Organic compound, application thereof and organic electroluminescent device containing organic compound

Abstract

The invention relates to an organic compound, application of the compound and an organic electroluminescent device containing the compound. The organic compound disclosed by the invention has a structure as shown in a formula (1-1) or a formula (1-2), wherein a ring A, a ring B, a ring C, a ring D and a ring E independently represent one of C5-C60 aromatic rings and C5-C60 heteroaromatic rings; y and Z each independently represent a single bond, a double bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; w represents a single bond; x represents N or C; n1, n2 and n3 are respectively and independently selected from 0 or 1. After the compound disclosed by the invention is prepared and applied to the organic electroluminescent device, the device has good performances of high color purity and high luminous efficiency and also has extremely long service life.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, in particular to an organic compound, and application of the light-emitting material and an organic electroluminescence device comprising the compound. BACKGROUND

[0002] Organic Light Emission Diodes (OLED) is a kind of device with sandwich structure, including positive and negative electrode film layers and organic functional material layer sandwiched between the electrode film layers. When a proper voltage is applied to the positive and negative electrodes of OLED, the holes generated at the anode and the electrons generated at the cathode combine in the light-emitting layer, and depending on the characteristics of the material, red, green and blue colors are generated. OLED has the advantages of self-emission, high brightness, wide viewing angle, high contrast, low energy consumption, thin light-emitting layer, flexibility, etc. In recent years, it has developed rapidly and is widely used in display fields such as lighting, smart phones, tablet computers, televisions, VR, wearable devices, etc. It is highly concerned in the field of new display technology and new lighting technology and is supported by the state.

[0003] In order to prepare a light-emitting device with high luminous efficiency and long service life, and to improve the performance of the device, the core light-emitting material is particularly important. A good efficiency and long life OLED device is usually the result of the optimization of device structure and various organic materials. The internal quantum efficiency (IQE) of traditional fluorescent materials is only 25%, and only singlet excitons can be utilized for light emission. Phosphorescent materials usually utilize strong spin-orbit coupling of noble metals (such as Ir, Pt) to enhance intersystem crossing, and utilize both singlet and triplet excitons for light emission, making the internal quantum efficiency reach 100%. On this basis, the industry has been committed to developing a new generation of organic electroluminescent materials to further improve the performance of the device.

[0004] With the development of technology, in order to meet the BT.2020 standard of the International Telecommunication Union Radio Communication Department (ITU-R) for the new generation of ultra-high definition (UHD) video production and display system, the light-emitting material needs to have a narrower half-peak width in addition to high efficiency and long life to achieve higher color purity. The half-peak width of the currently commercialized OLED material is usually wide (>40 nm), although the color purity can be improved by optical filter, but the brightness and efficiency will be reduced, which is not worth the loss.

[0005] In recent years, new OLED materials based on multiple resonance (MR) have become a hot spot in the field of organic electroluminescence, which have both high efficiency and narrow spectrum. However, MR-TADF materials usually have a relatively planar rigid structure, which can easily cause serious accumulation between molecules in the device, resulting in broadening of the device spectrum and significant decrease of efficiency. Therefore, how to avoid molecular accumulation and develop MR-TADF materials with high efficiency, long service life and narrow spectrum is the key to further improve the performance of OLED. SUMMARY

[0006] To solve the above technical problems, the present application provides an organic compound, which has narrow spectrum pure red light emission properties, and the specific technical solutions are as follows:

[0007] An organic compound has the structure shown in the following formula (1-1) or formula (1-2):

[0008]

[0009] In formula (1-1), formula (1-2):

[0010] Each of ring A, ring B, ring C, ring D and ring E independently represents one of C5-C60 aromatic ring and C5-C60 heteroaromatic ring;

[0011] Each of Y and Z independently represents a single bond, a double bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5;

[0012] W represents a single bond; X represents N or C; each of n1, n2 and n3 is independently selected from 0 or 1;

[0013] R1, R2, R3, R4 and R5 are not connected with adjacent groups or connected to form a ring; R2 and R3 are not connected or connected to form a ring; R4 and R5 are not connected or connected to form a ring;

[0014] Each of R1, R2, R3, R4 and R5 is independently selected from one of the following groups which are unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;

[0015] R a , R b , R c , R d , R e independently represent a single substituent to the maximum allowed number of substituents; R a , R b , Rc R d R e two adjacent ones are connected or not connected;

[0016] R a R b R c R d R e are independently connected to the ring structure to which they are attached by a single bond or are fused;

[0017] R a R b R c R d R e each independently is selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or one of the following groups which are unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C2-C10 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;

[0018] two adjacent R's are not connected or are connected to form a ring; R' is selected from deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of any two of the foregoing.

[0019] In the present invention, the "substituted or unsubstituted" group can be substituted with one substituent or can be substituted with multiple substituents, and when the substituents are multiple, they can be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be described again.

[0020] In the present invention, the expression "single bond or fused connection" generally refers to a substituent group directly connected to the parent structure by a single bond, or refers to a substituent group fused to the parent structure to form a polycyclic aromatic hydrocarbon structure with multiple aromatic rings sharing edges. The aromatic ring here includes a benzene ring type six-membered aromatic ring, and also includes five-membered, six-membered and other heteroaromatic rings containing N, O or S atoms.

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

[0022] In the present specification, the expression of a ring structure with a dash through it represents a bonding site at any position on the ring structure that can form a bond.

[0023] In the present specification, "each independently" means that the subject can be the same or different from each other when the subject has a plurality of subjects.

[0024] In the present specification, the expression of a chemical element, unless otherwise specified, generally includes the concept of its isotope, for example, the expression of "hydrogen (H)" includes the concept of its isotope 1H (protium or H), 2H (deuterium or D), and the like, and carbon (C) includes 12C, 13C, and the like, and the like, and thus further description will not be given.

[0025] In the present specification, a heteroatom generally refers to an atom or an atomic group selected from N, O, S, P, Si, and Se, and preferably selected from N, O, and S.

[0026] In the present specification, as examples of halogen, fluorine, chlorine, bromine, iodine, and the like can be given.

[0027] In the present specification, unless otherwise specified, both aryl and heteroaryl include the case of a single ring and a condensed ring.

[0028] In the present specification, 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, and the like.

[0029] The C3-C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, and the like.

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

[0031] 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] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

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

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

[0035] In this invention, the substituted or unsubstituted C6-C60 aryl (or C6-C50 aryl) includes monocyclic aryl and fused-ring aryl, preferably C6-C30 aryl, and more preferably C6-C20 aryl. A monocyclic aryl refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, and terphenyl. 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, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... 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'-spirodifluorenyl, and benzo[a]fluorenyl.

[0036] The C3-C60 heteroaryl (or C6-C50 heteroaryl) mentioned in the present application includes monocyclic heteroaryl and fused ring heteroaryl, preferably C3-C30 heteroaryl, further preferably C4-C20 heteroaryl, and more preferably C5-C12 heteroaryl. The monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl include furanyl, thienyl, pyrrolyl, pyridyl, etc. The fused 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 are groups that share two adjacent atoms and are fused to each other. Examples of fused ring heteroaryl include benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenoxazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, etc.

[0037] Specific examples of arylene in the present application can be divalent groups obtained by removing one hydrogen atom from the examples of aryl described above. The number of carbons of arylene includes but is not limited to C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of heteroarylene in the present application can be divalent groups obtained by removing one hydrogen atom from the examples of heteroaryl described above.

[0038] The aryloxy or heteroaryloxy in the present application can be a monovalent group composed of the above-mentioned aryl or heteroaryl and oxygen.

[0039] In the present application, arylamino represents a group formed by replacing one or two hydrogens on an amino group with aryl groups, wherein the connection site of the arylamino can be connected to the aryl group in the arylamino or to the N in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0040] The C6-C30 arylamino mentioned in the present application can be exemplified by phenylamino, methylphenylamino, naphthylamino, anthryl amino, phenanthryl amino, biphenylamino, etc.

[0041] The C3-C30 heteroarylamino mentioned in the present application can be exemplified by pyridylamino, pyrimidinylamino, dibenzofuranyl amino, etc.

[0042] The chain alkyl group mentioned in the present application includes straight chain alkyl group and branched chain alkyl group, unless otherwise specified. Specifically, the substituted or unsubstituted C1-C30 chain alkyl group, preferably the substituted or unsubstituted C1-C16 chain alkyl group, more preferably the substituted or unsubstituted C1-C10 chain alkyl group. Examples of the substituted or unsubstituted C1-C10 chain alkyl group include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, n-pentyl group, sec-pentyl group, neopentyl group, n-hexyl group, neohexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, and the like.

[0043] In the present application, the cycloalkyl group includes monocycloalkyl group and polycycloalkyl group; 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 in the ring; and the C3-C20 cycloalkyl group can be exemplified by, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group, and the like.

[0044] In the present specification, as the substituted or unsubstituted C1-C20 alkoxy group, preferably the substituted or unsubstituted C1-C10 alkoxy group, examples of the C1-C20 alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, t-butoxy group, pentoxy group, isopentoxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, and the like, of which methoxy group, ethoxy group, n-propoxy group, isopropoxy group, t-butoxy group, sec-butoxy group, isobutoxy group, isopentoxy group, and more preferably methoxy group are preferred.

[0045] In the present specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, examples of the C1-C10 silyl group can be a silyl group substituted with a group exemplified in the above C1-C10 chain alkyl group, specifically exemplified by methylsilyl group, dimethylsilyl group, trimethylsilyl group, ethylsilyl group, diethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, t-butyldiphenylsilyl group, and the like.

[0046] In the present specification, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, is a hydrocarbon group containing at least one C=C double bond, exemplarily including, but not limited to, ethenyl group, propenyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, butadienyl group, pentadienyl group, and the like.

[0047] It should be noted that the possible effects of each group / characteristic are described separately in the present application for the sake of convenience of explanation, but this does not mean that these groups / characteristics act in isolation. In fact, the reason for obtaining good performance is essentially an optimized combination of the whole molecule, which is the result of the synergistic effect between each group, rather than the effect of a single group.

[0048] Further, the compound of the present application has a structure represented by any one of the following formulae (2-1) and (2-2):

[0049]

[0050] wherein R a , R b , R c , R d , R e , Y, Z and X are defined as the same as in formula (1-1) or formula (1-2);

[0051] Y and Z each independently represent a single bond, NR1or CR2R3;

[0052] Preferably, Y and Z each represent a single bond.

[0053] Further preferably, in formula (1-1), formula (1-2), formula (2-1) and formula (2-2), the ring A, the ring B, the ring C and the ring D each independently are a structure represented by formula (a) or formula (b), and the dotted line represents the position of the group in the above general formula:

[0054]

[0055] In formula (a), U 1 , U 2 , U 3 , U 4 each independently is selected from CR 1 or N, and the adjacent two R 1 are not connected or connected by a chemical bond to form a ring.

[0056] R 1each independently selected from one of hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C1-C20 alkylamino, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C3-C30 heteroarylamino, unsubstituted or R"-substituted C6-C30 aryloxy, unsubstituted or R"-substituted C3-C30 heteroaryloxy, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C3-C60 heteroaryl;

[0057] In formula (b), W 1 is selected from O, S, NR 2 or CR 3 R 4 ; R 2 , R 3 , R 4 is not connected to the adjacent group or is connected by a chemical bond to form a ring; R 3 is not connected to R 4 or forms a ring therebetween;

[0058] R 2 , R 3 , R 4 each independently selected from one of unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C3-C60 heteroaryl;

[0059] R" is selected from any one or a combination of two of deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl.

[0060] It is further preferred that in formula (a), U 1 , U 2 , U 3 , U 4 each independently selected from CR 1 , R 1one or a combination of two of the following substituent groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzphenanthryl, pyrenyl, chrysenyl, fluorenyl, dibenzo-a- pyrenyl, tetracene, pentacene, benzopyrenyl, biphenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, truxenyl, isotruxenyl, spirotruxenyl, spiroisotruxenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazachrysenyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, or silyl;

[0061] in formula (b), R 2 , R 3 , R 4one or a combination of two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzphenanthryl, pyrenyl, chrysenyl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthrydinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy.

[0062] In the above general formula compound of the present application, preferably, each of the ring A, ring B, ring C, ring D independently represents one of C5 to C20 aromatic ring, C5 to C20 heteroaromatic ring, and ring E independently represents C6 to C30 aromatic ring.

[0063] Preferably, each of the ring A, ring B, ring C, ring D is independently selected from any one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, thiophene, benzanthracene group, phenanthrene group, benzophenanthrene group, pyrene group, coronene group, chrysene group, fluoranthene group, tetracene group, pentacene group, benzopyrene group, biphenyl group, biphenyl group, terphenyl group, triphenyl group, quaterphenyl group, dibiphenyl group, furan group, benzofuran group, isobenzofuran group, dibenzofuran group, thiophene group, benzothiophene group, isobenzothiophene group, dibenzothiophene group, pyrrole group, isoindole group, carbazole group, indolocarbazole group, pyridine group, quinoline group, isoquinoline group, acridine group, phenanthridine group, benzo-5,6-quinoline group, benzo-6,7-quinoline group, benzo-7,8-quinoline group, pyrazole group, indazole group, imidazole group, benzimidazole group, naphthimidazole group, phenanthroimidazole group, pyridylimidazole group, pyrazylimidazole group, quinoxalimidazole group, oxazole group, benzoxazole group, naphthoxazole group, anthroxazole group, phenanthroxazole group, 1,2-thiazole group, 1,3-thiazole group, benzothiazole group, pyridazine group, benzopyridazine group, pyrimidine group, benzopyrimidine group, quinoxaline group; ring E is selected from benzene ring.

[0064] More preferably, each of the ring A, ring B, ring C, ring D is independently selected from one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, thiophene; ring E is selected from benzene ring.

[0065] Further, the compound of the present application has a structure as shown in any one of the following formula (3-1), (3-2):

[0066]

[0067] wherein, R a , R b , R c , R d , R e , X are defined the same as in formula (1-1) or formula (1-2);

[0068] Preferably, in formula (3-2), X is selected from N.

[0069] In each of the above-mentioned general formula compounds of the present application, preferably, the R a , R b , R c , R d , R eeach independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, amino or one of the following groups unsubstituted or R'-substituted: C1-C6-chain alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-thioalkoxy, C6-C20-aryl- amino, C3-C20-heteroaryl-amino, C6-C30-aryl, C6-C30-aryloxy, C5-C30-heteroaryl;

[0070] Preferably, said R a , R b , R c , R d , R e each independently selected from the group consisting of hydrogen, deuterium or one or a combination of two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrooxazolyl, phenanthrooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthylidinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy.

[0071] Further, the compounds of the general formula of the present application can preferably be the following specific compounds 1 to 264, which are merely representative:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] The structural design innovation of the compound of the present application is that a spiro atom is introduced on one side of the N-B-N parent nucleus, connecting the two benzene rings, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the rigidity of the molecule, significantly narrowing the full width at half maximum (FWHM in 20-30 nm), and improving the light-emitting efficiency (PLQY>90%). And the adamantyl group connected at the spiro atom has large steric hindrance, which can significantly increase the distance between molecules, greatly weaken the intermolecular π-π interaction force, inhibit the spectral broadening in the device and the efficiency roll-off under high brightness, and further improve the device stability. Compared with other alkyl groups, adamantyl has stronger rigidity, which can reduce non-radiative transition caused by vibration and improve the light-emitting efficiency of the molecule. Compared with other aromatic rings, it can more effectively inhibit π-π stacking and is a better choice.

[0084] On the basis of the above-mentioned core parent nucleus structure, the use of different aromatic ring fusion on the carbazole or diarylamine fragments on both sides of the parent nucleus structure of the compound of the present application can effectively regulate the conjugated plane of the molecule, and then realize the red shift or blue shift of the light color, and realize the coverage of the whole visible light region. The main donor fragment of the compound of formula (1-1) of the present application is a derivative of carbazole or diphenylamine, and the electron-transporting ability of the benzimidazole derivative in the compound of formula (1-2) is weaker than that of the carbazole and diphenylamine derivative, which will cause a slight blue shift of the light color, but the electron-transporting ability of the benzimidazole derivative is better than that of the carbazole and diphenylamine derivative, which can enhance the electron-transporting ability in the device, thereby improving the performance of the device.

[0085] The electroluminescent spectrum of the OLED device prepared by using the compound has a relatively narrow half-peak width (<30 nm), and exhibits obvious multiple resonance thermally activated delayed fluorescence characteristics, thereby greatly enriching the skeleton system of multiple resonance narrow spectrum materials, greatly simplifying the synthesis process, and improving the reaction yield; the corresponding electroluminescent device has low starting voltage, high luminous efficiency and extremely long service life, can meet the requirements of current panel manufacturing enterprises on high-performance materials, and has good application prospect in industrialization.

[0086] The second object of the present application is to provide a use of the compound according to the first object, wherein the compound is used in an organic electroluminescent device. Preferably, the compound is used as a light-emitting layer material, preferably a light-emitting dye, in the organic electroluminescent device.

[0087] The third object of the present application is to provide an organic electroluminescent device. Specifically, the embodiments of the present application provide an organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer formed in sequence on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, 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 between the hole transport layer and the electron transport layer; preferably, the light-emitting layer contains the compound of any one of the general formula (1), the general formula (2), the formula (2-1) or the formula (2-2), or the light-emitting layer contains at least one of the specific compounds 1-264.

[0088] The fourth object of the present application is to provide a display device using the organic electroluminescent device of the present application. DETAILED DESCRIPTION

[0089] The specific preparation methods of the novel compounds of the present application will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation methods of the present application are not limited to these synthesis examples.

[0090] The various chemicals used in the present application, such as petroleum ether, tert-butylbenzene, sodium sulfate, toluene, dichloromethane, cesium carbonate, sodium hydride, boron tribromide, tetrahydrofuran, N,N-dimethylformamide, n-butyllithium, reaction intermediates and other basic chemical raw materials are purchased from Shanghai Titan Science and Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds is a ZAB-HS type mass spectrometer (manufactured by Micromass Company, UK).

[0091] The synthesis method of the compound of the present application is briefly described as follows. First, intermediate I is obtained by using nucleophilic substitution and Buchwald-Hartwig reaction. Then, after lithium-halogen exchange using n-butyl lithium, nucleophilic addition with aromatic ketone is carried out, and then ring closure by acidification to obtain intermediate II. Finally, under the action of tert-butyl lithium, electrophilic boronation with boron tribromide is carried out to obtain the target compound.

[0092] Synthesis of compound 2 of synthesis example 1

[0093]

[0094] In a two-necked flask, compound 1-bromo-3-chloro-2,4-difluorobenzene (10 mmol), 3,6-di-tert-butylcarbazole (10 mmol), cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under nitrogen atmosphere, and the temperature was raised to 150°C, and the reaction was carried out for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 100 mL of water, then washed twice with 10 mL of methanol, and dried to obtain the target compound 2-2, a light yellow solid.

[0095] In a two-necked flask, compound 2-2 (10 mmol), 3,6-di-tert-butylcarbazole (10 mmol), cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under nitrogen atmosphere, and the temperature was raised to 150°C, and the reaction was carried out for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 100 mL of water, then washed twice with 10 mL of methanol, and dried to obtain the target compound 2-3, a light yellow solid.

[0096] In a two-necked flask, compound 2-3 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran under nitrogen atmosphere, and cooled to -78°C, and n-butyl lithium pentane solution (1M, 6 ml) was added, and the reaction was carried out at this temperature for 1 hour. Adamantone (5 mmol) was dissolved in 40 ml of dry tetrahydrofuran previously cooled to -78°C, and then the solution was slowly injected into the solution of 2-3 at -78°C, and slowly warmed to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, and the solvent was evaporated under reduced pressure, and 100 ml of ice acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After the reaction was carried out for 2 hours, it was neutralized with saturated aqueous sodium carbonate solution, and extracted with dichloromethane, and the organic phase was collected, dried with anhydrous sodium sulfate, and then filtered and concentrated, and the compound was separated by silica gel column with petroleum ether:dichloromethane = 5:1 as developing agent to obtain compound 2-4.

[0097] Compound 2-4 (1 mmol) was dissolved in 20 mL of tert-butyl benzene in a sealed tube, cooled to -78 °C, then tert-butyllithium in pentane (1 M, 2.5 mL) was added, followed by warming to 30 °C for 1 hour. Again cooled to -78 °C, slowly added boron tribromide (3 mmol), then warmed to 30 °C and continued stirring for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, then warmed to 160 °C and reacted for 12 hours. The solvent was removed by vacuum evaporation, and the target compound 2 (HPLC analysis purity 99.44%) was obtained as a bright yellow solid. MALDI-TOF-MS results: molecular ion peak: 772.4928; elemental analysis results: theoretical value: C, 87.021; H, 7.961; B, 1.403; N, 3.622 (%); experimental value: C, 87.026; H, 7.966; B, 1.412; N, 3.634 (%).

[0098] Synthesis of compound 5 of synthesis example 2

[0099]

[0100] The synthesis of this compound was similar to example 1, and the target compound 5 (HPLC analysis purity 99.73%) was obtained as a bright yellow solid. MALDI-TOF-MS results: molecular ion peak: 598.258; elemental analysis results: theoretical value: C, 88.291; H, 5.223; B, 1.811; N, 4.683 (%); experimental value: C, 88.299; H, 5.225; B, 1.823; N, 4.686 (%).

[0101] Synthesis of compound 15 of synthesis example 3

[0102]

[0103] The synthesis of this compound was similar to example 1, and the target compound 15 (HPLC analysis purity 99.19%) was obtained as a bright yellow solid. MALDI-TOF-MS results: molecular ion peak: 648.2737; elemental analysis results: theoretical value: C, 88.891; H, 5.132; B, 1.671; N, 4.321 (%); experimental value: C, 88.9; H, 5.144; B, 1.678; N, 4.33 (%).

[0104] Synthesis of compound 23 of synthesis example 4

[0105]

[0106] The compound was synthesized in a similar manner as in Example 1 to give the target compound 23 (HPLC purity 99.43%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 661.3628; elemental analysis result: Theoretical value: C, 85.313; H, 6.702; B, 1.632; N, 6.353 (%); Experimental value: C, 85.32; H, 6.712; B, 1.638; N, 6.363 (%).

[0107] Synthesis of Example 5 compound 25

[0108]

[0109] The compound was synthesized in a similar manner as in Example 1 to give the target compound 25 (HPLC purity 99.25%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 812.4302; elemental analysis result: Theoretical value: C, 88.652; H, 6.573; B, 1.331; N, 3.451 (%); Experimental value: C, 88.662; H, 6.577; B, 1.335; N, 3.459 (%).

[0110] Synthesis of Example 6 compound 36

[0111]

[0112] The compound was synthesized in a similar manner as in Example 1 to give the target compound 36 (HPLC purity 99.08%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 994.5146; elemental analysis result: Theoretical value: C, 86.903; H, 6.383; B, 1.092; N, 5.632 (%); Experimental value: C, 86.906; H, 6.394; B, 1.105; N, 5.638 (%).

[0113] Synthesis of Example 7 compound 44

[0114]

[0115] The compound was synthesized in a similar manner as in Example 1 to give the target compound 44 (HPLC purity 99.19%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 824.343; elemental analysis result: Theoretical value: C, 81.533; H, 5.991; B, 1.313; N, 3.401; S, 7.772 (%); Experimental value: C, 81.536; H, 5.999; B, 1.319; N, 3.405; S, 7.777 (%).

[0116] Synthesis of compound 60 of synthesis example 8

[0117]

[0118] The compound was synthesized in a similar way as example 1 to give the target compound 60 (HPLC purity 99.61%), bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 766.3553; elemental analysis result: theory: C, 84.581; H, 6.182; B, 1.412; N, 3.651; S, 4.183 (%); experiment: C, 84.59; H, 6.193; B, 1.416; N, 3.663; S, 4.191 (%).

[0119] Synthesis of compound 62 of synthesis example 9

[0120]

[0121] The compound was synthesized in a similar way as example 1 to give the target compound 62 (HPLC purity 99.05%), bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 825.4254; elemental analysis result: theory: C, 87.262; H, 6.353; B, 1.311; N, 5.092 (%); experiment: C, 87.268; H, 6.364; B, 1.324; N, 5.095 (%).

[0122] Synthesis of compound 63 of synthesis example 10

[0123]

[0124] The compound was synthesized in a similar way as example 1 to give the target compound 63 (HPLC purity 99.75%), bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 873.4254; elemental analysis result: theory: C, 87.962; H, 6.001; B, 1.242; N, 4.812 (%); experiment: C, 87.967; H, 6.01; B, 1.247; N, 4.822 (%).

[0125] Synthesis of compound 73 of synthesis example 11

[0126]

[0127] The compound was synthesized in a similar manner as in Example 1 to give the target compound 73 (HPLC purity 99.28%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 766.3553; elemental analysis result: Theoretical value: C, 84.583; H, 6.182; B, 1.412; N, 3.653; S, 4.183 (%); Experimental value: C, 84.587; H, 6.192; B, 1.418; N, 3.66; S, 4.189 (%).

[0128] Synthesis of Example 12 compound 84

[0129]

[0130] The compound was synthesized in a similar manner as in Example 1 to give the target compound 84 (HPLC purity 99.23%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 825.4254; elemental analysis result: Theoretical value: C, 87.263; H, 6.352; B, 1.311; N, 5.093 (%); Experimental value: C, 87.273; H, 6.36; B, 1.315; N, 5.099 (%).

[0131] Synthesis of Example 13 compound 89

[0132]

[0133] The compound was synthesized in a similar manner as in Example 1 to give the target compound 89 (HPLC purity 99.5%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 766.3553; elemental analysis result: Theoretical value: C, 84.583; H, 6.182; B, 1.413; N, 3.652; S, 4.183 (%); Experimental value: C, 84.589; H, 6.188; B, 1.421; N, 3.659; S, 4.189 (%).

[0134] Synthesis of Example 14 compound 102

[0135]

[0136] The compound was synthesized in a similar manner as in Example 1 to give the target compound 102 (HPLC purity 99.6%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 898.4458; elemental analysis result: Theoretical value: C, 89.513; H, 6.173; B, 1.201; N, 3.123 (%); Experimental value: C, 89.525; H, 6.181; B, 1.21; N, 3.125 (%).

[0137] Synthesis of Example 15 compound 107

[0138]

[0139] The compound was synthesized in a similar manner as in Example 1 to give the target compound 107 (HPLC purity 99.22%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 825.4254; elemental analysis result: Theoretical value: C, 87.263; H, 6.351; B, 1.312; N, 5.093 (%); Experimental value: C, 87.272; H, 6.363; B, 1.316; N, 5.105 (%).

[0140] Synthesis of Example 16 compound 111

[0141]

[0142] The compound was synthesized in a similar manner as in Example 1 to give the target compound 111 (HPLC purity 99.27%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 825.4254; elemental analysis result: Theoretical value: C, 87.261; H, 6.351; B, 1.312; N, 5.093 (%); Experimental value: C, 87.268; H, 6.362; B, 1.318; N, 5.104 (%).

[0143] Synthesis of Example 17 compound 114

[0144]

[0145] The compound was synthesized in a similar manner as in Example 1 to give the target compound 114 (HPLC purity 99.64%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 823.4098; elemental analysis result: Theoretical value: C, 87.471; H, 6.122; B, 1.313; N, 5.102 (%); Experimental value: C, 87.483; H, 6.132; B, 1.316; N, 5.115 (%).

[0146] Synthesis of compound 121 of synthesis example 18

[0147]

[0148] The compound was synthesized in a similar manner to example 1 to obtain the target compound 121 (HPLC analysis purity 99.09%), light yellow solid. MALDI-TOF-MS result: molecular ion peak: 812.4302; elemental analysis result: theoretical value: C, 88.651; H, 6.572; B, 1.331; N, 3.451 (%); experimental value: C, 88.664; H, 6.582; B, 1.34; N, 3.461 (%).

[0149] Synthesis of compound 129 of synthesis example 19

[0150]

[0151] In a double-necked flask, compound 1-bromo-3-chloro-4-fluoro-2-iodobenzene (10 mmol), 3,6-di-tert-butylcarbazole (10 mmol), cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under a nitrogen atmosphere, and the temperature was raised to 150°C, and the reaction was carried out for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 100 mL of water, then washed twice with 10 mL of methanol, and dried to obtain the target compound 129-2, a light yellow solid.

[0152] In a double-necked flask, compound 129-2 (10 mmol), bis(4-phenyl)phenylamine (10 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2 mmol), sodium tert-butoxide (12 mmol) were sequentially added under a nitrogen atmosphere, 100 mL of dry toluene was added and the temperature was raised to 110°C, and the reaction was carried out for 12 hours. After cooling, the organic phase was separated and collected, the organic phase was dried with anhydrous sodium sulfate, then filtered and concentrated, the compound was separated by silica gel column with petroleum ether: dichloromethane = 10:1 as developing agent to obtain compound 129-3.

[0153] In a two-necked flask, compound 129-3 (5 mmol) was dissolved in 10 ml dry tetrahydrofuran under nitrogen atmosphere, cooled to -78 °C, and n-butyllithium pentane solution (1 M, 6 ml) was added. The reaction was allowed to proceed at this temperature for 1 hour. Adamantone (5 mmol) was dissolved in 40 ml dry tetrahydrofuran previously cooled to -78 °C, and the solution was slowly injected into the solution of 129-3 at -78 °C, slowly warmed to room temperature, and the reaction was allowed to proceed for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, and the solvent was evaporated under reduced pressure. 100 ml glacial acetic acid and 10 ml concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After 2 hours of reaction, the reaction was neutralized with saturated aqueous sodium carbonate solution, and the organic phase was separated and collected by dichloromethane extraction. The organic phase was dried over anhydrous sodium sulfate, and then filtered and concentrated. The compound was separated by silica gel column with petroleum ether: dichloromethane = 5: 1 as developing agent to obtain compound 129-4.

[0154] Compound 129-4 (1 mmol) was dissolved in 20 mL of tert-butyl benzene in a sealed tube, cooled to -78 °C, and then tert-butyllithium pentane solution (1 M, 2.5 mL) was added. After warming to 30 °C, the reaction was allowed to proceed for 1 hour. After cooling to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and the stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was allowed to proceed for 12 hours. The solvent was evaporated under vacuum, and the target compound 129 (HPLC analysis purity 99.41%) was obtained as a bright yellow solid by passing through a silica gel column with petroleum ether: dichloromethane = 10: 1 as developing agent. MALDI-TOF-MS results: molecular ion peak: 814.4458; elemental analysis results: theoretical value: C, 88.431; H, 6.803; B, 1.332; N, 3.443 (%); experimental value: C, 88.443; H, 6.807; B, 1.34; N, 3.446 (%).

[0155] Synthesis of compound 144 of synthesis example 20

[0156]

[0157] The synthesis of this compound was similar to Example 19 to obtain the target compound 144 (HPLC analysis purity 99.09%) as a bright yellow solid. MALDI-TOF-MS results: molecular ion peak: 992.4989; elemental analysis results: theoretical value: C, 87.081; H, 6.191; B, 1.092; N, 5.642 (%); experimental value: C, 87.086; H, 6.198; B, 1.104; N, 5.649 (%).

[0158] Synthesis of compound 157 of synthesis example 21

[0159]

[0160] The compound was synthesized in a similar manner as Example 19 to give the target compound 157 (HPLC purity 99.34%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 790.4458; elemental analysis result: theory: C, 88.082; H, 7.012; B, 1.373; N, 3.541 (%); experiment: C, 88.094; H, 7.019; B, 1.383; N, 3.547 (%).

[0161] Synthesis of Example 22 compound 165

[0162]

[0163] The compound was synthesized in a similar manner as Example 19 to give the target compound 165 (HPLC purity 99.17%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.4023; elemental analysis result: theory: C, 84.403; H, 6.701; B, 1.363; N, 3.522 (%); experiment: C, 84.41; H, 6.705; B, 1.374; N, 3.533 (%).

[0164] Synthesis of Example 23 compound 177

[0165]

[0166] The compound was synthesized in a similar manner as Example 19 to give the target compound 177 (HPLC purity 99.76%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 853.4567; elemental analysis result: theory: C, 87.203; H, 6.612; B, 1.271; N, 4.923 (%); experiment: C, 87.213; H, 6.622; B, 1.284; N, 4.926 (%).

[0167] Synthesis of Example 24 compound 180

[0168]

[0169] The compound was synthesized in a similar manner as Example 19 to give the target compound 180 (HPLC purity 99.32%), a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 855.4724; elemental analysis result: Theoretical value: C, 87.001; H, 6.831; B, 1.261; N, 4.913 (%); Experimental value: C, 87.011; H, 6.839; B, 1.271; N, 4.921 (%).

[0170] Synthesis of Example 25 compound 191

[0171]

[0172] The compound was synthesized in a similar manner as Example 19 to give the target compound 191 (HPLC purity 99.48%), a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 692.3397; elemental analysis result: Theoretical value: C, 83.222; H, 6.553; B, 1.562; N, 4.041; S, 4.633 (%); Experimental value: C, 83.225; H, 6.558; B, 1.567; N, 4.045; S, 4.645 (%).

[0173] Synthesis of Example 26 compound 202

[0174]

[0175] In a two-necked flask, compound 202-1 (10 mmol), bis(4-tert-butyl)phenylamine (10 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2 mmol), sodium tert-butoxide (12 mmol) were added successively under nitrogen atmosphere, 100 ml dry toluene was added and the temperature was raised to 110°C, and the reaction was carried out for 12 hours. After cooling, the organic phase was separated and collected, the organic phase was dried with anhydrous sodium sulfate, then filtered and concentrated, and the compound was separated by silica gel column with petroleum ether: dichloromethane = 10: 1 as developing agent to give compound 202-2.

[0176] In a two-necked flask, compound 202-2 (10 mmol), bis(4-tert-butyl)phenylamine (10 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2 mmol), sodium tert-butoxide (12 mmol) were added successively under nitrogen atmosphere, 100 ml dry toluene was added and the temperature was raised to 110°C, and the reaction was carried out for 12 hours. After cooling, the organic phase was separated and collected, the organic phase was dried with anhydrous sodium sulfate, then filtered and concentrated, and the compound was separated by silica gel column with petroleum ether: dichloromethane = 10: 1 as developing agent to give compound 202-3.

[0177] In a two-necked flask, compound 202-3 (5 mmol) was dissolved in 10 ml dry tetrahydrofuran under nitrogen atmosphere, cooled to -78 °C, and n-butyllithium pentane solution (1 M, 6 ml) was added. The reaction was allowed to proceed at this temperature for 1 hour. Adamantone (5 mmol) was dissolved in 40 ml dry tetrahydrofuran previously cooled to -78 °C, and the solution was slowly injected into the solution of 202-3 at -78 °C, slowly warmed to room temperature, and the reaction was allowed to proceed for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, and the solvent was evaporated under reduced pressure. 100 ml glacial acetic acid and 10 ml concentrated hydrochloric acid were added, and then warmed to reflux. After 2 hours of reaction, the reaction was neutralized with saturated aqueous sodium carbonate solution, and the organic phase was separated and collected by extraction with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate, followed by filtration and concentration. The compound was separated by silica gel column with petroleum ether: dichloromethane = 5: 1 as an eluent to obtain compound 202-4.

[0178] In a sealed tube, compound 202-4 (1 mmol) was dissolved in 20 mL of tert-butylbenzene, cooled to -78 °C, and tert-butyllithium pentane solution (1 M, 2.5 mL) was added, and then warmed to 30 °C for 1 hour. After cooling to -78 °C again, boron tribromide (3 mmol) was slowly added, and then warmed to 30 °C and stirred for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then warmed to 160 °C and reacted for 12 hours. The solvent was evaporated under vacuum, and the target compound 202 (HPLC analysis purity 99.17%) was obtained as a bright yellow solid by passing through a silica gel column with petroleum ether: dichloromethane = 10: 1 as an eluent. MALDI-TOF-MS results: molecular ion peak: 776.5241; elemental analysis results: theoretical value: C, 86.572; H, 8.432; B, 1.393; N, 3.612 (%); experimental value: C, 86.578; H, 8.436; B, 1.4; N, 3.616 (%).

[0179] Synthesis of compound 218 of synthesis example 27

[0180]

[0181] The compound was synthesized in the same manner as example 26 to obtain the target compound 218 (HPLC analysis purity 99.8%) as a bright yellow solid. MALDI-TOF-MS results: molecular ion peak: 882.3894; elemental analysis results: theoretical value: C, 87.063; H, 5.373; B, 1.222; N, 6.353 (%); experimental value: C, 87.075; H, 5.381; B, 1.232; N, 6.359 (%).

[0182] Synthesis of compound 235 of synthesis example 28

[0183]

[0184] The compound was synthesized in a similar way as example 26 to give the target compound 235 (HPLC purity 99.09%), light yellow solid. MALDI-TOF-MS result: molecular ion peak: 690.3781; elemental analysis result: the theoretical value: C, 85.203; H, 6.863; B, 1.561; N, 4.061 (%); the experimental value: C, 85.215; H, 6.865; B, 1.566; N, 4.072 (%).

[0185] Synthesis of compound 245 of synthesis example 29

[0186]

[0187] The compound was synthesized in a similar way as example 26 to give the target compound 245 (HPLC purity 99.76%), light yellow solid. MALDI-TOF-MS result: molecular ion peak: 702.4145; elemental analysis result: the theoretical value: C, 87.162; H, 7.311; B, 1.541; N, 3.993 (%); the experimental value: C, 87.169; H, 7.323; B, 1.547; N, 4.004 (%).

[0188] Synthesis of compound 257 of synthesis example 30

[0189]

[0190] The compound was synthesized in a similar way as example 26 to give the target compound 257 (HPLC purity 99.04%), light yellow solid. MALDI-TOF-MS result: molecular ion peak: 687.3785; elemental analysis result: the theoretical value: C, 85.583; H, 6.742; B, 1.571; N, 6.113 (%); the experimental value: C, 85.586; H, 6.753; B, 1.582; N, 6.121 (%).

[0191] Synthesis of compound 262 of synthesis example 31

[0192]

[0193] The compound was synthesized in a similar manner to Example 26 to obtain the target compound 262 (HPLC analytical purity 99.08%) as a bright yellow solid. MALDI-TOF-MS result: molecular ion peak: 739.4098; elemental analysis result: theoretical value: C, 86.051; H, 6.811; B, 1.463; N, 5.683 (%); experimental value: C, 86.063; H, 6.823; B, 1.465; N, 5.689 (%).

[0194] Device Examples

[0195] The technical effects and advantages of the present application are demonstrated and verified below by testing the actual use performance by specifically applying the compounds of the present application to an organic electroluminescent device.

[0196] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material can be further divided into multiple regions, such as the organic material layer can include a hole transport region, a light emitting layer, an electron transport region.

[0197] The material of the anode can be an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (Sn02), zinc oxide (ZnO), and any combination thereof. The material of the cathode can be a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.

[0198] The hole transport region is between the anode and the light emitting layer. The hole transport region can be a single layer structure of a 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 multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0199] 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 vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, and the like.

[0200] The light-emitting layer includes light-emitting dyes (i.e. dopants) that can emit different wavelengths of light spectrum, and can also include a host material. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, blue, etc. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or can be stacked together to form a color light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can emit different colors such as red, green, blue, etc. simultaneously.

[0201] The electron transport region can 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 can also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0202] Specifically, the method for manufacturing the organic electroluminescent device of the present application includes the following steps:

[0203] 1. The glass plate coated with an anode material is ultrasonically treated in a commercial cleaning agent, washed in deionized water, ultrasonically treated in a mixed solvent of acetone and ethanol to remove oil, baked in a clean environment until the water is completely removed, washed with ultraviolet light and ozone, and the surface is bombarded with a low-energy cation beam;

[0204] 2. The glass plate with the anode is placed in a vacuum chamber, vacuumed to 1 x 10-5 to 9 x 10-3 Pa, and a hole injection material is vacuum-deposited on the anode layer film to form a hole injection layer, with a deposition rate of 0.1 to 0.5 nm / s;

[0205] 3. A hole transport material is vacuum-deposited on the hole injection layer to form a hole transport layer, with a deposition rate of 0.1 to 0.5 nm / s,

[0206] 4. An electron blocking layer is vacuum-deposited on the hole transport layer, with a deposition rate of 0.1 to 0.5 nm / s;

[0207] 5. An organic light-emitting layer of the device is vacuum-deposited on the electron blocking layer, including a host material and a light-emitting dye. The deposition rate of the host material, the deposition rate of the sensitizer material, and the deposition rate of the dye are adjusted by a multi-source co-deposition method to achieve a preset doping ratio of the dye;

[0208] 6. A hole blocking layer is vacuum-deposited on the organic light-emitting layer, with a deposition rate of 0.1 to 0.5 nm / s;

[0209] 7. An electron transport material of the device is vacuum-deposited on the hole blocking layer to form an electron transport layer, with a deposition rate of 0.1 to 0.5 nm / s;

[0210] 8. LiF is vacuum evaporated on the electron transport layer as an electron injection layer at 0.1-0.5 nm / s, and Al layer is vacuum evaporated as a cathode of the device at 0.1-0.5 nm / s.

[0211] The present application also provides a display device comprising the organic electroluminescent device provided above. The display device can be specifically an OLED display and the like display device, and a television, digital camera, mobile phone, tablet computer and the like any product or component having a display function comprising the display device. The display device has the same advantages as the organic electroluminescent device described above relative to the prior art, and will not be described here again.

[0212] The organic electroluminescent device of the present application is further described below through specific examples.

[0213] Embodiments 1-60 of the present application are organic electroluminescent devices prepared using the compounds of the present application, and Comparative Examples 1-3 are parallel comparison devices prepared using the compounds P1, P2 and P3 of the prior art according to the same preparation method as the compounds of the present application. The structure schemes of all the prepared devices are shown in Table 1 below:

[0214] Table 1:

[0215]

[0216]

[0217]

[0218]

[0219] Wherein, the anode material is ITO; the hole injection layer material is HI, and the total thickness is generally 5-30 nm, which is designed to be 10 nm in the embodiments of the present application; the material of the hole transport layer is HT, and the total thickness is generally 5-100 nm, which is designed to be 40 nm in the embodiments of the present application; the material of the electron blocking layer is EBL, and the total thickness is generally 5-20 nm, which is designed to be 15 nm in the embodiments of the present application; the Host is a wide-bandgap host material of the organic light-emitting layer, and the thickness of the organic light-emitting layer is generally 1-100 nm, which is designed to be 30 nm in the embodiments of the present application; the material of the hole blocking layer is HBL, and the total thickness is generally 5-20 nm, which is designed to be 15 nm in the embodiments of the present application; the material of the electron transport layer is ET, and the thickness is generally 5-100 nm, which is designed to be 40 nm in the embodiments of the present application; the electron injection layer and the cathode material are selected to be LiF (0.5 nm) and metal aluminum (150 nm).

[0220] The structural formula of each type of organic material used in each of the above embodiments is as follows:

[0221]

[0222]

[0223] The performance of the devices prepared in Examples 1-62 and Comparative Examples 1-6 of the present application is shown in Table 2 below:

[0224] Table 2:

[0225]

[0226]

[0227]

[0228] Compared with Comparative Example 1, the compound in the present application introduces a spiroadamantane group on one side of the N-B-N structure in the parent nucleus, connects the two benzene rings, eliminates the repulsion between the original hydrogen atoms, significantly enhances the rigidity of the molecule, significantly narrows the full width at half maximum (FWHM in 20-30 nm), and improves the luminous efficiency (PLQY > 95%). Compared with Comparative Examples 2 and 3, the spiro atom is replaced with a spiroadamantane group, which has greater steric hindrance and stronger structural rigidity, and can significantly inhibit the reduction of fluorescence quantum efficiency caused by intermolecular stacking. The maximum external quantum efficiency in the device is significantly improved, and the efficiency roll-off is significantly reduced, indicating that the introduction of the bulky adamantane group can effectively inhibit the quenching of triplet excitons. And the lifetime of the device is significantly improved. In the sensitized device prepared using a TADF material as a sensitizer, the efficiency roll-off of the device is further reduced due to the high upconversion rate of the sensitizer, the device has a high external quantum efficiency even at high brightness, and the lifetime of the device is further improved.

[0229] The above experimental data show that the organic electroluminescent device prepared using the novel MR-TADF material provided by the present application has high color purity and high luminous efficiency, and also realizes low efficiency roll-off of the electroluminescent device, and has an extremely long device lifetime, proving the great advantage of the molecular structure in the present application in improving the efficiency and stability of the device. In view of its excellent efficiency, color purity and stability, the above-mentioned compounds should have good application prospects.

[0230] Although the present application is described in conjunction with the embodiments, the present application is not limited to the above embodiments, and it should be understood that those skilled in the art can make various modifications and improvements under the guidance of the concept of the present application, and the appended claims generalize the scope of the present application.

[0231] Obviously, the above embodiments are only examples for clearly illustrating the present application and are not intended to limit the present application. Based on the above description, other different forms of changes or variations can be made by those skilled in the art. Here, all the embodiments are not required to be enumerated. The changes or variations derived from the above are still within the protection scope of the present application.

Claims

1. An organic compound having a structure represented by any one of the following formulae (1-1) or (1-2): ###0001### (1-1) (1-2) in the formulae (1-1), (1-2): ring A, ring B, ring C, ring D, ring E each independently represents one of a C5 to C60 aromatic ring, a C5 to C60 heteroaromatic ring; Y and Z each independently represent a single bond, a double bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; W represents a single bond; X represents N or C; n1, n2, and n3 each independently is selected from 0 or 1; R1, R2, R3, R4, R5 are not connected to the adjacent group or are connected to form a ring; R2 and R3 are not connected or are connected to form a ring; R4 and R5 are not connected or are connected to form a ring; R1, R2, R3, R4, R5 each independently is selected from one of the following groups which is unsubstituted or substituted with R': C1 to C36 chain alkyl, C3 to C36 cycloalkyl, C6 to C30 arylamino, C6 to C60 aryl, C6 to C60 aryloxy, C5 to C60 heteroaryl; adjacent two R's are not connected or are connected to form a ring; R' is selected from any one or a combination of two of deuterium, halogen, cyano, amino, C2 to C20 alkenyl, C1 to C20 chain alkyl, C3 to C20 cycloalkyl, C1 to C20 alkoxy, C1 to C20 thioalkoxy, C1 to C20 alkylsilyl, C1 to C20 alkylamino, C6 to C60 arylamino, C3 to C60 heteroarylamino, C6 to C30 aryloxy, C6 to C60 aryl, C3 to C60 heteroaryl. In the formula (1), a structure represented by any one of the following formulae (2-1), (2-2): ###0002### (2-1) (2-2) Y and Z each independently represent a single bond, NR1, or CR2R3; Preferably, Y and Z each represent a single bond. In the formulae (1-1), (1-2), (2-1), (2-2), ring A, ring B, ring C, ring D each independently is a structure represented by formula (a) or formula (b), and the dotted line represents a fused position of the following group in the above general formula: R" is selected from any one or a combination of two of deuterium, halogen, cyano, amino, C2 to C20 alkenyl, C1 to C20 chain alkyl, C3 to C20 cycloalkyl, C1 to C20 alkoxy, C1 to C20 thioalkoxy, C1 to C20 alkylsilyl, C1 to C20 alkylamino, C6 to C60 arylamino, C3 to C60 heteroarylamino, C6 to C30 aryloxy, C6 to C60 aryl, C3 to C60 heteroaryl. Ring A, ring B, ring C, ring D each independently represents one of a C5 to C20 aromatic ring, a C5 to C20 heteroaromatic ring, and ring E independently represents a C6 to C30 aromatic ring. ​ ​ ​ R a , R b , R c , R d , R e each independently represents a single substituent to the maximum permissible number of substituents; said R a , R b , R c , R d , R e are each independently connected to the ring structure to which they are attached by a single bond or are fused. R a , R b , R c , R d , R e between two adjacent ones are connected or not connected; said R a , R b , R c , R d , R e each independently is selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino or one of the following groups which are unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C2-C10 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl; ​ 2. The organic compound according to claim 1, characterized by ​ wherein R a , R b , R c , R d , R e , Y, Z and X are each as defined in formula (1-1) or formula (1-2); ​ said R a , R b , R c , R d , R e are each independently connected by a single bond or fused to the ring structure to which they are attached, preferably by a single bond; ​ 3. The organic compound according to claim 1 or 2, characterized by ​ In formula (a), U 1 , U 2 , U 3 , U 4 are each independently selected from CR 1 or N, and two adjacent R 1 are not connected or are connected by a chemical bond to form a ring; R 1 each independently is selected from one of hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C1-C20 alkylamino, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C3-C30 heteroarylamino, unsubstituted or R"-substituted C6-C30 aryloxy, unsubstituted or R"-substituted C3-C30 heteroaryloxy, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C3-C60 heteroaryl; In formula (b), W 1 is selected from O, S, NR 2 or CR 3 R 4 ; R 2 , R 3 , R 4 is not connected to the adjacent group or is connected by a chemical bond to form a ring; R 3 is not connected to R 4 or is connected to form a ring; R 2 , R 3 , R 4 each independently is selected from one of unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C3-C60 heteroaryl; ​ 4. The organic compound according to claim 3, characterized by In formula (a), U 1 , U 2 , U 3 , U 4 each independently is selected from CR 1 , R 1 each independently is selected from hydrogen, deuterium, cyano, halogen or one or a combination of two of the following substituent groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzphenanthryl, pyrenyl, chrysenyl, fluoranthenyl, fluoranthene, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydrogen pyrenyl, tetrahydrogen pyrenyl, cis or trans indenofluorenyl, truxenyl, isotruxenyl, spirotruxenyl, spiroisotruxenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridyl, phenanthridyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrooxazolyl, phenanthrooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazachrysenyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, or silyl; In formula (b), R 2 , R 3 , R 4 each independently is selected from one or a combination of two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzphenanthryl, pyrenyl, chrysenyl, fluorenyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthrydinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy.

5. The compound of claim 1 or 3, wherein ​ Preferably, each of the ring A, ring B, ring C, ring D is independently selected from any one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, thiophene, benzanthracene group, phenanthrene group, benzophenanthrene group, pyrene group, coronene group, chrysene group, fluoranthene group, tetracene group, pentacene group, benzopyrene group, biphenyl group, biphenyl group, terphenyl group, triphenyl group, quaterphenyl group, dibiphenyl group, furan group, benzofuran group, isobenzofuran group, dibenzofuran group, thiophene group, benzothiophene group, isobenzothiophene group, dibenzothiophene group, pyrrole group, isoindole group, carbazole group, indolocarbazole group, pyridine group, quinoline group, isoquinoline group, acridine group, phenanthridine group, benzo-5,6-quinoline group, benzo-6,7-quinoline group, benzo-7,8-quinoline group, pyrazole group, indazole group, imidazole group, benzimidazole group, naphthimidazole group, phenanthroimidazole group, pyridylimidazole group, pyrazylimidazole group, quinoxalimidoazole group, oxazole group, benzoxazole group, naphthoxazole group, anthroxazole group, phenanthroxazole group, 1,2-thiazole group, 1,3-thiazole group, benzothiazole group, pyridazine group, benzopyridazine group, pyrimidine group, benzopyrimidine group, quinoxaline group; ring E is selected from benzene ring. More preferably, each of the ring A, ring B, ring C, ring D is independently selected from one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene, thiophene; ring E is selected from benzene ring.

6. The compound of claim 1, wherein has any one of the following formula (3-1), (3-2): wherein R a , R b , R c , R d , R e , and X are each the same as defined in Formula (1-1) or Formula (1-2); Preferably, in formula (3-2), X is selected from N.

7. The organic compound according to any one of claims 1, 3 or 6, wherein R a , R b , R c , R d , R e are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, amino or one of the following groups which are unsubstituted or R'-substituted: C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C20 arylamino, C3-C20 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl; and R a , R b , R c , R d , R e are connected or not connected between two adjacent ones; Preferably, said R a , R b , R c , R d , R e are each independently selected from hydrogen, deuterium or one or a combination of two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzphenanthryl, pyrenyl, chrysenyl, fluorenyl, xanthenyl, fluorxenyl, perilenyl, pentacenyl, biphenyl, biphenylenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridylimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrooxazolyl, phenanthrooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthrydinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy.

8. The compound according to claim 1, selected from the following specific structural compounds:

9. Use of the compound according to any one of claims 1-8 as a functional material in an organic electronic device, which is an organic electroluminescent device, an optical sensor, a solar cell, an organic thin film transistor or an organic field effect transistor; Further, the use of the compound is as a light-emitting layer material in an organic electroluminescent device, in particular as a light-emitting material in a light-emitting layer.

10. An organic electroluminescent device comprising a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer formed in sequence on the substrate; the light-emitting functional layers comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, the hole injection layer being formed on the anode layer, the hole transport layer being formed on the hole injection layer, the cathode layer being formed on the electron transport layer, the light-emitting layer being between the hole transport layer and the electron transport layer, wherein the light-emitting layer contains the compound according to any one of claims 1-8.

11. A display device comprising the organic electroluminescent device according to claim 10.

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