Organic electroluminescent device and electronic device

Abstract

The invention provides an organic light-emitting device and an electronic device. The organic light-emitting 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 is selected from a compound as shown in a formula 1; the second compound is selected from a compound shown in a formula 2. # imgabs0 #

Description

Technical Field

[0001] This application relates to the technical field of organic electroluminescent materials, and particularly to an organic electroluminescent device and an electronic device. Background Art

[0002] In recent years, organic electroluminescent devices (OLEDs) have become very popular emerging flat panel display products at home and abroad because OLED displays have characteristics such as 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 these two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a 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 respectively injected into the light-emitting layer from the anode and the cathode. Then, in the 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 externally.

[0004] Currently, there are still problems with poor performance during the use of organic electroluminescent devices, such as high driving voltage, low luminous efficiency, or short lifespan, etc. These all affect the application fields of the electromechanical electroluminescent devices. Therefore, it is still necessary to conduct further research in this field to improve the performance of organic electroluminescent devices. Summary of the Invention

[0005] Aiming at the above problems existing in the prior art, the purpose of this application is to provide an organic electroluminescent device and an electronic device to improve the performance of the device and the apparatus.

[0006] According to the first aspect of this application, there is provided an organic electroluminescent device, including a cathode, an anode, and an organic layer;

[0007] wherein, the cathode and the anode are disposed opposite to each other;

[0008] the organic layer is located between the cathode and the anode;

[0009] the organic layer includes an organic light-emitting layer;

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

[0011] The first compound has a structure shown in Formula 1:

[0012]

[0013] X is selected from C(R aR b )、O or S;

[0014] R1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a group represented by formula A;

[0015] R2 and R3 are the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms or a group represented by formula A;

[0016] Only one of the R1, R2 and R3 is a group represented by formula A;

[0017] R a and R b are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0018] Each of L, L1 and L2 is the same or different and is each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0019] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0020] The substituents in the R1, R2, R3, R a , R b , L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a haloaryl group having 6 to 20 carbon atoms or a trialkylsilyl group having 3 to 12 carbon atoms, and any two adjacent substituents in Ar1 and Ar2 form a 3- to 15-membered ring;

[0021] The second compound has the structure shown in formula 2:

[0022]

[0023] Ring A is a benzene ring, a dibenzofuran ring or a dibenzothiophene ring;

[0024] Ar3 and Ar4 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0025] L3 and L4 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0026] The substituents in L3, L4, Ar3 and Ar4 are the same or different, and each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring;

[0027] Each of R4, R5 and R6 is the same or different, and each independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0028] n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0029] n5 is selected from 0, 1 or 2;

[0030] n6 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0031] According to a second aspect of the present application, there is provided an electronic device including the organic electroluminescent device described in the first aspect.

[0032] The light-emitting layer of the organic electroluminescent device in this application contains both a first compound and a second compound. The first compound has a core group formed by the fusion of a dibenzo five-membered ring and a benzoxazole in a special manner. The compound formed by combining this parent nucleus with a triazine-based electron transport group can have strong carrier transport ability and high energy transfer ability while maintaining a relatively high first triplet energy level value. The second compound in the light-emitting layer is a benzindole carbazole fused ring compound, and the first compound and the second compound are mixed in a certain proportion to form a mixed light-emitting layer host material. First, the core group of the first compound has a planar structure while having a ring-like structure, and its first triplet energy level value is relatively matched with that of indole carbazole derivative compounds; second, the second compound belongs to a hole-transporting host material, and the fused carbazole derivative-based core structure can significantly increase the conjugation area of the target compound, enhance the intermolecular interaction force, and improve the carrier transport ability of the compound film. Therefore, when the first compound and the second compound of this application are combined as a mixed light-emitting host material, the aggregation of molecules is reduced, the localization of electrons and holes is avoided, and it is not easy to form carrier transport traps, which can significantly improve the carrier balance in the light-emitting layer, improve the stability of the film, and further improve the light-emitting efficiency and lifespan of the device. Description of the Drawings

[0033] The drawings are used to provide a further understanding of this application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain this application, but do not constitute a limitation to this application.

[0034] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of this application.

[0035] Figure 2 It is a schematic structural diagram of an electronic device according to an embodiment of this application.

[0036] Reference Signs

[0037] 100, Anode; 200, Cathode; 300, Functional Layer; 310, Hole Injection Layer

[0038] 321, First Hole Transport Layer; 322, Light-Emitting Auxiliary Layer; 320, Hole Transport Layer; 330, Organic Light-Emitting Layer

[0039] 340, Electron Transport Layer; 350, Electron Injection Layer; 400, Electronic Device Detailed Description of the Embodiments

[0040] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of this application.

[0041] In the figures, the regions and thicknesses of layers may be exaggerated for clarity. The same reference numerals in the figures denote the same or similar structures, and thus their detailed descriptions will be omitted.

[0042] According to a first aspect of the present application, there is provided an organic electroluminescent device, including a cathode, an anode, and an organic layer;

[0043] wherein, the cathode and the anode are disposed opposite to each other;

[0044] the organic layer is located between the cathode and the anode;

[0045] the organic layer includes an organic light-emitting layer;

[0046] the organic light-emitting layer includes a first compound and a second compound;

[0047] the first compound has a structure represented by Formula 1

[0048]

[0049] X is selected from C(R a R b ), O, or S;

[0050] R1 is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms or a group represented by Formula A;

[0051] R2 and R3 are the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a group represented by Formula A;

[0052] only one of R1, R2, and R3 is a group represented by Formula A;

[0053] R a and R b are the same or different and are each independently selected from an alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

[0054] Each of L, L1, and L2 is the same or different and is 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;

[0055] Ar1 and Ar2 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;

[0056] Said R1, R2, R3, R a , R b , L, L1, L2, Ar1, and Ar2 have substituents that 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 halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 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, or a trialkylsilyl group having 3 to 12 carbon atoms. Any two adjacent substituents in Ar1 and Ar2 form a 3- to 15-membered ring;

[0057] The second compound has the structure shown in Formula 2:

[0058]

[0059] Ring A is a benzene ring, a dibenzofuran ring, or a dibenzothiophene ring;

[0060] Ar3 and Ar4 are the same or different and are each 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;

[0061] L3 and L4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0062] The substituents in L3, L4, Ar3, and Ar4 are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms. Optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring;

[0063] Each of R4, R5 or R6 is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0064] n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0065] n5 is selected from 0, 1 or 2;

[0066] n6 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0067] In this application, the terms "optionally" and "optionally" mean that the subsequent described events or circumstances may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes both the scenario where any two adjacent substituents form a ring and the scenario where any two adjacent substituents exist independently of each other and do not form a ring. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly attached; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0068] In this application, the description methods "each... is independently", "each... is separately independently" and "each... is independently" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can also mean that within the same group, the specific options expressed between 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, chlorine", which means that in formula Q-1, there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options for each R" do not affect each other; in formula Q-2, there are q substituents R" on each benzene ring of the biphenyl, the number q of the R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options for each R" do not affect each other.

[0069] In the present application, a term such as "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc or unsubstituted aryl. Among them, the above-mentioned substituent, that is, Rc, may be, for example, deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, triphenylsilyl group, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, aryloxy group with 6 to 20 carbon atoms or arylthio group with 6 to 20 carbon atoms, etc. The number of substitutions can be one or more.

[0070] In the present application, "a plurality of" means more than 2, such as 2, 3, 4, 5, 6, etc.

[0071] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms.

[0072] The hydrogen atoms in the compound structure of the present application include various isotope atoms of hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0073] In the compound structural formula of the present application, "D" represents deuteration.

[0074] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, the aryl can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryls connected by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl connected by carbon-carbon bonds, or two or more fused-ring aryls connected by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bonds can also be regarded as the aryl in the present application. Among them, the fused-ring aryl can include, for example, bicyclic fused aryl (such as naphthyl), tricyclic fused aryl (such as phenanthryl, fluorenyl, anthryl), etc. The aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, and the like.

[0075] In the present application, the arylene involved refers to a divalent or polyvalent group formed by an aryl further losing one or more hydrogen atoms.

[0076] In the present application, the terphenyl includes

[0077] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 or 30. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 18 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.

[0078] In the present application, the fluorenyl group can be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group can be:

[0079] etc., but not limited thereto.

[0080] In the present application, the aryl as the substituent is, for example but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

[0081] In the present application, the heteroaryl is a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be one or more of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., and is not limited thereto.

[0082] In the present application, the heteroarylene involved refers to a divalent or polyvalent group formed by the heteroaryl further losing one or more hydrogen atoms.

[0083] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 3 to 30. In other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 12 to 18. In still other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 5 to 12.

[0084] In the present application, examples of the heteroaryl as a substituent include, but are not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.

[0085] In the present application, the substituted heteroaryl may be one or more hydrogen atoms in the heteroaryl substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.

[0086] 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. 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, etc.

[0087] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine or iodine.

[0088] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0089] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0090] In the present application, the number of carbon atoms 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, adamantyl.

[0091] In the present application, the number of carbon atoms of the deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuteriomethyl.

[0092] In the present application, the number of carbon atoms of the haloalkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0093] In the present application, an n-membered ring is a ring system formed by n atoms. For example, a phenyl group is a 6-membered ring. A 3- to 15-membered ring refers to a cyclic group having 3 to 15 ring atoms. Examples of the 3- to 15-membered ring include cyclopentane, cyclohexane, fluorene ring, benzene ring, and the like.

[0094] In the present application, refers to a chemical bond that connects to other groups.

[0095] In the present application, the non-positioning connecting bond involves a single bond extending from the ring system which indicates that one end of the connecting bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positioning connecting bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connection mode shown in formulas (f-1) to (f-10):

[0096]

[0097] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positioning connecting bond extending from the middle of one benzene ring, and the meaning it represents includes any possible connection mode shown in formulas (X'-1) to (X'-4):

[0098]

[0099] The non-positioning substituent in the present application refers to a substituent connected through a single bond extending from the center of the ring system, which indicates that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, and the meaning it represents includes any possible connection mode shown in formulas (Y-1) to (Y-7):

[0100]

[0101] In some embodiments of the present application, the first compound is selected from the structures shown in formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, or formula 1-9:

[0102]

[0103] In some embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted arylene having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene having 12 to 18 carbon atoms.

[0104] 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 each independently selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, or a substituted or unsubstituted heteroarylene having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0105] Optionally, the substituents in L, L1, and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, phenyl, or deuterated phenyl.

[0106] 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 each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolyl.

[0107] Optionally, the substituents in L, L1, and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, or phenyl.

[0108] In some embodiments of the present application, in the first compound represented by Formula 1, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0109]

[0110] Optionally, L is selected from a single bond or the group consisting of the following groups:

[0111]

[0112] In some embodiments of the present application, in the first compound represented by Formula 1, L is independently selected from a single bond or the group consisting of the following groups:

[0113]

[0114] In some embodiments of the present application, in the first compound represented by Formula 1, L1 and L2 are the same or different and each independently selected from a single bond or the group consisting of the following groups:

[0115]

[0116]

[0117] In some embodiments of the present application, in the first compound represented by Formula 1, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups 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 groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0118] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups having 1 to 4 carbon atoms, deuterated alkyl groups having 1 to 4 carbon atoms, alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, aryl groups having 6 to 15 carbon atoms, heteroaryl groups having 5 to 12 carbon atoms, trialkylsilyl groups having 3 to 8 carbon atoms, or deuterated aryl groups having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0119] In some embodiments of the present application, in the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and each independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophenyl groups.

[0120] Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, trifluoromethyl, trimethylsilyl, phenyl, or naphthyl.

[0121] In some embodiments of the present application, in the first compound represented by Formula 1, among Ar1 and Ar2, one is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; the other is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene.

[0122] 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, cyclohexyl, trifluoromethyl, trimethylsilyl, phenyl or naphthyl.

[0123] 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 each independently selected from the following groups:

[0124]

[0125]

[0126] 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 each independently selected from the following groups:

[0127]

[0128]

[0129] In some embodiments of the present application, in the first compound represented by Formula 1, R a and R b are the same or different and are each independently methyl, substituted or unsubstituted phenyl.

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

[0131] In some embodiments of the present application, in the first compound represented by Formula 1, R a and R b are the same.

[0132] In some embodiments of the present application, X is selected from C(CH3)2, O or S.

[0133] In some embodiments of the present application, in the first compound represented by Formula 1, R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl.

[0134] Optionally, the substituents in R1 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0135] In some embodiments of the present application, in the first compound represented by Formula 1, R2 and R3 are the same or different and are each independently selected from hydrogen, deuterium or the group represented by Formula A; and only one of R2 and R3 is the group represented by Formula A.

[0136] In some embodiments of the present application, in the first compound represented by Formula 1, one of R2 and R3 is selected from hydrogen or deuterium, and the other is the group represented by Formula A.

[0137] In some embodiments of the present application, in the first compound represented by Formula 1, being the same or different and each independently selected from the following groups:

[0138]

[0139] In some embodiments, the second compound represented by Formula 2 is selected from the structures represented by the following Formulas (2-1) to (2-13):

[0140]

[0141] In some embodiments, in the second compound represented by Formula 2, L3 and L4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene having 12 to 18 carbon atoms.

[0142] In some embodiments, in the second compound represented by Formula 2, L3 and L4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0143] Optionally, in the second compound represented by Formula 2, the substituents in L3 and L4 are the same or different, and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, phenyl, or naphthyl.

[0144] In some embodiments, in the second compound represented by Formula 2, L3 and L4 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted carbazolyl.

[0145] Optionally, in the second compound represented by Formula 2, the substituents in L3 and L4 are the same or different, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, or phenyl.

[0146] In some embodiments, in the second compound represented by Formula 2, L3 and L4 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0147]

[0148] In some embodiments, in the second compound represented by Formula 2, L3 and L4 are the same or different, and are each independently selected from a single bond or the following groups:

[0149]

[0150] In some embodiments, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.

[0151] In some embodiments, Ar3 and Ar4 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, a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.

[0152] In some embodiments, in the second compound represented by Formula 2, the substituents in Ar3 and Ar4 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or a trialkylsilyl group having 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0153] In some embodiments, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0154] Optionally, in the second compound represented by Formula 2, the substituents in Ar3 and Ar4 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trimethylsilyl group, a pentadeuterated phenyl group, a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0155] In some embodiments, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different and are each independently selected from the following groups:

[0156]

[0157] In some embodiments, in the second compound represented by Formula 2, Ar3 and Ar4 are the same or different and are each independently selected from the following groups:

[0158]

[0159]

[0160] In some embodiments, in the second compound represented by Formula 2, are the same or different and are each independently selected from the following groups:

[0161]

[0162] In some embodiments, in the second compound represented by Formula 2, one of Ar3 and Ar4 is selected from: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and the other is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.

[0163] In some embodiments, in the second compound represented by Formula 2, one of Ar3 and Ar4 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 phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl; and the other 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 phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0164] Optionally, in the second compound represented by Formula 2, the substituents of Ar3 and Ar4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl, phenyl or naphthyl.

[0165] In some embodiments, in the second compound represented by Formula 2, one of them is selected from:

[0166]

[0167] the other is selected from the following groups:

[0168]

[0169] In some embodiments, in the second compound represented by Formula 2, each of R4, R5 and R6 is the same or different and is each independently selected from hydrogen, deuterium, cyano, fluorine, trideuteriomethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0170] In some embodiments of the present application, the first compound is selected from the compounds represented by A-1 to A-204 in Claim 13.

[0171] In some embodiments of the present application, the second compound is selected from the compounds represented by B-1 to B-348 and C-1 to C-181 in Claim 13.

[0172] Further, in the organic electroluminescent device of the present application, the organic light-emitting layer contains a host material and a dopant. The host material contains a first compound and a second compound. Generally, based on the weight (mass) of the two compounds, the mass ratio of the first compound to the second compound is from 1:99 to 99:1, preferably from 10:90 to 90:10; preferably from 20:80 to 80:20; more preferably from 30:70 to 70:30; still more preferably from 40:60 to 60:40. Further, the mass ratio of the host material to the dopant in the organic light-emitting layer is from 90:10 to 99:1.

[0173] In some embodiments of the present application, the mass ratio of the first compound (the compound shown in Formula 1) to the second compound (the compound shown in Formula 2 or Formula 3) in the host of the light-emitting layer of the organic electroluminescent device is from 30:70 to 70:30.

[0174] Optionally, in the host material, the mass ratio of the first compound (Compound of Formula 1) to the second compound (the compound shown in Formula 2 or Formula 3) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35, 70:30, 75:25, 80:20.

[0175] In some embodiments of the present application, the host material and the guest material can be co-evaporated by 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 host material and the guest material during the evaporation process, or by controlling the evaporation rate ratio of the host material and the guest material.

[0176] Optionally, the organic light-emitting layer can be formed 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 film thickness of the host material and the guest material during the evaporation process, or by controlling the film thickness ratio of the host material and the guest material.

[0177] In order to obtain a host material mixture, the first compound and the second compound can be placed in an oscillator and mixed to obtain a mixture with a desired weight ratio.

[0178] In order to form each layer constituting the organic electroluminescent device of the present application, a dry film-forming method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, etc. can be used.

[0179] In addition, the first compound and the second compound can be used to form a film in the methods listed above, typically by co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in corresponding individual crucible sources and current is applied to multiple chambers simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chamber to evaporate the materials.

[0180] In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.

[0181] In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.

[0182] In a second aspect of the present application, an electronic device is provided, and the organic electroluminescent device described in the first aspect is included in the electronic device.

[0183] In another aspect of the present application, a composition is further provided. The composition includes a first compound and a second compound, and the first compound has a structure represented by Formula 1:

[0184]

[0185] X is selected from C(R a R b ), O or S;

[0186] R1 is selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms or a group represented by Formula A;

[0187] R2 and R3 are the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms or a group represented by Formula A;

[0188] Only one of R1, R2 and R3 is a group represented by Formula A;

[0189] R a and R b are the same or different and are each independently selected from an alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

[0190] Each of L, L1 and L2 is the same or different and is each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms;

[0191] Ar1 and Ar2 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0192] The substituents in R1, R2, R3, R a , R b , L, L1, L2, Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, halogen groups, cyano 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, cycloalkyl groups having 3 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, haloaryl groups having 6 to 20 carbon atoms, or trialkylsilyl groups having 3 to 12 carbon atoms. Optionally, any two adjacent substituents in Ar1 and Ar2 form a 3- to 15-membered ring;

[0193] The second compound has the structure shown in Formula 2:

[0194]

[0195] Ring A is a benzene ring, a dibenzofuran ring, or a dibenzothiophene ring;

[0196] Ar3 and Ar4 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0197] L3 and L4 are the same or different, and are each independently selected from a single bond, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms;

[0198] The substituents in L3, L4, Ar3 and Ar4 are the same or different, and are each independently selected from deuterium, cyano groups, 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, alkoxy groups having 1 to 10 carbon atoms, alkylthio 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, or cycloalkyl groups having 3 to 10 carbon atoms. Optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring;

[0199] Each of R4, R5, R6 and R7 is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0200] n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0201] n5 is selected from 0, 1 or 2;

[0202] n6 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0203] In some embodiments of the present application, the mass ratio of the first compound to the second compound in the composition is from 1:99 to 99:1; preferably from 10:90 to 90:10; more preferably from 20:80 to 80:20; still more preferably from 30:70 to 70:30, and even more preferably from 40:60 to 60:40.

[0204] In some embodiments, the mass ratio of the first compound (compound of formula 1) to the second compound (compound represented by formula 2 or formula 3) in the composition is from 30:70 to 70:30.

[0205] The present application also provides the use of the light-emitting layer composition in the light-emitting layer of an organic electroluminescent device.

[0206] The present application also provides an organic electroluminescent device comprising the composition.

[0207] The organic electroluminescent device provided by the present application comprises an anode and a cathode which are oppositely arranged, 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.

[0208] In some embodiments of the present application, the organic electroluminescent device sequentially comprises an anode (for example, an ITO / Ag / ITO substrate), a hole transport layer, a hole adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (for example, an Mg-Ag mixture) and an organic capping layer. The hole transport layer is located between the anode and the organic light-emitting layer, and the hole adjustment layer is located between the hole transport layer and the organic light-emitting layer.

[0209] According to a specific embodiment, such as Figure 1As shown, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a light-emitting auxiliary layer (also known as a hole auxiliary layer, a hole adjustment layer, an electron blocking layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked.

[0210] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function (work function) that helps 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); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0211] In this application, the first hole transport layer or the light-emitting auxiliary layer may each include one or more hole transport materials. The material of the hole transport layer 320 may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and specifically may be selected from the compounds shown below or any combination thereof:

[0212]

[0213] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0214] In one embodiment, the light-emitting auxiliary layer 322 is composed of HT-2.

[0215] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not make special restrictions thereon. The material of the hole injection layer 310 may be, for example, selected from the following compounds or any combination thereof;

[0216]

[0217] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1.

[0218] Optionally, the organic light-emitting layer 330 may include the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of the host material and the guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. 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.

[0219] The host material of the organic light-emitting layer 330 includes the first compound and the second compound.

[0220] The guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and the present application does not make special restrictions thereon. The guest material is also referred to as a doping material or a dopant. According to the emission type, it can be divided into a fluorescent dopant and a phosphorescent dopant. For example, specific examples of the phosphorescent dopant include, but are not limited to,

[0221]

[0222]

[0223] In an embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be, for example, RD.

[0224] In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be, for example, fac-Ir(ppy)3.

[0225] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and it may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, electron transport materials such as BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, etc., and the present application does not make special limitations thereon. The material of the electron transport layer 340 includes LiQ and other electron transport materials, and the other electron transport materials may be selected from, but are not limited to, the following compounds:

[0226]

[0227] In an embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0228] In the present application, the cathode 200 includes a cathode material, which is a material with a small work function that helps inject electrons into the functional layer. Specific examples of the cathode material include, but are not limited to, 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. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0229] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances. In an embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0230] The present application not only provides the organic electroluminescent device including the compound represented by Formula 1 and the compound represented by Formula 2 for the organic light-emitting layer. The present application also provides an electronic device including the organic electroluminescent device of the present application.

[0231] According to an embodiment, as Figure 2 shown, the provided electronic device is the electronic device 400. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, for example, but are not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0232] The following specifically describes the synthesis methods of the first compound and the second compound of the present application in combination with synthesis examples, but the present application is not limited thereby.

[0233] Synthesis Example

[0234] Those skilled in the art should recognize that the chemical reactions described in the present application can be used to appropriately prepare many heterocyclic compounds of the present application, and other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-illustrative compounds according to the present application can be successfully completed by those skilled in the art through modification methods, such as appropriately protecting interfering groups, by using other known reagents in addition to those described in the present application, or making some conventional modifications to the reaction conditions. Compounds for which the synthesis method is not mentioned in the present application are all raw material products obtained through commercial channels.

[0235] Synthesis of the first compound:

[0236] Synthesis of Sub-a1:

[0237]

[0238] Under a nitrogen atmosphere, RM-1 (13.76 g, 50 mmol) and dichloromethane (130 mL) were successively added to a 250 mL three-necked flask. The system was cooled to 0 °C, and N-bromosuccinimide (9.35 g, 52.5 mmol) was added in batches. After maintaining the temperature for reaction for 6 h, the system was slowly allowed to rise to room temperature. The reaction solution was poured into 250 mL of saturated aqueous sodium thiosulfate solution and stirred well for 30 min. It was extracted with dichloromethane (100 mL × 3 times). The combined organic phases were 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 dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-a1 (14.0 g; yield 79%).

[0239] Synthesis of Sub-b1:

[0240]

[0241] Under a nitrogen atmosphere, Sub-a1 (17.71 g, 50 mmol), 4-chloro-2-fluorophenylboronic acid (9.59 g, 55 mmol), tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), absolute ethanol (45 mL) and deionized water (45 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The combined organic phases were 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 dichloromethane / n-heptane as the mobile phase to obtain a yellow solid Sub-b1 (11.31 g, yield 56%).

[0242] With reference to the synthesis of Sub-b1, Reactant A shown in Table 1 was used to replace 4-chloro-2-fluorophenylboronic acid to synthesize Sub-b2 and Sub-b3 in Table 1.

[0243] Table 1. Synthesis of Sub-b2 and Sub-b3

[0244]

[0245]

[0246] Synthesis of Sub-c1:

[0247]

[0248] Under a nitrogen atmosphere, Sub-b1 (27.25 g, 67.5 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. During the addition, the temperature was strictly controlled within the range of 0 ± 5 °C. After the addition was complete, the mixture was kept at 0 ± 5 °C for 2 h, and then the system was allowed to warm 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 warmed 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 the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain the white solid product Sub-c1 (17.63 g, yield 67%).

[0249] With reference to the synthesis of Sub-c1, Reactant B shown in Table 2 was used to replace Sub-b1 to synthesize Sub-c2 and Sub-c3 in Table 2.

[0250] Table 2. Synthesis of Sub-c2 and Sub-c3

[0251]

[0252] Synthesis of Sub-d1:

[0253]

[0254] Under a nitrogen atmosphere, Sub-c1 (19.49 g, 50 mmol), cesium carbonate (32.58 g, 100 mmol) and DMSO (200 mL) were added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was raised to 80 °C for reaction for 4 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The combined organic phases were dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain the white solid Sub-d1 (16.27 g, yield 88%).

[0255] With reference to the synthesis of Sub-d1, Reactant C shown in Table 3 was used to replace Sub-c1 to synthesize Sub-d2 and Sub-d3 in Table 3.

[0256] Table 3. Synthesis of Sub-d2 and Sub-d3

[0257]

[0258] Synthesis of Sub-e1:

[0259]

[0260] Under a nitrogen atmosphere, Sub-d1 (18.50 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started. When the temperature of the system reached 40 °C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The temperature was further raised to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and it was stirred well for 30 min. Then, it was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of absolute ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-e1 (14.76 g, yield 64%) was obtained.

[0261] With reference to the synthesis of Sub-e1, Reactant D shown in Table 4 was used to replace Sub-d1 to synthesize Sub-e2 and Sub-e3 in Table 4.

[0262] Table 4. Synthesis of Sub-e2 and Sub-e3

[0263]

[0264] Synthesis of Compound A-1:

[0265]

[0266] Under a nitrogen atmosphere, Sub-e1 (12.10 g, 26.25 mmol), RM-2 (7.94 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were successively added to a 250 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The combined organic phases were 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 dichloromethane / n-heptane as the mobile phase to obtain a white solid A-1 (10.0 g, yield 65%, m / z = 617.20 [M+H] + )

[0267] Referring to the synthesis of compound A-1, using reactant E shown in Table 5 to replace Sub-e1 and reactant F to replace RM-2, the first compound of the present application in Table 5 was synthesized.

[0268] Table 5: Synthesis of the First Compound of the Present Application

[0269]

[0270]

[0271]

[0272]

[0273] Synthesis of the second compound:

[0274] Synthesis of Sub-f1:

[0275]

[0276] Under a nitrogen atmosphere, 9-bromo-7H-benzo[c]carbazole (29.62 g, 100 mmol), benzyl bromide (25.65 g, 150 mmol), potassium hydroxide (11.22 g, 200 mmol) and tetrahydrofuran (300 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was raised to 60 °C for reaction for 6 h. After the system was cooled to room temperature, it was extracted with tetrahydrofuran (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain white solid Sub-f1 (32.45 g, yield 84%).

[0277] Synthesis of Sub-g1:

[0278]

[0279] Under a nitrogen atmosphere, Sub-f1 (19.31 g, 50 mmol), 1-chloro-2-aminodibenzofuran (10.88 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and toluene (250 mL) were successively added to a 500 mL three-necked flask. 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 combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain white solid Sub-g1 (19.10 g; yield 73%).

[0280] With reference to the synthesis of Sub-g1, Sub-g2 to Sub-g9 were synthesized using reactant G shown in Table 6 to replace Sub-f1 and reactant H to replace 1-chloro-2-aminodibenzofuran.

[0281] Table 6: Synthesis of Sub-g2 to Sub-g9

[0282]

[0283] Synthesis of Sub-h1:

[0284]

[0285] Under a nitrogen atmosphere, Sub-g1 (26.15 g, 50 mmol), palladium acetate (0.56 g, 2.5 mmol), tricyclohexylphosphine tetrafluoroborate (CAS: 58656-04-5, 1.84 g, 5 mmol), cesium carbonate (32.58 g, 100 mmol) and N,N-dimethylacetamide (260 mL) were successively added to a 500 mL three-necked flask. 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 combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain off-white solid Sub-h1 (13.62 g; yield 56%).

[0286] With reference to the synthesis of Sub-h1, Sub-h2 to Sub-h9 were synthesized using reactant J shown in Table 7 to replace Sub-g1.

[0287] Table 7: Synthesis of Sub-h2 to Sub-h9

[0288]

[0289]

[0290] Synthesis of Sub-h10:

[0291]

[0292] Under a nitrogen atmosphere, add Sub-h3 (11.80 g, 25 mmol) and 200 mL of benzene-D6 to a 100 mL three-necked flask. After heating to 60 °C, add trifluoromethanesulfonic acid (22.51 g, 150 mmol) thereto, and continue heating to boiling and stirring for reaction for 24 hours. After the reaction system is cooled to room temperature, add 50 mL of heavy water thereto, stir for 10 minutes, and then add a saturated aqueous solution of K3PO4 to neutralize the reaction solution. Extract the organic layer with dichloromethane (50 mL × 3 times), combine the organic phases, dry over anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure to obtain a crude product. Use n-heptane / dichloromethane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid Sub-h10 (8.88 g, yield 73%).

[0293] Synthesis of Sub-j1:

[0294]

[0295] Under a nitrogen atmosphere, successively add Sub-h1 (24.33 g, 50 mmol), iodobenzene (12.24 g, 60 mmol), copper(I) iodide (1.90 g, 10 mmol), 18-crown-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 (240 mL) to a 500 mL three-necked flask, heat to reflux, and stir the reaction overnight; after the system is cooled to room temperature, pour the reaction solution into 500 mL of deionized water, filter by suction and collect the filter solid; dissolve the filter solid with dichloromethane and dry over anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure to obtain a crude product. Use n-heptane / dichloromethane as the mobile phase to purify the crude product by silica gel column chromatography to obtain an off-white solid Sub-j1 (20.54 g; yield 73%).

[0296] Referring to the synthesis of Sub-j1, use the reactant K shown in Table 8 to replace Sub-h1 to synthesize Sub-j2 and Sub-j3.

[0297] Table 8: Synthesis of Sub-j2 and Sub-j3

[0298]

[0299]

[0300] Synthesis of Sub-k1:

[0301]

[0302] Under a nitrogen atmosphere, Sub-j1 (28.13 g, 50 mmol), potassium tert-butoxide (56.10 g, 500 mmol) and DMSO (280 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was raised to 50 °C - 60 °C for reaction for 4 h. After the system was cooled to room temperature, the reaction solution was poured into 500 mL of deionized water, and a precipitate was formed; suction filtration was carried out and the filter solid was taken. The filter solid was dissolved in dichloromethane (200 mL), anhydrous sodium sulfate was added for drying, filtration was carried out and the filtrate was taken, 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 white solid Sub-k1 (18.20 g, yield 77%).

[0303] Referring to the synthesis of Sub-k1, reactant L shown in Table 9 was used to replace Sub-j1 to synthesize Sub-k2 and Sub-k3.

[0304] Table 9: Synthesis of Sub-k2 and Sub-k3

[0305]

[0306] Synthesis of Compound B-4:

[0307]

[0308] Under a nitrogen atmosphere, Sub-h3 (11.81 g, 25 mmol), 4-bromobiphenyl-D9 (6.60 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were successively added to a 250 mL three-necked flask. The temperature was raised to reflux and stirred overnight; after the system was cooled to room temperature, extraction was carried out with dichloromethane (100 mL × 3 times), the organic phases were combined and dried with anhydrous sodium sulfate, and after filtration, 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 white solid Compound B-4 (13.30 g; yield 84%, m / z = 634.28 [M+H] + )

[0309] Referring to the synthesis of Compound B-4, reactant M shown in Table 10 was used to replace Sub-h3, and reactant N was used to replace 4-bromobiphenyl to synthesize the second compound of the present application in Table 10.

[0310] Table 10 Synthesis of the Second Compound of This Application

[0311]

[0312]

[0313]

[0314]

[0315] 1H-NMR of Compound A-1: 1 H-NMR(400MHz, Methylene-Chloride-D2) δ ppm 8.83 - 8.67(m, 5H), 8.62(s, 1H), 8.53(d, 1H), 8.35(d, 2H), 825(d, 1H), 8.19(d, 1H), 8.12(d, 1H), 8.08(d, 1H), 8.0(d, 1H), 7.89(d, 1H), 7.67 - 7.54(m, 7H), 7.48(t, 1H), 7.38(t, 1H);

[0316] 1H-NMR of Compound B-81: 1 H-NMR(400MHz, Methylene-Chloride-D2) δ ppm 9.42(s, 1H), 8.29(d, 1H), 8.21(d, 1H), 8.06(d, 1H), 8.00(d, 1H), 7.96(s, 1H), 7.91(d, 1H), 7.88 - 7.77(m, 4H), 7.68(d, 2H), 7.66 - 7.38(m, 14H), 7.16(d, 2H), 7.08(s, 1H);

[0317] 1H-NMR of Compound C-91: 1 H-NMR(400MHz, Methylene-Chloride-D2) δ ppm 9.46(s, 1H), 8.51(d, 1H), 8.32 - 8.06(m, 7H), 7.94(s, 1H), 7.83(t, 1H), 7.69 - 7.46(m, 16H), 7.31(s, 1H).

[0318] Preparation and Evaluation of Organic Electroluminescent Devices

[0319] Example 1: Preparation of a Red Organic Electroluminescent Device

[0320] First, the anode is pretreated through the following process: with thicknesses in sequence of On the ITO / Ag / ITO substrate, surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The ITO substrate surface was cleaned with an organic solvent to remove impurities and oil on the ITO substrate surface.

[0321] On the experimental substrate (anode), PD:HT-1 was co-evaporated at a deposition rate ratio of 3%:97% to form a hole injection layer (HIL) with a thickness of Then, HT-1 was vacuum-evaporated on the hole injection layer to form a first hole transport layer with a thickness of for

[0322] Compound HT-2 was vacuum-evaporated on the first hole transport layer to form a light-emitting auxiliary layer with a thickness of for

[0323] Next, on the light-emitting auxiliary layer, using compound A-1 as the first host, compound C-67 as the second host, and RD as the dopant, a red light-emitting layer was prepared by co-evaporation method. Among them, the first host: the second host was mixed evenly according to the weight ratio of 50:50 to obtain a composition; the composition of the host material: RD was co-evaporated at a deposition rate ratio of 98%:2% to form a red light-emitting layer (EML) with a thickness of for

[0324] On the light-emitting layer, compound ET-1 and LiQ were co-evaporated at a deposition rate ratio of 1:1 to form an electron transport layer (ETL) with a thickness of Yb was evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate ratio of 1:9 and vacuum-evaporated on the electron injection layer to form a cathode with a thickness of for

[0325] In addition, a CP with a thickness of was vacuum-evaporated on the above-mentioned cathode, thus completing the fabrication of the red organic light-emitting device.

[0326] Examples 2 to 24

[0327] Except that when fabricating the light-emitting layer, the compound combinations in Table 11 below were used to replace the compound combinations in Example 1, an organic light-emitting device was prepared using the same method as in Example 1.

[0328] Comparative Examples 1 to 4

[0329] Except that when fabricating the light-emitting layer, the light-emitting layer host combinations in Table 11 below were used to replace the compound A-1 and C-67 combinations in Example 1 respectively, an organic light-emitting device was prepared using the same method as in Example 1.

[0330] Among them, when preparing each example and comparative example, the structures of the compounds used are as follows:

[0331]

[0332]

[0333] The performance of the red organic light-emitting devices prepared in Examples 1 to 24 and Comparative Examples 1 to 4 was tested. Specifically, the IVL performance of the devices was tested under the condition of 10 mA / cm 2 and the T95 device lifetime was tested under the condition of 20 mA / cm 2 The test results are shown in Table 11.

[0334] Table 11 Test Results of the Devices of the Present Application

[0335]

[0336]

[0337] As can be seen from Table 11 above, compared with Comparative Examples 1 to 4, when the first compound and the second compound of the present invention are used as the host materials of the light-emitting layer of the organic light-emitting device, the device efficiency is increased by at least 14.9% and the lifetime is increased by at least 13.2%.

[0338] The experimental results verify that there is a relatively well-matched first triplet energy level value and energy transfer property between the first compound and the second arylamine compound of the present application; compared with the parent nucleus types of compounds N1, N2, and N3 in Comparative Examples 1 to 4, the parent nucleus fusion mode of the first compound of the present application can better improve the carrier transport ability and energy transfer ability of the electron transport type host material (the first compound). Further, when the first compound is combined with the second compound of the indolocarbazole fused heterocyclic type, the performance of the device is better than that of the second compound of the indolocarbazole fused benzene ring type. The device obtained by the former can achieve a longer service life and better luminous efficiency. The reason is that the combination of the indolocarbazole fused heterocyclic type parent nucleus and the first compound as the light-emitting layer host can improve the energy transfer efficiency and reduce the energy loss of the light-emitting layer.

[0339] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

1. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer; Among them, The cathode and the anode are disposed opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer includes a first compound and a second compound; The first compound has a structure represented by Formula 1: X is selected from C(R a R b ), O or S; R1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a group represented by Formula A; R2 and R3 are the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a group represented by Formula A; Only one of R1, R2, and R3 is a group represented by Formula A; R a and R b are the same or different and each independently selected from an alkyl group having 1 to 10 carbon atoms, 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 of L, L1, and L2 is the same or different and is 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; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in R1, R2, R3, R a , R b , L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 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 or a trialkylsilyl group having 3 to 12 carbon atoms, and any two adjacent substituents in Ar1 and Ar2 form a 3- to 15-membered ring; The second compound has a structure represented by Formula 2: Ring A is a benzene ring, a dibenzofuran ring, or a dibenzothiophene ring; Ar3 and Ar4 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; L3 and L4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in L3, L4, Ar3, and Ar4 are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms. Optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring; Each of R4, R5, and R6 is the same or different and is independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; n5 is selected from 0, 1, or 2; n6 is selected from 0, 1, 2, 3, 4, 5, or 6.

2. The organic electroluminescent device according to claim 1, wherein In the first compound shown in Formula 1, L, L1 and L2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene or a substituted or unsubstituted carbazolyl; Optionally, the substituents in L, L1 and L2 are the same or different and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl or phenyl.

3. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, L1 and L2 are the same or different and each independently selected from a single bond or the group consisting of the following groups: Optionally, L is selected from a single bond or the group consisting of the following groups:

4. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 are the same or different and each independently selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl; Optionally, the substituents in Ar1 and Ar2 are the same or different and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, trifluoromethyl, trimethylsilyl, phenyl or naphthyl.

5. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 are the same or different and each independently selected from the following groups:

6. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, one of R2 and R3 is selected from hydrogen or deuterium, and the other is a group represented by Formula A; Optionally, R1 is selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, and the substituents in R1 are the same or different and each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; Optionally, X is selected from C(CH3)2, O or S.

7. The organic electroluminescent device according to claim 1, wherein, In the second compound shown in Formula 2, Ar3 and Ar4 are the same or different and each independently selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzothiazolyl; Optionally, the substituents in Ar3 and Ar4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

8. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, Ar3 and Ar4 are each independently selected from the following groups:

9. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, L3 and L4 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene; Optionally, the substituents in L3 and L4 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

10. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, L3 and L4 are the same or different and are independently selected from a single bond or the group consisting of the following groups:

11. The organic electroluminescent device according to claim 1, wherein, Identical or different and each independently selected from the following groups:

12. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, each of R4, R5 and R6 is the same or different and is independently selected from hydrogen, deuterium, cyano, fluorine, trideuteriomethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

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

14. An electronic device, characterized in that, An organic electroluminescent device according to any one of claims 1 to 13.

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