents in Ar4 and Ar5 are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a pentadeuterated phenyl group.

[0097] In other embodiments of the present application, in Formula 2, Ar4 and Ar5 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 quaterphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0098] 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, phenyl or pentadeuterated phenyl.

[0099] In some embodiments of the present application, in Formula 2, Ar4 and Ar5 are the same or different and are independently selected from the group consisting of the following groups:

[0100] Specifically, in Formula 2, Ar4 and Ar5 are the same or different and are independently selected from the group consisting of the following groups:

[0101] In some embodiments of the present application, in Formula 2 are independently selected from the group consisting of:

[0102] Specifically, in Equation 2 are independently selected from the group consisting of:

[0103] In some embodiments of the present application, the second compound is selected from the group consisting of the following compounds:

[0104] In some embodiments of the present application, the host material and the guest material can be co-evaporated through a multi-source evaporation process so that the host material and the guest material are uniformly dispersed in the organic light-emitting layer. The doping ratio can be regulated by controlling the evaporation rate of the guest material during the evaporation process, or by controlling the evaporation rate ratio of the host material and the guest material.

[0105] Optionally, the organic light-emitting layer can be evaporated by a multi-source co-evaporation method to form an organic light-emitting layer including a host material and a guest material. The doping ratio can be regulated by controlling the evaporation rate of the guest material during the evaporation process, or by controlling the evaporation rate ratio of the host material to the guest material to regulate the doping ratio.

[0106] The relative amounts of the first compound and the second compound in the organic light-emitting layer of the organic electroluminescent device of the present application are not particularly limited and can be selected according to the specific application of the organic electroluminescent device. Generally, the evaporation rate ratio (%) of the first compound and the second compound can be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0107] In some preferred embodiments of the present application, the evaporation rate ratio (%) of the first compound to the second compound is 40:60, 45:65, 50:50, 55:45 or 60:40.

[0108] In other embodiments of the present application, the first compound and the second compound can be evenly mixed by mechanical stirring to form a main material mixture, and the main material mixture and the guest material are evaporated into an organic light-emitting layer by a multi-source co-evaporation method to form an organic light-emitting layer including the main material mixture and the guest material. The doping ratio can be regulated by controlling the evaporation rate of the guest material during the evaporation process, or by controlling the evaporation rate ratio of the main material mixture and the guest material to regulate the doping ratio.

[0109] Among them, the first compound and the second compound in the main material mixture can be mixed according to mass percentage. The present application does not specifically limit the relative content of the two types of compounds in the main material mixture, and can be selected according to the specific application of the organic electroluminescent device. Generally, based on the total weight of the main material mixture, the mass percentage of the first compound can be 1% to 99%, and the mass percentage of the second compound can be 1% to 99%. For example, in the main material mixture, the mass ratio (%) of the first compound to the second compound can be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.

[0110] In one embodiment of the present application, the organic electroluminescent device is a phosphorescent device.

[0111] In a specific embodiment of the present application, the organic electroluminescent device is a green phosphorescent organic electroluminescent device.

[0112] 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.

[0113] In a specific embodiment of the present application, as shown in Figure 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one organic layer 300 between the anode layer and the cathode layer, and the organic 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.

[0114] Optionally, the anode 100 includes the following anode material, which is preferably a material with a large work function that facilitates hole injection into the organic 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 are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0115] Optionally, the hole transport layer 320 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and this application does not impose any particular limitation on this. For example, in some embodiments of this application, the hole transport layer 320 is composed of HT-1.

[0116] Optionally, the luminescence-assisting layer 330 (also known as a hole-adjusting layer, electron-blocking layer, hole-assisting layer, hole-buffering layer, luminescence-adjusting layer, or second hole-transporting layer) may include one or more hole-transporting materials. The hole-transporting materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and this application does not impose any particular limitation on this. For example, in some embodiments of this application, the luminescence-assisting layer 330 is composed of HT-2.

[0117] Alternatively, 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. Alternatively, the organic light-emitting layer 340 may be composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, which in turn transfers energy to the guest material, thereby enabling the guest material to emit light.

[0118] 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 this application does not impose any particular limitation thereto.

[0119] In some embodiments of the present application, in a green organic electroluminescent device, the organic light-emitting layer 340 comprises the first compound, the second compound and the guest material GD-01 of the present application.

[0120] 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. The electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not impose any particular limitation on this. For example, in some embodiments of the present application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0121] Alternatively, cathode 200 includes a cathode material having a small work function that facilitates electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode comprising silver and magnesium is used as the cathode.

[0122] 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitations thereon. In some embodiments of this application, the hole injection layer 310 may be composed of PD and HT-1.

[0123] 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic matter. In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).

[0124] A second aspect of the present application further provides an electronic device, which includes the organic electroluminescent device described in the present application.

[0125] For example, as shown in FIG2 , the electronic device provided in this application is a first electronic device 400, which includes any of the organic electroluminescent devices described in the above-mentioned 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, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. Since the first electronic device 400 includes the above-mentioned organic electroluminescent device, it has the same beneficial effects, and this application will not repeat them here.

[0126] The present application will be described in detail below in conjunction with embodiments; however, the following description is intended to explain the present application rather than to limit the scope of the present application in any way.

[0127] Synthesis of the first compound

[0128] Synthesis of intermediate IM-a-no:

[0129] Under nitrogen, 2,3-dichloronitrobenzene (20.0 g, 104.2 mmol), d5-phenylboronic acid pinacol ester (47.9 g, 229.2 mmol), tetrakis(triphenylphosphine)palladium (4.8 g, 4.2 mmol), potassium carbonate (57.6 g, 416.7 mmol), tetrabutylammonium bromide (13.4 g, 41.2 mmol), toluene (320 mL), ethanol (80 mL), and deionized water (80 mL) were added to a round-bottom flask. The mixture was heated to 75°C–80°C and stirred for 72 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the layers were 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 mixture as the mobile phase to obtain the intermediate IM-a-no (17.7 g, yield: 60%) as a colorless oil.

[0130] Referring to the synthesis method of intermediate IM-a-no, reactant A was used to replace 2,3-dichloronitrobenzene to synthesize the intermediates shown in Table 1 below:

[0131] Table 1

[0132] Synthesis of intermediate IM-a-nh:

[0133] Under nitrogen protection, intermediate IM-a-no (16.0 g, 56.1 mmol), triphenylphosphine (36.8 g, 140.2 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask. The mixture was stirred and heated to 175°C to 180°C for 36 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. The solvent was removed under high temperature and reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain the white solid intermediate IM-a-nh (9.2 g, yield: 65%).

[0134] Referring to the synthesis method of intermediate IM-a-nh, reactant B was used to replace intermediate IM-a-no to synthesize the intermediates shown in Table 2 below:

[0135] Table 2

[0136] Synthesis of compound A20:

[0137] Under nitrogen, intermediate IM-a-nh (5.0 g, 19.8 mmol), compound sub 1 (12.9 g, 29.7 mmol, CAS: 217088-83-7), and N,N-dimethylformamide (50 mL) were added to a round-bottom flask. The mixture was stirred and cooled to -5°C to 0°C. Sodium hydride (0.6 g, 23.7 mmol) was added and stirred at -5°C to 0°C for 1 hour. The temperature was then raised to 20°C to 25°C and allowed to react for 24 hours. The reaction was terminated, the reaction mixture was washed with water, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixture as the eluent, followed by recrystallization using a toluene / n-heptane mixture as the mobile phase to obtain Compound A20 (7.9 g, yield: 61%) as a white solid.

[0138] Referring to the synthesis method of compound A20, the compounds shown in Table 3 below were synthesized by replacing intermediate IM-a-nh with reactant C and compound sub 1 with reactant D:

[0139] Table 3

[0140] Synthesis of compound A46:

[0141] Under nitrogen protection, intermediate IM-a-nh (5.0 g, 19.8 mmol), compound sub 2 (8.7 g, 20.8 mmol, CAS: 191061-39-00), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g, 0.4 mmol), sodium tert-butoxide (2.9 g, 29.7 mmol) and xylene (50 mL) were added to a round-bottom flask, and the mixture was stirred and reacted at 135° C. to 140° C. for 16 hours; the mixture was cooled to room temperature, washed with water and then separated, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent, and then the product was recrystallized and purified using a toluene / n-heptane solvent system to obtain white solid compound A46 (9.8 g, yield: 78%).

[0142] Referring to the synthesis method of compound A46, reactant E in Table 4 below was used to replace intermediate IM-a-nh, and reactant F was used to replace compound sub2 to synthesize the compounds shown in Table 4 below:

[0143] Table 4

[0144] Synthesis of reactant F-89 used in compound B89

[0145] Under nitrogen, 2-chloro-4,6-di(phenyl-2,3,4,5,6-D5)-1,3,5-triazine (20.0 g, 72.0 mmol), 3'-chlorobiphenyl-4-boronic acid (17.6 g, 75.6 mmol), tetrakis(triphenylphosphine)palladium (0.8 g, 0.7 mmol), potassium carbonate (19.9 g, 144.0 mmol), tetrabutylammonium bromide (0.2 g, 0.7 mmol), toluene (200 mL), ethanol (80 mL), and deionized water (40 mL) were added to a round-bottom flask. The reaction mixture was heated to 75°C-80°C and stirred for 5 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the layers were separated. The organic phase was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain a white solid intermediate F-89 (24.8 g, yield: 80%).

[0146] Synthesis of intermediate sub a1:

[0147] Under nitrogen, compound sub 3 (20.0 g, 74.7 mmol, CAS: 3842-55-5), 3-fluoro-4-biphenylboronic acid (16.9 g, 78.4 mmol), tetrakis(triphenylphosphine)palladium (0.9 g, 0.7 mmol), potassium carbonate (20.6 g, 149.4 mmol), tetrabutylammonium bromide (0.2 g, 0.7 mmol), toluene (200 mL), ethanol (80 mL), and deionized water (40 mL) were added to a round-bottom flask. The reaction mixture was heated to 75°C-80°C and stirred for 10 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the layers were separated. The organic phase was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixture as the mobile phase to obtain the white solid intermediate sub a1 (21.7 g, yield: 72%).

[0148] Referring to the synthesis method of intermediate sub a1, reactant G was substituted for 3-fluoro-4-biphenylboronic acid to synthesize the intermediates shown in Table 5 below:

[0149] Table 5

[0150] Synthesis of compound B73

[0151] Under nitrogen protection, compound IM-b-nh (22.5 g, 89.2 mmol), compound sub a1 (20 g, 49.6 mmol), tripotassium phosphate (52.6 g, 247.8 mmol) and N-methylpyrrolidone (200 mL) were added to a round-bottom flask, the reaction solution was heated to 195 ° C, and stirred for 12 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 then 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 mixed solvent of dichloromethane / n-heptane to obtain a solid product B73 (18.3 g, yield: 58%).

[0152] Referring to the synthesis method of compound B73, reactant H was substituted for compound sub a1 to synthesize the compounds shown in Table 6 below:

[0153] Table 6

[0154] Synthesis of intermediate ai:

[0155] Under nitrogen protection, 2,3-dichloronitrobenzene (20.0 g, 104.2 mmol), D5-phenylboronic acid pinacol ester (21.8 g, 104.2 mmol), tetrakis(triphenylphosphine)palladium (2.4 g, 2.1 mmol), potassium carbonate (28.8 g, 208.3 mmol), tetrabutylammonium bromide (6.7 g, 20.8 mmol), toluene (160 mL), ethanol (40 mL) and deionized water (40 mL) were added to a round-bottom flask, and the reaction solution was heated to 75° C. to 80° C. and stirred for 48 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 then 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 solvent system to obtain a white solid intermediate ai (18.8 g, yield: 76%).

[0156] Synthesis of intermediate aii:

[0157] Under nitrogen, intermediate ai (18.0 g, 75.4 mmol), triphenylphosphine (49.5 g, 188.5 mmol), and o-dichlorobenzene (150 mL) were added to a round-bottom flask. The mixture was stirred and heated to 175°C-180°C for 36 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the layers were separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure at high temperature. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixture to obtain intermediate aii (11.1 g, yield: 72%) as a white solid.

[0158] Synthesis of intermediate SL1:

[0159] Intermediate aii (10.0 g, 48.6 mmol), 4-biphenylboronic acid (10.1 g, 51.1 mmol), palladium acetate (0.1 g, 0.5 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.5 g, 1.0 mmol), cesium carbonate (23.8 g, 72.9 mmol), toluene (80 mL), ethanol (20 mL), and deionized water (20 mL) were added to a round-bottom flask under nitrogen. The mixture was heated to 75°C-80°C and stirred for 48 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the layers were separated. The organic phase was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixture to obtain intermediate SL1 (12.1 g, yield: 77%) as a white solid.

[0160] Synthesis of compound AA21:

[0161] Under nitrogen, intermediate SL1 (5.0 g, 15.5 mmol), intermediate sub 4 (6.5 g, 15.5 mmol, CAS: 1443049-84-0), tris(dibenzylideneacetone)dipalladium (0.1 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g, 0.3 mmol), sodium tert-butoxide (2.2 g, 23.2 mmol), and xylene (50 mL) were added to a round-bottom flask. The mixture was stirred at 135°C to 140°C for 7 hours. The mixture was cooled to room temperature, washed with water, and then separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as an eluent, and then the product was recrystallized and purified using a toluene / n-heptane mixed solvent to obtain white solid compound AA21 (7.6 g; yield: 70%).

[0162] The mass spectrum data of the first compound are shown in Table 7 below:

[0163] Table 7

[0164] Synthesis of the second compound

[0165] Synthesis of compound a3:

[0166] Under nitrogen, raw material a-1 (20.0 g, 48.9 mmol, CAS: 2071630-78-7), raw material b-1 (15.1 g, 48.9 mmol, CAS: 1762-84-1), tris(dibenzylideneacetone)dipalladium (0.4 g, 0.5 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.4 g, 1.0 mmol), sodium tert-butoxide (7.0 g, 73.4 mmol) and xylene (200 mL) were added to a round-bottom flask, and the mixture was stirred at 140°C for 6 hours. The mixture was cooled to room temperature, washed with water and separated, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as an eluent, and then the product was recrystallized and purified using a toluene / n-heptane mixed solvent to obtain a white solid compound a3-1 (23.1 g, yield: 74%).

[0167] Trifluoromethanesulfonic anhydride (86.8g, 307.8mmol) and heavy water (30.8g, 1538.9mmol) were added at 0°C and stirred for 5 hours to prepare a solution. Compound a3-1 (20g, 31.4mmol) was added to 120mL of 1,2,4-trichlorobenzene, and the mixture was stirred. Then, the prepared mixed solution of trifluoromethanesulfonic anhydride and heavy water was slowly added dropwise to the mixed solution of compound a3-1 and 1,2,4-trichlorobenzene, and the mixture was stirred while being heated to 140°C, and then the temperature was maintained. After reacting for 14 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound a3 (10.97g, yield: 54%).

[0168] Referring to the synthesis method of compound a3, the compounds shown in Table 8 below were synthesized by using reactant a in Table 8 below instead of compound a-1 and reactant b in Table 8 below instead of compound b-1:

[0169] Table 8

[0170] The mass spectrum data of the second compound are shown in Table 9 below.

[0171] Table 9

[0172] Preparation of organic electroluminescent devices

[0173] Example 1: Preparation of green organic electroluminescent device

[0174] The device was prepared by the following process

[0175] When the thickness of ITO / Ag / ITO is On the experimental substrate, ultraviolet, ozone and O2:N2 plasma are used for surface treatment to increase the work function of the anode, and organic solvents can be used to clean the surface of the experimental substrate to remove impurities and oil stains on the surface of the experimental substrate.

[0176] Compound HT-1 and PD were co-evaporated on the experimental substrate at an evaporation rate ratio of 97%:3% to form a film with a thickness of The hole injection layer is then deposited with compound HT-1 to form a hole injection layer with a thickness of The hole transport layer is formed by evaporating compound HT-2 on the hole transport layer to form a hole transport layer with a thickness of light-emitting auxiliary layer.

[0177] On the light-emitting auxiliary layer, compound a3 (second compound), compound A2 (first compound), and GD-01 (doped guest) were co-evaporated at an evaporation rate ratio of 60%:40%:10% to form a layer with a thickness of organic light-emitting layer.

[0178] On the organic light emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 50%:50% to form a film with a thickness of electron transport layer.

[0179] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at an evaporation rate ratio of 10%:90% to form a thickness of cathode.

[0180] Compound CP-1 is evaporated on the cathode to form a thickness of An organic covering layer is formed, thereby completing the preparation of a green organic electroluminescent device.

[0181] Example 2 to Example 40:

[0182] An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the organic light-emitting layer, the first compound, the second compound, and the ratio of the evaporation rates of the first compound and the second compound in Table 10 were used instead of the first compound, the second compound, and the ratio of the evaporation rates of the first compound and the second compound in Example 1.

[0183] Comparative Examples 1 and 2:

[0184] An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the organic light-emitting layer, the first compound, the second compound, and the ratio of the evaporation rates of the first compound and the second compound in Table 10 were used instead of the first compound, the second compound, and the ratio of the evaporation rates of the first compound and the second compound in Example 1.

[0185] The compounds used to prepare the devices of each embodiment and comparative example are as follows:

[0186] The green organic electroluminescent devices prepared in Examples 1 to 40 and Comparative Examples 1 to 2 were tested for their performance. Specifically, at 15 mA / cm 2 The IVL performance of the device was tested under the conditions of 20mA / cm 2 The T95 device life was tested under the conditions of , and the test results are shown in Table 10 below.

[0187] Table 10

[0188] As can be seen from the above table, compared with Comparative Examples 1 to 2, the device current efficiency of Examples 1 to 40 is improved by at least 8.9%, and the T95 life is improved by at least 33.5%.

[0189] The organic light-emitting layer of the organic electroluminescent device of the present application comprises a first compound and a second compound, wherein the core structure of the first compound is a phenylcarbazole connected to a triazine group via a nitrogen atom, wherein one of the phenyl rings on the carbazole ring is fully deuterated, and the other phenyl ring is connected to an aryl group. The aromatic group on one side of the carbazole group serves as a substituent, which expands the range of aromatic conjugation in the molecular structure while reducing the molecular symmetry, giving the material better energy transfer properties and reducing crystallinity; the special asymmetric deuteration of the carbazole group can effectively improve the stability of the molecular structure and further reduce the molecular symmetry, thereby significantly improving the photoelectric stability and film-forming properties of the material. The first compound of the present application has excellent carrier transport properties, energy transfer properties, and photoelectric stability, and is suitable for use as a main material for the light-emitting layer in an organic electroluminescent device. The organic electroluminescent device using it as the main material has significantly improved life characteristics while maintaining a low driving voltage and high luminous efficiency. The second compound of the present application selects an indolecarbazole compound with a specific fusion method, and the parent nucleus of the compound is fully deuterated, which can significantly improve the stability of the compound. The combination of these two deuterated compounds exhibits high and balanced carrier mobility. Using these two materials as a mixed host material for green organic electroluminescent devices can reduce the operating voltage of the device, while improving its luminous efficiency and lifetime. In particular, the first compound, in which the aromatic group on the carbazole side is a pentadeuterated phenyl group, exhibits even better device performance when combined with the second compound.

[0190] Specifically, compared to Comparative Example 1, the device prepared in this application significantly reduces the driving voltage and improves the luminous efficiency. This may be due to the deuteration of specific sites in the phenylcarbazole core structure in the first compound of this application, which, when used in combination with the second compound having strong hole-vacancy properties, can significantly extend the service life of the organic electroluminescent device.

[0191] Compared with Comparative Example 2, the device prepared in this application has significantly improved service life. The reason for this may be that the first compound of this application is deuterated at a specific site of the carbazole group, and the triazine and carbazole are connected by a single bond or an arylene group. When used with the second compound having strong hole-vacancy properties, the photoelectric stability of the device can be significantly improved.

[0192] The above describes in detail some embodiments of the present application in conjunction with the accompanying drawings. However, the present application is not limited to the specific details of the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the scope of protection 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 is a compound represented by 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 pentadeuterated phenyl, biphenyl or terphenyl; 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 a compound represented by Formula 2: 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, and 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 and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L4, L5, Ar4 and Ar5 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.

2. The organic electroluminescent device according to claim 1, characterized in that: In 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; 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, a phenyl group or a pentadeuterated phenyl group.

3. The organic electroluminescent device according to claim 1, characterized in that: In 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, phenyl or pentadeuterated phenyl.

4. The organic electroluminescent device according to claim 1, characterized in that: 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, 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.

5. The organic electroluminescent device according to claim 1, characterized in that: In formula 1 are independently selected from the group consisting of:

6. The organic electroluminescent device according to claim 1, characterized in that: In formula 1 Selected from the group consisting of:

7. The organic electroluminescent device according to claim 1, characterized in that: In Formula 1, Ar3 is selected from the group consisting of the following groups:

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

9. The organic electroluminescent device according to claim 1, characterized in that: 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 carbazolylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenylene group; 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.

10. The organic electroluminescent device according to claim 1, characterized in that: In Formula 2, Ar4 and Ar5 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 quaterphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; 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, phenyl or pentadeuterated phenyl.

11. The organic electroluminescent device according to claim 1, characterized in that: In formula 2 The same or different, and are independently selected from the following groups:

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

13. The organic electroluminescent device according to claim 1, characterized in that: The organic layer further includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron transport layer and an electron injection layer.

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

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