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.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to an organic electroluminescent device and electronic apparatus. Background Technology

[0002] In recent years, organic light-emitting devices (OLEDs) have become a very popular emerging flat panel display product both domestically and internationally. This is because OLED displays have characteristics such as self-illumination, wide viewing angle, short response time, high efficiency, and wide color gamut.

[0003] Organic light-emitting diodes (OLEDs) typically include an anode, a cathode, and an organic layer formed between these two electrodes. This 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 host and dopant materials), a hole blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the OLED, holes and electrons are injected into the light-emitting layer from the anode and cathode, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. These excitons, in an excited state, release energy, causing the light-emitting layer to emit light.

[0004] Currently, organic electroluminescent devices still suffer from poor performance issues during use, such as excessively high driving voltage, low luminous efficiency, or short lifespan. These problems limit their application areas, so further research is necessary to improve their performance. Summary of the Invention

[0005] In view of the above-mentioned problems in the prior art, the purpose of this application is to provide an organic electroluminescent device and electronic device to improve the performance of the device and the apparatus.

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

[0007] The cathode and the anode are arranged opposite to each other;

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

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

[0010] The organic light-emitting layer comprises 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 single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms;

[0015] L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms;

[0016] The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0017] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups, groups shown in Formula A or groups shown in Formula B, having 6 to 30 carbon atoms.

[0018]

[0019] Indicates a chemical bond;

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

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

[0022] Ar is selected from substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms.

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

[0024] Ar3 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0025] The substituents in Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 18 carbon atoms, deuteryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, or cycloalkyl with 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, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 18 carbon atoms, deuteralkyl groups with 6 to 18 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms, or cycloalkyl groups with 5 to 10 carbon atoms;

[0027] n1 represents the number of R1s, and n1 can be 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 R3s, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0030] n4 represents the number of R4s, 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] Among them, ring W has the structure shown in equation C, and any two adjacent # positions in equation C are the same as those in equation 2. *The positions are closely intertwined;

[0034] Q is selected from O or S;

[0035] L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0036] Ar4 and Ar5 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0037] Each of R5, R6, and R7 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0038] n5 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0039] n6 is selected from 0, 1, or 2;

[0040] n7 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0041] The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.

[0042] According to a second aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the first aspect.

[0043] The light-emitting layer of the organic electroluminescent device of this application includes the first compound and the second compound. The first compound has an electron transport material with naphtho[2,1-d]oxazole linked to triazine at the 9-position. The second compound has a core structure formed by the fusion of 7H-benzo[C]carbazole with dibenzofuran or dibenzothiophene through a pyrrole ring. The first compound and the second compound are mixed in a certain proportion to form a hybrid light-emitting host material. First, the first compound in the luminescent layer is an electron transport host material with a unique group connection method. On the one hand, it maintains a high first triplet energy level while possessing strong carrier transport and high energy transfer capabilities. On the other hand, this unique connection method allows the compound structure to have a certain degree of distortion, inhibiting excessive packing between compound molecules and suppressing crystallization, thereby endowing the compound film with high stability. Second, the second compound in the luminescent layer is a hole transport host material with a core formed by the fusion of 7H-benzo[C]carbazole and dibenzofuran or dibenzothiophene through a pyrrole ring. This core has a large conjugated area and enables the compound to maintain a relatively suitable first excited triplet energy level. The two host compounds in the luminescent layer work together to enhance intermolecular interactions, improve the energy transfer efficiency of the luminescent layer, and enhance the carrier transport capability of the luminescent layer. Therefore, when the first and second compounds of this application are combined as a hybrid luminescent host material, the carrier balance in the luminescent layer can be significantly improved, the stability of the film can be enhanced, and thus the luminous efficiency and lifetime of the device can be improved. Attached Figure Description

[0044] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0045] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0046] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0047] Figure Labels

[0048] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0049] 321. First hole transport layer; 322. Hole adjustment layer; 320. Hole transport layer; 330. Organic light-emitting layer.

[0050] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0051] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided to make this application more comprehensive and complete, and to fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0052] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

[0053] According to a first aspect of this application, an organic electroluminescent device is provided, comprising a cathode, an anode, and an organic layer;

[0054] The cathode and the anode are arranged opposite to each other;

[0055] The organic layer is located between the cathode and the anode;

[0056] The organic layer includes an organic light-emitting layer;

[0057] The organic light-emitting layer comprises a first compound and a second compound;

[0058] The first compound has the structure shown in Formula 1.

[0059]

[0060] Either X or Z is -N=, and the other is O or S;

[0061] L1 and L2 are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms;

[0062] L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms;

[0063] The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0064] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups, groups shown in Formula A or groups shown in Formula B, having 6 to 30 carbon atoms.

[0065]

[0066] Ring A and ring T are each independently selected from benzene rings or naphthalene rings;

[0067] Y is selected from O, S, or N (Ar);

[0068] Ar is selected from substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms.

[0069] The substituents in Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0070] Ar3 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0071] The substituents in Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 18 carbon atoms, deuteryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring;

[0072] R1, R2, R3, and R4 are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 18 carbon atoms, deuteralkyl groups with 6 to 18 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms, or cycloalkyl groups with 5 to 10 carbon atoms;

[0073] n1 represents the number of R1s, and n1 can be selected from 0, 1, 2 or 3;

[0074] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;

[0075] n3 represents the number of R3s, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0076] n4 represents the number of R4s, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0077] The second compound has the structure shown in Formula 2:

[0078]

[0079] Among them, ring W has the structure shown in equation C, and any two adjacent # positions in equation C are the same as those in equation 2. *The positions are closely intertwined;

[0080] Q is selected from O or S;

[0081] L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0082] Ar4 and Ar5 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0083] Each of R5, R6, and R7 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0084] n5 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0085] n6 is selected from 0, 1, or 2;

[0086] n7 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0087] The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.

[0088] In this application, the terms "optional" and "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently 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 spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0089] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0090] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl group having a substituent Rc or an unsubstituted aryl group. The substituents mentioned above, i.e., Rc, can be, for example, deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms, etc. The number of substituents can be one or more.

[0091] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0092] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms.

[0093] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0094] In the structural formula of the compound in this application, "D" indicates deuteration.

[0095] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0096] In this application, the term "arylene" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0097] In this application, terphenyl includes

[0098] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0099] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0100] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0101] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0102] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0103] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl group) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 12 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 12 to 24.

[0104] In this application, the heteroaryl groups used as substituents include, but are not limited to, pyridyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0105] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0106] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0107] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0108] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0109] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0110] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0111] In this application, the number of carbon atoms in the deuterated alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0112] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.

[0113] In this application, an n-membered ring refers to a ring system formed by n atoms. For example, a phenyl ring is a 6-membered ring. A 3- to 15-membered ring refers to a cyclic group having 3 to 15 ring atoms. Examples of 3- to 15-membered rings include cyclopentane (5-membered ring), cyclohexane (6-membered ring), fluorene ring (13-membered ring), and benzene ring (6-membered ring).

[0114] In this application, It refers to the chemical bond that connects with other groups.

[0115] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0116]

[0117] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0118]

[0119] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0120]

[0121] In some embodiments, the compound represented by Formula 1 is selected from the structures shown in Formulas (1-1) to (1-2):

[0122]

[0123] In some embodiments, in the first compound shown in Formula 1, L1 and L2 are each independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0124] In some embodiments, in the first compound shown in Formula 1, L is selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10 or 12 carbon atoms.

[0125] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, phenyl or deuterated phenyl.

[0126] In some embodiments, in the first compound shown in Formula 1, L, L1 and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl or substituted or unsubstituted pyridinylene.

[0127] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

[0128] In some embodiments, in the first compound shown in Formula 1, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0129]

[0130] L is selected from the group consisting of single bonds or the following groups:

[0131]

[0132] In some embodiments, in the first compound shown in Formula 1, L, L1, and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0133]

[0134] In some embodiments, in the first compound shown in Formula 1, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted pyridinylene.

[0135] Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

[0136] In some embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, the group shown in Formula A or the group shown in Formula B.

[0137] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, or deuteralkyl with 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0138] In some embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, the group shown in Formula A, or the group shown in Formula B.

[0139] The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl;

[0140]

[0141] Optionally, in Formula A and Formula B, ring A and ring T are each independently selected from benzene ring or naphthalene ring;

[0142] Y is selected from O, S, or N (Ar);

[0143] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl;

[0144] The substituents in Ar, each of R3 and R4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

[0145] In some embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, or the following groups:

[0146]

[0147]

[0148] The substituents in Ar1 and Ar2 are the same as or different from each of R3 and R4, and are independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl;

[0149] n3 represents the number of R3s, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0150] n4 represents the number of R4s, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0151] In some more specific embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0152]

[0153] In some embodiments, in the first compound shown in Formula 1, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0154]

[0155]

[0156] In some embodiments, in the first compound shown in 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 dibenzothiophene, and the substituents in Ar3 are the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.

[0157] In some embodiments, in the first compound shown in Formula 1, Ar3 is selected from the following groups:

[0158]

[0159] In some embodiments, in the first compound shown in Formula 1, Ar3 is selected from the following groups:

[0160]

[0161]

[0162] In some embodiments, in the first compound shown in Formula 1, Each is independently selected from the following groups:

[0163]

[0164] In some embodiments, in the first compound shown in Formula 1, each R1 and R2 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, or naphthyl.

[0165] In some embodiments, the second compound shown in Formula 2 is selected from the structures shown in Formulas (S-1) to (S-12):

[0166]

[0167] In some embodiments, in the second compound shown in Formula 2, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0168] In some embodiments, in the second compound shown in Formula 2, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0169] Optionally, in the second compound shown in Formula 2, the substituents in L4 and L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, phenyl or naphthyl.

[0170] In some embodiments, in the second compound shown in Formula 2, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl.

[0171] Optionally, in the second compound shown in Formula 2, the substituents in L4 and L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0172] In some embodiments, in the second compound shown in Formula 2, L4 and L5 are each independently selected from the group consisting of single bonds or the following groups:

[0173]

[0174] In some embodiments, in the second compound shown in Formula 2, L4 and L5 are each independently selected from single bonds or the following groups:

[0175]

[0176] In some embodiments, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.

[0177] In some embodiments, Ar4 and Ar5 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.

[0178] In some embodiments, in the second compound shown in Formula 2, the substituents in Ar4 and Ar5 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, or trialkylsilyl with 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0179] In some embodiments, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazole.

[0180] Optionally, in the second compound shown in Formula 2, the substituents in Ar4 and Ar5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, biphenyl or naphthyl.

[0181] In some embodiments, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and each is independently selected from the following groups:

[0182]

[0183] In some embodiments, in the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and each is independently selected from the following groups:

[0184]

[0185]

[0186] In some embodiments, the second compound shown in Formula 2, They may be the same or different, and each is independently selected from the following groups:

[0187]

[0188] In some embodiments, in the second compound shown in Formula 2, one of Ar4 and Ar5 is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and the other is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.

[0189] In some embodiments, in the second compound shown in Formula 2, one of Ar4 and Ar5 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 phenanthyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, and the other is selected from: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazole.

[0190] Optionally, in the second compound shown in Formula 2, the substituents in Ar4 and Ar5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl.

[0191] In some embodiments, the second compound shown in Formula 2, One of them is selected from:

[0192]

[0193] The other is selected from the following groups:

[0194]

[0195] In some embodiments, in the second compound shown in Formula 2, each of R5, R6 and R7 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0196] In some embodiments, the first compound is selected from the compounds shown in claims A-1 to A-336 of claim 14.

[0197] In some embodiments, the second compound is selected from the compounds shown in claims B1- to B-352 of claim 14.

[0198] Furthermore, in the organic light-emitting device of this application, the organic light-emitting layer comprises a host material and a dopant. The host material comprises a first compound and a second compound. Typically, based on the weight (mass) of the two compounds, the mass ratio of the first compound to the second compound is 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 20:80 to 80:20; further preferably 30:70 to 70:30, more preferably 40:60 to 60:40. Even more preferably, the mass ratio of the host material to the dopant in the organic light-emitting layer is 90:10 to 99:1.

[0199] In some embodiments, the mass ratio of the first compound (compound of formula 1) and the second compound (compound of formula 2) in the light-emitting layer of the organic electroluminescent device is 30:70 to 70:30.

[0200] Optionally, in the main material, the mass ratio of the first compound (compound of formula 1) and the second compound (compound of formula 2) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35, 70:30, or 80:20.

[0201] In some embodiments of this application, the host material and the guest material can be deposited together 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 adjusted by controlling the evaporation rate of the host material and the guest material during the evaporation process, or by controlling the ratio of the evaporation rate of the host material and the guest material.

[0202] Optionally, the organic light-emitting layer can be deposited using 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 controlled by adjusting the film thickness of the host material and the guest material during the evaporation process, or by adjusting the film thickness ratio of the host material and the guest material.

[0203] To obtain a mixture of main materials, the first and second compounds can be placed in an oscillator and mixed to obtain a mixture in the desired weight ratio.

[0204] To form each layer constituting the organic electroluminescent device of this application, dry film formation methods such as vacuum deposition, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0205] In some embodiments of this application, the organic electroluminescent device is a phosphorescent device.

[0206] In some specific embodiments of this application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.

[0207] In a second aspect of this application, an electronic device is provided, the electronic device comprising the organic electroluminescent device described in the first aspect.

[0208] In another aspect of this application, a composition is also provided, the composition comprising a first compound and a second compound, the first compound having the structure shown in Formula 1.

[0209]

[0210] Either X or Z is -N=, and the other is O or S;

[0211] L1 and L2 are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms;

[0212] L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms;

[0213] The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, and cycloalkyl with 5 to 10 carbon atoms;

[0214] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups, groups shown in Formula A or groups shown in Formula B, having 6 to 30 carbon atoms.

[0215]

[0216] Ring A and ring T are each independently selected from benzene rings or naphthalene rings;

[0217] Y is selected from O, S, or N (Ar);

[0218] Ar is selected from substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms;

[0219] The substituents in Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0220] Ar3 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0221] The substituents in Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 18 carbon atoms, deuteryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring;

[0222] R1, R2, R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 18 carbon atoms, deuteralkyl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms;

[0223] n1 represents the number of R1s, and n1 can be selected from 0, 1, 2 or 3;

[0224] n2 represents the number of R2, and n2 is selected from 0, 1 or 2;

[0225] n3 represents the number of R3s, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0226] n4 represents the number of R4s, and n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0227] The second compound has the structure shown in Formula 2:

[0228]

[0229] Among them, ring W has the structure shown in equation C, and any two adjacent # positions in equation C are the same as those in equation 2. *The positions are closely intertwined;

[0230] Q is selected from O or S;

[0231] L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0232] Ar4 and Ar5 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0233] Each of R5, R6, and R7 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0234] n5 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0235] n6 is selected from 0, 1, or 2;

[0236] n7 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0237] The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, in Ar4 and Ar5, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.

[0238] Optionally, the mass ratio of the first compound to the second compound in the composition is 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 20:80 to 80:20, and even more preferably 40:60 to 60:40.

[0239] In some embodiments, the mass ratio of the first compound (compound of formula 1) and the second compound (compound of formula 2) in the composition is 30:70 to 70:30.

[0240] This application also provides the use of the light-emitting layer composition in the light-emitting layer of an organic electroluminescent device.

[0241] This application also provides an organic electroluminescent device comprising the composition.

[0242] The organic electroluminescent device provided in this application includes an anode and a cathode disposed opposite to each other, and an organic layer. The organic layer includes an organic light-emitting layer, which comprises a first compound and a second compound.

[0243] In some embodiments of this application, the organic electroluminescent device sequentially comprises an anode (e.g., an ITO / Ag / ITO substrate), a hole transport layer, a hole conditioning layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (e.g., a Mg-Ag mixture), and an organic capping layer. The hole transport layer is located between the anode and the organic light-emitting layer, and the hole conditioning layer is located between the hole transport layer and the organic light-emitting layer.

[0244] According to a specific implementation method, such as Figure 1 As 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 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 stacked in sequence.

[0245] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; 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-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0246] In this application, the first hole transport layer or the hole conditioning layer may each include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0247]

[0248]

[0249] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0250] In one embodiment, the hole adjustment layer 322 is composed of HT-2.

[0251] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. The material of the hole injection layer 310 can be selected from, for example, the following compounds or any combination thereof;

[0252]

[0253] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1.

[0254] 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 a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0255] The emissive layer can be prepared using a co-evaporation method to prepare a red emissive layer. In some embodiments, a first compound is used as a first host, and a second compound is used as a second host. The first and second hosts are mixed uniformly in a certain weight ratio to obtain an emissive layer host composition. The host composition and dopant are then simultaneously vapor-deposited at a certain vapor deposition rate to form an emissive layer (EML) of a certain thickness. In other embodiments, the first compound, the second compound, and the dopant are simultaneously vapor-deposited at a certain vapor deposition rate to form an emissive layer (EML) of a certain thickness.

[0256] The main material of the organic light-emitting layer 330 includes the first compound and the second compound.

[0257] 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; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. For example, specific examples of phosphorescent dopant include, but are not limited to,

[0258]

[0259] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be, for example, RD.

[0260] 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.

[0261] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. These electron transport materials can be selected from, but are not limited to, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, etc., and this application does not impose any specific limitations on them. The material of the electron transport layer 340 includes LiQ and other electron transport materials, which can be selected from, but are not limited to, the following compounds:

[0262]

[0263]

[0264] In one embodiment of this application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0265] In this application, the cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0266] Optionally, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 includes ytterbium (Yb).

[0267] This application not only provides the organic electroluminescent device comprising the compound represented by Formula 1 and the compound represented by Formula 2 for the organic light-emitting layer, but also provides an electronic device comprising the organic electroluminescent device of this application.

[0268] According to one implementation method, such as Figure 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, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0269] The synthesis methods of the first and second compounds of this application are described in detail below with reference to the synthesis examples, but this application is not limited thereto.

[0270] Synthesis Examples

[0271] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0272] Synthesis of the first compound:

[0273] Synthesis of Sub-a1:

[0274]

[0275] Under a nitrogen atmosphere, RM-1 (16.21 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (160 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, 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.

[0276] Synthesis of Sub-b1:

[0277]

[0278] 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), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain an orange-yellow solid (16.2 g, yield 77%).

[0279] Referring to the synthesis of Sub-c1, Sub-b2 to Sub-b14 were synthesized by replacing RM-2 with reactant A as shown in Table 1 and replacing 4-chlorophenylboronic acid with reactant B.

[0280] Table 1: Synthesis of Sub-b2 to Sub-b14

[0281]

[0282]

[0283] Synthesis of compound A-4:

[0284]

[0285] 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-dicyclohexylphosphine-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 added sequentially to a 250 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give a white solid (9.0 g, yield 65%, m / z = 553.20 [M+H)). + ).

[0286] Referring to the synthesis of compound A-4, reactant C shown in Table 2 was used to replace RM-3 to synthesize the first compound of this application shown in Table 2.

[0287] Table 2: Synthesis of the first compound of this application

[0288]

[0289]

[0290]

[0291]

[0292]

[0293] Synthesis of the second compound:

[0294] Synthesis of Sub-c1:

[0295]

[0296] Under a nitrogen atmosphere, 9-bromo-7H-benzo[C]carbazole (29.62 g, 100 mmol), benzyl bromosulfate (25.65 g, 150 mmol), potassium hydroxide (11.22 g, 200 mmol), and tetrahydrofuran (300 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the reaction was carried out at 60 °C for 6 h. After the system cooled to room temperature, extraction with tetrahydrofuran (100 mL × 3 times) was performed. The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. Purification of the crude product by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase yielded a white solid (32.45 g, 84% yield).

[0297] Synthesis of Sub-d1:

[0298]

[0299] Under a nitrogen atmosphere, Sub-c1 (19.31 g, 50 mmol), 1-chloro-2-aminodibenzofuran (10.88 g, 50 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and toluene (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-d1 (19.10 g; yield 73%).

[0300] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d10 were synthesized by replacing Sub-a1 with reactant D shown in Table 3 and replacing 1-chloro-2-aminodibenzofuran with reactant E.

[0301] Table 3: Synthesis of Sub-d2 to Sub-d10

[0302]

[0303]

[0304] Synthesis of Sub-e1:

[0305]

[0306] Under a nitrogen atmosphere, Sub-d1 (26.15 g, 50 mmol), palladium acetate (0.56 g, 2.5 mmol), tricyclohexylphosphine tetrafluoroborate (CAS: 58656-04-5, 1.84 g, 5 mmol), cesium carbonate (32.58 g, 100 mmol), and N,N-dimethylacetamide (260 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-e1 (13.62 g; yield 56%).

[0307] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e10 were synthesized by replacing Sub-d1 with reactant F shown in Table 4.

[0308] Table 4: Synthesis of Sub-e2 to Sub-e10

[0309]

[0310]

[0311] Synthesis of Sub-e11:

[0312]

[0313] Under a nitrogen atmosphere, Sub-e3 (11.80 g, 25 mmol) and Benzene-D6 were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to reflux and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 minutes. A saturated aqueous solution of K3PO4 was then added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the combined organic phases were dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid, Sub-e11 (8.88 g, yield 73%).

[0314] Synthesis of Sub-f1:

[0315]

[0316] Under a nitrogen atmosphere, Sub-e1 (24.33 g, 50 mmol), iodobenzene (12.24 g, 60 mmol), cuprous iodide (1.90 g, 10 mmol), 18-crown ether-6 (1.32 g, 5 mmol), 1,10-phenanthroline (3.96 g, 20 mmol), potassium carbonate (15.20 g, 110 mmol), and N,N-dimethylformamide (240 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water, filtered, and the filtrate was collected. The filtrate was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a grayish-white solid (20.54 g; yield 73%).

[0317] Referring to the synthesis of Sub-f1, Sub-f2 and Sub-f3 were synthesized by replacing Sub-e1 with reactant G shown in Table 5.

[0318] Table 5: Synthesis from Sub-f2 to Sub-f3

[0319]

[0320] Synthesis of Sub-g1:

[0321]

[0322] Under a nitrogen atmosphere, Sub-f1 (28.13 g, 50 mmol), potassium tert-butoxide (56.10 g, 500 mmol), and DMSO (280 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the reaction was carried out at 50–60 °C for 4 h. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water, resulting in a precipitate. The precipitate was filtered and collected. The precipitate was dissolved in dichloromethane (200 mL), dried over anhydrous sodium sulfate, filtered again, and the filtrate was collected. The solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid (18.20 g, yield 77%).

[0323] Referring to the synthesis of Sub-g1, Sub-g2 and Sub-g3 were synthesized by replacing Sub-f1 with reactant H shown in Table 6.

[0324] Table 6: Synthesis of Sub-g2 and Sub-g3

[0325]

[0326] Synthesis of compound B-4:

[0327]

[0328] Under a nitrogen atmosphere, Sub-e3 (11.81 g, 25 mmol), 4-bromobiphenyl-D9 (6.60 g, 27.5 mmol), tris(dibenzylacetone)palladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol), and xylene (120 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by filtration under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase, yielding a white solid (13.30 g; yield 84%, m / z = 634.28 [M+H]). + ).

[0329] Referring to the synthesis of compound B-4, reactant J was used instead of Sub-e3 and reactant K was used instead of 4-bromobiphenyl, as shown in Table 7, to synthesize the second compound of this application as shown in Table 7.

[0330] Table 7 Synthesis of the second compound of this application

[0331]

[0332]

[0333]

[0334]

[0335]

[0336] NMR of compound A-242: 1 H-NMR (400MHz, CD2Cl2) δppm: 9.36 (s, 1H), 8.86-8.78 (m, 4H), 8.57 (d, 1H), 8.04 (d, 1H), 7 .95-7.84(m,7H),7.77(t,1H),7.70-7.44(m,9H),7.41(d,1H),7.18(t,1H),7.08(t,2H).

[0337] NMR of compound B-81: 1H-NMR (400MHz, CD2Cl2) δppm: 9.42 (s, 1H), 8.29 (d, 1H), 8.21 (d, 1H), 8.06 (d, 1H), 8.00 (d, 1H), 7.96 (s, 1H), 7.91 (d, 1H), 7.88-7.77 (m, 4H), 7.68 (d, 2H), 7.66-7.38 (m, 14H), 7.16 (d, 2H), 7.08 (s, 1H).

[0338] Fabrication and evaluation of organic electroluminescent devices:

[0339] Example 1: Fabrication of a red organic electroluminescent device

[0340] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0341] PD:HT-1 was co-deposited on the experimental substrate (anode) at a deposition rate ratio of 2%:98%, forming a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer. The first hole transport layer.

[0342] Compound HT-2 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. Hole adjustment layer.

[0343] Next, on the second hole transport layer, compound A-4 was used as the first host, compound B-4 as the second host, and RD as the dopant, and a red emitting layer was prepared by co-evaporation. The first host and the second host were mixed uniformly at a weight ratio of 50:50 to obtain the host material composition for the emitting layer. The host material composition and RD were simultaneously evaporated at a evaporation rate of 100%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0344] On the light-emitting layer, compound ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) is formed, and then magnesium (Mg) and silver (Ag) are mixed at a evaporation rate ratio of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0345] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CPL is used to complete the fabrication of a red organic electroluminescent device.

[0346] Examples 2-40

[0347] Except that the organic electroluminescent device was prepared using the same method as in Example 1, except that the combination of compounds in Table 8 below was used instead of the main material composition in Example 1 when fabricating the light-emitting layer.

[0348] Comparative Examples 1-3

[0349] Except that, when fabricating the light-emitting layer, the composition of compounds A-4 and B-4 in Example 1 is replaced by the light-emitting layer main combination in Table 8 below, the organic electroluminescent device is prepared using the same method as in Example 1.

[0350] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0351]

[0352] The performance of the red organic electroluminescent devices prepared in Examples 1-40 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 8.

[0353] Table 8

[0354]

[0355]

[0356] Referring to Table 8 above, when the compounds of the present invention are used as the host material for red organic electroluminescent devices, the efficiency (Cd / A) is increased by at least 12.8% and the lifetime is increased by at least 14.9%.

[0357] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution 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; in, The cathode and the anode are arranged opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer comprises 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 single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms; L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms; The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups, groups shown in Formula A or groups shown in Formula B, having 6 to 30 carbon atoms. Indicates a chemical bond; Ring A and ring T are each independently selected from benzene rings or naphthalene rings; Y is selected from O, S, or N (Ar); Ar is selected from substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms. The substituents in Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; Ar3 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms; The substituents in Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 18 carbon atoms, deuteryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, or cycloalkyl with 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, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 18 carbon atoms, deuteralkyl groups with 6 to 18 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms, or cycloalkyl groups with 5 to 10 carbon atoms; n1 represents the number of R1s, and n1 can be 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 R3s, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 represents the number of R4s, 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: Among them, ring W has the structure shown in equation C, and any two adjacent # positions in equation C are the same as those in equation 2. *The positions are closely intertwined; Q is selected from O or S; L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar4 and Ar5 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Each of R5, R6, and R7 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms; n5 is selected from 0, 1, 2, 3, 4, 5 or 6; n6 is selected from 0, 1, or 2; n7 is selected from 0, 1, 2, 3, 4, 5 or 6; The substituents in L4, L5, Ar4, and Ar5 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 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, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorene, a substituted or unsubstituted phenanthylene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted pyridinylene. Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl 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 the group consisting of single bonds or the following groups: L is selected from the group consisting of single bonds or the following groups:

4. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, the group shown in Formula A or the group shown in Formula B. The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl; Optionally, in Formula A and Formula B, ring A and ring T are each independently selected from benzene ring or 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 of R3 and R4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

5. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Ar1 and Ar2 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, or the following groups: The substituents in Ar1 and Ar2, and the same or different R3 and R4, are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl; n3 represents the number of R3s, and n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n4 represents the number of R4s, 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 dibenzothiopheneyl, and the substituents in Ar3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.

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

7. The organic electroluminescent device according to claim 1, wherein, In the first compound shown in Formula 1, Each is independently selected from the following groups: Preferably, each of R1 and R2 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, or naphthyl.

8. The organic electroluminescent device according to claim 1, wherein, In the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and each is 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 phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar4 and Ar5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, biphenyl or naphthyl.

9. The organic electroluminescent device according to claim 1, wherein, In the second compound shown in Formula 2, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in L4 and L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

10. The organic electroluminescent device according to claim 1, wherein, In the second compound shown in Formula 2, L4 and L5 are each independently selected from the group consisting of single bonds or the following groups:

11. The organic electroluminescent device according to claim 1, wherein, In the second compound shown in Formula 2, Ar4 and Ar5 may be the same or different, and each is independently selected from the following groups:

12. The organic electroluminescent device according to claim 1, wherein, In the second compound shown in Formula 2, They may be the same or different, and each is independently selected from the following groups:

13. The organic electroluminescent device according to claim 1, wherein, The organic light-emitting layer comprises a host material and a dopant, wherein the host material includes the first compound and the second compound; the mass ratio of the first compound and the second compound is 10:90 to 90:

10.

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:

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

Images