An organic electroluminescent device

Abstract

This invention provides an organic electroluminescent device. The organic electroluminescent device comprises a first compound having the structure shown in Formula I and a second compound having the structure shown in Formula II, wherein the first compound is a polysubstituted benzodiazole structure, and the second compound is an amine compound having a benzofuran group, a benzothiophene group, a carbazole group, or a fluorene group. This invention provides that the first and second compounds have better structural matching, better hole injection capability, and excellent charge generation capability. Combining the first and second compounds to prepare the organic electroluminescent device can reduce the device voltage, improve device efficiency, and extend device lifespan.

Description

Technical Field

[0001] This invention belongs to the field of OLED technology, specifically including an organic electroluminescent device. Background Technology

[0002] Currently disclosed organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as the electron transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). When a bias voltage was applied to the device, green light was emitted, laying the foundation for the development of modern organic light-emitting diodes (OLEDs). Today, OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. As OLEDs are self-emissive solid-state devices, their emergence has provided a tremendous impetus to the development of the display and lighting fields. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for applications on flexible substrates.

[0004] OLEDs are classified into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. Fluorescent OLEDs only use singlet state emission; the triplet states generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%, and this extremely low IQE hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported a phosphorescent OLED that uses triplet emission from a complexed heavy metal as the emitter, enabling the harvesting of both singlet and triplet states and achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed significantly to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high internal quantum efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high internal quantum efficiency.

[0005] The color of OLED emission can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to obtain the desired spectrum. Green OLEDs, yellow OLEDs, red OLEDs, and phosphorescent materials have all been successfully commercialized. However, blue phosphorescent devices still suffer from problems such as blue unsaturation, short device lifespan, and high operating voltage. Furthermore, the efficiency of phosphorescent OLEDs decreases rapidly at high brightness levels, and their emission spectrum saturation, device efficiency, and lifespan do not yet meet application requirements.

[0006] p-type doped materials (PD materials) are a crucial class of materials in OLED devices, primarily used in conjunction with hole transport materials to form hole injection layers or p-type charge generation layers. In the fabrication of OLED display panels using PD materials, a typical process involves co-evaporating and thermally sublimating the PD material and hole transport material onto the substrate surface to form a thin film, followed by the gradual deposition of other functional layers and the light-emitting layer. Good device performance requires an excellent hole injection layer, necessitating a good match between the LUMO energy level of the PD material and the HOMO energy level of the hole transport material to improve hole injection performance. This significantly reduces device voltage and power consumption. Different hole injection layers utilize different hole transport materials, necessitating the pairing of different PD materials. Therefore, researching the pairing of PD materials and hole transport materials to achieve suitable hole injection and reduce voltage becomes critical. Summary of the Invention

[0007] The present invention aims to provide an organic electroluminescent device to solve at least some of the above-mentioned problems. The organic electroluminescent device comprises a first compound having structural formula I and a second compound having structural formula II. The hole injection layer formed by the combination of these two compounds can effectively reduce the device voltage, improve device efficiency and lifetime. Simultaneously, the charge generation layer formed by the combination of these two compounds can also reduce the voltage of series-connected devices, resulting in excellent device performance.

[0008] Therefore, a first aspect of the present invention provides an organic electroluminescent device comprising:

[0009] anode,

[0010] cathode,

[0011] and a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a first compound and a second compound, wherein the general structural formula of the first compound is shown in Formula I:

[0012]

[0013] In formula I,

[0014] W is selected from O, S, or Se each time it appears, either the same or different.

[0015] Z 1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 Or N;

[0016] R 1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0017] R 2 Each time it appears, it is selected from the following groups, either the same or different: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0018] R, R', R 3Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0019] Adjacent R 1 R 2 R 3 They can be arbitrarily connected to form a loop;

[0020] When R 1 Z when CF3 2 Not C-CF3;

[0021] The general structural formula of the second compound is shown in Formula II:

[0022]

[0023] In formula II,

[0024] X 1 Each occurrence is selected from O, S, NAr, either identically or differently. 3 CR c R d or SiR c R d ;

[0025] L, L 1 L 2 Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0026] Ar1 Ar 2 and Ar 3 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof, either identically or differently.

[0027] a represents 1 or 2; preferably 1;

[0028] b represents 0, 1, 2, 3, or 4;

[0029] c represents 0, 1, 2, or 3;

[0030] R a R b R c R d Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, hydroxyl, mercapto, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0031] Adjacent R a R b R c R d They can be arbitrarily connected to form a loop;

[0032] In structures I and II, hydrogen may be partially or completely replaced by deuterium.

[0033] Furthermore, each occurrence of R is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0034] Furthermore, each time R appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0035] Furthermore, when R has substituents, the substituents in R include at least one electron-withdrawing group.

[0036] Furthermore, the first compound has the structure shown in Formula I-1:

[0037]

[0038] In Equation I-1,

[0039] W is selected from O, S, or Se each time it appears, either identically or differently;

[0040] R 1 Each time it appears, it is selected from cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0041] R 2 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; and when R 2 When selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is substituted with one or more R... 3 replace;

[0042] R', R 3Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0043] Adjacent R 1 R 2 R 3 They can be arbitrarily connected to form a loop;

[0044] When R 1 Z when CF3 2 Not C-CF3.

[0045] Furthermore, the first compound may also have a structure of formula I-1-1 or I-1-2 as shown below:

[0046]

[0047] in,

[0048] W is selected from O, S, or Se each time it appears, either identically or differently;

[0049] Z 1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 ;

[0050] R 1Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0051] R 2 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; and when R 2 When selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is substituted with one or more R... 3 replace;

[0052] R 4 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0053] R', R 3 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0054] Adjacent R 1 R 2 R 3 R 4 They can be arbitrarily connected to form a loop;

[0055] When R 1 Z when CF3 2 Not C-CF3.

[0056] Furthermore, the first compound may also have the following structure: I-1-3

[0057]

[0058] in,

[0059] W is selected from O, S, or Se each time it appears, either identically or differently;

[0060] Z 1 Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 ;

[0061] R 1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0062] R 2 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; and when R 2 When selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is substituted with one or more R... 3 replace;

[0063] R 4 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0064] R', R 3Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0065] Adjacent R 1 R 2 R 3 R 4 They can be arbitrarily connected to form a loop;

[0066] When R 1 When it's CF3, R 4 It's not CF3.

[0067] Furthermore, Z 1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 .

[0068] Furthermore, R' is selected from the group consisting of, in the same or different ways each time it appears: fluorine, cyano, SCN, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aroxy with 6-30 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms, and combinations thereof;

[0069] Furthermore, R' is selected from the group consisting of the following groups, either identically or differently each time it appears: fluorine, cyano, SCN, trifluoromethyl, 2,3,5,6-tetrafluoro-4-cyanophenyl, 2,3,5,6-tetrafluoropyridyl, cyanophenyl, fluorophenyl, and combinations thereof;

[0070] Furthermore, W is selected from O or S each time it appears, either identically or differently; Z 1 Z 2 and Z 3 At least one of them is selected from CR 3 ;

[0071] Furthermore, W is selected from O; Z 1 Z 2 and Z 3 Selected from CR 3 ;

[0072] Furthermore, R 1 Each time it appears, it is selected from the group consisting of: cyano, substituted or unsubstituted alkoxy group having 1-20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, and combinations thereof; and the substituents of the substituted alkoxy, substituted aryl or substituted heteroaryl group contain at least one electron-withdrawing group;

[0073] Furthermore, R 1 Each time it appears, it is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, either identically or differently.

[0074] R 4 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0075] Furthermore, the R 2 Each occurrence is selected from the group consisting of: substituted aryl groups having 6-30 carbon atoms, substituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; said aryl or heteroaryl group is substituted with one or more R 3 replace;

[0076] R 3Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, isocyano, SCN, OCN, SF5, boroalkyl, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof;

[0077] Adjacent substituent R 1 R 3 They can be arbitrarily connected to form a ring.

[0078] Furthermore, the R 3 At least one of them, each time appearing, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, substituted alkyl having 1-20 carbon atoms, substituted alkoxy having 1-20 carbon atoms, substituted aryl having 6-30 carbon atoms, substituted heteroaryl having 3-30 carbon atoms, and combinations thereof; and the substituents of the substituted alkyl, substituted heteroalkyl, substituted alkoxy, substituted aryl or substituted heteroaryl contain at least one electron-withdrawing group.

[0079] Further, in the first compound of the organic electroluminescent device, the electron-withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, azirrocycloyl, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, azirrocycloyl, and azirrocycloyl: Alkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 cyclic carbon atoms, heteroalkyl groups having 1-20 carbon atoms, aralkyl groups having 7-30 carbon atoms, alkoxy groups having 1-20 carbon atoms, aryloxy groups having 6-30 carbon atoms, alkenyl groups having 2-20 carbon atoms, alkynyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, alksilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, and combinations thereof.

[0080] Further, the electron-withdrawing group is selected from the group consisting of: fluorine, cyano, isocyano, SCN, OCN, SF5 and any of the following groups substituted by one or more of fluorine, cyano, isocyano, SCN, OCN, SF5: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 cyclic carbon atoms, heteroalkyl having 1-20 carbon atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aroxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkoxyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0081] Furthermore, the electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazine, and combinations thereof.

[0082] Furthermore, R, R 3 Each occurrence is either identical or different from the group consisting of the following structures:

[0083]

[0084]

[0085]

[0086] In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium;

[0087] and / or R 1 Each time it appears, the same or different groups are selected from A3 to A20 and B1 to B160 as described above;

[0088] and / or R 2 Each time it appears, the group consisting of B1 to B160 is selected in the same or different ways;

[0089] This indicates the connection points between the above structure and other structures.

[0090] Further, the first compound in the organic electroluminescent device is characterized in that the organic compound is selected from the group consisting of compounds P1 to P1276; compounds P1 to P1276 have a structure represented by formula I-1-4; wherein W and Z 1 Z 2 Z 3 R 1 R 2 These correspond to atoms or groups selected from the table below:

[0091]

[0092] Table 1

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111] In compounds P1 to P1276, hydrogen may be partially or completely replaced by deuterium.

[0112] Furthermore, the second compound has a structure shown in one of Formulas II-1 to II-5:

[0113]

[0114] Among them, L, L 1 L 2Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0115] Ar 1 Ar 2 and Ar 3 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof, either identically or differently.

[0116] b is 0, 1, 2, 3, or 4;

[0117] c is 0, 1, 2, or 3;

[0118] R a R b R c R d Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, hydroxyl, mercapto, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0119] Adjacent R a R b R c R d They can be arbitrarily connected to form a ring.

[0120] Furthermore, the second compound has the structure shown in Formula II-1, II-3 or Formula II-5.

[0121] Furthermore, Ra R b R c R d Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted groups having Alkenyl groups with 2-20 carbon atoms, substituted or unsubstituted alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino groups with 0-20 carbon atoms, and combinations thereof.

[0122] Furthermore, R a R b R c R d Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0123] Furthermore, R c R dEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. Alkynyl groups with 1 carbon atom, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino groups with 0-20 carbon atoms, and combinations thereof.

[0124] Furthermore, R c R d Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0125] Furthermore, one or more CH2 groups among the alkyl, alkoxy, alkenyl, and alkynyl groups can be -R e C=C-、-C≡C-、Si(R e 2. C=O, C=NR e -C(=O)O-, -C(=O)NR e -、NR e -P(=O)(R e Replace with -, -O-, -S-, SO or SO2.

[0126] Furthermore, the R a R b R c R d Each can be controlled by one or more R e Replace, R eEach time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, fluorine, acyl, carbonyl, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aroxy with 6-30 carbon atoms, substituted or unsubstituted... The following are considered compounds: an alkenyl group having 2-20 carbon atoms; a substituted or unsubstituted alkynyl group having 2-20 carbon atoms; a substituted or unsubstituted aryl group having 6-30 carbon atoms; a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms; a substituted or unsubstituted alksilyl group having 3-20 carbon atoms; a substituted or unsubstituted arylsilyl group having 6-20 carbon atoms; a substituted or unsubstituted alkylgermanium group having 3-20 carbon atoms; a substituted or unsubstituted arylgermanium group having 6-20 carbon atoms; a substituted or unsubstituted amino group having 0-20 carbon atoms; and combinations thereof; wherein one or more CH2 groups among the alkyl, alkoxy, alkenyl, and alkynyl groups may be -R f C=C-、-C≡C-、Si(R f 2. C=O, C=NR f -C(=O)O-, -C(=O)NR f -、NR f -P(=O)(R f Replace with -, -O-, -S-, SO or SO2.

[0127] Furthermore, the R e Each can be controlled by one or more R f Replace, R fEach time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, fluorine, acyl, carbonyl, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoyl, alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocyclic having 3-20 ring atoms, aralkyl having 7-30 carbon atoms, and so on. Alkoxy groups, aryloxy groups having 6-30 carbon atoms, alkenyl groups having 2-20 carbon atoms, alkynyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, alksilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, alkylgermanyl groups having 3-20 carbon atoms, arylgermanyl groups having 6-20 carbon atoms, amino groups having 0-20 carbon atoms, and combinations thereof.

[0128] Furthermore, L, L 1 L 2 Each time it appears, it is selected from the same or different groups of single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene, and combinations thereof.

[0129] Furthermore, among them L, L 1 L 2 Each can be controlled by one or more R a Group substitution.

[0130] Furthermore, L, L 1 L 2 Each occurrence is selected from one of the following structures: single bond, substituted, or unsubstituted, either identically or differently:

[0131]

[0132] “…” indicates L, L 1 L 2 The bond positions to other atoms or groups, respectively;

[0133] Furthermore, in the above structure, hydrogen may be partially or completely replaced by deuterium, fluorine, methyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, N-phenylcarbazole, trimethylsilyl, or triphenylsilyl.

[0134] Furthermore, Ar 1 Ar2 Ar 3 Each time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, and combinations thereof.

[0135] Furthermore, Ar 1 Ar 2 Ar 3 Each time it appears, it is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[a]fluorenyl, and combinations thereof, either identically or differently.

[0136] Furthermore, among which Ar 1 Ar 2 Ar 3 Each can be controlled by one or more R a Group substitution.

[0137] Furthermore, Ar 1 Ar 2 Ar 3 Each occurrence is selected, either identically or differently, from one of the following substituted or unsubstituted structures:

[0138]

[0139]

[0140]

[0141] "*—" indicates Ar 1 Ar 2 Ar 3 respectively with L 1 L 2 The connection key position of , N;

[0142] In the above structures, hydrogen may be partially or completely replaced by deuterium, fluorine, methyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, N-phenylcarbazole, trimethylsilyl, or triphenylsilyl.

[0143] Ar 1 Ar 2 Ar 3In the structure, the unsubstituted hydrogen in the ring pointed to by "*—" can optionally pass through "*—" and L. 1 L 2 N-connection, for example

[0144] It can represent any of the following structures:

[0145]

[0146] For example It can represent any of the following structures:

[0147]

[0148] "*" indicates L 1 L 2 N and Ar respectively 1 Ar 2 Ar 3 The bonding positions of the linkages. Further, the second compound has one of the structures shown in the following formula:

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] In the above structure, hydrogen can be partially or completely replaced by deuterium.

[0167] Furthermore, the first organic layer is a hole injection layer, which contains a first compound and a second compound; the mass doping ratio of the first compound to the second compound is 1:1000 to 1000:1.

[0168] Furthermore, the mass doping ratio of the first compound to the second compound is 1:100 to 1:10.

[0169] Furthermore, the organic electroluminescent device includes at least two light-emitting units, and a charge generation layer is disposed between the at least two light-emitting units, wherein the charge generation layer includes a p-type charge generation layer and an n-type charge generation layer; the p-type charge generation layer includes a first compound and a second compound; the mass doping ratio of the first compound to the second compound is 1:1000 to 1000:1.

[0170] Furthermore, the mass doping ratio of the first compound to the second compound is from 1:100 to 1:5.

[0171] Furthermore, a second organic layer is also included between the anode and the cathode, the material of which is selected from compounds having triarylamine units, spirodifluorene compounds, pentanebenzene compounds, oligothiophene compounds, oligophenyl compounds, oligophenylenevinyl compounds, oligofluorene compounds, porphyrin complexes or metal phthalocyanine complexes.

[0172] Furthermore, a second organic layer is also included between the anode and the cathode, the second organic layer being adjacent to the first organic layer, the second organic layer being a hole transport layer, and the material of the second organic layer being selected from the second compound.

[0173] Furthermore, the present invention also provides a display component comprising the organic electroluminescent device described in any of the preceding claims.

[0174] Furthermore, the present invention also provides a composition comprising a first compound and a second compound, wherein the first compound has the general structural formula shown in Figure I:

[0175]

[0176] In formula I,

[0177] W is selected from O, S, or Se each time it appears, either the same or different.

[0178] Z1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 Or N;

[0179] R 1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0180] R 2 Each time it appears, it is selected from the following groups, either the same or different: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0181] R, R', R 3 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0182] Adjacent R 1 R 2 R 3 They can be arbitrarily connected to form a loop;

[0183] When R 1 Z when CF3 2 Not C-CF3;

[0184] The general structural formula of the second compound is shown in Formula II:

[0185]

[0186] In formula II,

[0187] X 1 Each occurrence is selected from O, S, NAr, either identically or differently. 3 CR c R d or SiR c R d ;

[0188] L, L 1 L 2 Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;

[0189] Ar 1 Ar 2 and Ar 3 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof, either identically or differently.

[0190] a is 1 or 2;

[0191] b is 0, 1, 2, 3, or 4;

[0192] c is 0, 1, 2, or 3;

[0193] R a R b R c R dEach time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, hydroxyl, mercapto, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0194] Adjacent R a R b R c R d They can be arbitrarily connected to form a loop;

[0195] In structures I and II, hydrogen may be partially or completely replaced by deuterium.

[0196] For details on the substituents and specific structures in this composition, please refer to the description of the first and second compounds contained in the first organic layer of the organic electroluminescent device.

[0197] The beneficial effects of this invention are as follows:

[0198] This invention provides an organic electroluminescent device comprising a first organic layer, which includes a first compound and a second compound. The first compound has the structure shown in Formula I, and the second compound has the structure shown in Formula II. The first compound is a multi-substituted benzodiazole structure, and the second compound is an amine compound having a benzofuran group, a benzothiophene group, a carbazole group, or a fluorene group. The first compound provided by this invention has a novel substituent structure, which can adjust the doping capability of the material, while the second compound has excellent hole transport capability. The combination of the first and second compounds allows for better structural matching, resulting in superior device performance. This combination, when used in the fabrication of organic electroluminescent devices, can reduce device voltage and improve device efficiency and lifetime, whether used as a hole injection layer or a charge generation layer. Attached Figure Description

[0199] Figure 1 This is a schematic diagram of an organic electroluminescent device according to one embodiment of this specification, wherein the device 100 includes a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190.

[0200] Figure 2 This is a schematic diagram of an organic light-emitting device with an encapsulation layer according to an embodiment of this specification, wherein the device 200 includes a substrate 201, an anode 210, a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light-emitting layer 250, a hole blocking layer 260, an electron transport layer 270, an electron injection layer 280, a cathode 290, and an encapsulation layer 202.

[0201] Figure 3 This is a schematic diagram of a series organic light-emitting device with an encapsulation layer according to an embodiment of this specification. The device 300 includes a substrate 301, an anode 310, a first hole injection layer 311, a first hole transport layer 312, a first electron blocking layer 313, a first light-emitting layer 314, a first hole blocking layer 315, a first electron transport layer 316, an N-type charge generation layer 320, a P-type charge generation layer 321, a second hole injection layer 330, a second hole transport layer 331, a second electron blocking layer 332, a second light-emitting layer 333, a second hole blocking layer 334, a second electron transport layer 335, a second electron injection layer 336, a cathode 337, and an encapsulation layer 302. Detailed Implementation

[0202] To more clearly illustrate the present invention, the following description, in conjunction with preferred embodiments and accompanying drawings, further clarifies the invention. Those skilled in the art should understand that the specific description below is illustrative rather than restrictive and should not be construed as limiting the scope of protection of the present invention. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of the specification to those skilled in the art. Various modifications can be made based on the embodiments and comparative examples in this specification, and the scope of protection of the present invention should not be limited to the embodiments and comparative examples detailed below.

[0203] The organic compounds of this invention are suitable for use in light-emitting elements, display panels, and electronic devices, particularly organic electroluminescent devices. The electronic devices of this invention are devices comprising a layer of at least one organic compound; these devices may also comprise layers of inorganic materials or layers formed entirely of inorganic materials. Preferred electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells (O-DSSCs), organic optical detectors, organic photosensors, organic field quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasma emitting devices. Organic electroluminescent devices (OLEDs) are particularly preferred.

[0204] Definition of the term "substituent group"

[0205] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0206] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred.

[0207] Cycloalkyl – as used herein, includes cyclic alkyl groups. A cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred.

[0208] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl.

[0209] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl.

[0210] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably one having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may optionally be substituted.

[0211] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0212] Aromatic or aryl-aryl – as used herein – refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0213] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0214] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0215] A heteroaryl or heteroaryl group—as used herein—refers to a divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0216] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0217] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0218] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0219] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0220] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0221] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0222] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0223] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0224] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphoxy group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryl, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphoxy group. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms. Cycloalkyl groups having 3-20 carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 carbon atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, and unsubstituted alkyne groups having 6-30 carbon atoms. Aryl, unsubstituted heteroaryl with 3-30 carbon atoms, unsubstituted alkylsilyl with 3-20 carbon atoms, unsubstituted arylsilyl with 6-20 carbon atoms, unsubstituted alkylgermanium with 3-20 carbon atoms, unsubstituted arylgermanium with 6-20 carbon atoms, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphoxy, and combinations thereof with 0-20 carbon atoms.

[0225] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0226] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon, nitrogen, oxygen, phosphorus, and boron can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to its ability to enhance device efficiency and stability.

[0227] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0228] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0229] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0230]

[0231] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0232]

[0233] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0234]

[0235] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0236]

[0237] The first and second compounds used in this invention can be obtained by referring to the preparation methods in the prior art, and will not be described in detail here.

[0238] The fabrication method of organic electroluminescent devices is not limited. The fabrication method in the following embodiments is merely an example and should not be construed as limiting. Those skilled in the art can reasonably improve the fabrication method of the following embodiments based on existing technology. For example, the proportions of various materials in each organic layer are not particularly limited, and those skilled in the art can reasonably select them within a certain range based on existing technology. In the device embodiments, the device characteristics are tested using conventional equipment in the art and methods well known to those skilled in the art. Since those skilled in the art are familiar with the above-mentioned equipment usage, testing methods, and other related content, and can obtain the inherent data of the sample definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0239] Device Example A

[0240] Device Example 1

[0241] This embodiment provides an organic electroluminescent device, the fabrication method of which is as follows: An ITO substrate is patterned to have a light-emitting area of ​​2mm × 2mm, then washed with isopropanol, UV, and ozone respectively. Afterwards, the ITO substrate is mounted on a substrate support of a vacuum deposition apparatus, and the pressure is adjusted to make the vacuum rate 1 × 10⁻⁶. -7 First, a hole injection layer is formed on the ITO layer (anode) formed on the substrate by vacuum deposition of compounds P28 and HT-1 (mass ratio of compound P28 to compound HT-1 is 2:98) provided in Example 1 of the present invention with a thickness of 10 nm. Next, a hole transport layer is formed on the hole injection layer by vacuum deposition of HT-1 with a thickness of 110 nm. Then, an electron blocking layer is formed on the hole transport layer by vacuum deposition of compound EB-1 with a thickness of 10 nm. Finally, on the electron blocking layer, compounds BD-1 and BH are vacuum deposited with a thickness of 20 nm. A mixture is used to form a light-emitting layer (the mass ratio of BD-1 to BH is 2:98); then, a hole-blocking layer is formed on the light-emitting layer by vacuum deposition of compound HB-1 with a thickness of 5 nm; next, an electron transport layer is formed on the hole-blocking layer by vacuum deposition of compound ET-1 and Liq (the mass ratio of ET-1 to Liq is 5:5) with a thickness of 30 nm; then, an electron injection layer is formed on the electron transport layer by depositing LiF with a thickness of 1 nm; finally, an electron cathode is formed on the electron injection layer by depositing aluminum (Al) with a thickness of 150 nm, thus fabricating an organic electroluminescent device.

[0242] Device Example 2

[0243] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P48, and the mass ratio of compound P48 to HT-1 in the hole injection layer is 2:98.

[0244] Device Example 3

[0245] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P68, and the mass ratio of compound P68 to HT-1 in the hole injection layer is 2:98.

[0246] Device Example 4

[0247] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P75, and the mass ratio of compound P75 to HT-1 in the hole injection layer is 2:98.

[0248] Device Example 5

[0249] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P567, and the mass ratio of compound P567 to HT-1 in the hole injection layer is 2:98.

[0250] Device Example 6

[0251] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P68, compound HT-1 is replaced with compound HT-2, and the mass ratio of compound P68 to HT-2 in the hole injection layer is 2:98.

[0252] Device Example 7

[0253] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P68, compound HT-1 is replaced with compound HT-3, and the mass ratio of compound P68 to HT-3 in the hole injection layer is 2:98.

[0254] Device Example 8

[0255] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P68, compound HT-1 is replaced with compound HT-4, and the mass ratio of compound P68 to HT-4 in the hole injection layer is 2:98.

[0256] Device Example 9

[0257] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P68, compound HT-1 is replaced with compound HT-5, and the mass ratio of compound P68 to HT-5 in the hole injection layer is 2:98.

[0258] Device Example 10

[0259] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P75, compound HT-1 is replaced with compound HT-5, and the mass ratio of compound P75 to HT-5 in the hole injection layer is 2:98.

[0260] Device Example 11

[0261] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P567, compound HT-1 is replaced with compound HT-5, and the mass ratio of compound P567 to HT-5 in the hole injection layer is 2:98.

[0262] Device Comparison Example 1

[0263] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound PD-1, and the mass ratio of compound PD-1 to HT-1 in the hole injection layer is 2:98.

[0264] Device Comparison Example 2

[0265] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound PD-1, compound HT-1 is replaced with compound HT-5, and the mass ratio of compound PD-1 to HT-5 in the hole injection layer is 2:98.

[0266] Device Comparison Example 3

[0267] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound PD-2, compound HT-1 is replaced with compound HT-5, and the mass ratio of compound PD-2 to HT-5 in the hole injection layer is 2:98.

[0268] Device Comparison Example 4

[0269] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound PD-3, compound HT-1 is replaced with compound HT-5, and the mass ratio of compound PD-3 to HT-5 in the hole injection layer is 2:98.

[0270] Device Comparison Example 5

[0271] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P68, compound HT-1 is replaced with compound HD-1, and the mass ratio of compound P68 to HD-1 in the hole injection layer is 2:98.

[0272] Device Comparison Example 6

[0273] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound P567, compound HT-1 is replaced with compound HD-2, and the mass ratio of compound P567 to HD-2 in the hole injection layer is 2:98.

[0274] Device Comparison Example 7

[0275] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound PD-2, compound HT-1 is replaced with compound HD-1, and the mass ratio of compound PD-2 to HD-1 in the hole injection layer is 2:98.

[0276] Device Comparison Example 8

[0277] The preparation method is the same as in Device Example 1, except that compound P28 in the hole injection layer is replaced with compound PD-3, compound HT-1 is replaced with compound HD-2, and the mass ratio of compound PD-3 to HD-2 in the hole injection layer is 2:98.

[0278] The molecular structural formulas of the materials used in this invention and the materials in each layer of the device are as follows:

[0279]

[0280]

[0281] The electrode preparation method and the deposition method of each functional layer in this embodiment are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, and will not be described in detail here.

[0282] Device performance

[0283] The organic electroluminescent devices provided in Device Examples 1-11 and Comparative Examples 1-8 were tested using standard methods. For this purpose, J = 10 mA / cm² was used. 2 The driving voltage and current efficiency (CE) of the organic electroluminescent device were determined at a current density of J = 25 mA / cm². 2 The lifetime (LT95) of the organic electroluminescent device was determined at a given current density.

[0284] The testing instruments and methods used to perform performance testing on the above-mentioned OLED devices are as follows:

[0285] Brightness was tested using a PhotoResearch PR-635 spectral scanner;

[0286] Current density and turn-on voltage: tested using a Keithley 2400 digital source meter;

[0287] The performance test results of the above devices are listed in Table 2.

[0288] Table 2 Device performance test results

[0289]

[0290] The device performance test results in Table 2 above show that:

[0291] Compared with the organic electroluminescent devices provided in Comparative Examples 1-4, the organic electroluminescent devices prepared by the first and second compounds provided by this invention in Examples 1-11 showed a 2% to 6% decrease in driving voltage, a corresponding 5% to 13% increase in current efficiency, and a significant 27% to 69% increase in lifetime. This indicates that the first compound provided by this invention has superior doping ability and device performance compared to Comparative Examples PD-1, PD-2, and PD-3, and can better combine with the second compound to form a hole injection layer. This also demonstrates that the multi-substituted benzodiazole structure provided by this invention can better match the structure of the second compound; even the difference between F and CF3 can produce different performance characteristics.

[0292] Compared with the organic electroluminescent devices provided in Comparative Examples 5 and 6, the organic electroluminescent devices prepared by the first and second compounds provided by the present invention in Examples 1-11 have a driving voltage that is reduced by 6% to 9%, a current efficiency that is increased by 8% to 14%, and a lifetime that is significantly increased by 67% to 80%. This indicates that the second compound provided by the present invention has better hole transport performance than Comparative Examples HD-1 and HD-2, and is more suitable as a hole transport material.

[0293] Compared with the organic electroluminescent devices provided in Comparative Examples 7 and 8, the organic electroluminescent devices prepared by the first and second compounds provided by the present invention in Examples 1-11 have a driving voltage that is 7% to 10% lower, a current efficiency that is 18% to 25% higher, and a lifetime that is significantly improved by 78% to 110%. When the combination of the first and second compounds provided by the present invention is used to prepare a hole injection layer, it is better matched with each other than the comparative examples and has better hole injection performance.

[0294] Device Example B

[0295] Device Example B1

[0296] This embodiment provides a tandem organic electroluminescent device, which is fabricated as follows: An ITO substrate is patterned to have a light-emitting area of ​​2mm × 2mm, then washed with isopropanol, UV light, and ozone, respectively. The ITO substrate is then mounted on a substrate support in a vacuum deposition apparatus, and the pressure is adjusted to achieve a vacuum rate of 1 × 10⁻⁶. -7 First, a hole injection layer is formed on the ITO layer (anode) formed on the substrate by vacuum deposition of compounds P68 and HT-1 (mass ratio of compound P68 to HT-1 is 2:98) provided in Embodiment B1 of the present invention with a thickness of 10 nm. Next, a hole transport layer is formed on the hole injection layer by vacuum deposition of HT-1 with a thickness of 25 nm. Then, an electron blocking layer is formed on the hole transport layer by vacuum deposition of compound EB-1 with a thickness of 5 nm. Finally, a mixture of compound BD-1 and compound BH is vacuum deposited on the electron blocking layer with a thickness of 20 nm. A light-emitting layer is formed (the mass ratio of BD-1 to BH is 2:98); then, a hole-blocking layer is formed on the light-emitting layer by vacuum deposition of compound HB-1 with a thickness of 5 nm; next, an electron transport layer is formed on the hole-blocking layer by vacuum deposition of compound ET-1 and Liq (the mass ratio of ET-1 to Liq is 5:5) with a thickness of 14 nm; then, an N-type charge generation layer is formed on the electron transport layer by depositing compound N-CG and Yb (the mass ratio of N-CG to Yb is 99:1) with a thickness of 10 nm; then, an N-type charge generation layer is formed on the N-type charge generation layer by vacuum deposition of compound N-CG and Yb (the mass ratio of N-CG to Yb is 99:1) with a thickness of 10 nm. A P-type charge generation layer is formed by vacuum deposition of compounds P68 and HT-1 (mass ratio of P68 to HT-1 is 5:95) to a thickness of m, according to the embodiments of the invention. Then, a second hole transport layer is formed by vacuum deposition of compound HT-1 to a thickness of 35 nm on the P-type charge generation layer. Next, a second electron blocking layer is formed by vacuum deposition of compound EB-1 to a thickness of 5 nm on the second hole transport layer. Finally, a second light-emitting layer (BD-1) is formed by vacuum deposition of a mixture of compound BD-1 and compound BH to a thickness of 20 nm on the second electron blocking layer. The mass ratio of HB-1 to BH is 2:98. Next, a second hole blocking layer is formed on the second light-emitting layer by vacuum deposition of compound HB-1 with a thickness of 5 nm. Then, on the second hole blocking layer, a second electron transport layer is formed by vacuum deposition of compound ET-1 and Liq (mass ratio of ET-1 to Liq is 5:5) with a thickness of 30 nm. Then, an electron injection layer is formed by depositing LiF with a thickness of 1 nm on the second electron transport layer. Finally, an organic electroluminescent device is formed by depositing aluminum (Al) with a thickness of 150 nm on the electron injection layer.

[0297] Device Example B2

[0298] The preparation method is the same as in Device Example B1, except that compound P68 in the P-type charge generation layer is replaced with compound P567, and the mass ratio of compound P567 to HT-1 in the P-type charge generation layer is 5:95.

[0299] Device Example B3

[0300] The preparation method is the same as in Device Example B1, except that compound HT-1 in the P-type charge generation layer is replaced with compound HT-4, and the mass ratio of compound P68 to HT-4 in the P-type charge generation layer is 5:95.

[0301] Device Example B4

[0302] The preparation method is the same as in Device Example B1, except that compound HT-1 in the P-type charge generation layer is replaced with compound HT-5, and the mass ratio of compound P68 to HT-5 in the P-type charge generation layer is 5:95.

[0303] Device Comparison C1

[0304] The preparation method is the same as in Device Example B1, except that compound P68 in the P-type charge generation layer is replaced with compound PD-2, and the mass ratio of compound PD-2 to HT-1 in the P-type charge generation layer is 5:95.

[0305] Device Comparison Example C2

[0306] The preparation method is the same as in Device Example B1, except that compound P68 in the P-type charge generation layer is replaced with compound PD-3, and the mass ratio of compound PD-3 to HT-1 in the P-type charge generation layer is 5:95.

[0307] Device Comparison Example C3

[0308] The preparation method is the same as in Device Example B1, except that compound HT-1 in the P-type charge generation layer is replaced with compound HD-2, and the mass ratio of compound P68 to HD-2 in the P-type charge generation layer is 5:95.

[0309] Device Comparison Example C4

[0310] The preparation method is the same as in Device Example B1, except that compound P68 in the P-type charge generation layer is replaced with compound PD-3, compound HT-1 is replaced with compound HD-2, and the mass ratio of compound PD-3 to HD-2 in the P-type charge generation layer is 5:95.

[0311] The molecular structural formulas of the materials used in this invention and the remaining materials of the device are as follows:

[0312]

[0313] Device performance

[0314] The organic electroluminescent devices provided in Device Examples B1-B4 and Device Comparative Examples C1-C4 were tested using standard methods. For this purpose, J = 10 mA / cm² was used. 2 The driving voltage and current efficiency (CE) of the organic electroluminescent device were determined at a current density of J = 35 mA / cm². 2 The lifetime (LT97) of the organic electroluminescent device was determined at a given current density. The performance test results of the above devices are listed in Table 3.

[0315] Table 3 Device performance test results

[0316]

[0317]

[0318] The device performance test results in Table 3 above show that:

[0319] Compared with the organic electroluminescent devices provided by comparative examples C1 and C2, the organic electroluminescent device Example B1 prepared by the first and second compounds provided by the present invention exhibits a 9% and 8% reduction in driving voltage, a corresponding 16% and 19% increase in current efficiency, and a significant 12% and 15% increase in lifetime. This indicates that the first compound P68 provided by the present invention has superior doping ability compared to comparative examples PD-2 and PD-3, resulting in better device performance when forming the P-type charge generation layer of a tandem organic electroluminescent device. Compared with the organic electroluminescent devices provided by comparative examples C1 and C2, the present invention… The organic electroluminescent devices B2, B3, and B4 prepared from the first and second compounds provided by the present invention exhibit a 7% to 10% reduction in driving voltage, a corresponding 17% to 26% improvement in current efficiency, and a significant 12% to 22% increase in lifetime. This further demonstrates that the first compound provided by the present invention has superior doping ability compared to the comparative compound, resulting in better device performance when forming the P-type charge generation layer of a tandem organic electroluminescent device. It also indicates that the multi-substituted benzodiazole structure provided by the present invention can achieve better structural matching when combined with the second compound to form a charge generation layer, leading to different performance characteristics.

[0320] Compared with the organic electroluminescent device provided by Comparative Example C3, the organic electroluminescent devices B1, B3, and B4 prepared by the first and second compounds provided by the present invention have a 20% to 21% lower driving voltage, a corresponding 40% to 45% increase in current efficiency, and a significant 44% to 53% increase in lifetime. This indicates that the second compound provided by the present invention has better hole transport performance and has better device performance than the comparative compound when forming the P-type charge generation layer of the tandem organic electroluminescent device.

[0321] Compared with the organic electroluminescent device provided by Comparative Example C4, the driving voltage of the organic electroluminescent devices B1-B4 prepared by the first and second compounds provided by the present invention is reduced by 22% to 23%, the current efficiency is also improved by 56% to 65%, and the lifetime is significantly improved by 72% to 82%. This indicates that the combination of the first and second compounds provided by the present invention is more suitable for forming the P-type charge generation layer of the series organic electroluminescent device than the combination of compounds in the comparative example.

[0322] This invention provides a first compound with excellent hole transport layer material doping capability, with different substituents in its structure producing different effects. The second compound has excellent hole transport capability. Moreover, when the first and second compounds are combined, excellent hole injection can be achieved. At the same time, it can also serve as a charge generation layer in a series device. The organic electroluminescent device prepared by this invention can not only reduce the device voltage and improve the device efficiency, but also significantly improve the device lifetime, and has a wide range of application value.

[0323] The above description is merely a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the scope of the technology disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.

Claims

1. An organic electroluminescent device, characterized in that, include: anode, cathode, and a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a first compound and a second compound, the general structural formula of the first compound being shown in Formula I: In formula I, W is selected from O, S, or Se each time it appears, either identically or differently; Z 1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 Or N; R 1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof. R 2 Each time it appears, it is selected from the following groups, either the same or different: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; R, R', R 3 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof. Adjacent R 1 R 2 R 3 They can be arbitrarily connected to form a loop; When R 1 Z when CF3 2 Not C-CF3; The general structural formula of the second compound is shown in Formula II: In formula II, X 1 Each occurrence is selected from O, S, NAr, either identically or differently. 3 CR c R d or SiR c R d ; L, L 1 L 2 Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Ar 1 Ar 2 and Ar 3 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof, either identically or differently. 'a' represents 1 or 2; b represents 0, 1, 2, 3, or 4; c represents 0, 1, 2, or 3; R a R b R c R d Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, hydroxyl, mercapto, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof. Adjacent R a R b R c R d They can be arbitrarily connected to form a loop; In Formula I and Formula II, hydrogen may be partially or completely replaced by deuterium.

2. The organic electroluminescent device according to claim 1, characterized in that, The R, each time it appears, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; Preferably, the R is selected, in the same or different ways, from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Preferably, when R has substituents, the substituents in R include at least one electron-withdrawing group.

3. The organic electroluminescent device according to claim 1, characterized in that, The first compound has the structure shown in Formula I-1: In Equation I-1, W is selected from O, S, or Se each time it appears, either identically or differently; R 1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof. R 2 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; and when R 2 When selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is substituted with one or more R... 3 replace; R', R 3 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof. Adjacent R 1 R 2 R 3 They can be arbitrarily connected to form a loop; When R 1 Z when CF3 2 Not C-CF3.

4. The organic electroluminescent device according to claim 1, characterized in that, The first compound has a structure as shown in one of the formulas I-1-1 to I-1-3 below: in, W is selected from O, S, or Se each time it appears, either identically or differently; Z 1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 ; R 1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof. R 2 Each time it appears, it is selected from the group consisting of: substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; and when R 2 When selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is substituted with one or more R... 3 replace; R 4 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; R', R 3 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof. Adjacent R 1 R 2 R 3 R 4 They can be arbitrarily connected to form a loop; In I-1-1 and I-1-2, when R 1 Z when CF3 2 Not C-CF3; In I-1-3, when R 1 When R is CF3 4 Not CF3.

5. The organic electroluminescent device according to claim 1, characterized in that, Z 1 Z 2 and Z 3 Each time it appears, it is selected from CR in the same or different ways. 3 .

6. The organic electroluminescent device according to claim 1, characterized in that, R' is selected, in the same or different manner, from the group consisting of: fluorine, cyano, SCN, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Preferably, R' is selected from the group consisting of fluorine, cyano, SCN, trifluoromethyl, 2,3,5,6-tetrafluoro-4-cyanophenyl, 2,3,5,6-tetrafluoropyridyl, cyanophenyl, fluorophenyl, and combinations thereof, each time it appears.

7. The organic electroluminescent device according to claim 1, characterized in that, The W is selected from O or S each time it appears, either identically or differently; Z 1 Z 2 and Z 3 At least one of them is selected from CR 3 ; Preferably, W is selected from O; Z 1 Z 2 and Z 3 Selected from CR 3 .

8. The organic electroluminescent device according to claim 1, characterized in that, The R 3 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, isocyano, SCN, OCN, SF5, boroalkyl, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof; Preferably, the R 3 At least one of them, each time appearing, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, substituted alkyl having 1-20 carbon atoms, substituted alkoxy having 1-20 carbon atoms, substituted aryl having 6-30 carbon atoms, substituted heteroaryl having 3-30 carbon atoms, and combinations thereof; and the substituents of the substituted alkyl, substituted heteroalkyl, substituted alkoxy, substituted aryl or substituted heteroaryl contain at least one electron-withdrawing group.

9. The organic electroluminescent device according to claim 1, characterized in that, R, R 3 Each occurrence is either identical or different from the group consisting of the following structures: In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium; and / or R 1 Each time it appears, the same or different groups are selected from A3 to A20 and B1 to B160 as described above; and / or R 2 Each time it appears, the group consisting of B1 to B160 is selected in the same or different ways; This indicates the connection points between the above structure and other structures.

10. The organic electroluminescent device according to claim 4, characterized in that, The first compound is selected from the group consisting of compounds P1 to P1276; said compounds P1 to P1276 have a structure represented by formula I-1-4; wherein W, Z 1 Z 2 Z 3 R 1 R 2 These correspond to atoms or groups selected from the table below: In compounds P1 to P1276, hydrogen may be partially or completely replaced by deuterium.

11. The organic electroluminescent device according to claim 1, characterized in that, The second compound has a structure shown in one of Formulas II-1 to II-5: Among them, L, L 1 L 2 Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Ar 1 Ar 2 and Ar 3 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof, either identically or differently. b is 0, 1, 2, 3, or 4; c is 0, 1, 2, or 3; R a R b R c R d Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, halogen, hydroxyl, mercapto, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof. Adjacent R a R b R c R d They can be arbitrarily connected to form a ring.

12. The organic electroluminescent device according to claim 1 or 11, characterized in that, R a R b R c R d Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted groups having Alkenyl groups with 2-20 carbon atoms, substituted or unsubstituted alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alksilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino groups with 0-20 carbon atoms, and combinations thereof; Preferably, R a R b R c R d Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

13. The organic electroluminescent device according to claim 1 or 11, characterized in that, L, L 1 L 2 Each time it appears, it is selected from the same or different groups of single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene, and combinations thereof.

14. The organic electroluminescent device according to claim 1 or 11, characterized in that, Ar 1 Ar 2 Ar 3 Each time it appears, it is selected from the same or different groups of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, and combinations thereof.

15. The organic electroluminescent device according to claim 1 or 11, characterized in that, Ar 1 Ar 2 Ar 3 Each occurrence is selected, either identically or differently, from one of the following substituted or unsubstituted structures: "*—" indicates Ar 1 Ar 2 Ar 3 respectively with L 1 L 2 The connection key position of , N; In the above structures, hydrogen may be partially or completely replaced by deuterium, fluorine, methyl, tert-butyl, cyclohexyl, adamantyl, phenyl, biphenyl, trimethylsilyl, or triphenylsilyl.

16. The organic electroluminescent device according to claim 1 or 11, characterized in that, The second compound has one of the structures shown in the following formula: In the above structure, hydrogen can be partially or completely replaced by deuterium.

17. The organic electroluminescent device according to claim 1, characterized in that, The first organic layer is a hole injection layer, which contains a first compound and a second compound; the mass doping ratio of the first compound to the second compound is 1:1000 to 1000:

1. Preferably, the mass doping ratio of the first compound to the second compound is 1:100 to 1:

10.

18. The organic electroluminescent device according to claim 1, characterized in that, The organic electroluminescent device includes at least two light-emitting units, and a charge generation layer is disposed between the at least two light-emitting units. The charge generation layer includes a p-type charge generation layer and an n-type charge generation layer. The p-type charge generation layer includes a first compound and a second compound. The mass doping ratio of the first compound to the second compound is 1:1000 to 1000:

1. Preferably, the mass doping ratio of the first compound to the second compound is 1:100 to 1:

5.

19. The organic electroluminescent device according to claim 1, characterized in that, A second organic layer is further included between the anode and the cathode. The material of the second organic layer is selected from compounds having triarylamine units, spirodifluorene compounds, pentanebenzene compounds, oligothiophene compounds, oligophenyl compounds, oligophenylene vinylidene compounds, oligofluorene compounds, porphyrin complexes, or metal phthalocyanine complexes.

20. The organic electroluminescent device according to claim 1, characterized in that, A second organic layer is further included between the anode and the cathode. The second organic layer is a hole transport layer and is adjacent to the first organic layer. The material of the second organic layer is selected from a second compound.

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