Organic electroluminescent device and electronic device

Abstract

The present application provides an organic electroluminescent device and an electronic device. The organic electroluminescent device comprises a cathode, an anode, and an organic layer; the organic layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a first compound and a second compound; the first compound is selected from among a compound represented by formula 1; the second compound is selected from among an arylamine compound represented by formula 2.

Description

Organic electroluminescent devices and electronic devices

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202410330363.5 filed on March 21, 2024. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field

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

[0004] In recent years, organic electroluminescent devices (OLEDs) have become a very popular emerging flat-panel display product both at home and abroad. This is because OLED displays have the characteristics of self-luminescence, wide viewing angle, short response time, high efficiency, and wide color gamut.

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

[0006] Currently, organic electroluminescent devices (OLEDs) still face performance issues such as excessively high driving voltages, low luminous efficiency, and short lifespans, which hinder their application. Therefore, further research is necessary to improve the performance of OLEDs. Summary of the Invention

[0007] In view of 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 device.

[0008] According to a first aspect of the present application, there is provided an organic electroluminescent device comprising a cathode, an anode and an organic layer;

[0009] Wherein, the cathode and the anode are arranged opposite to each other;

[0010] The organic layer is located between the cathode and the anode;

[0011] The organic layer includes an organic light-emitting layer;

[0012] The organic light-emitting layer includes a first compound and a second compound;

[0013] The first compound has a structure shown in Formula 1

[0014] In Formula 1, each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

[0015] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different;

[0016] L, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0017] 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;

[0018] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 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, 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 in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar1 and Ar2 form a saturated or unsaturated 3-15 membered ring;

[0019] The second compound has a structure shown in Formula 2:

[0020] In formula 2, Ar4 and Ar5 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;

[0021] L3, L4 and L5 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;

[0022] The substituents in L3, L4, L5, Ar4 and Ar5 are the same or different and are each independently selected from 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, 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 in Ar4 and Ar5 form a saturated or unsaturated 3 to 15-membered ring;

[0023] Group B is selected from the structure shown in Formula 2-1, Formula 2-2 or Formula 2-3:

[0024] In formula 2-1, ring Q is a naphthalene ring;

[0025] Ar3 is 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;

[0026] The substituents in Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms;

[0027] each R1 and R2 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, 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;

[0028] n1 is selected from 0, 1, 2, 3 or 4;

[0029] n2 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0030] In formula 2-2, one of Z and Y is -N=, and the other is O or S;

[0031] Ar is 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;

[0032] The substituents in Ar are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms;

[0033] Each of R3, R4 and R5 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, 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;

[0034] n3 and n4 are each independently selected from 0, 1 or 2;

[0035] n5 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0036] According to a second aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the first aspect.

[0037] The core structure of the first compound of the organic electroluminescent device of this application, phenanthro[3,2-b]benzofuran The parent nucleus is connected to the electron-deficient heteroaryl of the triazine class as an electron-transporting luminescent host material; the second compound is a triarylamine compound, and the first compound and the second compound are mixed in a certain ratio to form a mixed luminescent host material. The special fusion mode of phenanthrene and benzofuran ensures that the parent nucleus of phenanthrene[3,2-b]benzofuran has a relatively suitable first excited triplet energy level, which is suitable as a fragment of the luminescent host material. In addition, the parent nucleus structure of phenanthrene[3,2-b]benzofuran has a large conjugated system. After connecting it to the electron-deficient heteroaryl of the triazine class, it can enhance the intermolecular force and improve the electron mobility of the compound. In the device of the present application, the first triplet energy level value of the first compound in the luminescent layer is relatively matched with the energy level of the second compound, the aromatic amine compound. The combination of these two host materials is conducive to energy transfer and improves the efficiency of hole and electron combination. In addition, the hole-transporting luminescent host material triarylamine used in the device of the present application contains an aromatic group with a large conjugated plane, such as triphenylene oxazole, pentahelidinone, or benzocarbazole, which can enhance the intermolecular interaction force and improve the carrier transport ability of the compound film. Therefore, when the organic electroluminescent device of the present application uses the first compound and the second compound as a mixed luminescent host material, it can significantly improve the energy transfer efficiency of the luminescent layer, promote the carrier balance in the luminescent layer, broaden the exciton recombination area, improve the exciton energy utilization efficiency, improve the stability of the film, and thus improve the luminous efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0039] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0040] FIG2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0041] Reference numerals 100, anode 200, cathode 300, functional layer 310, hole injection layer 321, first hole transport layer 322, luminescence auxiliary layer 320, hole transport layer 330, organic light emitting layer 340, electron transport layer 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0042] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete and will fully convey the concepts of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a full understanding of the embodiments of the present application.

[0043] In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus their detailed description will be omitted.

[0044] According to a first aspect of the present application, there is provided an organic electroluminescent device comprising a cathode, an anode and an organic layer;

[0045] Wherein, the cathode and the anode are arranged opposite to each other;

[0046] The organic layer is located between the cathode and the anode;

[0047] The organic layer includes an organic light-emitting layer;

[0048] The organic light-emitting layer includes a first compound and a second compound;

[0049] The first compound has a structure shown in Formula 1

[0050] In Formula 1, each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

[0051] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different;

[0052] L, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0053] 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;

[0054] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 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, 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 in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar1 and Ar2 form a saturated or unsaturated 3-15 membered ring;

[0055] The second compound has a structure shown in Formula 2:

[0056] In formula 2, Ar4 and Ar5 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;

[0057] L3, L4 and L5 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;

[0058] The substituents in L3, L4, L5, Ar4 and Ar5 are the same or different and are each independently selected from 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, 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 in Ar4 and Ar5 form a saturated or unsaturated 3 to 15-membered ring;

[0059] Group B is selected from the structure shown in Formula 2-1, Formula 2-2 or Formula 2-3:

[0060] In formula 2-1, ring Q is a naphthalene ring;

[0061] Ar3 is 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;

[0062] The substituents in Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms;

[0063] each R1 and R2 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, 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;

[0064] n1 is selected from 0, 1, 2, 3 or 4;

[0065] n2 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0066] In formula 2-2, one of Z and Y is -N=, and the other is O or S;

[0067] Ar is 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;

[0068] The substituents in Ar are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms;

[0069] Each of R3, R4 and R5 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, 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;

[0070] n3 and n4 are each independently selected from 0, 1 or 2;

[0071] n5 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0072] In this application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include 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 connected; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0073] In this application, the descriptions “each independently is”, “each independently is” and “each independently is” are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0074] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl group having the substituent Rc or an unsubstituted aryl group. The substituent Rc can be, for example, 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, 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, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms. The number of substituents can be one or more.

[0075] In this application, "plurality" refers to two or more, for example, 2, 3, 4, 5, 6, etc.

[0076] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0077] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0078] “D” in the structural formula of the compound of the present application represents deuteration.

[0079] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be considered as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene Peryl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl, Ji et al.

[0080] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0081] In this application, terphenyl includes

[0082] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group can be 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. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0083] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0084] In the present application, examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

[0085] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or multiple aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. For example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0086] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0087] In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (heteroarylene group) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 5 to 12.

[0088] In the present application, examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0089] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, or the like.

[0090] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0091] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0092] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0093] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0094] In the present application, the number of carbon atoms in the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0095] In the present application, the number of carbon atoms in a deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl.

[0096] In the present application, the carbon number of the haloalkyl group having 1 to 10 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.

[0097] In this application, an n-membered ring is a ring system consisting of n atoms. For example, a phenyl group is a 6-membered ring. A 3- to 15-membered ring refers to a cyclic group with 3 to 15 ring atoms. Examples of 3- to 15-membered rings include cyclopentane, cyclohexane, fluorene, and benzene rings.

[0098] In this application, Refers to the chemical bonds that connect to other groups.

[0099] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. This means that one end of the link can be connected to any position in the ring system that the link passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0100] For 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-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0101] A non-positional substituent herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within 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 via a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7):

[0102] 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 group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0103] In some embodiments of the present application, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group.

[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 phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolylene group or a substituted or unsubstituted pyridylene group.

[0105] In some embodiments of the present application, 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.

[0106] In some embodiments of the present application, in the first compound represented by Formula 1, L is selected from a single bond or the following groups:

[0107] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:

[0108] In some more specific embodiments of the present application, in the first compound represented by Formula 1, L is independently selected from a single bond or the following groups:

[0109] In some more specific 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 the group consisting of a single bond or the following groups:

[0110] In some embodiments of the present application, in the first compound shown in Formula 1, Ar1 and Ar2 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, 25, 26, 27, 28, 29, or 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0111] In some embodiments of the present application, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0112] In some embodiments of the present application, in the first compound shown in Formula 1, in the first compound shown in Formula 1, Ar1 and Ar2 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 phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted triphenyl 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.

[0113] In some embodiments of the present application, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0114] 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 group consisting of the following groups:

[0115] 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 group consisting of the following groups:

[0116] In some embodiments of the present application, in the first compound represented by Formula 1, Each is independently selected from the group consisting of:

[0117] In some embodiments of the present application, in the first compound represented by Formula 1, Selected from the group consisting of:

[0118] In some embodiments of the present application, in the first compound represented by Formula 1, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0119] In some embodiments of the present application, in the second compound represented by Formula 2, Ar4 and Ar5 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, 25, 26, 27, 28, 29 or 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0120] In some embodiments of the present application, the substituents in Ar4 and Ar5 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0121] In some embodiments of the present application, in the second compound shown in Formula 2, Ar4 and Ar5 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 phenanthrenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted benzoxazolyl group, and a substituted or unsubstituted benzothiazolyl group.

[0122] In some embodiments of the present application, the substituents in Ar4 and Ar5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0123] In some embodiments of the present application, in the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are each independently selected from the group consisting of the following groups:

[0124] In some embodiments of the present application, in the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are each independently selected from the group consisting of the following groups:

[0125] In some embodiments of the present application, in the second compound represented by Formula 2, when group B is selected from the structure represented by Formula 2-1, Ar4 is selected from the group consisting of the following groups:

[0126] In some embodiments of the present application, in the second compound represented by Formula 2, L3, L4 and L5 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0127] In some embodiments of the present application, the substituents in L3, L4 and L5 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, or a phenyl group.

[0128] In some embodiments of the present application, in the second compound shown in Formula 2, L3, L4 and L5 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted dibenzofuranyl group.

[0129] In some embodiments of the present application, the substituents in L3, L4 and L5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0130] In some embodiments of the present application, in the second compound represented by Formula 2, L3, L4 and L5 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:

[0131] In some embodiments of the present application, in the second compound represented by Formula 2, L3 is selected from the group consisting of a single bond or the following groups:

[0132] In some embodiments of the present application, in the second compound represented by Formula 2, L4 and L5 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:

[0133] In some specific embodiments of the present application, in the second compound represented by Formula 2, The same or different, are independently selected from the group consisting of the following groups:

[0134] In some embodiments of the present application, in formula 2-1, each R1 and R2 are the same or different and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl or naphthyl.

[0135] In some embodiments of the present application, in Formula 2-1, Ar3 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 phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0136] In some embodiments of the present application, the substituents in Ar3 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, naphthyl or trimethylsilyl.

[0137] In some specific embodiments of the present application, in the second compound represented by Formula 2, Ar3 in Formula 2-1 is selected from the group consisting of the following groups:

[0138] In some embodiments of the present application, in formula 2-2, R3, R4 and R5 are the same or different and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl or naphthyl.

[0139] In some embodiments of the present application, in Formula 2-2, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene.

[0140] In some embodiments of the present application, the substituents in Ar are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, naphthyl or trimethylsilyl.

[0141] In some specific embodiments of the present application, in the second compound represented by Formula 2, Ar in Formula 2-2 is selected from the group consisting of the following groups:

[0142] In some embodiments of the present application, in the second compound represented by Formula 2, group B is selected from the group consisting of the following groups:

[0143] In some embodiments of the present application, the first compound is selected from the group consisting of the following compounds A-1 to A-456:

[0144] In some embodiments of the present application, the second compound is selected from the group consisting of the following compounds B-1 to B-228, C-1 to C-240, and D-1 to D-60:

[0145] In one embodiment, in the organic electroluminescent device of the present application, the organic light-emitting layer comprises a host material and a dopant. The host material comprises a first compound and a second compound. Typically, based on the weight (mass) of the two compounds, the mass ratio of the first compound to the second compound is 1:99 to 99:1, preferably 10:90 to 90:10; preferably 20:80 to 80:20; further preferably 30:70 to 70:30; and more preferably 40:60 to 60:40. Furthermore, the mass ratio of the host material to the dopant in the organic light-emitting layer is 90:10 to 99:1.

[0146] In some embodiments of the present application, the mass ratio of the first compound (the compound represented by Formula 1) to the second compound (the compound represented by Formula 2) in the main body of the light-emitting layer of the organic electroluminescent device is 30:70 to 70:30.

[0147] In some embodiments of the present application, in the host material, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound represented by Formula 2) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35, 70:30, 75:25, or 80:20.

[0148] In some embodiments of the present application, the host material and the guest material can be co-evaporated through a multi-source evaporation process so that the host material and the guest material are uniformly dispersed in the organic light-emitting layer. The doping ratio can be regulated by controlling the evaporation rates 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.

[0149] In some embodiments of the present application, the organic light-emitting layer can be evaporated by a multi-source co-evaporation method to form an organic light-emitting layer including a host material and a guest material. The doping ratio can be regulated by controlling the 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.

[0150] To obtain the host material mixture, the first compound and the second compound may be placed in an oscillator and mixed to obtain a mixture with a desired weight ratio.

[0151] 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, slit coating, spin coating, dip coating, flow coating method, etc. can be used.

[0152] Alternatively, the first compound and the second compound may be subjected to film formation in the above-listed methods, typically by co-evaporation or hybrid evaporation. Co-evaporation is a hybrid deposition method in which two or more materials are placed in a single crucible source and current is simultaneously applied to multiple chambers to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in a single crucible source prior to evaporation and current is applied to the chambers to evaporate the materials.

[0153] In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.

[0154] In some embodiments of the present application, the organic electroluminescent device is a red phosphorescent organic electroluminescent device or a green phosphorescent organic electroluminescent device.

[0155] In a second aspect of the present application, an electronic device is provided, wherein the electronic device comprises the organic electroluminescent device described in the first aspect.

[0156] In another aspect of the present application, a composition is further provided, comprising a first compound and a second compound, wherein the first compound has a structure shown in Formula 1

[0157] In Formula 1, each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

[0158] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different;

[0159] L, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0160] 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;

[0161] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 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, 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 in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar1 and Ar2 form a saturated or unsaturated 3-15 membered ring;

[0162] The second compound has a structure shown in Formula 2:

[0163] In formula 2, Ar4 and Ar5 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;

[0164] L3, L4 and L5 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;

[0165] The substituents in L3, L4, L5, Ar4 and Ar5 are the same or different and are each independently selected from 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, 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 in Ar4 and Ar5 form a saturated or unsaturated 3 to 15-membered ring;

[0166] Group B is selected from the structure shown in Formula 2-1, Formula 2-2 or Formula 2-3:

[0167] In formula 2-1, ring Q is a naphthalene ring;

[0168] Ar3 is 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;

[0169] The substituents in Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms;

[0170] each R1 and R2 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, 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;

[0171] n1 is selected from 0, 1, 2, 3 or 4;

[0172] n2 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0173] In formula 2-2, one of Z and Y is -N=, and the other is O or S;

[0174] Ar is 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;

[0175] The substituents in Ar are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms;

[0176] Each of R3, R4 and R5 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, 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;

[0177] n3 and n4 are each independently selected from 0, 1 or 2;

[0178] n5 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0179] In some embodiments of the present application, the mass ratio of the first compound to the second compound in the composition is 1:99 to 99:1; preferably 10:90 to 90:10; preferably 20:80 to 80:20; further preferably 30:70 to 70:30, and more preferably 40:60 to 60:40.

[0180] In some embodiments, the mass ratio of the first compound (the compound of Formula 1) to the second compound (the compound of Formula 2) in the composition is 30:70 to 70:30.

[0181] The present application also provides use of the composition in a light-emitting layer of an organic electroluminescent device.

[0182] The present application also provides an organic electroluminescent device comprising the composition.

[0183] The organic electroluminescent device provided in the present application comprises an anode and a cathode arranged opposite to each other, the cathode, the anode and an organic layer, wherein the organic layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises a first compound and a second compound.

[0184] In some embodiments of the present application, an organic electroluminescent device includes, in order, an anode (e.g., 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 (e.g., a 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.

[0185] According to a specific embodiment, as shown in Figure 1, 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 stacked in sequence.

[0186] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto. In some embodiments of the present application, the anode is a transparent electrode comprising indium tin oxide (indium tin oxide) (ITO).

[0187] In the present application, the first hole transport layer or the light-emitting auxiliary layer may include one or more hole transport materials, respectively. The hole transport layer 320 material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:

[0188] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0189] In one embodiment, the light-emitting auxiliary layer 322 is composed of HT-2.

[0190] In one embodiment, 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 made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example:

[0191] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0192] In one embodiment of the present application, the organic light-emitting layer 330 may include the host material and the guest material. In some embodiments of the present application, the organic light-emitting layer 330 is composed of the host material and the guest material. Holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may 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.

[0193] In one embodiment of the present application, the host material of the organic light-emitting layer 330 includes the first compound and the second compound.

[0194] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into fluorescent dopants and phosphorescent dopants. For example, specific examples of the phosphorescent dopant include, but are not limited to,

[0195] In one 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 can be RD, for example.

[0196] 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 can be, for example, fac-Ir(ppy)3.

[0197] In one embodiment of the present application, the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but not limited to, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives and other electron transport materials, and the present application does not impose any special restrictions on this. 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 not limited to, the following compounds:

[0198] In one embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0199] In the present application, cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. In some embodiments of the present application, a metal electrode comprising magnesium and silver is included as the cathode.

[0200] In one embodiment of the present application, 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic matter. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0201] The present application not only provides the organic electroluminescent device comprising the compound represented by Formula 1 and the compound represented by Formula 2 for use in the organic light-emitting layer, but also provides an electronic device comprising the organic electroluminescent device of the present application.

[0202] According to one embodiment, as shown in FIG2 , the provided electronic device is an 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, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, and the like.

[0203] The synthesis methods of the first compound and the second compound of the present application are described in detail below with reference to the synthesis examples, but the present application is not limited thereto.

[0204] Synthesis Example

[0205] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds described herein, and that other methods for preparing the compounds described herein are considered within the scope of this application. For example, the synthesis of compounds not exemplified herein can be successfully accomplished by one skilled in the art through modifications such as appropriate protection of interfering groups, the use of known reagents other than those described herein, or conventional modifications of reaction conditions. Compounds for which no synthetic method is described herein are commercially available raw materials.

[0206] Synthesis of the first compound:

[0207] Synthesis of Sub-a1:

[0208] Under nitrogen, to a 500 mL three-necked flask were added 2-bromo-3-methoxyphenanthrene (14.34 g, 50 mmol), 4-chloro-2-fluorophenylboric acid (9.58 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL). Stirring and heating were initiated, and the temperature was raised to reflux and the reaction was allowed to proceed overnight. After the system cooled to room temperature, extraction was performed with dichloromethane (100 mL × 3 times). The organic phases were combined, 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 (12.1 g, yield 72%).

[0209] Referring to the synthesis method of Sub-a1, reactant A shown in Table 1 was used instead of 4-chloro-2-fluorophenylboronic acid to synthesize Sub-a2 to Sub-a4.

[0210] Table 1: Synthesis of Sub-a2 to Sub-a4

[0211] Synthesis of Sub-b1:

[0212] Under a nitrogen atmosphere, Sub-a1 (22.73 g, 67.5 mmol) and dry dichloromethane (220 mL) were added to a 500 mL three-necked flask. The system was cooled to 0±5°C and a dichloromethane solution of boron tribromide (135 mL, 1 M) was added dropwise using a constant pressure dropping funnel. The temperature was strictly controlled within the range of 0±5°C during the addition. After the addition was completed, the temperature 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 a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid product Sub-b1 (16.77 g, yield 77%).

[0213] Referring to the synthesis method of Sub-b1, reactant B shown in Table 2 was used instead of Sub-a1 to synthesize Sub-b2 to Sub-b4.

[0214] Table 2: Synthesis of Sub-b2 to Sub-b4

[0215] Synthesis of Sub-c1:

[0216] Under a nitrogen atmosphere, Sub-b1 (16.14 g, 50 mmol), cesium carbonate (32.58 g, 100 mmol), and DMSO (160 mL) were added to a 250 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to 80°C for 4 h. After the system cooled to room temperature, extraction was performed with dichloromethane (100 mL x 3). The organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain Sub-c1 (13.47 g, 89% yield) as a white solid.

[0217] Referring to the synthesis method of Sub-c1, reactant C shown in Table 3 was used instead of Sub-b1 to synthesize Sub-c2 to Sub-c4.

[0218] Table 3: Synthesis of Sub-c2 to Sub-c4

[0219] Synthesis of Sub-d1:

[0220] Under nitrogen atmosphere, Sub-c1 (15.1 g, 50 mmol), pinacol diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (150 mL) were added in sequence to a 500 mL three-necked flask. Stirring and heating were started. When the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The filter cake was filtered under reduced pressure to obtain a filter cake. The filter cake was cleaned with dichloromethane, and anhydrous magnesium sulfate was added to remove moisture. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was slurried once with n-heptane to obtain Sub-d1 (14.4 g, 73% yield) as a white solid.

[0221] Referring to the synthesis method of Sub-d1, reactant D shown in Table 4 was used instead of Sub-c1 to synthesize Sub-d2 to Sub-d4.

[0222] Table 4: Synthesis of Sub-d2 to Sub-d4

[0223] Synthesis of Sub-e1:

[0224] Under a nitrogen atmosphere, RM-1 (18.44 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), tetrahydrofuran (45 mL), and deionized water (45 mL) were added sequentially to a 1000 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for overnight reaction. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, 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 Sub-e1 (19.80 g, 89% yield) as a white solid.

[0225] Referring to the synthesis method of Sub-e1, Sub-e2 to Sub-e11 were synthesized by using reactant E shown in Table 5 instead of RM-1 and reactant F instead of 3-chlorophenylboronic acid.

[0226] Table 5: Synthesis of Sub-e2 to Sub-e11

[0227] Synthesis of compound A-4:

[0228] Under a nitrogen atmosphere, Sub-d1 (10.84 g, 27.5 mmol), RM-2 (9.04 g, 25 mmol), palladium acetate (0.12 g, 0.5 mmol), (2-dicyclohexylphosphino-2',4',6'triisopropylbiphenyl) (Xphos, 0.48 g, 1 mmol), potassium carbonate (6.91 g, 50 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were added sequentially to a 500 mL three-necked flask, and the temperature was raised to reflux and stirred to react overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off 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 compound A-4 (10.83 g; yield 73%, m / z = 594.20 [M+H] + ).

[0229] Referring to the synthesis method of compound A-4, reactant G shown in Table 6 was used instead of Sub-d1, and reactant H was used instead of RM-2 to synthesize the first compound of the present application shown in the following table.

[0230] Table 6: Synthesis of the first compound of the present application

[0231] Synthesis of Sub-f1:

[0232] Under nitrogen, RM-3 (16.20 g, 50 mmol), 4-chloro-2-formaldehydephenylboronic acid (10.14 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), TBAB (1.61 g, 5 mmol), toluene (160 mL), anhydrous ethanol (40 mL), and deionized water (40 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL x 3). The organic phases were combined, 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 dichloromethane / n-heptane as the mobile phase to obtain Sub-f1 (10.94 g, 57% yield) as a white solid.

[0233] Referring to the synthesis method of Sub-f1, Sub-f2 to Sub-f7 were synthesized by using reactant J shown in Table 7 instead of RM-3 and reactant K instead of 4-chloro-2-formaldehyde phenylboronic acid.

[0234] Table 7: Synthesis of Sub-c2 to Sub-c7

[0235] Synthesis of Sub-g1:

[0236] Under a nitrogen atmosphere, Sub-f1 (49.9 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.38 g, 217 mmol), and anhydrous tetrahydrofuran (500 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was cooled to 0°C in an ice-water bath. A 1 M solution of potassium tert-butoxide in anhydrous tetrahydrofuran (220 mL) was then slowly added dropwise. After the addition was complete, the mixture was slowly warmed to room temperature and stirred for 6 h. The reaction mixture was poured into 1000 mL of deionized water and extracted with ethyl acetate (250 mL x 3). The organic phases were combined, 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 Sub-g1 (39.1 g, 73% yield) as a red solid.

[0237] Referring to the synthesis method of Sub-g1, reactant L shown in Table 8 was used instead of Sub-f1 to synthesize Sub-g2 to Sub-g7.

[0238] Table 8: Synthesis of Sub-g2 to Sub-g7

[0239] Synthesis of Sub-h1:

[0240] Under a nitrogen atmosphere, Sub-g1 (49.0 g, 119 mmol), Eaton's reagent (4.5 mL) and chlorobenzene (500 mL) were added to a 1000 mL three-necked flask in sequence, and the temperature was raised to reflux and the reaction was continued with stirring for 4 h. After the reaction system reached room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off 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 solid Sub-h1 (21.70 g, yield 48%).

[0241] Referring to the synthesis method of Sub-h1, Sub-h2 to Sub-h7 were synthesized by using reactant M shown in Table 9 instead of Sub-g1.

[0242] Table 9: Synthesis of Sub-h2 to Sub-h7

[0243] Synthesis of Sub-i1:

[0244] Under nitrogen atmosphere, Sub-h1 (19.0 g, 50 mmol), diboronic acid pinacol ester (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (200 mL) were added in sequence to a 500 mL three-necked flask. Stirring and heating were started. When the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved in 200 mL of toluene, and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-i1 (16.0 g, 68% yield) was obtained.

[0245] Referring to the synthesis method of Sub-h1, Sub-i2 to Sub-i6 were synthesized by using reactant N shown in Table 10 instead of Sub-h1.

[0246] Table 10: Synthesis of Sub-i2 to Sub-i6

[0247] Synthesis of Sub-j1:

[0248] Under a nitrogen atmosphere, 4-bromochlorobenzene (9.57 g, 50 mmol), Sub-i1 (25.92 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (250 mL), anhydrous ethanol (62.5 mL), and deionized water (62.5 mL) were added sequentially to a 1000 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, 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 Sub-j1 (18.9 g, 83% yield) as a white solid.

[0249] Referring to the synthesis of Sub-j1, Sub-j2 to Sub-j10 were synthesized by using reactant O shown in Table 11 instead of 4-bromochlorobenzene and reactant P instead of Sub-i1.

[0250] Table 11: Synthesis of Sub-j2 to Sub-j10

[0251] Synthesis of Sub-k1:

[0252] Under nitrogen, a 500 mL three-necked flask was charged with Sub-h1 (19.0 g, 50 mmol), 4-aminobiphenyl (8.46 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and toluene (200 mL). The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous sodium 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 / dichloromethane as the mobile phase to obtain Sub-k1 (19.22 g, 75% yield) as a gray solid.

[0253] Referring to the synthesis method of Sub-k1, Sub-k2 to Sub-k26 were synthesized by using reactant Q shown in Table 12 instead of Sub-h1 and reactant R instead of 4-aminobiphenyl.

[0254] Table 12: Synthesis of Sub-k2 to Sub-k26

[0255] Synthesis of compound B-3:

[0256] Under nitrogen atmosphere, Sub-k1 (12.81 g, 25 mmol), 2-bromonaphthalene (5.18 g, 25 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were added to a 500 mL three-necked flask in sequence, the temperature was raised to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid B-3 (13.90 g; yield 87%, m / z = 639.24 [M+H] + ).

[0257] Referring to the synthesis method of compound B-3, the second compound of the present application in Table 13 was synthesized by using reactant S shown in Table 13 instead of Sub-k1 and reactant T instead of 2-bromonaphthalene.

[0258] Table 13: Synthesis of the second compound of the present application

[0259] Compound A-47 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 8.91 (s, 1H), 8.89-8.87 (m, 3H), 8.20 (d, 2H), 8.57 (d, 1H), 8.45 (d, 1H) ,8.41(d,1H),8.30(d,1H),8.02(d,1H),7.92(d,1H),7.87(s,1H),7.75(d,1H),7.72-7.43(m,13H);

[0260] Compound B-91 NMR: 1H-NMR (400MHz, CD2Cl2) δppm: 8.66 (d, 1H), 8.26-8.20 (m, 2H), 8.00 (s, 2H), 7.98 (s, 1H), 7.86-7.76 (m, 3H),7.72(d,1H),7.67(d,1H),7.56-7.34(m,11H),7.33-7.27(m,3H),7.18(d,1H),7.08-6.98(m,4H);

[0261] Compound C-10 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 8.54 (t, 2H), 8.17 (d, 1H), 8.00-7.68 (m, 8H), 7.57-7.13 (m, 18H);

[0262] Compound D-13 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 8.76(d,1H),8.54(d,1H),7.99(d,1H),7.95(s,1H),7 .89-7.75(m,6H),7.70(t,1H),7.63(d,1H),7.60-7.25(m,18H),7.22-7.12(m,2H).

[0263] Preparation and evaluation of organic electroluminescent devices:

[0264] Example 1: Preparation of red organic electroluminescent device

[0265] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0266] PD:HT-1 was co-evaporated on the experimental substrate (anode) at an evaporation rate ratio of 2%:98% to form a film with a thickness of The hole injection layer (HIL) is then vacuum-deposited with HT-1. The first hole transport layer.

[0267] Compound HT-2 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of light-emitting auxiliary layer.

[0268] Next, on the light-emitting auxiliary layer, compound A-4 was used as the first host, compound B-3 as the second host, and RD as the dopant, and a co-evaporation method was used to prepare a red light-emitting layer. The first host and the second host were mixed in a weight ratio of 50:50 to obtain a composition; the composition of the host material and RD were simultaneously evaporated at an evaporation rate of 98%:2% to form a layer with a thickness of red light emitting layer (EML).

[0269] On the light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 1:9 evaporation rate and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0270] In addition, the thickness of the vacuum evaporation layer on the cathode is CP, thereby completing the manufacture of red organic electroluminescent devices.

[0271] Examples 2 to 64

[0272] An organic electroluminescent device was prepared using the same method as in Example 1, except that the compound combination in Table 14 below was used instead of the compound combination in Example 1 when preparing the light-emitting layer.

[0273] Comparative Examples 1 to 3

[0274] An organic electroluminescent device was prepared by the same method as in Example 1, except that the light-emitting layer host combinations shown in Table 14 were used instead of the combination of compounds A-4 and B-3 in Example 1.

[0275] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:

[0276] The performance of the red organic electroluminescent devices prepared in Examples 1 to 64 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 14.

[0277] Table 14

[0278] As shown in Table 14, compared with the mixed host materials of the light-emitting layer of Comparative Examples 1 to 3, when the first compound and the second compound of the present invention are used as mixed host materials of the red organic electroluminescent device, the luminous efficiency (Cd / A) of the device is improved by at least 14.5%, and the T95 life span is improved by at least 13.0%.

[0279] The experimental results confirm that the first compound of the present application and the three aromatic amine second compounds have relatively matched first triplet energy level values ​​and energy transfer properties. Compared with the three compound combinations in Comparative Examples 1 to 3, the parent core fusion mode of the first compound of the present application can better enhance the carrier transport capacity and energy transfer capacity of the electron transport host material. When the organic electroluminescent device of the present application uses the first compound and the second compound as a hybrid luminescent host material, it can significantly improve the energy transfer efficiency of the light-emitting layer, promote carrier balance in the light-emitting layer, broaden the exciton recombination area, improve the exciton energy utilization efficiency, improve the stability of the film, and thus improve the luminous efficiency and life of the device.

Claims

1. An organic electroluminescent device comprising a cathode, an anode and an organic layer; in, The cathode and the anode are arranged opposite to each other; The organic layer is located between the cathode and the anode; The organic layer 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 shown in Formula 1: In Formula 1, each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different; L, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 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 Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 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, 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 in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar1 and Ar2 form a saturated or unsaturated 3-15 membered ring; The second compound has a structure shown in Formula 2: In formula 2, Ar4 and Ar5 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, L4 and L5 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, L5, Ar4 and Ar5 are the same or different and are each independently selected from 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, 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 in Ar4 and Ar5 form a saturated or unsaturated 3 to 15-membered ring; Group B is selected from the structure shown in Formula 2-1, Formula 2-2 or Formula 2-3: In formula 2-1, ring Q is a naphthalene ring; Ar3 is 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 Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms; each R1 and R2 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, 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; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1, 2, 3, 4, 5 or 6; In formula 2-2, one of Z and Y is -N=, and the other is O or S; Ar is 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 Ar are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms; Each of R3, R4 and R5 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, 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; n3 and n4 are each independently selected from 0, 1 or 2; n5 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 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 group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolylene group or a substituted or unsubstituted pyridylene group; Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl or phenyl.

3. The organic electroluminescent device according to claim 1 or 2, wherein: In the first compound represented by Formula 1, L is selected from the group consisting of a single bond or the following groups: Optionally, L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:

4. The organic electroluminescent device according to any one of claims 1 to 3, wherein: In the first compound represented by Formula 1, Ar1 and Ar2 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 phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene 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; Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

5. The organic electroluminescent device according to any one of claims 1 to 4, wherein: In the first compound represented by Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following groups:

6. The organic electroluminescent device according to any one of claims 1 to 5, wherein: In the first compound represented by Formula 1, are the same or different and are independently selected from the group consisting of:

7. The organic electroluminescent device according to any one of claims 1 to 6, wherein: In the second compound represented by Formula 2, Ar4 and Ar5 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted benzoxazolyl group, or a substituted or unsubstituted benzothiazolyl group; Optionally, the substituents in Ar4 and Ar5 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

8. The organic electroluminescent device according to any one of claims 1 to 7, wherein: In the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are each independently selected from the group consisting of the following groups:

9. The organic electroluminescent device according to any one of claims 1 to 8, wherein: In the second compound represented by Formula 2, L3, L4 and L5 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted dibenzofuranylene group; Alternatively, the substituents in L3, L4 and L5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl; Preferably, L3, L4 and L5 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:

10. The organic electroluminescent device according to any one of claims 1 to 9, wherein: In Formula 2-1, R1 and R2 are the same or different and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl, or naphthyl; Preferably, in formula 2-2, R3, R4 and R5 are the same or different and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl or naphthyl.

11. The organic electroluminescent device according to any one of claims 1 to 10, wherein: In formula 2-1, Ar3 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 phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Preferably, in formula 2-2, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; Optionally, the substituents in Ar and Ar3 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, naphthyl or trimethylsilyl.

12. The organic electroluminescent device according to any one of claims 1 to 11, wherein: In the second compound represented by Formula 2, The same or different, are independently selected from the group consisting of the following groups:

13. The organic electroluminescent device according to any one of claims 1 to 12, wherein: In the second compound represented by Formula 2, group B is selected from the group consisting of: Preferably, Ar3 is selected from the group consisting of: Preferably, Ar is selected from the group consisting of:

14. The organic electroluminescent device according to any one of claims 1 to 13, wherein: The first compound is selected from the group consisting of: Optionally, the second compound is selected from the group consisting of:

15. An electronic device, characterized in that The organic electroluminescent device comprises the organic electroluminescent device according to any one of claims 1 to 14.

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