Organic electroluminescent device and electronic device

Abstract

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

Description

Technical Field

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

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

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

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

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

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

[0007] wherein, the cathode and the anode are oppositely arranged;

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

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

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

[0011] the first compound has the structure shown in Formula 1

[0012]

[0013] Either X or Z is —N═, and the other is O or S;

[0014] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 18 carbon atoms;

[0015] L is selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 12 carbon atoms;

[0016] The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms or a cycloalkyl group having 5 to 10 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, a group represented by Formula 1-1 or a group represented by Formula 1-2;

[0018]

[0019] represents a chemical bond;

[0020] Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring;

[0021] Y is selected from O, S or N(Ar);

[0022] Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,

[0023] The substituents in Ar are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;

[0024] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0025] The substituents in Ar1, Ar2 and Ar3 are the same or different and are each 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, triphenylsilyl, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring;

[0026] R1, R2, R3 and R4 are each 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, triphenylsilyl, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;

[0027] n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3;

[0028] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;

[0029] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0030] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0031] The second compound has the structure shown in Formula 2:

[0032]

[0033] Wherein, ring B has the structure shown in Formula 2-1 or Formula 2-2;

[0034] L4, L5 and L6 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, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0035] Ar4, Ar5 and Ar6 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0036] The substituents in L4, L5, L6, Ar4, Ar5 and Ar6 are the same or different, and are each independently selected from deuterium, cyano group, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, haloaryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

[0037] According to the second aspect of the present application, there is provided an electronic device including the organic electroluminescent device described in the first aspect.

[0038] The light-emitting layer of the organic electroluminescent device of the present application contains the first compound and the second compound. The first compound is an electron-transporting organic light-emitting layer host material in which naphtho[2,1-d]oxazole is connected to triazine through the 9-position. The second compound is a compound formed by connecting diarylamine with benzophenanthrooxazole or pentaspiroene as the mother nucleus. The first compound and the second compound are mixed in a certain ratio to form a mixed light-emitting host material. First, the first compound used in the light-emitting layer of the device of the present application has a special connection mode. On the one hand, it can have strong carrier transport ability and high energy transfer ability while maintaining a relatively high first triplet energy level value of the material; on the other hand, this special connection mode can make the compound structure have a certain degree of twist, inhibit the excessive stacking between compound molecules, and inhibit the crystallization of the compound, thereby endowing the compound film with high stability; secondly, the hole-transporting host material used in the present application contains the mother nucleus of benzophenanthrooxazole or pentaspiroene. These two mother nuclei have a large conjugated area, which can enhance the intermolecular interaction force and improve the carrier transport ability of the compound film; in addition, the mother nuclei of benzophenanthrooxazole and pentaspiroene are not completely planar structures. Affected by the interaction between the terminal hydrogen atoms, the terminal benzene rings and the main plane all show a certain degree of twist. This twisted structure can help the compound form an amorphous film. Therefore, when the first compound and the second compound of the present application are combined as a mixed light-emitting host material, the carrier balance in the light-emitting layer can be significantly improved, the exciton recombination region can be broadened, the exciton energy utilization efficiency can be improved, the stability of the film can be improved, and thus the light-emitting efficiency and lifespan of the device can be improved. Description of the Drawings

[0039] The drawings are used to provide a further understanding of the present application and constitute a part of the specification. They are used together with the following specific embodiments to explain the present application, but do not constitute a limitation to the present application.

[0040] Figure 1It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0041] Figure 2 It is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0042] Reference numerals

[0043] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer

[0044] 321, First hole transport layer; 322, Luminescence assisting layer; 320, Hole transport layer; 330, Organic light-emitting layer

[0045] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed embodiments

[0046] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of the present application.

[0047] In the figures, the regions and layer thicknesses may be exaggerated for clarity. The same reference numerals in the figures denote the same or similar structures, and thus their detailed descriptions will be omitted.

[0048] 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;

[0049] wherein, the cathode and the anode are disposed opposite to each other;

[0050] the organic layer is located between the cathode and the anode;

[0051] the organic layer includes an organic light-emitting layer;

[0052] the organic light-emitting layer includes a first compound and a second compound;

[0053] the first compound has a structure represented by Formula 1:

[0054]

[0055] Either X or Z is —N═, and the other is O or S;

[0056] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 18 carbon atoms;

[0057] L is selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 12 carbon atoms;

[0058] The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;

[0059] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by Formula 1-1 or a group represented by Formula 1-2;

[0060]

[0061] Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring;

[0062] Y is selected from O, S or N(Ar);

[0063] Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms,

[0064] The substituents in Ar are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;

[0065] Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0066] The substituents in Ar1, Ar2 and Ar3 are the same or different and are each 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, triphenylsilyl, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring;

[0067] R1, R2, R3 and R4 are each 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, triphenylsilyl, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;

[0068] n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3;

[0069] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;

[0070] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0071] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0072] The second compound has the structure shown in Formula 2:

[0073]

[0074] wherein, Ring B has the structure shown in Formula 2-1 or Formula 2-2;

[0075] L4, L5 and L6 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, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0076] Ar4, Ar5 and Ar6 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0077] The substituents in L4, L5, L6, Ar4 and Ar5, and Ar5 and Ar6 are the same or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, haloaryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms; optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

[0078] In this application, the terms "optionally" and "optionally" mean that the subsequent events or circumstances may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes both the scenario where any two adjacent substituents form a ring and the scenario where any two adjacent substituents exist independently of each other without forming a ring. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly attached; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0079] In this application, the description methods "each... independently is", "respectively independently is" and "each independently is" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options expressed by the same symbol do not affect each other, or it can also mean that among the same group, the specific options expressed by the same symbol do not affect each other. For example, wherein each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine, which means that 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 the biphenyl, the number q of the R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0080] In the present application, a term such as "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, namely Rc, may be, for example, deuterium, cyano group, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 20 carbon atoms or arylthio group having 6 to 20 carbon atoms, etc. The number of substitutions may be one or more.

[0081] In the present application, "a plurality of" means more than 2, such as 2, 3, 4, 5, 6, etc.

[0082] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms.

[0083] The hydrogen atoms in the compound structure of the present application include various isotope atoms of hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0084] In the present application, "D" in the compound structural formula represents deuteration.

[0085] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl may be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, the aryl may be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryls conjugated through carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl conjugated through carbon-carbon bonds, or two or more fused-ring aryls conjugated through carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as the aryl in the present application. Among them, the fused-ring aryl may include, for example, bicyclic fused aryl (such as naphthyl), tricyclic fused aryl (such as phenanthryl, fluorenyl, anthryl), etc. The aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of the aryl include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrenyl, benzo[a]pyrenyl, yl, etc.

[0086] In the present application, the arylene involved refers to a divalent or polyvalent group formed by an aryl further losing one or more hydrogen atoms.

[0087] In the present application, the terphenyl includes

[0088] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 18 carbon atoms. In some other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.

[0089] In the present application, the fluorenyl group can be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group can be etc., but is not limited thereto.

[0090] In the present application, the aryl as a substituent is, for example but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

[0091] In the present application, the heteroaryl refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be one or more of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., and is not limited thereto.

[0092] In the present application, the heteroarylene involved refers to a divalent or polyvalent group formed by further removing one or more hydrogen atoms from the heteroaryl.

[0093] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 3 to 30. In some other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 12 to 18. In some other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 12 to 24.

[0094] In the present application, the heteroaryl as a substituent includes, for example but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.

[0095] In the present application, the substituted heteroaryl may be one or more than two hydrogen atoms in the heteroaryl are substituted by groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0096] In the present application, the alkyl having 1 to 10 carbon atoms may include a straight-chain alkyl having 1 to 10 carbon atoms and a branched-chain alkyl having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl include but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, etc.

[0097] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.

[0098] In the present application, specific examples of the trialkylsilyl include but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0099] In the present application, specific examples of the haloalkyl include but are not limited to, trifluoromethyl.

[0100] In the present application, the number of carbon atoms of the cycloalkyl having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl include but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

[0101] In the present application, the number of carbon atoms of the deuterated alkyl 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 include but are not limited to, trideuteriomethyl.

[0102] In the present application, the number of carbon atoms in the haloalkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0103] In the present application, an n-membered ring refers to a ring system formed by n atoms. For example, a phenyl group is a 6-membered ring. A 3- to 15-membered ring refers to a cyclic group having 3 to 15 ring atoms. Examples of the 3- to 15-membered ring include cyclopentane (5-membered ring), cyclohexane (6-membered ring), fluorene ring (13-membered ring), benzene ring (6-membered ring), and the like.

[0104] In the present application, refers to a chemical bond that connects to other groups.

[0105] In the present application, the non-positioning connecting bond refers to a single bond extending from the ring system which means that one end of the connecting bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positioning connecting bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connection mode shown in formulas (f-1) to (f-10):

[0106]

[0107] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positioning connecting bond extending from the middle of one benzene ring, and the meaning it represents includes any possible connection mode shown in formulas (X'-1) to (X'-4):

[0108]

[0109] The non-positioning substituent in the present application refers to a substituent connected through a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, and the meaning it represents includes any possible connection mode shown in formulas (Y-1) to (Y-7):

[0110]

[0111] In some embodiments, the compound represented by formula 1 is selected from the structures represented by the following formulas 1-A to 1-B:

[0112]

[0113] In some embodiments, in the first compound represented by Formula 1, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0114] In some embodiments, in the first compound represented by Formula 1, L is selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene having 5, 6, 7, 8, 9, 10 or 12 carbon atoms.

[0115] Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, phenyl or deuterated phenyl.

[0116] In some embodiments, in the first compound represented by Formula 1, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted carbazolyl or a substituted or unsubstituted pyridinyl;

[0117] 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, trideuteriomethyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

[0118] In some embodiments, in the first compound represented by Formula 1, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:

[0119]

[0120] L is selected from a single bond or the group consisting of the following groups:

[0121]

[0122] In some embodiments, in the first compound represented by Formula 1, L, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:

[0123]

[0124] In some embodiments, in the first compound of Formula 1, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolyl or substituted or unsubstituted pyridinyl.

[0125] Optionally, the substituents in L are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl or phenyl.

[0126] In some embodiments, in the first compound of Formula 1, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, the group of Formula 1-1 or the group of Formula 1-2.

[0127] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, cyano, a haloalkyl having 1 to 4 carbon atoms, a deuterated alkyl having 1 to 4 carbon atoms, an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 15 carbon atoms, a heteroaryl having 5 to 12 carbon atoms, a trialkylsilyl having 3 to 8 carbon atoms or a deuterated aryl having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0128] In some embodiments, in the first compound of Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, the group of Formula 1-1 or the group of Formula 1-2;

[0129] 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, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl, phenyl or naphthyl;

[0130]

[0131] Optionally, in Formula 1-1 and Formula 1-2, ring A and ring T are each independently selected from a benzene ring or a naphthalene ring;

[0132] Y is selected from O, S or N(Ar);

[0133] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl;

[0134] The substituents in Ar, each R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl or phenyl.

[0135] In some embodiments, in the first compound of formula 1, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl or the following groups:

[0136]

[0137] The substituents in Ar1 and Ar2 and each R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuteriophenyl or naphthyl;

[0138] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0139] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0140] In some more specific embodiments, in the first compound of formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0141]

[0142]

[0143] In some embodiments, in the first compound of formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0144]

[0145]

[0146] In some embodiments, in the first compound of Formula 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and the substituents in Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl or naphthyl.

[0147] In some embodiments, in the first compound of Formula 1, Ar3 is selected from the following groups:

[0148]

[0149] In some embodiments, in the first compound of Formula 1, Ar3 is selected from the following groups:

[0150]

[0151] In some embodiments, in the first compound of Formula 1, each is independently selected from the following groups:

[0152]

[0153] In some embodiments, in the first compound of Formula 1, each of R1 and R2 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterophenyl or naphthyl.

[0154] In some embodiments, the second compound of Formula 2 is selected from the structures shown in the following formulas (S-1) to (S-9):

[0155]

[0156]

[0157] In some embodiments, Ar4, Ar5 and Ar6 are each independently selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, substituted or unsubstituted heteroaryl having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0158] In some embodiments, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0159] Optionally, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiophenyl, and substituted or unsubstituted benzocarbazolyl.

[0160] In some embodiments, the substituents in Ar4, Ar5, and Ar6 are each independently selected from deuterium, fluorine, cyano, haloalkyl groups having 1 to 4 carbon atoms, deuterated alkyl groups having 1 to 4 carbon atoms, alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, heteroaryl groups having 5 to 12 carbon atoms, and trialkylsilyl groups having 3 to 8 carbon atoms. Optionally, any two adjacent substituents in Ar4 and Ar5 form a benzene ring or a fluorene ring.

[0161] Optionally, the substituents in Ar4, Ar5, and Ar6 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, or trimethylsilyl; optionally, any two adjacent substituents in Ar4 and Ar5 form a benzene ring, a cyclopentane, a cyclohexane, or a fluorene ring.

[0162] In some embodiments, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

[0163]

[0164] The substituted group W has one or more than two substituents, and each substituent is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and when the number of substituents in group W is greater than 1, each substituent is the same or different.

[0165] In some embodiments, Ar4 and Ar5 are the same or different and are each independently selected from the following groups:

[0166]

[0167] Optionally, Ar6 is selected from the following groups:

[0168]

[0169] In some embodiments, Ar4 and Ar5 are each independently selected from the following groups:

[0170]

[0171]

[0172] Optionally, Ar6 is selected from the following groups:

[0173]

[0174] In some embodiments, L4, L5, and L6 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and a substituted or unsubstituted heteroarylene having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0175] In some embodiments, L4, L5, and L6 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene having 12 to 18 carbon atoms.

[0176] In some embodiments, the substituents in L4, L5, and L6 are each independently selected from deuterium, fluorine, cyano, a haloalkyl having 1 to 4 carbon atoms, a deuterated alkyl having 1 to 4 carbon atoms, an alkyl having 1 to 4 carbon atoms, an aryl having 6 to 10 carbon atoms, and a trialkylsilyl having 3 to 8 carbon atoms.

[0177] In some embodiments, L4, L5, and L6 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothiophenylene, and a substituted or unsubstituted dibenzofuranylene.

[0178] Optionally, the substituents in L4, L5 and L6 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0179] In some embodiments, L6 is selected from the group consisting of a single bond or the following groups:

[0180]

[0181] In some embodiments, L4 and L5 are each independently selected from the group consisting of a single bond or the following groups:

[0182]

[0183] In some embodiments, L6 is selected from a single bond, phenylene, deuterated phenylene or naphthylene.

[0184] In some embodiments, L6 is selected from a single bond or the following groups:

[0185]

[0186] In some embodiments, L4 and L5 are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene.

[0187] Optionally, the substituents in L4 and L5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0188] In some embodiments, L4 and L5 are each independently selected from a single bond or the following groups:

[0189]

[0190] In some embodiments, identical or different, and each independently selected from the following groups:

[0191]

[0192] In some embodiments, selected from the following groups:

[0193]

[0194]

[0195] In some embodiments, the first compound is selected from the compounds represented by A-1 to A-336 in claim 14.

[0196] In some embodiments, the second compound is selected from the compounds represented by B-1 to B-294 and C-1 to C-360 in claim 14.

[0197] Furthermore, 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. Generally, based on the weight (mass) of the two compounds, the mass ratio of the first compound to the second compound is from 1:99 to 99:1, preferably from 10:90 to 90:10, more preferably from 20:80 to 80:20; still more preferably from 30:70 to 70:30, and even more preferably from 40:60 to 60:40. Further, the mass ratio of the host material to the dopant in the organic light-emitting layer is from 90:10 to 99:1.

[0198] In some embodiments, the mass ratio of the first compound (compound of formula 1) to the second compound (compound of formula 2) in the host of the light-emitting layer of the organic electroluminescent device is from 20:80 to 80:20.

[0199] Optionally, in the host material, the mass ratio of the first compound (compound of formula 1) to the second compound (compound of formula 2) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35, 70:30, 80:20.

[0200] In some embodiments of the present application, the host material and the guest material can be co-evaporated by a multi-source evaporation process, so that the host material and the guest material are uniformly dispersed in the organic light-emitting layer. The doping ratio can be regulated by controlling the evaporation rate of the host material and the guest material during the evaporation process, or by controlling the evaporation rate ratio of the host material and the guest material.

[0201] Optionally, the organic light-emitting layer can be evaporated by a multi-source co-evaporation method to form an organic light-emitting layer comprising 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.

[0202] In order to obtain the host material mixture, the first compound and the second compound can be placed in an oscillator and mixed to obtain a mixture with the desired weight ratio.

[0203] To form each layer of the organic electroluminescent device constituting the present application, dry film formation methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc. can be used.

[0204] In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.

[0205] In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.

[0206] In a second aspect of the present application, an electronic device is provided, and the organic electroluminescent device described in the first aspect is included in the electronic device.

[0207] In another aspect of the present application, a composition is further provided. The composition includes a first compound and a second compound, and the first compound has a structure represented by Formula 1

[0208]

[0209] Either X or Z is —N═, and the other is O or S;

[0210] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;

[0211] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;

[0212] The substituents in L, L1, and L2 are the same or different, and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a cycloalkyl group having 5 to 10 carbon atoms;

[0213] Ar1 and Ar2 are the same or different, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by Formula 1-1, or a group represented by Formula 1-2;

[0214]

[0215] Ring A and ring T are each independently selected from a benzene ring or a naphthalene ring;

[0216] Y is selected from O, S, or N(Ar);

[0217] Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms;

[0218] The substituents in Ar are the same or different, and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms;

[0219] 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;

[0220] The substituents in Ar1, Ar2 and Ar3 are the same or different, and are each independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring;

[0221] R1, R2, R3 and R4 are independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms;

[0222] n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3;

[0223] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;

[0224] n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0225] n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0226] The second compound has the structure shown in Formula 2:

[0227]

[0228] Among them, ring B has the structure shown in Formula 2-1 or Formula 2-2;

[0229] L4, L5 and L6 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms;

[0230] Ar4, Ar5 and Ar6 are the same or different, and each independently selected from a substituted or unsubstituted aryl having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

[0231] The substituents in L4, L5, L6, Ar4, Ar5 and Ar6 are the same or different, and each independently selected from deuterium, cyano group, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, haloaryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

[0232] Optionally, the mass ratio of the first compound to the second compound in the composition is from 1:99 to 99:1, preferably from 10:90 to 90:10, more preferably from 20:80 to 80:20, and still more preferably from 40:60 to 60:40.

[0233] In some embodiments, the mass ratio of the first compound (compound of Formula 1) to the second compound (compound of Formula 2) in the composition is from 20:80 to 80:20.

[0234] The present application also provides the use of the luminescent layer composition in the luminescent layer of an organic electroluminescent device.

[0235] The present application also provides an organic electroluminescent device comprising the composition.

[0236] The organic electroluminescent device provided by the present application includes an anode and a cathode disposed opposite to each other, a cathode, an anode and an organic layer. The organic layer includes an organic light-emitting layer, and the organic light-emitting layer includes a first compound and a second compound.

[0237] In some embodiments of the present application, the organic electroluminescent device sequentially includes an anode (e.g., 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., 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.

[0238] According to a specific embodiment, as Figure 1 shown, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a hole adjustment layer (also known as a hole auxiliary layer or a light-emitting auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked.

[0239] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function (work function) that helps hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, it includes a transparent electrode including indium tin oxide (ITO) as the anode.

[0240] In the present application, the first hole transport layer or the hole adjustment layer may respectively include one or more hole transport materials, and the hole transport layer materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and specifically may be selected from the following compounds or any combination thereof:

[0241]

[0242] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0243] In one embodiment, the hole adjustment layer 322 is composed of HT-2.

[0244] Optionally, a hole injection layer 310 is further disposed 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 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and this application does not make special restrictions on this. The material of the hole injection layer 310 can be selected from the following compounds or any combination thereof, for example;

[0245]

[0246] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0247] Optionally, the organic light-emitting layer 330 may include the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of the host material and the guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.

[0248] The preparation method of the light-emitting layer can be to prepare a red light-emitting layer by a co-evaporation method. In some embodiments, a first compound is used as the first host, a second compound is used as the second host, and the first host and the second host are mixed evenly according to a certain weight ratio to obtain a light-emitting layer host composition; the composition of the host material and the dopant are co-evaporated at a certain evaporation rate ratio to form a light-emitting layer (EML) with a certain thickness. In other embodiments, the first compound, the second compound and the dopant are co-evaporated at a certain evaporation rate ratio to form a light-emitting layer (EML) with a certain thickness.

[0249] The host material of the organic light-emitting layer 330 includes the first compound and the second compound.

[0250] The guest material of the organic light-emitting layer 330 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative or other materials, and this application does not make special restrictions on this. The guest material is also called a doping material or a dopant. It can be divided into a fluorescent dopant and a phosphorescent dopant according to the light-emitting type. For example, specific examples of the phosphorescent dopant include, but are not limited to,

[0251]

[0252]

[0253] 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, for example, RD.

[0254] 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.

[0255] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from, but not limited to, electron transport materials such as BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, etc. The present application does not make special limitations on this. The material of the electron transport layer 340 contains LiQ and other electron transport materials, and the other electron transport materials can be selected from, but not limited to, the following compounds:

[0256]

[0257] In one embodiment of the present application, the electron transport layer 340 is composed of ET and LiQ.

[0258] In the present application, the cathode 200 includes a cathode material, which is a material with a small work function that helps electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0259] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 can include inorganic materials such as alkali metal sulfides and alkali metal halides, or can include complexes of alkali metals and organic substances. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0260] The present application not only provides the organic electroluminescent device including the compounds represented by Formula 1 and the compounds represented by Formula 2 for the organic light-emitting layer. The present application also provides an electronic device including the organic electroluminescent device of the present application.

[0261] According to one embodiment, asFigure 2 As shown, the provided electronic device is electronic device 400. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and can include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0262] The following combines synthesis examples to specifically illustrate the synthesis methods of the first compound and the second compound of the present application, but the present application is not limited thereby.

[0263] Synthesis Example

[0264] Those skilled in the art should recognize that the chemical reactions described in the present application can be used to appropriately prepare many heterocyclic compounds of the present application, and other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-illustrative compounds according to the present application can be successfully completed by those skilled in the art through modification methods, such as appropriately protecting interfering groups, by using other known reagents in addition to those described in the present application, or making some conventional modifications to the reaction conditions. Compounds for which the synthesis method is not mentioned in the present application are all raw material products obtained through commercial channels.

[0265] Synthesis of the first compound:

[0266] Synthesis of Sub-a1:

[0267]

[0268] Under a nitrogen atmosphere, RM-1 (16.21 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (160 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started. When the system was heated to 40 °C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The temperature was continued to be raised to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and it was stirred well for 30 min. Then, it was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of absolute ethanol to obtain a gray solid; the crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column. After concentration, a white solid Sub-a1 (13.55 g, yield 73%) was obtained.

[0269] Synthesis of Sub-b1:

[0270]

[0271] Under a nitrogen atmosphere, RM-2 (17.20 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), absolute ethanol (35 mL) and deionized water (35 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for 8 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure after filtration 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 an orange-yellow solid Sub-b1 (16.2 g, yield 77%).

[0272] With reference to the synthesis of Sub-c1, Reactant A shown in Table 1 was used to replace RM-2, and Reactant B was used to replace 4-chlorophenylboronic acid to synthesize Sub-b2 to Sub-b14

[0273] Table 1: Synthesis of Sub-b2 to Sub-b14

[0274]

[0275]

[0276] Synthesis of Compound A-4:

[0277]

[0278] Under a nitrogen atmosphere, Sub-a1 (9.75 g, 26.25 mmol), RM-3 (8.60 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were successively added to a 250 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for 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, and the solvent was removed by distillation under reduced pressure after filtration to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid A-4 (9.0 g, yield 65%, m / z = 553.20 [M+H] + )

[0279] With reference to the synthesis of reference compound A-4, substitute reactant C shown in Table 2 for RM-3 to synthesize the first compound of this application in Table 2.

[0280] Table 2: Synthesis of the First Compound of this Application

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287] Synthesis of the second compound:

[0288] Synthesis of Sub-c1:

[0289]

[0290] Under a nitrogen atmosphere, add RM-1 (16.20 g, 50 mmol), 4-chloro-2-formylphenylboronic acid (10.14 g, 55 mmol), tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (160 mL), absolute ethanol (40 mL), and deionized water (40 mL) into a 500 mL three-necked flask in sequence. Start stirring and heating, and raise the temperature to reflux for 8 h. After the system cools to room temperature, extract with dichloromethane (100 mL × 3 times). Combine the organic phases, dry with anhydrous magnesium sulfate, filter, and distill off the solvent under reduced pressure to obtain the crude product. Purify the crude product by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid Sub-c1 (10.94 g, yield 57%).

[0291] With reference to the synthesis of Sub-c1, substitute reactant D shown in Table 3 for RM-1 and reactant E for 4-chloro-2-formylphenylboronic acid to synthesize Sub-c2 to Sub-c7.

[0292] Table 3. Synthesis of Sub-c2 to Sub-c7

[0293]

[0294]

[0295] Synthesis of Sub-d1:

[0296]

[0297] Under a nitrogen atmosphere, into a 1000 mL three-necked flask, Sub-c1 (49.9 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.38 g, 217 mmol) and anhydrous tetrahydrofuran (500 mL) were successively added, and the system was cooled to 0 °C with an ice-water bath; then an anhydrous tetrahydrofuran solution of potassium tert-butoxide (1 M, 220 mL) was slowly added dropwise to the system; after the addition was completed, the system was slowly warmed to room temperature and stirred for reaction for 6 h. The reaction solution was poured into 1000 mL of deionized water, extracted with ethyl acetate (250 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 n-heptane as the mobile phase to obtain a red solid Sub-d1 (39.1 g, yield 73%).

[0298] With reference to the synthesis of Sub-d1, using the reactant F shown in Table 4 to replace Sub-d1, Sub-d2 to Sub-d7 were synthesized.

[0299] Table 4. Synthesis of Sub-d2 to Sub-d7

[0300]

[0301] Synthesis of Sub-e1:

[0302]

[0303] Under a nitrogen atmosphere, into a 1000 mL three-necked flask, Sub-e1 (49.0 g, 119 mmol), Eaton's reagent (4.5 mL) and chlorobenzene (500 mL) were successively added, and the temperature was raised to reflux and stirred for reaction for 4 h. After the reaction system was cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, then extracted with dichloromethane (250 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 solid Sub-e1 (21.70 g, yield 48%).

[0304] With reference to the synthesis of Sub-e1, using the reactant G shown in Table 5 to replace Sub-d1, Sub-e2 to Sub-e7 were synthesized.

[0305] Table 5. Synthesis of Sub-e2 to Sub-e7

[0306]

[0307] Synthesis of Sub-f1:

[0308]

[0309] Under a nitrogen atmosphere, Sub-e1 (19.0 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (200 mL) were successively added to a 500 mL three-necked flask. Stirring and heating were started. When the temperature of the system reached 40 °C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The temperature was further raised to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and it was stirred well for 30 min. Then, it was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of absolute ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-f1 (16.0 g, yield 68%) was obtained.

[0310] With reference to the synthesis of Sub-f1, Sub-f2 to Sub-f5 were synthesized using the reactant H shown in Table 6 to replace Sub-e1.

[0311] Table 6. Synthesis of Sub-f2 to Sub-f5

[0312]

[0313]

[0314] Synthesis of Sub-g1:

[0315]

[0316] Under a nitrogen atmosphere, 4-bromochlorobenzene (9.57 g, 50 mmol), Sub-f1 (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), absolute ethanol (62.5 mL) and deionized water (62.5 mL) were successively added to a 1000 mL three-necked flask. Stirring and heating were started, 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, 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-g1 (18.9 g, yield 83%).

[0317] With reference to the synthesis of Sub-g1, the reactant J shown in Table 7 was used to replace Sub-f1, and the reactant K was used to replace 4-bromochlorobenzene to synthesize Sub-g2 to Sub-g5.

[0318] Table 7. Synthesis of Sub-g2 to Sub-g5

[0319]

[0320]

[0321] Synthesis of Sub-h1:

[0322]

[0323] Under a nitrogen atmosphere, Sub-e1 (19.0 g, 50 mmol), 4-aminobiphenyl (8.46 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and toluene (200 mL) were successively added to a 500 mL three-necked flask. The temperature was raised to reflux and stirred overnight. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray solid Sub-h1 (19.22 g; yield 75%).

[0324] With reference to the synthesis of Sub-h1, the reactant L shown in Table 8 was used to replace Sub-e1, and the reactant M was used to replace 4-aminobiphenyl to synthesize Sub-h2 to Sub-h17.

[0325] Table 8. Synthesis of Sub-h2 to Sub-h17

[0326]

[0327]

[0328]

[0329] Synthesis of Compound B-12:

[0330]

[0331] Under a nitrogen atmosphere, Sub-h1 (12.81 g, 25 mmol), 1-(3-bromophenyl)naphthalene (7.08 g, 25 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.916 g, 0.5 mmol), (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were successively added to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain white solid B-12 (14.65 g; yield 82%, m / z = 715.27 [M+H] + ).

[0332] Referring to the synthesis of Compound B-12, the reactant N shown in Table 9 was used to replace Sub-h1, and the reactant O was used to replace 1-(3-bromophenyl)naphthalene to synthesize the compounds of the present application in Table 9.

[0333] Table 9: Synthesis of the Second Compounds of the Present Application

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341] 1H NMR of Compound A-161 H-NMR (400 MHz, Methylene-Chloride-D2) δ ppm 8.85 (d, 2H), 8.76 (d, 2H), 8.22 (t, 2H), 8.12 (s, 1H), 8.02 - 7.64 (m, 11H), 7.61 - 7.43 (m, 5H), 7.25 (t, 1H), 7.12 (t, 2H);

[0342] 1H-NMR of Compound B-45: 1 H-NMR (400 MHz, Methylene-Chloride-D2) δ ppm 8.79 (d, 1H), 8.22 - 8.16 (m, 2H), 8.03 - 7.97 (m, 3H), 7.94 - 7.88 (m, 2H), 7.85 - 7.80 (m, 3H), 7.75 (d, 1H), 7.58 - 7.24 (m, 18H);

[0343] 1H-NMR of Compound C-234: 1 H-NMR (400 MHz, Methylene-Chloride-D2) δ ppm 8.44 (d, 1H), 8.39 (d, 1H), 8.07 (d, 1H), 7.99 - 7.82 (m, 9H), 7.64 - 7.20 (m, 21H).

[0344] Preparation and Evaluation of Organic Electroluminescent Devices:

[0345] Example 1: Preparation of Red Organic Electroluminescent Devices

[0346] First, the anode is pretreated through the following process: On the ITO / Ag / ITO substrate with successive thicknesses of , surface treatment is carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, the surface of the ITO substrate can be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0347] On the experimental substrate (anode), PD:HT-1 is co-evaporated at a deposition rate ratio of 2%:98% to form a hole injection layer (HIL) with a thickness of . Then, HT-1 is vacuum-evaporated on the hole injection layer to form the first hole transport layer with a thickness of .

[0348] Compound HT-2 is vacuum-evaporated on the first hole transport layer to form a light-emitting auxiliary layer with a thickness of .

[0349] Next, on the light-emitting auxiliary layer, a red light-emitting layer is prepared by co-evaporation using compound A-4 as the first host, compound C-3 as the second host, and RD as the dopant. Among them, the first host: the second host is mixed evenly at a weight ratio of 50:50 to obtain the host material composition of the light-emitting layer. The host material composition of the light-emitting layer: RD is co-evaporated at an evaporation rate ratio of 100%:2% to form a thickness of of the red light-emitting layer (EML).

[0350] On the light-emitting layer, compound ET and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form thick electron transport layer (ETL). Yb is evaporated on the electron transport layer to form a thickness of of the electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at an evaporation rate ratio of 1:9 and vacuum-evaporated on the electron injection layer to form a thickness of of the cathode.

[0351] In addition, a CPL with a thickness of is vacuum-evaporated on the above cathode, thus completing the manufacture of the red organic light-emitting device.

[0352] Examples 2 to 40

[0353] Except that when fabricating the light-emitting layer, the compound combinations in Table 10 below are used to replace the host material composition in Example 1, an organic light-emitting device is prepared using the same method as in Example 1.

[0354] Comparative Examples 1 to 3

[0355] Except that when fabricating the light-emitting layer, the light-emitting layer host combinations in Table 10 below are used to replace the compositions of compound A-4 and C-3 in Example 1 respectively, an organic light-emitting device is prepared using the same method as in Example 1.

[0356] Among them, when preparing each example and comparative example, the structures of the compounds used are as follows:

[0357]

[0358] The red organic light-emitting devices prepared in Examples 1 to 40 and Comparative Examples 1 to 3 are subjected to performance tests. Specifically, the IVL performance of the devices is tested under the condition of 10 mA / cm 2 . The T95 device lifetime is tested under the condition of 20 mA / cm 2 . The test results are shown in Table 10.

[0359] Table 10 Test Results of Device Examples of the Present Application

[0360]

[0361]

[0362]

[0363] As can be seen from Table 10 above, when the compound of the present invention is used as the host material of a red organic electroluminescent device, the efficiency (Cd / A) is increased by at least 14.5%, and the T95 lifetime is increased by at least 15.2%.

[0364] The preferred embodiments of the present invention have been described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, and these simple modifications all fall within the protection scope of the present invention.

Claims

1. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer; Among them, The cathode and the anode are disposed opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer includes a first compound and a second compound; The first compound has the structure shown in Formula 1: Either X or Z is —N═, and the other is O or S; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene having 3 to 18 carbon atoms; L is selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene having 3 to 12 carbon atoms; The substituents in L, L1, and L2 are the same or different, and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 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, a group shown in Formula 1-1, or a group shown in Formula 1-2; Represents a chemical bond; Ring A and Ring T are each independently selected from a benzene ring or a naphthalene ring; Y is selected from O, S, or N(Ar); Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, The substituents in Ar are the same or different, and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; 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 Ar1, Ar2, and Ar3 are the same or different, and are each independently selected from hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5- to 13-membered ring; R1, R2, R3 and R4 are each independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl, an aryl group having 6 to 18 carbon atoms, a deuterated aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms; n1 represents the number of R1, and n1 is selected from 0, 1, 2 or 3; n2 represents the number of R2, and n2 is selected from 0, 1 or 2; n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The second compound has the structure shown in Formula 2: Wherein, ring B has the structure shown in Formula 2-1 or Formula 2-2; L4, L5 and L6 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, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar4, Ar5 and Ar6 are the same or different, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L4, L5, L6, Ar4, Ar5 and Ar6 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 halogenated alkyl 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, triphenylsilyl, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms; Optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

2. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, L, L1 and L2 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 phenanthrylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted pyridinyl 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, wherein, In the first compound shown in Formula 1, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups: L is selected from a single bond or the group consisting of the following groups:

4. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, a group represented by Formula 1-1 or a group represented by Formula 1-2; 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, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl, phenyl or naphthyl; Optionally, in Formula 1-1 and Formula 1-2, ring A and ring T are each independently selected from a benzene ring or a naphthalene ring; Y is selected from O, S or N(Ar); Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl; The substituents in Ar, each R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, trimethylsilyl, pentadeuteriophenyl or phenyl.

5. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl or the following group: The substituents in Ar1 and Ar2, each R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuteriophenyl or naphthyl; n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 represents the number of R4, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; Preferably, 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; The substituents in Ar3 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuteriophenyl or naphthyl.

6. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 are the same or different and are each independently selected from the following groups: Optionally, Ar3 is selected from the following groups:

7. The organic electroluminescent device according to claim 1, wherein In the first compound represented by Formula 1, each independently selected from the following groups: Preferably, each R1 and R2 are independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteriomethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuteriophenyl or naphthyl.

8. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, Ar4, Ar5 and Ar6 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 fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl 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 benzo[1,2-b:4,5-b']dibenzofuranyl group, a substituted or unsubstituted benzo[1,2-b:4,5-b']dibenzothiophenyl group, a substituted or unsubstituted benzo[9,10]carbazolyl group; Optionally, the substituents in Ar4, Ar5 and Ar6 are the same or different and are each independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, trideuteriomethyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group, dibenzofuranyl group, dibenzothiophenyl group or trimethylsilyl group; optionally, any two adjacent substituents in Ar4 and Ar5 form a benzene ring, a cyclopentane ring, a cyclohexane ring or a fluorene ring.

9. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, L4, L5 and L6 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 phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group; Optionally, the substituents in L4, L5 and L6 are each independently selected from deuterium, fluorine, cyano group, trimethylsilyl group, trideuteriomethyl group, trifluoromethyl group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group or naphthyl group.

10. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, L6 is selected from a single bond or the group consisting of the following groups: Optionally, L4 and L5 are each independently selected from a single bond or the group consisting of the following groups:

11. The organic electroluminescent device according to claim 1, wherein, In the second compound represented by Formula 2, Ar4 and Ar5 are the same or different and are each independently selected from the following groups: Optionally, Ar6 is selected from the following groups:

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

13. The organic electroluminescent device according to claim 1, wherein, The organic light-emitting layer contains a host material and a dopant, and the host material includes the first compound and the second compound; the mass ratio of the first compound to the second compound is 20:80 to 80:

20.

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

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

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