Organic compound and tandem organic electroluminescent device

Abstract

The present disclosure relates to the technical field of photoelectric display devices. The present disclosure relates an organic compound, and also relates to a tandem organic electroluminescent device, specifically comprising a charge generation layer. The organic compound of the present disclosure has a structure as shown in general formula (1). According to the tandem organic electroluminescent device of the present disclosure, the voltage of the device can be effectively reduced, the efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

An organic compound and a stacked organic electroluminescent device Technical Field

[0001] The present disclosure relates to an organic compound, belonging to the technical field of organic light-emitting materials. The present disclosure also relates to a stacked organic electroluminescent device, specifically including a charge generation layer. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them ideal for fabrication on flexible substrates, enabling the design and production of aesthetically pleasing and impressive optoelectronic products, offering unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors (FETs), organic photovoltaic cells, and organic sensors. OLEDs have experienced particularly rapid development and have achieved commercial success in the information display field. OLEDs can produce highly saturated red, green, and blue colors, and full-color displays made with them require no additional backlight source, offering vibrant colors, a thin film structure, and excellent flexibility. The core of an OLED device is a thin film structure containing a variety of organic functional materials. Common functionalized organic materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as luminescent host materials and luminescent guest materials (dyes). When electricity is applied, electrons and holes are injected and transported to the luminescent region, where they recombine, generating excitons and emitting light.

[0003] New OLED screens are required to function even in bright sunlight. Medium and large-sized OLED screens also place higher demands on brightness and lifespan. This has led to the development of a new OLED structure: the stacked OLED structure. This stacked device structure connects multiple light-emitting units via a charge generation layer (CGL). Compared to traditional single-unit devices, stacked OLEDs with multiple light-emitting units often achieve significantly higher current efficiency and brightness, while requiring significantly less current density to maintain the same brightness. Furthermore, the multiple light-emitting core layers facilitate exciton separation, reducing the exciton density within the device's internal light-emitting layer and significantly extending operating life, effectively avoiding the trade-off between high brightness and long life. Compared to single-layer OLED devices, devices with a double-layer stacked structure can achieve a 2x increase in brightness and a 4x increase in lifespan. If applied to smartphones, this structure could reduce power consumption by approximately 30%, enabling smaller batteries and thinner bodies. Currently, LCG has mass-produced laminated OLEDs in automotive products. Apple and BOE are trying to apply this technology to display screens of mobile phones and other products. Laminated device technology is an important direction for the future development of high-brightness displays and white light OLED devices.

[0004] People are increasingly demanding the performance of these products. Current OLED materials and device structures cannot fully address the efficiency, lifespan, and cost challenges of OLED products. Through ongoing research, the researchers of this publication have discovered an ingenious molecular design for the charge generation layer, which is described in detail below. Surprisingly, the compounds disclosed in this publication are highly suitable for OLED applications and can effectively improve device performance.

[0005] Summary of the Invention

[0006] The present disclosure provides an o-phenanthroline organic compound having a structure as shown in the general formula (1):

[0007] In formula (1), R1, R2, R3, and R4 are each independently selected from one or a combination of two of hydrogen, deuterium, a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0008] and at least two of R2, R3, and R4 are not H at the same time;

[0009] Two adjacent ones of R2, R3, and R4 are not connected, or two adjacent ones of R2, R3, and R4 are connected to form a ring;

[0010] When R2, R3, and R4 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, R2, R3, and R4 are each independently connected to the connected benzene ring by a single bond or fusion;

[0011] X1, X2, X3, and X4 are each independently N or CR, and at least one of them is N;

[0012] R is selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cyclic alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

[0013] When substituents are independently present on the above-mentioned R1-R4 and R, the substituents are independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 aromatic boron, and C3-C30 heteroaryl.

[0014] Furthermore, the compound disclosed herein has a structure as shown in formula (1-1):

[0015] In formula (1-1), the definitions of R1, R2, X1, X2, X3, and X4 are the same as those in formula (1);

[0016] R5, R6, R7, and R8 are each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; any two adjacent ones of R5, R6, R7, and R8 are not connected, or any two adjacent ones of R5, R6, R7, and R8 are connected to form a ring.

[0017] In the present disclosure, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the present disclosure, they all have the same meaning, and the selection range of the substituents is as shown above and will not be repeated one by one. In the present disclosure, the expressions Ca to Cb represent that the number of carbon atoms of the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents. In the present disclosure, the expression of a ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond. In the present disclosure, "each independently" means that when there are multiple subjects, they may be the same or different from each other. In the present disclosure, the expression of chemical elements, unless otherwise specified, usually includes the concept of their isotopes. For example, the expression "hydrogen (H)" includes its isotopes. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13C, etc., will not be repeated here. The heteroatom in this disclosure generally refers to an atom or atomic group selected from N, O, S, P, Si and Se, and in some embodiments can be selected from N, O, S. In this disclosure, examples of halogen include: fluorine, chlorine, bromine, iodine, etc. In this disclosure, unless otherwise specified, aryl and heteroaryl include both single ring and condensed ring.

[0018] In the present disclosure, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58. The C3-C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58. The C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc. The C3-C20 may be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc. The C6-C30 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc. The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc. The C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0019] In the present disclosure, the substituted or unsubstituted C6-C60 aryl group includes a monocyclic aryl group and a condensed ring aryl group. In some embodiments, it can be selected from a C6-C30 aryl group, and in some embodiments, it can be selected from a C6-C20 aryl group. The so-called monocyclic aryl group refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as: phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. A condensed ring aryl group refers to a molecule containing at least two aromatic rings, and the aromatic rings are not independent of each other but share two adjacent carbon atoms and are fused to each other. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacenyl group is selected from 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The derivative group of fluorene is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirobifluorene and benzofluorenyl.

[0020] The C3 to C60 heteroaryl groups mentioned in the present disclosure include monocyclic heteroaryl groups and condensed ring heteroaryl groups. In some embodiments, they can be selected from C3-C30 heteroaryl groups, in some embodiments, they can be C4-C20 heteroaryl groups, and in some embodiments, they can be C5-C12 heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are connected by a single bond. Examples of monocyclic heteroaryl groups include furyl, thienyl, pyrrolyl, pyridyl, etc. A condensed ring heteroaryl group refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but are groups that share two adjacent atoms and are fused to each other. Examples of fused ring heteroaryl groups include benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, and indolocarbazolyl.

[0021] The aryloxy group in the present disclosure includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0022] In the present disclosure, an arylamino group represents a group formed by substituting one or two aryl groups for the hydrogen on an amino group, wherein the attachment point of the arylamino group can be connected to the aryl group in the arylamino group or to the N group in the arylamino group, and the exemplary carbon number and specific group of the aryl group in the arylamino group are the same as those described above. The C6-C30 arylamino groups mentioned in the present disclosure include, for example, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrenylamino, biphenylamino, etc. The C3-C30 heteroarylamino groups mentioned in the present disclosure include, for example, pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0023] The chain alkyl groups mentioned in this disclosure include straight-chain alkyl groups and branched-chain alkyl groups unless otherwise specified. Specifically, the substituted or unsubstituted C1-C30 chain alkyl groups can be selected from substituted or unsubstituted C1-C16 chain alkyl groups, and in some embodiments, can be substituted or unsubstituted C1-C10 chain alkyl groups. Examples of the substituted or unsubstituted C1-C10 chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, and 2-ethylhexyl.

[0024] In the present disclosure, the cycloalkyl group includes a monocycloalkyl group and a polycycloalkyl group; wherein, a monocycloalkyl group refers to an alkyl group containing a single cyclic structure; a polycycloalkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; the C3-C20 cycloalkyl group can be exemplified by: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0025] In the present disclosure, the substituted or unsubstituted C1-C20 alkoxy group can be selected from substituted or unsubstituted C1-C10 alkoxy groups. Examples of C1-C10 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, and the like. In some embodiments, the group can be selected from methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, and isopentyloxy groups, and in some embodiments, the group can be selected from methoxy.

[0026] It should be noted that, while the potential effects of various groups / features are described separately for ease of explanation, this does not imply that these groups / features function in isolation. In fact, the key to achieving good performance is the optimized combination of the entire molecule, resulting from the synergistic effects of the various groups, rather than the effects of any single group.

[0027] In a specific embodiment, in formula (1) and formula (1-1), X1, X2, X3, and X4 are all N. In a specific embodiment, one or more of the hydrogen atoms in the phenanthroline group are deuterated.

[0028] In a specific embodiment, in formula (1) and formula (1-1), R1 is hydrogen.

[0029] In a specific embodiment, in formula (1) and formula (1-1), R2, R3, R4, R5, R6, R7, and R8 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, furyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, and phenanthroline, or a combination of two thereof.

[0030] Specific structures of the organic compounds disclosed herein include, but are not limited to, compounds M1 to M279:

[0031] In a second aspect, the present disclosure provides a stacked organic electroluminescent device, wherein a specific material combination is used to form the charge generation layer. This device structure can effectively reduce the device voltage while improving the device efficiency and lifespan.

[0032] A stacked organic electroluminescent device comprises the following structure: an anode, a cathode, at least two light-emitting units arranged between the anode and the cathode, and a charge generation layer arranged between adjacent electroluminescent units, wherein each electroluminescent unit comprises at least a hole transport layer, an electron transport layer and an organic light-emitting layer, wherein the charge generation layer is composed of a dopant host and a dopant, the dopant being a lanthanide metal, and the dopant host having a structure as shown in formula (1).

[0033] In formula (1), R1, R2, R3, and R4 are each independently selected from one or a combination of two of hydrogen, a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0034] and at least two of R2, R3, and R4 are not H at the same time;

[0035] Two adjacent ones of R2, R3, and R4 are not connected, or two adjacent ones of R2, R3, and R4 are connected to form a ring;

[0036] When R2, R3, and R4 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, R2, R3, and R4 are each independently connected to the connected benzene ring by a single bond or fusion;

[0037] X1, X2, X3, and X4 are each independently N or CR, and at least one of them is N;

[0038] R is selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cyclic alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

[0039] When substituents are independently present on the above-mentioned R1-R4 and R, the substituents are independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 aromatic boron, and C3-C30 heteroaryl.

[0040] Furthermore, in the stacked organic electroluminescent device described in the present disclosure, the dopant in the charge generation layer is selected from one of the following metals: La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb or Lu; in some embodiments, it can be selected from Yb; the doping mass percentage of the dopant in the charge generation layer in the main material is 1%-50%; in some embodiments, it can be selected from 1%-30%, and in some embodiments, it can be selected from 1%-10%.

[0041] In some embodiments, the host material in the charge generation layer has a structure as shown in formula (1-1):

[0042] In formula (1-1), the definitions of R1, R2, X1, X2, X3, and X4 are the same as those in formula (1);

[0043] R5, R6, R7, and R8 are each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

[0044] Two adjacent ones of R5, R6, R7, and R8 are not connected, or two adjacent ones of R5, R6, R7, and R8 are connected to form a ring.

[0045] The preparation process of the host material in the charge generation layer disclosed above is simple and easy, the raw materials are readily available, and it is suitable for mass production and expansion, and is very suitable for industrial applications.

[0046] The stacked organic electroluminescent device disclosed herein employs a special charge generation layer disposed between adjacent light-emitting units in the device. The charge generation layer is formed by combining a doped host material having a bisphenanthroline structure with Yb. The coordination effect of the bisphenanthroline structure in the doped host material effectively inhibits the migration of Yb atoms, thereby improving the device voltage and lifespan. Furthermore, substituents are introduced into the central bisphenanthroline ring to improve electron transport performance, thereby reducing device voltage and increasing device efficiency and lifespan.

[0047] In a second aspect, the present disclosure provides a use of the organic compound as described above, wherein the compound is used in an organic electronic device.

[0048] In some embodiments, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper, and in some embodiments, it can be applied to an organic electroluminescent device.

[0049] In some embodiments, the compound is used as an electron transport layer material in an organic electroluminescent device or a charge generation layer material in a stacked device.

[0050] As a fourth aspect of the present disclosure, a display device utilizing the aforementioned laminated organic electroluminescent device is provided. The display device fabricated using the laminated organic electroluminescent device exhibits low operating voltage, high luminous efficiency, and an improved service life, meeting the high-performance material requirements of current panel and display manufacturers. DETAILED DESCRIPTION

[0051] The technical solution of the present disclosure is further described below through specific implementation methods. Those skilled in the art should understand that the embodiments are only used to help understand the present disclosure and should not be regarded as specific limitations of the present disclosure.

[0052] The organic compounds provided by the present disclosure can be obtained by known methods, for example, by known organic synthesis methods. An exemplary synthesis route is given below, but those skilled in the art can also obtain the organic compounds by other known methods.

[0053] In one embodiment, the polycyclic aromatic compound can be prepared by the following synthetic route:

[0054] Wherein, R1, R2, R3, and R4 have the same definitions as above; Pd(PPh3)4 is tetrakistriphenylphosphine palladium, and K2CO3 is potassium carbonate.

[0055] It should be noted that obtaining the compounds is not limited to the synthesis methods and raw materials used in this disclosure. Those skilled in the art may also select other methods or routes to obtain the polycyclic aromatic compounds disclosed herein. Compounds for which no synthesis methods are mentioned in this disclosure are raw materials obtained from commercial sources or are prepared in-house using these raw materials according to known methods.

[0056] The solvents and reagents used in the present disclosure can all be purchased from the chemical product market.

[0057] The specific preparation methods of the compounds disclosed herein will be described in detail below using multiple synthesis examples as examples, but the preparation methods disclosed herein are not limited to these synthesis examples.

[0058] The structures of the intermediates and compounds in the present disclosure were analyzed using an ABSCIEX mass spectrometer (4000QTRAP).

[0059] Synthesis Example 1: Synthesis of M1

[0060] Synthesis of intermediate M1-1:

[0061] At room temperature, M1-0 (20.0 g), phenylboronic acid (5.0 g), Pd(PPh3)4 (2.4 g), K2CO3 (11.3 g), and 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (PE:DCM = 50:1, v:v) was performed to obtain a crude product. Ethanol was added to slurry to obtain 13.7 g of a white solid, with a yield of 86.1%.

[0062] The molecular ion mass determined by mass spectrometry was 387.91 (theoretical value: 387.93).

[0063] Synthesis of M1:

[0064] At room temperature, M1-1 (10.0 g), A1 (7.9 g), Pd(PPh3)4 (1.5 g), K2CO3 (7.1 g), and 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (MeOH:DCM = 20:1, v:v) was performed to obtain the crude product, which was then washed with petroleum ether to afford 12.9 g of a white solid (85.3% yield).

[0065] The molecular ion mass determined by mass spectrometry was: 586.17 (theoretical value: 586.22).

[0066] Synthesis Example 2: Synthesis of M9

[0067] Synthesis of intermediate M9-1:

[0068] At room temperature, M9-0 (20.0 g), A1 (21.4 g), Pd(PPh3)4 (4.0 g), K2CO3 (19.3 g), and 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (MeOH:DCM = 20:1, v:v) was performed to obtain the crude product, which was then washed with petroleum ether to afford 30.1 g of a white solid (yield 88.8%).

[0069] The molecular ion mass determined by mass spectrometry was: 484.10 (theoretical value: 484.17).

[0070] Synthesis Example 3: Synthesis of M51

[0071] Synthesis of intermediate M51-1:

[0072] At room temperature, M51-0 (20.0 g), A2 (16.7 g), Pd(PPh3)4 (3.2 g), K2CO3 (15.2 g), and 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (PE:DCM = 50:1, v:v) was performed to obtain a crude product. Ethanol was added to slurry to obtain 20.7 g of a white solid, with a yield of 81.7%.

[0073] The molecular ion mass determined by mass spectrometry was 461.92 (theoretical value: 461.94).

[0074] Synthesis of M51:

[0075] M51-1 (10.0 g), A1 (13.3 g), Pd(PPh3)4 (1.3 g), K2CO3 (6.0 g), and 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1 L single-necked flask at room temperature. The atmosphere was replaced with nitrogen three times and heated to 90°C overnight. The reaction mixture was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and purified by column chromatography (MeOH:DCM = 20:1, v:v) to afford the crude product. The crude product was then washed with petroleum ether to afford 11.2 g of a white solid (78.3% yield).

[0076] The molecular ion mass determined by mass spectrometry was 660.20 (theoretical value: 660.23).

[0077] Synthesis Example 4: Synthesis of M123

[0078] At room temperature, M123-0 (10.0 g), A1 (27.6 g), Pd(PPh3)4 (2.6 g), K2CO3 (6.2 g), and 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (PE:DCM = 50:1, v:v) was performed to obtain a crude product. Ethanol was added to slurry to obtain 15.3 g of a white solid, with a yield of 80.7%.

[0079] The molecular ion mass determined by mass spectrometry was 840.21 (theoretical value: 840.27).

[0080] Synthesis Example 5: Synthesis of M157

[0081] Synthesis of intermediate M157-1:

[0082] At room temperature, M157-0 (20.0 g), A3 (9.9 g), Pd(PPh3)4 (2.8 g), K2CO3 (13.4 g), and 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (PE:DCM = 50:1, v:v) was performed to obtain a crude product. Ethanol was added to slurry to obtain 14.3 g of a white solid, with a yield of 81.3%.

[0083] The molecular ion mass determined by mass spectrometry was 560.16 (theoretical value: 560.20).

[0084] Synthesis of M157:

[0085] At room temperature, M157-1 (10.0 g), A1 (16.9 g), Pd(PPh3)4 (1.6 g), K2CO3 (7.6 g), and 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction mixture was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (MeOH:DCM = 20:1, v:v) was performed to obtain the crude product, which was then washed with petroleum ether to afford 12.2 g of a white solid (78.8% yield).

[0086] The molecular ion mass determined by mass spectrometry was 560.23 (theoretical value: 560.20).

[0087] Synthesis Example 6: Synthesis of M218

[0088] Synthesis of intermediate M218-1:

[0089] At room temperature, M218-0 (20.0 g), A4 (15.4 g), Pd(PPh3)4 (3.2 g), K2CO3 (15.2 g), and 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (PE:DCM = 50:1, v:v) was performed to obtain a crude product. Ethanol was added to slurry to obtain 21.3 g of a white solid, with a yield of 88.7%.

[0090] The molecular ion mass determined by mass spectrometry was 437.86 (theoretical value: 437.94).

[0091] Synthesis of M218:

[0092] M218-1 (10.0 g), A1 (14.0 g), Pd(PPh3)4 (1.3 g), K2CO3 (6.3 g), and 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1 L single-necked flask at room temperature. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction mixture was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (MeOH:DCM = 20:1, v:v) was performed to obtain the crude product, which was then washed with petroleum ether to afford 11.4 g of a white solid (78.5% yield).

[0093] The molecular ion mass determined by mass spectrometry was 636.25 (theoretical value: 636.23).

[0094] Synthesis Example 7: Synthesis of M266

[0095] Synthesis of intermediate M266-1:

[0096] At room temperature, M266-0 (20.0 g), A1 (38.2 g), Pd(PPh3)4 (3.6 g), K2CO3 (17.3 g), and 1,4-dioxane / water (1000 ml, 4 / 1) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 90°C for overnight reaction. The reaction mixture was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and column chromatography (MeOH:DCM = 20:1, v:v) was performed to obtain the crude product, which was then washed with petroleum ether to afford 27.6 g of a white solid (85.2% yield).

[0097] The molecular ion mass determined by mass spectrometry was 518.13 (theoretical value: 518.13).

[0098] Synthesis of M266:

[0099] At room temperature, M266-1 (10.0 g), A5 (3.7 g), Pd2(dba)3 (0.6 g), tri-tert-butylphosphine (1.9 g), sodium tert-butoxide (7.8 g), and toluene (400 mL) were added to a 1 L single-necked flask. The atmosphere was replaced with nitrogen three times and heated to 100°C for overnight reaction. The reaction mixture was cooled to room temperature, concentrated, extracted with dichloromethane, and washed with copious amounts of water. The organic phase was dried, concentrated, and then column chromatography (PE:DCM = 10:1, v:v) was performed to obtain the crude product. The crude product was then washed with petroleum ether to afford 10.3 g of a white solid, yielding 79.0%.

[0100] The molecular ion mass determined by mass spectrometry was 676.26 (theoretical value: 676.24).

[0101] Device Examples

[0102] Implementation Method

[0103] An OLED consists of a first electrode, a second electrode, and an organic material layer between the electrodes. This organic material layer can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, an electron transport region, and a charge generation layer.

[0104] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate used for the display can also be provided with thin film transistors (TFTs).

[0105] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0106] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0107] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of the following: a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0108] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0109] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below. Alternatively, one or more of the compounds HT-1 to HT-51 can be doped with one or more of the compounds HI-1 to HI-3 described below.

[0110] The light-emitting layer includes a luminescent dye (i.e., a dopant) that can emit light at different wavelengths, and may also include a host material. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0111] Depending on the technology, the light-emitting layer material can be made of fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, and other materials. An OLED device can use a single light-emitting technology or a combination of multiple technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0112] In one aspect of the present disclosure, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0113] In one aspect of the present disclosure, the barrier layer surrounding the light-emitting layer may be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0114] The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of TDE1-TDE49 listed below.

[0115] In one aspect of the present disclosure, an electron blocking layer (EBL) is positioned between the hole transport layer and the light-emitting layer. The EBL may be composed of, but is not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0116] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. This region may be a single-layer electron transport layer (ETL), including those containing only one compound and those containing multiple compounds. The region may also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0117] In one aspect of the present disclosure, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0118] In one aspect of the present disclosure, a hole-blocking layer (HBL) is positioned between the electron-transporting layer and the light-emitting layer. The hole-blocking layer may be composed of, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46, or a mixture of, but not limited to, one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46.

[0119] The device may further include an electron injection layer located between the electron transport layer and the cathode. Materials for the electron injection layer include, but are not limited to, one or more combinations of the following.

[0120] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0121] When the device contains multiple light-emitting units, each light-emitting unit is composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, and an electron transport layer. The charge generation layer is located between two light-emitting units and is mainly composed of a doping body and a dopant. The material that can be used for the doping body is the same as the material that can be used for the above-mentioned electron transport layer, and the dopant is a metal.

[0122] Device Examples

[0123] In the device embodiment, an organic electroluminescent device is prepared, comprising an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0124] (1) A glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0125] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, a mixture of compound HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above-mentioned anode layer as a hole injection layer at a deposition rate of 0.1 nm / s and a deposition film thickness of 10 nm;

[0126] (3) Vacuum evaporation of compound HT-4 on the hole injection layer as a hole transport layer at a deposition rate of 0.1 nm / s and a total deposition thickness of 60 nm;

[0127] (4) Vacuum evaporation of compound HT-14 on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a total deposition thickness of 5 nm;

[0128] (5) vacuum evaporating a light-emitting layer on the electron blocking layer. The light-emitting layer includes a binary mixture of a host material BFH-4 and a dye BFD-16, BFH-4:BFD-16 (100:3, w / w), with an evaporation rate of 0.1 nm / s and a total film thickness of 20 nm.

[0129] (6) Vacuum evaporation of compound ET-23 as a hole blocking layer on the light-emitting layer at a rate of 0.1 nm / s and a total film thickness of 5 nm;

[0130] (7) Vacuum evaporating a mixture of the compounds provided herein (specifically, compounds M1-M279 identified in Table 1) as an electron transport layer on the hole blocking layer at a rate of 0.1 nm / s and a total film thickness of 25 nm;

[0131] (8) LiF was vacuum evaporated on the electron transport layer as an electron injection layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0132] (9) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0133] Device Examples 1-11, Device Comparative Examples 1-2

[0134] An organic electroluminescent device was prepared. The only difference between the device example and the device example is that the materials of the electron transport layer are the compounds shown in Table 1; the other layers, thicknesses, materials and preparation methods are the same as those of the device example.

[0135] In device comparative examples 1-2, the following prior art compounds D1 and D2 are used as electron transport layer materials instead of the compounds in the present disclosure. The specific structural formulas are shown below:

[0136] D1 to D3 are compounds described in patent documents CN13651836A and KR102019005335, respectively. The methods for obtaining them refer to the corresponding patent documents.

[0137] Device performance test:

[0138] (1) Operating voltage: The voltage applied to the device at a brightness of 1000 nit;

[0139] (2) LT97 life: Use a luminance meter at 40mA / cm 2 Initial brightness of the device at a given current density. Maintaining a constant current, measure the time (in hours) for the device brightness to drop to 97% of the initial brightness. Taking the LT97 life test value of Comparative Example 1 as 1.0, calculate the ratio of the LT97 life test values ​​of the other devices to the LT97 life test value of Comparative Example 1.

[0140] (3) External quantum efficiency: The external quantum efficiency (EQE, %) of the device was obtained by using the integrating sphere method.

[0141] The test results are shown in Table 1.

[0142] Table 1:

[0143] Combined with the data in Table 1, it can be seen that the compounds provided by the present disclosure, as electron transport layer materials of organic electroluminescent devices, can reduce the operating voltage of the device, significantly extend the lifespan, improve the luminous efficiency, and the device has better stability and efficiency.

[0144] Device Example 12

[0145] A stacked organic electroluminescent device is prepared, comprising an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a charge generation layer, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0146] (1) A glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0147] (2) placing the glass substrate with the anode in a vacuum chamber and evacuating the chamber to a pressure of less than 1×10-5 Pa, and vacuum-depositing a mixture of HT-4 and HI-3 (97 / 3, w / w) as a hole injection layer on the anode layer at a deposition rate of 0.1 nm / s to a film thickness of 10 nm;

[0148] (3) Vacuum evaporation of compound HT-4 on the hole injection layer as a hole transport layer at a deposition rate of 0.1 nm / s and a total deposition thickness of 30 nm;

[0149] (4) Vacuum evaporation of compound HT-40 as an electron blocking layer on the hole transport layer at a deposition rate of 0.1 nm / s and a total deposition thickness of 5 nm;

[0150] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer comprises a ternary mixture of PH-61:PH-3:GPD-12 (100:100:20, w / w / w) at a deposition rate of 0.1 nm / s and a total film thickness of 40 nm;

[0151] (6) Vacuum evaporation of compound ET-23 as a hole blocking layer on the light-emitting layer at a rate of 0.1 nm / s and a total film thickness of 5 nm;

[0152] (7) A mixture of compounds ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole-blocking layer as an electron transport layer at a deposition rate of 0.1 nm / s to a total film thickness of 25 nm;

[0153] (8) Vacuum evaporation of a charge generation layer on the electron injection layer. The charge generation layer is a binary mixture of transition metal M1:Yb (100:3, w / w) at a deposition rate of 0.1 nm / s and a thickness of 10 nm.

[0154] (9) A mixture of compounds HT-4:HI-3 (92.5 / 7.5, w / w) was vacuum-deposited on the charge generation layer as a hole injection layer at a deposition rate of 0.1 nm / s to a film thickness of 10 nm.

[0155] (9) Vacuum evaporating layers (3) to (7) in sequence on the charge generation layer;

[0156] (10) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0157] Device Examples 13-20, Device Comparative Examples 3-4

[0158] The preparation methods of the organic electroluminescent devices of Examples 13-20 differ from those of Device Example 12 only in that they use the compounds shown in Table 2; other layers, thicknesses, materials, and preparation methods are the same as those of Device Example 12.

[0159] In device comparative examples 3-4, the above-mentioned prior art compounds D1 and D2 were used as charge generation layer materials instead of the compounds disclosed herein.

[0160] Device performance test:

[0161] (1) Working voltage: Use current density of 10mA / cm 2 The voltage applied to the device under the conditions;

[0162] (2) LT97 life: Use a luminance meter at 40mA / cm 2 Initial brightness of the device at a given current density. Maintaining a constant current, measure the time (in hours) for the device brightness to drop to 97% of the initial brightness. Taking the LT97 life test value of Comparative Example 1 as 1.0, calculate the ratio of the LT97 life test values ​​of the other devices to the LT97 life test value of Comparative Example 1.

[0163] (3) External quantum efficiency: The external quantum efficiency (EQE, %) of the device was obtained by using the integrating sphere method.

[0164] The test results are shown in Table 2.

[0165] Table 2:

[0166] Combined with the data in Table 2, it can be seen that using the compounds provided by the present disclosure as the charge generation layer material of the stacked organic electroluminescent device, the device has obvious advantages in terms of operating voltage, efficiency and lifespan.

[0167] Compared with compound D1, the compound disclosed herein removes the substituent on o-phenanthroline, thereby reducing the intermolecular steric hindrance and increasing the coordination ability between the molecule and Yb, thereby inhibiting the migration of Yb under the action of an electric field and facilitating the reduction of the driving voltage.

[0168] Compared with compound D2, the disclosed compound requires substitution at multiple sites on the central benzene ring, which is beneficial to expand the conjugated skeleton of the molecule, reduce the LUMO energy level, increase electron mobility, and improve the carrier balance in the device.

[0169] The specific embodiments described above further illustrate the purpose, technical solutions and beneficial effects of the present disclosure. It should be understood that the above are only specific embodiments of the present disclosure and are not intended to limit the present disclosure. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present disclosure should be included in the scope of protection of the present disclosure.

Claims

1. An organic compound having a structure as shown in the general formula (1): In formula (1), R1, R2, R3, and R4 are each independently selected from one or a combination of hydrogen, deuterium, a substituted or unsubstituted C1-C20 linear alkyl group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, or a substituted or unsubstituted C3-C30 heteroaryl group; And at least two of R2, R3, and R4 are not H at the same time; Two adjacent ones of R2, R3, and R4 are not connected, or two adjacent ones of R2, R3, and R4 are connected to form a ring; When R2, R3, and R4 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, R2, R3, and R4 are each independently connected to the connected benzene ring by a single bond or by fusion; X1, X2, X3, and X4 are each independently N or CR, and at least one of them is N; The R is selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; When the above-mentioned R1-R4 and R each independently have a substituent, the substituent is each independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 aromatic boron, and C3-C30 heteroaryl.

2. The organic compound according to claim 1, characterized in that It has a structure as shown in formula (1-1): In formula (1-1), the definition ranges of R1, R2, X1, X2, X3, and X4 are the same as those in formula (1); R5, R6, R7, and R8 are each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C20 alkenyl, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Two adjacent ones of R5, R6, R7, and R8 are not connected, or two adjacent ones of R5, R6, R7, and R8 are connected to form a ring.

3. The organic compound according to claim 1 or 2, characterized in that In formula (1) and formula (1-1), X1, X2, X3, and X4 are all N.

4. The organic compound according to claim 1 or 2, characterized in that In formula (1) and formula (1-1), R1 is hydrogen.

5. The organic compound according to claim 1 or 2, characterized in that In formula (1) and formula (1-1), R2, R3, R4, R5, R6, R7, and R8 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, and phenanthroline, or a combination of two thereof.

6. The organic compound according to claim 3, characterized in that In the formula (1) and the formula (1-1), one or more of the hydrogen atoms in the phenanthroline group are deuterated.

7. The organic compound according to claim 1 or 2, characterized in that The compound has the structure shown below:

8. A stacked organic electroluminescent device, comprising the following structure: an anode, a cathode, at least two electroluminescent units arranged between the anode and the cathode, and a charge generation layer arranged between two adjacent electroluminescent units, wherein each electroluminescent unit comprises at least a hole transport layer, an electron transport layer and an organic light-emitting layer, characterized in that: The charge generation layer is composed of a main material and a dopant, wherein the dopant is a lanthanide metal, and the main material has a structure as shown in formula (1): In formula (1), R1, R2, R3, and R4 are each independently selected from hydrogen, a substituted or unsubstituted C1-C20 linear alkyl group, a substituted or unsubstituted C3-C20 cyclic alkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C1-C20 alkyl One or a combination of two of amino, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroaryl; And at least two of R2, R3, and R4 are not H at the same time; Two adjacent ones of R2, R3, and R4 are not connected, or two adjacent ones of R2, R3, and R4 are connected to form a ring; When R2, R3, and R4 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, R2, R3, and R4 are each independently connected to the connected benzene ring by a single bond or by fusion; X1, X2, X3, and X4 are each independently N or CR, and at least one of them is N; The R is selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; When substituents are independently present on the above-mentioned R1-R4 and R, the substituents are independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C60 aromatic boron, and C3-C30 heteroaryl.

9. The stacked organic electroluminescent device according to claim 8, characterized in that: In formula (1), X1, X2, X3, and X4 are all N; The dopant in the charge generation layer is selected from one of the following metals: La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb or Lu; The doping mass percentage of the dopant in the charge generation layer in the host material is 1%-50%.

10. The stacked organic electroluminescent device according to claim 8, characterized in that: The dopant in the charge generation layer is selected from Yb; The doping mass percentage of the dopant in the charge generation layer in the main material is 1%-30%, and preferably the doping mass percentage is 1%-10%.

11. The stacked organic electroluminescent device according to claim 8, characterized in that: The main material in the charge generation layer has a structure as shown in formula (1-1): In formula (1-1), the definition ranges of R1, R2, X1, X2, X3, and X4 are the same as those in formula (1); R5, R6, R7, and R8 are each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Two adjacent ones of R5, R6, R7, and R8 are not connected, or two adjacent ones of R5, R6, R7, and R8 are connected to form a ring.

12. Use of the organic compound according to claim 1, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the application is as an electron transport layer material in an organic electronic device or as a charge generation layer material in a stacked device.

13. A display device, characterized in that: The display device comprises the stacked organic electroluminescent device as claimed in claim 8.

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