Organic compound and laminated organic electroluminescent device

Abstract

The invention relates to an organic compound, and also relates to a laminated organic light-emitting device, which specifically comprises a charge generation layer. Belongs to the technical field of photoelectric display devices. The organic compound has a structure as shown in a general formula (1). According to the laminated organic light-emitting device, the voltage of the device can be effectively reduced, the efficiency of the device is improved, and the service life of the device is prolonged. # imgabs0 #

Description

Technical Field

[0001] The invention relates to an organic compound, belonging to the technical field of organic light-emitting materials. The invention also relates to a laminated organic electroluminescent device, specifically comprising 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 very suitable for manufacturing on flexible substrates. Beautiful and cool optoelectronic products can be designed and produced according to demand, gaining unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

[0003] The core of OLED devices 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, luminescent host materials and luminescent guest (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] With the widespread use of OLEDs in small and medium-sized display screens, new OLED screens require normal use under strong light, while medium and large-sized OLED screens have higher requirements for brightness and life. Therefore, a new OLED structure, the stacked OLED structure, came into being. The stacked device structure connects multiple light-emitting units in layers through a charge generation layer (CGL). Compared with traditional single-light-emitting unit devices, stacked OLEDs with multiple light-emitting units often have doubled current efficiency and luminous brightness. At the same brightness, the required current density is also reduced by multiples; at the same time, multiple luminous center layers are also conducive to exciton separation, reducing the exciton density in the light-emitting layer inside the device, significantly increasing the working life, and effectively avoiding the trade-off between high brightness and long life. Compared with single-layer OLED devices, the brightness of double-layer stacked structure devices can be increased by 2 times and the service life can be extended by 4 times. If it is applied to smartphones, it can reduce power consumption by about 30%, which means that the mobile phone can be equipped with a smaller battery and the body thickness can be thinner. Currently, LCG has mass-produced laminated OLED automotive products. Apple and BOE are trying to use this technology in 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.

[0005] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, life span, cost, etc. Through careful thinking and continuous experiments, the researchers of the present invention have discovered an ingenious molecular design scheme for the charge generation layer, which is described in detail below. Surprisingly, the compounds disclosed in the present invention are very suitable for application in OLED and can effectively improve the performance of the device. Summary of the invention

[0006] The present invention provides an organic compound, specifically a phenanthroline compound, having a structure as shown in the general formula (1):

[0007]

[0008] 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 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 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0009] And at least two of R2, R3, and R4 are not H at the same time;

[0010] 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;

[0011] 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;

[0012] X1, X2, X3, and X4 are each independently N or CR, and at least one of them is N;

[0013] 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;

[0014] 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.

[0015] Furthermore, the compound of the present invention has a structure as shown in formula (1-1):

[0016]

[0017] In formula (1-1), the definition ranges of R1, R2, X1, X2, X3, and X4 are the same as those in formula (1);

[0018] 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;

[0019] 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.

[0020] In the present invention, 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 invention, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0021] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0022] In the present specification, 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.

[0023] In the present specification, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0024] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes thereof. For example, the expression "hydrogen (H)" includes its isotopes. 1 H (hydrogen or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13 C, etc., no further details.

[0025] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0026] In the present specification, examples of halogen include fluorine, chlorine, bromine, and iodine.

[0027] In the present invention, unless otherwise specified, aryl and heteroaryl include both monocyclic and condensed ring forms.

[0028] In the present invention, 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, etc.

[0029] The C3-C60 can all 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, etc.

[0030] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0031] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0032] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0033] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0034] The C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0035] In the present invention, the substituted or unsubstituted C6-C60 aryl includes a monocyclic aryl and a condensed aryl, preferably a C6-C30 aryl, and more preferably a C6-C20 aryl. The so-called monocyclic aryl 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 includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl 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. Condensed aryl 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 to condense each other. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, peryl, 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 fluorene derivative group 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.

[0036] The C3-C60 heteroaryl mentioned in the present invention includes monocyclic heteroaryl and condensed ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and more preferably C5-C12 heteroaryl. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl. When the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl include furanyl, thienyl, pyrrolyl, pyridyl, etc. Condensed ring heteroaryl 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 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, indolocarbazolyl and the like.

[0037] The aryloxy group in the present invention includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0038] In the present invention, arylamino represents a group formed by substituting one or two aryl groups for hydrogen on amino, wherein the connection point of the arylamino can be connected to the aryl group in the arylamino or to N in the arylamino, and the exemplary carbon number and specific group of the aryl group in the arylamino are the same as described above.

[0039] Examples of the C6-C30 arylamino group mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, and biphenylamino.

[0040] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.

[0041] The chain alkyl mentioned in the present invention, unless otherwise specified, includes straight chain alkyl and branched chain alkyl. Specifically, the substituted or unsubstituted C1-C30 chain alkyl is preferably a substituted or unsubstituted C1-C16 chain alkyl, and more preferably a substituted or unsubstituted C1-C10 chain alkyl. The substituted or unsubstituted C1-C10 chain alkyl includes, for example, 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, 2-ethylhexyl, etc.

[0042] In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein the monocycloalkyl group refers to an alkyl group containing a single cyclic structure; the 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.

[0043] In the present specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of the C1-C10 alkoxy group 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, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0044] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0045] Furthermore, in formula (1) and formula (1-1), X1, X2, X3, and X4 are all N.

[0046] Furthermore, in formula (1) and formula (1-1), R1 is hydrogen.

[0047] Furthermore, 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.

[0048] Further, as preferred structures of the organic compounds of the present invention, the following specific compounds M1-M279 can be cited, but are not limited to these compounds:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] In a second aspect, the present invention provides a stacked organic electroluminescent device, in which a charge generation layer is formed by a specific material combination. The use of such a device structure can effectively reduce the device voltage and improve the device efficiency and life.

[0074] 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 doping body and a dopant, the dopant is a lanthanide metal, and the doping body has a structure as shown in formula (1).

[0075]

[0076] 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 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 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0077] And at least two of R2, R3, and R4 are not H at the same time;

[0078] 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;

[0079] 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;

[0080] X1, X2, X3, and X4 are each independently N or CR, and at least one of them is N;

[0081] 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;

[0082] 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.

[0083] Furthermore, in the stacked organic electroluminescent device of the present invention, 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; preferably Yb;

[0084] The doping mass percentage of the dopant in the charge generation layer in the main material is 1%-50%, preferably 1%-30%, and more preferably 1%-10%.

[0085] Preferably, the host material in the charge generation layer has a structure as shown in formula (1-1):

[0086]

[0087] In formula (1-1), the definition ranges of R1, R2, X1, X2, X3, and X4 are the same as those in formula (1);

[0088] 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;

[0089] 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.

[0090] The preparation process of the main material in the charge generation layer of the present invention is simple and easy, the raw materials are easily available, it is suitable for mass production and is very suitable for industrial applications.

[0091] The stacked organic electroluminescent device of the present invention adopts a special charge generation layer scheme arranged between adjacent light-emitting units in the device, and the charge generation layer is formed by matching a doped host material with a bisphenanthroline structure and Yb. Through the coordination effect of the bisphenanthroline structure in the doped host material, the migration of Yb can be effectively suppressed, so that the voltage and life of the device are improved. At the same time, by introducing a substituent on the biphenyl ring in the middle of the bisphenanthroline structure, the electron transmission performance is improved, thereby reducing the device voltage and increasing the device efficiency and life.

[0092] In a second aspect, the present invention provides a use of the organic compound as described above, wherein the compound is used in an organic electronic device.

[0093] Preferably, 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 is further preferably applied to an organic electroluminescent device.

[0094] Preferably, the compound is used as an electron transport layer material in an organic electroluminescent device or as a charge generation layer material in a stacked device.

[0095] As a fourth aspect of the present invention, a display device using the laminated organic electroluminescent device of the present invention is provided. The display device prepared using the laminated organic electroluminescent device of the present invention has low operating voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturers for high-performance materials. DETAILED DESCRIPTION

[0096] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0097] The organic compound provided by the present invention can be obtained by a known method, for example, by a known organic synthesis method. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other known methods.

[0098] In a specific embodiment, the polycyclic aromatic compound can be prepared by the following synthetic route:

[0099]

[0100] Wherein, R1, R2, R3, and R4 have the same definitions as above; Pd(PPh3)4 is tetrakistriphenylphosphine palladium, and K2CO3 is potassium carbonate.

[0101] It should be noted that obtaining the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the polycyclic aromatic compounds proposed in the present invention. The compounds for which the synthesis method is not mentioned in the present invention are all raw materials obtained from commercial channels, or are prepared by these raw materials according to known methods.

[0102] The solvents and reagents used in the present invention can all be purchased from the chemical product market.

[0103] The specific preparation methods of the compounds of the present invention are described in detail below using a number of synthesis examples, but the preparation methods of the present invention are not limited to these synthesis examples.

[0104] The structural analysis of the intermediates and compounds in the present invention was performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0105] Synthesis Example 1: Synthesis of M1

[0106]

[0107] Synthesis of intermediate M1-1:

[0108] At room temperature, M1-0 (20.0 g), phenylboronic acid (5.0 g), Pd (PPh3) 4 (2.4 g), K2CO3 (11.3 g), 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (PE: DCM = 50: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 13.7 g of a white solid with a yield of 86.1%.

[0109] The molecular ion mass determined by mass spectrometry was: 387.91 (theoretical value: 387.93).

[0110] Synthesis of M1:

[0111] At room temperature, M1-1 (10.0 g), A1 (7.9 g), Pd (PPh3) 4 (1.5 g), K2CO3 (7.1 g), 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, heated to 90°C and reacted overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (MeOH: DCM = 20: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 12.9 g of a white solid with a yield of 85.3%.

[0112] The molecular ion mass determined by mass spectrometry was: 586.17 (theoretical value: 586.22).

[0113] Synthesis Example 2: Synthesis of M9

[0114]

[0115] Synthesis of intermediate M9-1:

[0116] At room temperature, M9-0 (20.0 g), A1 (21.4 g), Pd (PPh3) 4 (4.0 g), K2CO3 (19.3 g), 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, heated to 90°C and reacted overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (MeOH: DCM = 20: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 30.1 g of a white solid with a yield of 88.8%.

[0117] The molecular ion mass determined by mass spectrometry was: 484.10 (theoretical value: 484.17).

[0118] Synthesis Example 3: Synthesis of M51

[0119]

[0120] Synthesis of intermediate M51-1:

[0121] At room temperature, M51-0 (20.0 g), A2 (16.7 g), Pd (PPh 3) 4 (3.2 g), K 2 CO 3 (15.2 g), 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 90 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (PE: DCM = 50: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 20.7 g of a white solid with a yield of 81.7%.

[0122] The molecular ion mass determined by mass spectrometry was: 461.92 (theoretical value: 461.94).

[0123] Synthesis of M51:

[0124] At room temperature, M51-1 (10.0 g), A1 (13.3 g), Pd (PPh3) 4 (1.3 g), K2CO3 (6.0 g), 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, heated to 90°C and reacted overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (MeOH: DCM = 20: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 11.2 g of a white solid with a yield of 78.3%.

[0125] The molecular ion mass determined by mass spectrometry was: 660.20 (theoretical value: 660.23).

[0126] Synthesis Example 4: Synthesis of M123

[0127]

[0128] At room temperature, M123-0 (10.0 g), A1 (27.6 g), Pd (PPh 3) 4 (2.6 g), K 2 CO 3 (6.2 g), 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 90 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (PE: DCM = 50: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 15.3 g of a white solid with a yield of 80.7%.

[0129] The molecular ion mass determined by mass spectrometry was: 840.21 (theoretical value: 840.27).

[0130] Synthesis Example 5: Synthesis of M157

[0131]

[0132] Synthesis of intermediate M157-1:

[0133] At room temperature, M157-0 (20.0 g), A3 (9.9 g), Pd (PPh 3) 4 (2.8 g), K 2 CO 3 (13.4 g), 1, 4-dioxane / water (500 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 90 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (PE: DCM = 50: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 14.3 g of a white solid with a yield of 81.3%.

[0134] The molecular ion mass determined by mass spectrometry was: 560.16 (theoretical value: 560.20).

[0135] Synthesis of M157:

[0136] At room temperature, M157-1 (10.0 g), A1 (16.9 g), Pd (PPh3) 4 (1.6 g), K2CO3 (7.6 g), 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, heated to 90°C and reacted overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (MeOH: DCM = 20: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 12.2 g of a white solid with a yield of 78.8%.

[0137] The molecular ion mass determined by mass spectrometry was: 560.23 (theoretical value: 560.20).

[0138] Synthesis Example 6: Synthesis of M218

[0139]

[0140] Synthesis of intermediate M218-1:

[0141] At room temperature, M218-0 (20.0 g), A4 (15.4 g), Pd (PPh3) 4 (3.2 g), K2CO3 (15.2 g), 1,4-dioxane / water (500 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 90°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (PE: DCM = 50: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 21.3 g of a white solid with a yield of 88.7%.

[0142] The molecular ion mass determined by mass spectrometry was: 437.86 (theoretical value: 437.94).

[0143] Synthesis of M218:

[0144] At room temperature, M218-1 (10.0 g), A1 (14.0 g), Pd (PPh3) 4 (1.3 g), K2CO3 (6.3 g), 1,4-dioxane / water (250 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, heated to 90°C and reacted overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (MeOH: DCM = 20: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 11.4 g of a white solid with a yield of 78.5%.

[0145] The molecular ion mass determined by mass spectrometry was: 636.25 (theoretical value: 636.23).

[0146] Synthesis Example 7: Synthesis of M266

[0147]

[0148] Synthesis of intermediate M266-1:

[0149] At room temperature, M266-0 (20.0 g), A1 (38.2 g), Pd (PPh3) 4 (3.6 g), K2CO3 (17.3 g), 1,4-dioxane / water (1000 ml, 4 / 1) were added to a 1L single-mouth bottle, replaced with nitrogen three times, heated to 90°C and reacted overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (MeOH: DCM = 20: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 27.6 g of a white solid with a yield of 85.2%.

[0150] The molecular ion mass determined by mass spectrometry was: 518.13 (theoretical value: 518.13).

[0151] Synthesis of M266:

[0152] At room temperature, M266-1 (10.0 g), A5 (3.7 g), Pd2 (dba) 3 (0.6 g), tri-tert-butyl phosphine (1.9 g), sodium tert-butoxide (7.8 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated, extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, which was washed with petroleum ether to obtain 10.3 g of a white solid, with a yield of 79.0%.

[0153] The molecular ion mass determined by mass spectrometry was: 676.26 (theoretical value: 676.24).

[0154] Device Embodiment

[0155] Implementation

[0156] OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material 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, a charge generation layer, etc.

[0157] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0158] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material 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 is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0159] 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.

[0160] 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 a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of 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.

[0161] 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.

[0162]

[0163]

[0164]

[0165]

[0166] 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 compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0167]

[0168] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0169] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0170] In one aspect of the present invention, 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.

[0171]

[0172] In one aspect of the present invention, the barrier layer around the light-emitting layer can be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0173]

[0174]

[0175]

[0176]

[0177] 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.

[0178]

[0179]

[0180]

[0181] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but 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.

[0182] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0183] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0184]

[0185]

[0186]

[0187]

[0188] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0189] 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.

[0190] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0191] 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.

[0192] Device Embodiment

[0193] An organic electroluminescent device comprises 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:

[0194] (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;

[0195] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the vacuum chamber to a pressure less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-4:HI-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0196] (3) vacuum evaporating compound HT-4 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0197] (4) vacuum evaporating compound HT-14 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0198] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein 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 evaporation film thickness of 20 nm;

[0199] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0200] (7) vacuum evaporating a mixture of the compounds (M1-M279) provided by the present invention and ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0201] (8) Vacuum evaporating LiF on the electron transport layer as an electron injection layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0202] (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.

[0203] Device Examples 1-11, Device Comparative Examples 1-2

[0204] An organic electroluminescent device, which differs from the device embodiment only in that the materials of the electron transport layer are the compounds shown in Table 1; other layers, thicknesses, materials and preparation methods are the same as those of the device embodiment.

[0205] In device comparative examples 1-2, the following prior art compounds D1 and D2 are used as electron transport layer materials to replace the compounds of the present invention, and the specific structural formula is shown below:

[0206]

[0207] Device performance test:

[0208] (1) Operating voltage: the voltage applied to the device at a brightness of 1000 nit;

[0209] (2) LT97 life: Use a brightness meter at 40mA / cm 2 The initial brightness value of the device under the current density is measured by maintaining a constant current and measuring the time for the device brightness to drop to 97% of the initial brightness, in hours; the LT97 life test value of the device comparative example 1 is recorded as 1.0, and the ratio of the LT97 life test value of other devices to the LT97 life test value of the device comparative example 1 is calculated;

[0210] (3) External quantum efficiency: The external quantum efficiency (EQE, %) of the device was measured using the integrating sphere method.

[0211] The test results are shown in Table 1.

[0212] Table 1:

[0213]

[0214] Combined with the data in Table 1, it can be seen that the compounds provided by the present invention, as electron transport layer materials of organic electroluminescent devices, can reduce the operating voltage of the device, significantly extend the life, improve the luminous efficiency, and the device has better stability and efficiency.

[0215] Device Example 12

[0216] A stacked organic electroluminescent device comprises 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:

[0217] (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;

[0218] (2) placing the glass substrate with the anode in a vacuum chamber, evacuating the vacuum to less than <1×10-5Pa, and vacuum evaporating a mixture of compounds HT-4:HI-3 (97 / 3, w / w) on the anode layer as a hole injection layer at a evaporation rate of 0.1nm / s and a evaporation film thickness of 10nm;

[0219] (3) vacuum evaporating compound HT-4 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 30 nm;

[0220] (4) vacuum evaporating compound HT-40 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0221] (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), with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 40 nm;

[0222] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0223] (7) vacuum evaporating a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0224] (8) vacuum evaporating a charge generation layer on the electron injection layer, wherein 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;

[0225] (9) placing the glass substrate with the anode in a vacuum chamber, evacuating the vacuum to less than <1×10-5Pa, and vacuum evaporating a mixture of compounds HT-4:HI-3 (92.5 / 7.5, w / w) on the anode layer as a hole injection layer at a evaporation rate of 0.1nm / s and a evaporation film thickness of 10nm;

[0226] (9) vacuum evaporating layers (3) to (7) in sequence on the charge generation layer;

[0227] (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.

[0228] Device Examples 13-20, Device Comparative Examples 3-4

[0229] An organic electroluminescent device, which differs from device embodiment 12 only in that the compounds are shown in Table 2; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 12.

[0230] In device comparative examples 3-4, the above-mentioned prior art compounds D1 and D2 are used as charge generation layer materials instead of the compounds of the present invention.

[0231] Device performance test:

[0232] (1) Working voltage: Use current density of 10mA / cm 2 The voltage applied to the device under the conditions;

[0233] (2) LT97 life: Use a brightness meter at 40mA / cm 2 The initial brightness value of the device under the current density is measured by maintaining a constant current and measuring the time for the device brightness to drop to 97% of the initial brightness, in hours; the LT97 life test value of the device comparative example 1 is recorded as 1.0, and the ratio of the LT97 life test value of other devices to the LT97 life test value of the device comparative example 1 is calculated;

[0234] (3) External quantum efficiency: The external quantum efficiency (EQE, %) of the device was measured using the integrating sphere method.

[0235] The test results are shown in Table 2.

[0236] Table 2:

[0237]

[0238]

[0239] Combined with the data in Table 2, it can be seen that using the compound provided by the present invention as the charge generation layer material of the stacked organic electroluminescent device, the device has obvious advantages in terms of operating voltage, efficiency and life span.

[0240] Compared with compound D1, the compound of the present invention removes the substituent on o-phenanthroline, so that the intermolecular steric hindrance is reduced, the coordination ability between the molecule and Yb is increased, and the migration of Yb under the action of the electric field can be inhibited, which is beneficial to the reduction of the driving voltage.

[0241] Compared with compound D2, the compound of the present invention 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 the electron mobility, and improve the carrier balance in the device.

[0242] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above description is only a specific embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

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 two of hydrogen, 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, and 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 1 or 2, characterized in that The compound has the structure shown below:

7. 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 one or a combination of two of 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 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, and 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 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.

8. The stacked organic electroluminescent device according to claim 7, 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%.

9. The stacked organic electroluminescent device according to claim 7, 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%; More preferably, the doping mass percentage is 1%-10%.

10. The stacked organic electroluminescent device according to claim 7, 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.

11. 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.

12. A display device, characterized in that: The display device comprises the stacked organic electroluminescent device as claimed in claim 7.

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