An organic compound, application thereof, and an organic electroluminescence device using the same

Abstract

This invention relates to an organic compound, and more specifically, to a compound for use in organic electroluminescent devices (OLEDs) and OLEDs employing such compounds. The organic compound of this invention has the following structure. The compound employs a B-N resonance structure, which is beneficial for improving luminous efficiency and narrowing the spectrum. Simultaneously, the alternating HOMO and LUMO distributions of the molecule on adjacent atoms give the molecule certain TADF properties, which are beneficial for improving luminous efficiency and extending lifetime. When the compound of this invention is used in organic electroluminescent devices, particularly as a light-emitting layer material, it can effectively improve carrier transport balance in the device, thereby ensuring that the device achieves excellent results with high luminous efficiency and low start-up voltage.

Description

Technical Field

[0001] This invention relates to an organic compound, and more particularly to a compound for use in organic electroluminescent devices and organic electroluminescent devices employing such compounds. Background Technology

[0002] Currently, optoelectronic devices using organic materials are becoming increasingly popular for several reasons. Many of the materials used to manufacture these devices are relatively inexpensive, giving optoelectronic devices a potential cost advantage compared to inorganic devices. Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, meet, and recombine in the organic layer to emit light. Due to their advantages such as high brightness, fast response, wide viewing angle, simple manufacturing process, and flexibility, OLED devices have attracted significant attention in the fields of new display technology and new lighting technology. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and will further expand into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] With the continuous advancement of OLEDs in both lighting and display fields, research on their core materials has become increasingly focused. In the structures of organic light-emitting diodes (OLEDs) for display and lighting, blue fluorescence is typically combined with red and green phosphorescent materials. Recently, a literature report describes an ultrapure blue fluorescent dye (BN) compound based on TADF (Thermally Activated Delayed Fluorescence). This type of compound is based on triphenylboron and contains two nitrogen atoms, forming a rigid polycyclic aromatic skeleton. Nitrogen atoms exhibit an opposite resonance effect to boron atoms, and this opposite resonance effect is enhanced at their para positions. Therefore, this effect can clearly separate HOMO and LUMO orbitals. Calculated molecular orbitals of DABNA-1 show that LUMO orbitals are distributed at the boron atom and its ortho and para positions, while HOMO orbitals are distributed at the nitrogen atom and its meta positions. The emission of DABNA-1 is at 459 nm with a full width at half maximum (FWHM) of 28 nm, CIE coordinates (0.13, 0.09), and a maximum external quantum yield of 13.5%. The emission of DABNA-2 after the introduction of substituents is at 467 nm with a full width at half maximum (FWHM) of 28 nm and CIE coordinates of (0.12, 0.13), and the maximum external quantum yield is increased to 20.2%. However, the molecule's emission is too bluish and its hole transport performance is poor, which is not conducive to mass production applications.

[0004]

[0005] Boron (BN) compounds, based on triphenylboron, contain two nitrogen atoms, forming a rigid polycyclic aromatic skeleton. The nitrogen atom exhibits a resonance effect opposite to that of the boron atom, and this opposite resonance effect is enhanced at the para position. Therefore, this effect can clearly separate HOMO and LUMO orbitals. However, the emission spectra of BN-formed compounds are excessively blue, and their hole transport performance is poor, hindering mass production applications. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention provides an organic compound belonging to thermally activated delayed fluorescence materials. This invention also provides a method for applying this type of compound to OLED devices and an organic electroluminescent device employing this type of compound.

[0007] The organic compound of this invention has the structure shown in general formula (1):

[0008]

[0009] In equation (1):

[0010] Ring A, ring D, ring E and ring F are each independently selected from one of substituted or unsubstituted C5-C30 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings, and ring A and ring D are not connected to form a ring;

[0011] When substituents are present on rings A, D, E, and F, the substituents are selected from halogens, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. The substituents are independently linked to the connected aromatic or heteroaromatic rings to form a ring or not. When there are multiple substituents, any two adjacent substituents can be linked to each other to form a ring through chemical bonds.

[0012] X is selected from O, S, NR 1 CR 2 R 3 SiR 4 R 5 One of them;

[0013] The R 1 ~R 5Each of the following is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0014] When the above groups contain substituents, the substituents are selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0015] The rings A, D, E, and F are each independently selected from one of the substituted or unsubstituted C5-C14 aromatic rings and the substituted or unsubstituted C3-C14 heteroaromatic rings.

[0016] Preferably, ring A, ring D, ring E, and ring F are each independently selected from one of substituted or unsubstituted C5-C8 aromatic rings and substituted or unsubstituted C5-C8 heteroaromatic rings;

[0017] When substituents are present on rings A, D, E, and F, the substituents are selected from halogens, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. The substituents are independently linked to the connected aromatic or heteroaromatic rings to form a ring or not. When there are multiple substituents, any two adjacent substituents can be linked to each other to form a ring through chemical bonds.

[0018] When the above groups contain substituents, the substituents are selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0019] Furthermore, the general formula compounds of the present invention have the structure shown in formula (1-1):

[0020]

[0021] In equation (1-1), the definitions of ring A, ring D, and X are the same as those in equation (1);

[0022] The Z 1 ~Z 5 Selected independently from CR 6 Or N, the R 6 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 6 The R can be independently linked to an aromatic ring or heteroaromatic ring to form a ring, or not linked to an aromatic ring to form a ring. 6 When there are multiple, any two adjacent ones can be linked together by chemical bonds to form a ring;

[0023] When the above groups contain substituents, the substituents are selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0024] Furthermore, the general formula compounds of the present invention have structures as shown in formulas (1-2):

[0025]

[0026] In equation (1-2), the definition of X is the same as that in equation (1), and the definition of Z is... 1 ~Z 5 The definition is the same as the definition in equation (1-1);

[0027] The Y 1 ~Y 8 Selected independently from CR 7 Or N, the R 7Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 7 The R can be independently linked to an aromatic ring or heteroaromatic ring to form a ring, or not linked to an aromatic ring to form a ring. 7 When there are multiple, any two adjacent ones can be linked together by chemical bonds to form a ring;

[0028] When the above groups contain substituents, the substituents are selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0029] Furthermore, in equations (1), (1-1), and (1-2), X is preferably selected from O, S, and NR. 1 One of them; more preferably, X is NR. 1 .

[0030] Preferably, X is NR 1 The R 1 The structure is shown in equation (4-1):

[0031]

[0032] In equation (4-1), Z 21 ~Z 25 Selected independently from CR 8 Or N, the R 8 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 8 The R can be independently linked to an aromatic ring or heteroaromatic ring to form a ring, or not linked to an aromatic ring to form a ring. 8 When there are multiple, any two adjacent ones can be linked together by chemical bonds to form a ring;

[0033] When the above groups contain substituents, the substituents are selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0034] Further optimization, X is optimized from NR. 1 At that time, the R 1 The structure is shown in equation (4-2):

[0035]

[0036] In equation (4-2), Z 21 ~Z 24 The definitions are all the same as those in equation (4-1);

[0037] The R is selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, and substituted or unsubstituted C1-C20 silyl; when a substituent is present on R, the substituent is selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl;

[0038] Preferably, in formula (4-2), R is selected from substituted or unsubstituted groups of the following:

[0039]

[0040] One of them,

[0041] * indicates the bond position of the substituent group;

[0042] When the above groups contain substituents, the substituents are selected from one or a combination of at least two of the following: halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0043] Furthermore, in equations (1-1) and (1-2), the Z... 1 ~Z 5 Selected independently from CR6 Or N, the R 6 Independently preferred from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; more preferably, the Z 1 ~Z 5 Selected independently from CR 6 The R 6 Independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C5-C30 aryl. Preferably, the Z 1 ~Z 5 Selected independently from CR 6 The R 6 It is hydrogen.

[0044] Furthermore, in equation (1-2), the Y 1 ~Y 8 Selected independently from CR 7 Or N, the R 7 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; more preferably, Y 1 ~Y 8 Selected independently from CR 7 Or N, the R 7 It is independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C5-C30 aryl.

[0045] Preferred, Y 1 ~Y 8 Selected independently from CR 7 The R 7 It is independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C5-C30 aryl.

[0046] Furthermore, in equation (1-2), the Y... 1 Y 4 Y 5 Y 8 Selected independently from CR 7 Or N, the R 7The Y is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl. 2 Y 3 Y 6 Y 7 Selected independently from CR 17 The R 17 The R is independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C5-C30 aryl, wherein the R 17 It can independently connect with the connected aromatic ring to form a ring or not connect to form a ring;

[0047] Preferably, the Y 2 and Y 7 Independent selection from CR 17 The R 17 The Y is independently selected from one of the following: substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C5-C30 aryl. 3 and Y 6 Independently selected from CH;

[0048] Or, the Y 3 and Y 6 Independent selection from CR 17 The R 17 The Y is independently selected from one of the following: substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C5-C30 aryl. 2 and Y 7 Independently selected from CH;

[0049] Preferably, the Y 2 Y 3 Y 6 Y 7 Each substituent is independently selected from CH or from one of the following substituent groups:

[0050]

[0051] * indicates the bond position of the substituent group;

[0052] More preferably, the Y 3 and Y 6 Independently selected from CH, the Y 2 and Y 7 Independently selected from one of the following substituent groups:

[0053]

[0054]

[0055] Or, the Y 2 and Y 7 Independently selected from CH, the Y 3 and Y 6 Independently selected from one of the following substituent groups:

[0056]

[0057] * indicates the bond position where the substituent group is attached.

[0058] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0059] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0060] In this specification, the way a ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0061] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0062] In this invention, a monocyclic aryl group refers to a molecule containing one or at least two phenyl groups. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by single bonds, such as phenyl, diphenyl, terphenyl, etc. Fused-ring aryl groups refer to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused together by sharing ring edges, such as naphthyl, anthracene, etc. 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 other groups are independent of each other and connected by single bonds, such as pyridine, furan, thiophene, etc. Fused-ring heteroaryl groups refer to a molecule formed by the fusion of at least one phenyl group and at least one heteroaryl group, or a molecule formed by the fusion of at least two heteroaryl rings, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0063] The heteroatoms in the present invention generally refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0064] The atomic names described in the present invention include their corresponding various isotopes. For example, hydrogen (H) includes 1 H (protium or also denoted as H), 2 H (deuterium or also denoted as D), etc.; carbon (C) includes 12 C, 13 C, etc.

[0065] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0066] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and polycyclic aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. 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 are connected by single bonds. Exemplarily, 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. The polycyclic aryl group refers to a group in which the molecule contains at least two aromatic rings and the aromatic rings are not independent of each other but are fused to each other by sharing two adjacent carbon atoms. Exemplarily, such as: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, -yl, tetracenyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthryl is selected from 1-anthryl, 2-anthryl, and 9-anthryl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl is selected from 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl. The derivative groups of fluorene are 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'-spirobifluorenyl, and benzofluorenyl.

[0067] The C3-C60 heteroaryl groups mentioned in this invention include monocyclic heteroaryl groups and fused-ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and even more preferably C5-C12 heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When a 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 connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl group refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share a group consisting of two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0068] Specific examples of aryl groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned aryl examples to obtain a divalent group. Specific examples of heteroaryl groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned heteroaryl examples to obtain a divalent group.

[0069] The aryl group in this invention can be exemplified by the monovalent group composed of the above-mentioned aryl and heteroaryl groups and oxygen.

[0070] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0071] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinylamino, pyrimidinylamino, and dibenzofuranylamino.

[0072] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C20 chain alkyl groups are preferably substituted or unsubstituted C1-C16 chain alkyl groups. Examples of 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, 2-ethylhexyl, etc.

[0073] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0074] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C10 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and isopentoxy are preferred, and methoxy is more preferred.

[0075] In this specification, the substituted or unsubstituted C1-C20 silanes and the substituted or unsubstituted C1-C10 silanes are examples of silanes substituted with groups listed in the above C1-C10 silanes, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0076] Examples of preferred structures for the compounds involved in this invention include, but are not limited to, the following compounds:

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] As another aspect of the present invention, the application of the compound as described above in an organic electroluminescent device is also provided. Specifically, the application as a light-emitting layer material in an organic electroluminescent device is preferred, and the application as a light-emitting dye and / or sensitizer in the light-emitting layer of an organic electroluminescent device is more preferred.

[0084] As another aspect of the present invention, an organic electroluminescent device is also provided, comprising a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer contains a compound of general formula (1) as described above, or a compound containing the structure shown in P1 to P139 as described above.

[0085] Specifically, one embodiment of the present invention provides an organic electroluminescent device, including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains a compound of the general formula of the present invention shown in formula (1), formula (1-1), or formula (1-2) above, or contains a compound with a structure of P1 to P139 as shown above.

[0086] The present invention also discloses a display screen or display panel, wherein the display screen or display panel employs the organic electroluminescent device as described above; preferably, the display screen or display panel is an OLED display.

[0087] The present invention also discloses an electronic device having a display screen or display panel, wherein the display screen or display panel employs an organic electroluminescent device as described above.

[0088] OLED devices prepared using the compounds of this invention have low start-up voltage, high luminous efficiency, and better lifespan, which can meet the current requirements of panel manufacturers for high-performance materials.

[0089] The specific reasons why the compounds of the present invention exhibit excellent performance as luminescent dyes and / or sensitizers in the luminescent layer of organic electroluminescent devices are not yet clear, but it is speculated that the following reasons may be true:

[0090] The compounds of this invention introduce a naphthalene ring into the core structure, increasing molecular rigidity and thus improving luminescence efficiency and narrowing the spectrum. The compounds of this invention employ a BN resonance structure, causing the HOMO and LUMO atoms to alternately distribute on adjacent atoms, giving the molecule certain TADF properties, which is beneficial for improving luminescence efficiency and extending lifetime.

[0091] It should be noted that while the possible effects of each group / feature have been described separately for ease of explanation in this application, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0092] In addition, the preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are readily available, and it is suitable for mass production scale-up. Detailed Implementation

[0093] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0094] However, it should be noted that obtaining this compound is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the novel compounds proposed in this invention. Compounds for which synthetic methods are not mentioned in this invention are all raw material products obtained through commercial means, or self-made using these raw material products according to known methods.

[0095] The solvents and reagents used in the synthesis examples, such as dichloromethane, petroleum ether, ethanol, tetrahydrofuran, N,N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole, etc., can all be purchased from domestic chemical product markets, such as from Sinopharm Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, and Bailingwei Reagent Company. Alternatively, those skilled in the art can also synthesize them using well-known methods.

[0096] The analysis and detection of synthetic intermediates and compounds were performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0097] The synthesis method of the compounds of the present invention will be briefly described below.

[0098] Synthesis Example.

[0099] Representative synthetic pathways:

[0100]

[0101] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0102] Synthesis Examples

[0103] Synthesis Example 1: Synthesis of Compound P1

[0104]

[0105] Synthesis of intermediate P1-1:

[0106] At room temperature, 50 g of 1,8-dibromo-7-chloronaphthalene, 156.05 mmol, phenylboronic acid, 43.13 g of potassium carbonate, 1.80 g of tetraphenylphosphine palladium, 500 ml of dioxane, and 100 ml of water were added to a 2 L single-necked flask. The mixture was reacted overnight at 110 °C. Heating was stopped, and after cooling to room temperature, the mixture was filtered through 100-200 mesh silica gel. The solvent was evaporated, and the mixture was subjected to silica gel column chromatography (PE) with the sample mixed to obtain 31.21 g of a white solid product. The molecular ion mass determined by mass spectrometry was 317.61 (theoretical value: 317.61).

[0107] Synthesis of intermediate P1-2:

[0108] At room temperature, P1-1 (30 g, 94.46 mmol), diphenylamine (15.98 g, 94.46 mmol), Pd2(dba)3 (4.32 g, 4.72 mmol), tri-tert-butylphosphine tetrafluoroborate (4.29 g, 9.45 mmol), sodium tert-butoxide (18.16 g, 188.91 mmol), and xylene (600 ml) were added to a 2 L single-necked flask. The flask was purged with nitrogen three times and heated to 130 °C overnight. The reaction mixture was cooled to room temperature and filtered through 100-200 mesh silica gel. The filtrate was concentrated with silica gel and subjected to column chromatography (PE:DMC = 10:1) to obtain 40 g of crude product. Recrystallization from toluene / ethanol yielded 35 g of white solid. The molecular ion mass determined by mass spectrometry was 405.92 (theoretical value: 405.93).

[0109] Synthesis of compound P1:

[0110] Add P1-2 (30.00 g, 73.91 mmol) to a 1000 mL three-necked flask, add o-xylene (300 mL), purge with nitrogen three times, and add n-butyllithium solution (147.81 mmol) dropwise to the flask under ice-water bath using a coarse needle. Stir for 1 hour. Under ice-water bath, add boron tribromide (55.54 g, 221.72 mmol) using a coarse needle to the reaction mixture, stir for 30 minutes, heat to 45 °C and stir for 50 minutes. Under ice-water bath, add N,N-diisopropylethylamine (28.66 g, 221.72 mmol) to the reaction system, stir for 30 minutes, heat to 120 °C, and react overnight. Stop heating, and after the system cools to room temperature, quench with water (500 mL). The liquid was separated, and the lower organic phase was collected. The aqueous phase was extracted three times with ethyl acetate (500 ml). The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated with silica gel and subjected to column chromatography to obtain 13 g of crude product. Recrystallization from toluene / ethanol yielded 7.14 g of yellow solid. The molecular ion mass determined by mass spectrometry was 379.27 (theoretical value: 379.27).

[0111] Synthesis Example 2: Synthesis of Compound P4

[0112]

[0113] Synthesis of intermediate P4-1:

[0114] At room temperature, 1,8-dibromo-7-chloronaphthalene (50 g, 156.05 mmol), 4-tert-butylphenylboronic acid (27.78 g, 156.05 mmol), potassium carbonate (43.13 g, 312.10 mmol), tetrakis(triphenylphosphine)palladium (1.80 g, 1.56 mmol), 500 ml dioxane, and 100 ml water were added to a 2 L single-necked flask. The mixture was reacted overnight at 110 °C. Heating was stopped, and after cooling to room temperature, the mixture was filtered through 100-200 mesh silica gel. The solvent was evaporated, and the mixture was subjected to silica gel column chromatography (PE) with the sample mixed, yielding 36.56 g of a white solid product. Mass spectrometry analysis determined the molecular ion mass to be 373.72 (theoretical value: 373.72).

[0115] Synthesis of intermediate P4-2:

[0116] At room temperature, P4-1 (30 g, 80.27 mmol), di-tert-butylaniline (22.59 g, 80.27 mmol), Pd2(dba)3 (3.68 g, 4.01 mmol), tri-tert-butylphosphine tetrafluoroborate (3.65 g, 8.03 mmol), sodium tert-butoxide (15.43 g, 160.55 mmol), and xylene (600 ml) were added to a 2 L single-necked flask. The flask was purged with nitrogen three times and heated to 130 °C overnight. The reaction mixture was cooled to room temperature and filtered through 100-200 mesh silica gel. The filtrate was concentrated with silica gel and subjected to column chromatography (PE:DMC = 10:1) to obtain 44 g of crude product. Recrystallization from toluene / ethanol yielded 41.2 g of a white solid. The molecular ion mass determined by mass spectrometry was 574.25 (theoretical value: 574.25).

[0117] Synthesis of compound P4:

[0118] P4-2 (30.00 g, 52.24 mmol) was added to a 1000 mL three-necked flask, along with o-xylene (300 mL). The flask was purged with nitrogen three times. Under an ice-water bath, a solution of n-butyllithium (104.48 mmol) was added dropwise using a coarse needle. The mixture was stirred for 1 hour. Under an ice-water bath, boron tribromide (39.26 g, 156.73 mmol) was drawn up using a coarse needle and added to the reaction mixture. The mixture was stirred for 30 minutes, then heated to 45 °C and stirred for 50 minutes. Under an ice-water bath, N,N-diisopropylethylamine (20.26 g, 156.73 mmol) was drawn up and added to the reaction system. The mixture was stirred for 30 minutes, then heated to 120 °C and reacted overnight. Heating was stopped, and the system was allowed to cool to room temperature before quenching with 500 mL of water. The liquid was separated, and the lower organic phase was collected. The aqueous phase was extracted three times with ethyl acetate (500 ml). The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated with silica gel and subjected to column chromatography to obtain 16 g of crude product. Recrystallization from toluene / ethanol yielded 8.12 g of yellow solid. The molecular ion mass determined by mass spectrometry was 547.59 (theoretical value: 547.59).

[0119] Synthesis Example 3: Synthesis of Compound P49

[0120]

[0121] Synthesis of intermediate P49-1:

[0122] At room temperature, P1-1 (30 g, 94.46 mmol), naphthaniline (20.71 g, 94.46 mmol), Pd2(dba)3 (4.32 g, 4.72 mmol), tri-tert-butylphosphine tetrafluoroborate (4.29 g, 9.45 mmol), sodium tert-butoxide (18.16 g, 188.91 mmol), and xylene (600 ml) were added to a 2 L single-necked flask. The flask was purged with nitrogen three times and heated to 130 °C overnight. The reaction mixture was cooled to room temperature and filtered through 100-200 mesh silica gel. The filtrate was concentrated with silica gel and subjected to column chromatography (PE:DMC = 10:1) to obtain 45 g of crude product. Recrystallization from toluene / ethanol yielded 32.5 g of a white solid. Mass spectrometry analysis determined the molecular ion mass to be 460.00 (theoretical value: 455.99).

[0123] Synthesis of compound P49:

[0124] Add P49-1 (30.00 g, 65.79 mmol) to a 1000 mL three-necked flask, add o-xylene (300 mL), purge with nitrogen three times, and add n-butyllithium solution (131.58 mmol) dropwise to the flask under ice-water bath using a coarse needle. Stir for 1 hour. Under ice-water bath, add boron tribromide (49.45 g, 197.37 mmol) using a coarse needle to the reaction mixture, stir for 30 minutes, heat to 45 °C and stir for 50 minutes. Under ice-water bath, add N,N-diisopropylethylamine (25.51 g, 197.37 mmol) to the reaction system, stir for 30 minutes, heat to 120 °C, and react overnight. Stop heating, and after the system cools to room temperature, quench with water (500 mL). The liquid was separated, and the lower organic phase was collected. The aqueous phase was extracted three times with ethyl acetate (500 ml). The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated with silica gel and subjected to column chromatography to obtain a crude product of 15 g. Recrystallization from toluene / ethanol yielded 6.08 g of a yellow solid. The molecular ion mass determined by mass spectrometry was 429.33 (theoretical value: 429.33).

[0125] Device Examples

[0126] Implementation

[0127] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. This organic material layer can be further divided into multiple regions. For example, the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.

[0128] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0129] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0130] Organic material layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic material layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0131] The hole transport region is located between the anode and the emissive 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. Alternatively, the hole transport region can be a multilayer structure including at least one 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 emissive layer.

[0132] The material for the hole transport region may be selected from, but is 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 as shown in HT-1 to HT-51 below; or any combination thereof.

[0133]

[0134]

[0135]

[0136] 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 be one or more compounds of HT-1 to HT-51 mentioned above, or one or more compounds of HI-1 to HI-3 mentioned below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 mentioned below.

[0137]

[0138] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0139] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0140] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0141]

[0142] In one aspect of the invention, the light-emitting layer employs thermally activated delayed fluorescence emission technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85 described above.

[0143]

[0144]

[0145]

[0146]

[0147] In one aspect of the invention, the luminescent layer employs thermally activated delayed fluorescence emission technology. The fluorescent dopant in the luminescent layer may be selected from, but is not limited to, one or more combinations of TDE1-TDE37 listed below.

[0148]

[0149]

[0150] 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 employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77 may be employed.

[0151] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0152] In one aspect of the present invention, 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.

[0153]

[0154]

[0155]

[0156]

[0157] 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 employ, but is 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 may be employed.

[0158] The device may also include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations of the following.

[0159] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Yb, Mg.

[0160] Computational Chemistry:

[0161] This invention employs Gaussian O3 to perform quantum chemical calculations on the compounds. Time-correlated density functional theory was used to perform theoretical calculations on the compounds listed in Table 1, and the results are shown in Table 1. The structural formula of the comparative compound C2 is as follows:

[0162]

[0163] Synthesis of compound C2: The specific method is based on the synthesis method in patent document KR1020190078541A, and its description is omitted here.

[0164] Table 1 shows the quantum chemical calculation results of the compounds and comparative examples of this invention.

[0165] Table 1:

[0166]

[0167]

[0168] The fluorescence emission wavelength of the material is related to the first singlet state energy level; the higher the energy level, the shorter the fluorescence emission wavelength and the more bluish the emission. The phosphorescence emission wavelength of the material is related to the first triplet state energy level; the higher the energy level, the shorter the phosphorescence emission wavelength and the more bluish the emission. As can be seen from the calculation results in Table 1, the examples of the compounds of this invention have higher singlet state energies compared to the comparative compound C2, suggesting a shorter emission wavelength and making them more suitable as luminescent materials for blue OLED devices. This may be because the nitrogen atom in the compounds of this invention is located between the benzene ring and the naphthalene ring. This unique connection method results in higher first singlet and first triplet state energy levels in such compounds, thus producing a more bluish emission, which better meets the needs of deep blue OLED devices.

[0169] The fabrication process of the organic electroluminescent device in this embodiment is as follows:

[0170] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a acetone:ethanol mixed solvent, baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0171] The glass substrate with the anode was placed in a vacuum chamber and evacuated to a vacuum level of <1×10⁻⁶. -5Pa, on the aforementioned anolyte film, a 10 nm HT-4:HI-3 (97 / 3, w / w) mixture was vacuum thermally deposited as a hole injection layer, a 60 nm HT-4 compound as a hole transport layer, and a 5 nm HT-14 compound as an electron blocking layer; a 20 nm BFH-4:P1 (100:3, w / w) binary mixture was deposited as a light-emitting layer, a 5 nm ET-23 compound as a hole blocking layer, a 25 nm ET-69:ET-57 (50 / 50, w / w) compound as an electron transport layer, a 1 nm LiF compound as an electron injection layer, and a 150 nm aluminum metal as a cathode. The total deposition rate of all organic layers and LiF was controlled at 0.1 nm / s, and the deposition rate of the metal electrode was controlled at 1 nm / s.

[0172] The preparation process of Device Examples 2-18 and Comparative Examples 1-2 is the same as that of Device Example 1, except that P1 in the light-emitting layer is replaced with compounds P17, P81, P4, P85, P86, P87, P88, P90, P89, P36, P139, P11, P125, P8, P16, P20, P9 of the present invention and comparative compounds C1 and C2 of the prior art.

[0173] The structure of compound C1 is shown below:

[0174]

[0175] Synthesis of compound C1: The specific method is based on the synthesis method in patent document KR1020190078541A, and its description is omitted here.

[0176] Device testing methods (including equipment and testing conditions):

[0177] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0178] Under the same brightness, the driving voltage and external quantum efficiency of organic electroluminescent devices prepared from the compound and comparative materials were determined using a digital source meter, luminance meter, and PR650. Specifically, the voltage was increased at a rate of 0.1 V per second, and the driving voltage and external quantum efficiency were measured when the brightness of the organic electroluminescent device reached 1000 cd / m². 2 The voltage at that time is the driving voltage.

[0179] The performance of the organic electroluminescent devices prepared in the above-mentioned device embodiments and comparative examples is shown in Table 2 below.

[0180] Table 2:

[0181]

[0182]

[0183] As shown in Table 1, when the material schemes and fabrication processes of other functional layers in the organic electroluminescent device structure are exactly the same, compared with the comparative example, the BN-type organic material of the present invention has higher luminous efficiency in organic electroluminescent devices due to its rigid structure, and thus exhibits higher external quantum efficiency in OLED devices.

[0184] The present invention has been illustrated with the above embodiments to explain the detailed method of the present invention. However, the present invention is not limited to the detailed method described above, that is, it does not mean that the present invention must rely on the detailed method described above to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound having a structure represented by the following formula (1-2): Y 1 、Y 4 、Y 5 、Y 8 are each independently selected from CH or N; The said Y 2 and Y 7 are independently selected from CR 17 or N, and the said R 17 is independently selected from one of C1-C10 linear alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl, and the said Y 3 and Y 6 are independently selected from CH or N; or, the said Y 3 and Y 6 are independently selected from CR 17 or N, and the said R 17 is independently selected from one of C1-C10 linear alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C5-C30 aryl, and the said Y 2 and Y 7 are independently selected from CH or N; The said Z 1 ~Z 5 are each independently selected from CR 6 or N, and the said R 6 is independently selected from one of hydrogen and C1-C20 linear alkyl groups; X is selected from one of O, S, NR 1 , CR 2 R 3 , SiR 4 R 5 ; The R 2 ~R 5 are each independently selected from C1-C20 linear alkyl groups; R 1 is the structure shown in the following formula (4-1): In formula (4-1), Z 21 ~Z 25 are each independently selected from CR 8 , and the R 8 are independently selected from one of hydrogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, and C6-C60 aryl.

2. The organic compound according to claim 1, wherein X is selected from one of O, S, NR 1 ; R 1 is the structure shown in the following formula (4-2): In formula (4-2), Z 21 , Z 22 , Z 24 , Z 25 are all defined in the same way as in formula (4-1); The R is selected from one of C1-C20 linear alkyl groups and C3-C20 cycloalkyl groups.

3. The organic compound according to claim 2, X is NR 1 ; In formula (4-2), the R is selected from one of the following groups: ； Represents the position of the access key for the substitution group.

4. The organic compound according to claim 1, wherein Z 1 ~Z 5 are each independently selected from CR 6 , and R 6 is hydrogen.

5. The organic compound according to claim 1, wherein Y 2 and Y 7 are each independently selected from one of the following substituents: Represents the position of the access key for the substituent group.

6. The organic compound according to claim 1, wherein Y 3 and Y 6 are independently selected from CH, and Y 2 and Y 7 are independently selected from one of the following substituted groups: ； Alternatively, said Y 2 and Y 7 are independently selected from CH, said Y 3 and Y 6 are independently selected from one of the following substituted groups: Represents the access key position of the substitution group.

7. An organic compound having the following structure: 。 8. Use of the compound according to any one of claims 1-7 in 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; The compound is used as a light-emitting dye in the light-emitting layer of an organic electroluminescent device.

9. An organic electroluminescent device, which device comprises a first electrode, a second electrode and one or more organic functional layers inserted between the first electrode and the second electrode, the organic functional layers including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and the light-emitting layer contains the compound according to any one of claims 1-7.

Images