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), wherein ring A, ring B, ring C and ring I respectively and independently represent a benzene ring, a naphthalene ring or an anthracene ring; a ring D, a ring E, a ring F and a ring G independently represent one of C5-C20 aromatic rings and C4-C20 heteroaromatic rings respectively; ring Z and ring W each independently represent a benzene ring, a naphthalene ring or an anthracene ring; x and Y are respectively and independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; and when X is a single bond, Y is selected from CO, SO2, S, NR1, CR2R3 or SiR4R5. The organic electroluminescent device adopting the compound disclosed by the invention has good performance of high color purity and high luminous efficiency, also realizes low-efficiency roll-off, and has extremely long device service life. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and particularly relates to an organic compound, and also relates to the application of such a light-emitting material and an organic electroluminescent device comprising the compound. Background Art

[0002] Organic light-emitting devices (OLEDs: Organic Light Emission Diodes) are devices with a sandwich-like structure, including positive and negative electrode layers and an organic functional material layer sandwiched between the electrode layers. When an appropriate voltage is applied to the positive and negative electrodes of the OLED, holes generated by the anode and electrons generated by the cathode combine in the light-emitting layer, and three colors of red, green, and blue are generated according to the characteristics of the material. OLEDs have the advantages of self-luminescence, high brightness, wide viewing angle, high contrast, low power consumption, thin light-emitting layer, and flexibility. In recent years, they have developed rapidly and are currently widely used in display fields such as lighting, smartphones, tablets, TVs, VR, and wearable devices, and have received much attention in the fields of new display technologies and new lighting technologies, and have received strong support from the country.

[0003] To prepare a light-emitting device with high luminous efficiency and long service life and improve the performance of the device, the core light-emitting material is particularly crucial. A high-efficiency and long-life OLED device is usually the result of the optimized combination of the device structure and various organic materials. For traditional fluorescent materials, their internal quantum efficiency (IQE) is only 25%, and they can only utilize singlet excitons for luminescence. Phosphorescent materials usually utilize the strong spin-orbit coupling of noble metals (such as Ir, Pt) to enhance intersystem crossing, and at the same time utilize both singlet and triplet excitons for luminescence, so that the internal quantum efficiency reaches 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 promulgated by the Radiocommunication Sector of the International Telecommunication Union (ITU-R) for the new generation of ultra-high definition (UHD) video production and display systems, for light-emitting materials, in addition to high efficiency and long life, a narrower full width at half maximum is also required to achieve higher color purity. However, the full width at half maximum of currently commercialized OLED materials is usually relatively wide (>40 nm). Although the color purity can also be improved by an optical filter, it will lead to a decrease in brightness and efficiency, which is not worth the loss.

[0005] In recent years, novel OLED materials based on multiple resonance (MR) have become a research hotspot in the field of organic electroluminescence due to their advantages of high efficiency and narrow spectra. Introducing chirality into the MR structure not only results in high-efficiency and narrow-spectrum emission but also endows the emission with circular polarization, making it have unique luminescent properties and attracting more and more researchers' attention. SUMMARY OF THE INVENTION

[0006] To solve the above technical problems, the present invention provides an organic compound with narrow-spectrum pure red light emission properties. The specific technical solution is as follows:

[0007] An organic compound having the structure shown in the following formula (1):

[0008]

[0009] In formula (1), ring A, ring B, ring C, and ring I each independently represent a benzene ring, a naphthalene ring, or an anthracene ring;

[0010] Ring D, ring E, ring F, and ring G each independently represent one of an aromatic ring with 5 to 20 carbon atoms or a heteroaromatic ring with 4 to 20 carbon atoms;

[0011] Ring Z and ring W each independently represent a benzene ring, a naphthalene ring, or an anthracene ring;

[0012] X and Y each independently are selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; and when X is a single bond, Y is selected from CO, SO2, S, NR1, CR2R3, or SiR4R5;

[0013] m and n each independently are 0 or 1;

[0014] R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R z 、R w each independently represent a mono-substituent to the maximum allowable number of substituents; the R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R iTwo adjacent ones among them are not connected or are connected by a chemical bond to form a ring; R z and R w are not connected or are connected by a chemical bond to form a ring;

[0015] The said R a and R b and R c and R d and R e and R f and R g and R h and R i and R z and R w are each independently connected to the connected ring structure by a chemical bond, or are fused to form a ring structure connection through O, S, Se, NR1, CR2R3 or SiR4R5;

[0016] The said R1, R2, R3, R4, R5 are not connected to adjacent groups or are connected by a chemical bond to form a ring; There is no connection or connection to form a ring between R2 and R3; There is no connection or connection to form a ring between R4 and R5;

[0017] The said R1, R2, R3, R4, R5 are each independently selected from one of the following groups which are unsubstituted or substituted by R': C1-C36 linear alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;

[0018] R a and R b and R c and R d and R e and R f and R g and R h and R i and R z and R w are each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino or one of the following groups which are unsubstituted or substituted by R': C1-C36 linear alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, Cl-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;

[0019] Two adjacent R's are not connected or connected by a chemical bond; R' is selected from any one or a combination of two of deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 linear 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, and C3-C60 heteroaryl.

[0020] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents, they may 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 substituents is as shown above and will not be elaborated one by one.

[0021] In this specification, the expression of Ca~Cb represents that the group has a carbon atom number of a~b. Generally, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0022] In this specification, the expression of a ring structure crossed by "—" indicates that the connection site is at any position on the ring structure capable of forming a bond.

[0023] In this specification, "independently of each other" means that when the subject has multiple, they may be the same or different from each other.

[0024] In the present invention, for the expression of chemical elements, unless otherwise specified, it usually includes the concept of its isotopes. For example, the expression of "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H), 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be elaborated further.

[0025] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0026] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0027] In the present invention, unless otherwise specified, aryl and heteroaryl both include monocyclic and fused-ring cases.

[0028] In the present invention, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

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

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

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

[0032] Any of C6-C30 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

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

[0034] Any of C2-C10 may be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0035] In the present invention, the substituted or unsubstituted C6-C60 aryl group (or C6-C50 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 means 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 group, biphenyl group, terphenyl group, etc. Specifically, the biphenyl group includes 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. The polycyclic aryl group means 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 group, anthryl group, phenanthryl group, indenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, Groups such as a base, a tetracenyl group, and their derivative groups. The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracenyl group is selected from a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the pyrenyl group is selected from a 1-pyrenyl group, a 2-pyrenyl group, and a 4-pyrenyl group; the tetracenyl group is selected from a 1-tetracenyl group, a 2-tetracenyl group, and a 9-tetracenyl group. The derivative group of fluorene is selected from a 9,9-dimethylfluorenyl group, a 9,9-diethylfluorenyl group, a 9,9-dipropylfluorenyl group, a 9,9-dibutylfluorenyl group, a 9,9-dipentylfluorenyl group, a 9,9-dihexylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-dinaphthylfluorenyl group, a 9,9'-spirobifluorenyl group, and a benzofluorenyl group.

[0036] The C3-C60 heteroaryl group (or C6-C50 heteroaryl group) mentioned in the present invention includes a monocyclic heteroaryl group and a fused-ring heteroaryl group, preferably a C3-C30 heteroaryl group, more preferably a C4-C20 heteroaryl group, and even more preferably a C5-C12 heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as an aryl group, a heteroaryl group, an alkyl group, etc.), the heteroaryl group and other groups are independent of each other and are connected by a single bond. Examples of the monocyclic heteroaryl group include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, etc. The fused-ring heteroaryl group means that the molecule contains at least one aromatic heterocycle and an aromatic ring (an aromatic heterocycle or an aromatic ring), and the two are not independent of each other but are fused to each other by sharing two adjacent atoms. Examples of the fused-ring heteroaryl group include a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an acridinyl group, an isobenzofuryl group, an isobenzothienyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, a phenazinyl group, a 9-phenylcarbazolyl group, a 9-naphthylcarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, etc.

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

[0038] The aryloxy group or heteroaryloxy group in the present invention can be a monovalent group formed by an oxygen atom and the above aryl group or heteroaryl group.

[0039] In the present invention, the arylamino group represents a group formed by substituting one or two hydrogen atoms on the amino group with an aryl group, and the connection site of the arylamino group can be connected to the aryl group in the arylamino group or to the N in the arylamino group. The exemplary number of carbon atoms and specific groups of the aryl group in the arylamino group are the same as those above.

[0040] Examples of the C6-C30 arylamine mentioned in the present invention include, for example, phenylamine, methylphenylamine, naphthylamine, anthrylamine, phenanthrylamine, biphenylamine, etc.

[0041] Examples of the C3-C30 heteroarylamine mentioned in the present invention include, for example, pyridylamine, pyrimidinylamine, dibenzofuranylamine, etc.

[0042] In the present invention, the linear alkyl group, unless otherwise specified, includes a straight-chain alkyl group and a branched-chain alkyl group. Specifically, the substituted or unsubstituted C1-C30 linear alkyl group is preferably a substituted or unsubstituted C1-C16 linear alkyl group, and more preferably a substituted or unsubstituted C1-C10 linear alkyl group. Examples of the substituted or unsubstituted C1-C10 linear alkyl group include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0043] In the present invention, the cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group; wherein, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure; the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0044] In the present specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of the C1-C20 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are preferred, and methoxy is more 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 by the groups exemplified in the above C1-C10 linear alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and other groups.

[0046] In this specification, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, is a hydrocarbon group containing at least 1 C═C double bond, and exemplarily includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0047] It should be noted that in this application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between each group, rather than the effect of a single group.

[0048] Furthermore, the organic compound of the present invention has a structure shown in formula (2-1) or formula (2-2):

[0049]

[0050] Wherein, ring D, ring E, ring F, ring G, R a , R c , R d , R e , R f , R g , R i , R z , R w , m, and n are defined in the same way as those in formula (1);

[0051] X is selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; Y is selected from a single bond, NR1 or CR2R3; and when X is a single bond, Y is selected from NR1 or CR2R3;

[0052] Preferably, m is 0 or 1, X is selected from a single bond, NR1 or CR2R3; n is 1, and Y is selected from a single bond.

[0053] More preferably, it is characterized in that in formula (1), formula (2-1), and formula (2-2), ring D, ring E, ring F, and ring G are each independently a structure shown in formula (a) or formula (b), and the dotted line represents the fusion position of the following groups in formula (1), formula (2), and formula (2-2):

[0054]

[0055] In formula (a), U 1 , U 2 , U 3 , U 4 are each independently selected from CR 1 or N, and two adjacent Rs1 are not connected to each other or are connected by a chemical bond to form a ring;

[0056] R 1 each independently selected from hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R”-substituted C1-C20 linear 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), X 1 is selected from O, S, NR 2 or CR 3 R 4 ; R 2 and R 3 and R 4 are not connected to the adjacent groups or are connected by a chemical bond to form a ring; R 3 and R 4 are not connected or are connected to form a ring;

[0058] R 2 and R 3 and R 4 each independently selected from unsubstituted or R”-substituted C1-C20 linear 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 deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 linear 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, any one or a combination of two of them.

[0060] Continuing preferably, in formula (a), U 1 and U 2 and U 3 and U 4 each independently selected from CR 1 where R 1Each independently selected from one or a combination of two of hydrogen, deuterium, cyano, halogen or the following substituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indeno[1,2-b]fluorene, trindene, isotrindene, spirotrindene, spiroisotrindene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indeno[1,2-b]carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraaza[1,2,3,4-def]chrysene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthroline, 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, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy or silyl;

[0061] In formula (b), R 2 , R 3 , R 4Each independently selected from one or a combination of two of the following substituted groups: halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy.

[0062] In the general formula compound of the present invention, preferably, both the ring Z and the ring W are benzene rings; or one of the ring Z and the ring W is a naphthalene ring and the other is a benzene ring;

[0063] Preferably, the R z , R w Each independently selected from hydrogen, deuterium, halogen, cyano, amino or one of the following groups which are unsubstituted or substituted by R': C1-C6 linear alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C1-C10 alkylsilyl, C2-C6 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl; R' is selected from any one of deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl;

[0064] More preferably, the Rz and R w are each independently selected from one or a combination of two of hydrogen, deuterium, or the following substituted groups: cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, vinyl, propenyl, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, carbazolyl, pyridyl, quinolinyl, acridinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthrolinyl, 1,3,5-triazinyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, tert-butylphenyl, cyanophenyl, pyrrolidine, trimethylsilyl, triphenylsilyl, piperidine, or methoxy;

[0065] R z and R w are not connected or are connected by a chemical bond to form a ring.

[0066] In the general formula compound of the present invention, preferably, the R a , R b , R c , R d , R e , R f , R g , R i are each independently selected from hydrogen, deuterium, halogen, cyano, amino, or one of the following unsubstituted or R'-substituted groups: C1-C6 linear 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;

[0067] Preferably, the R a , R b , R c , R d , R e , R f , R g , R iEach independently selected from one or a combination of two of hydrogen, deuterium or the following substituents: halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthrooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, aza-carbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy;

[0068] R1, R2, R3, R4, and R5 are each independently selected from one or a combination of two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthrooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy.

[0069] Furthermore, the general formula compounds of the present invention can preferably be the following specific structural compounds A1 - A68, B1 - B88, C1 - C64, D1 - D60, E1 - E60, F1 - F60, which are only representative:

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] The innovative structural design of this type of compound of the present invention is as follows: The use of a naphthalene- or anthracene-fused indolocarbazole group connected to a boron-nitrogen core can not only expand the π-conjugation of the entire molecule, shifting the photochromism to pure red light emission with a standard of 620 - 630 nm, but also, due to the MR multiple resonance effect of indolocarbazole, significantly narrowing the full width at half maximum of the emission, achieving ultra-narrowband pure red light emission. The naphthalene- or anthracene-fused structure in the core of the present invention can also further expand the naphthalene ring fragment, and increasing the conjugated fragment can further shift the photochromism to deep red light of about 640 nm.

[0087] Meanwhile, introducing a spiro atom on one side of the N - B - N core connects the two benzene rings on both sides, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the molecular rigidity, significantly narrowing the full width at half maximum (FWHM is 20 - 30 nm), and improving the luminescence efficiency (PLQY > 90%). Due to the spatial structure of the spiro atom's tetrahedron, the introduction of the spiro atom forms two orthogonal planes at the spiro atom, significantly increasing the intermolecular distance and reducing the intermolecular interaction force, which can reduce the interaction between the host and the dye and between the dyes in the device, thus significantly improving the luminescence efficiency and the lifetime of the device. Different spiro atom fragments have different triplet energy levels, which can regulate the distribution of triplet excitons in the molecule, thereby affecting the exciton lifetime and further regulating the lifetime of the device. And the introduction of the spiro atom fragment will not have a great impact on the photochromism, and can significantly improve the lifetime of the device without changing the photochromism and FWHM. The fragment structure that can be connected at the spiro atom in the structure designed by the compound of the present invention can preferably be the following structure, where "*" represents the site connected to the spiro atom:

[0088]

[0089] The electroluminescence spectrum of the OLED device prepared with the compound of the present invention has a narrow full width at half maximum (<30 nm), showing obvious multiple resonance thermally activated delayed fluorescence characteristics, thus greatly enriching the framework system of multiple resonance narrow spectrum materials. At the same time, the synthesis process is greatly simplified and the reaction yield is improved. The corresponding electroluminescent device has a low turn-on voltage, high luminous efficiency and extremely long service life, which can meet the requirements of current panel manufacturing enterprises for high-performance materials and shows good application prospects in industrialization.

[0090] The second object of the present invention is to provide an application of the compound described in the first object, and 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.

[0091] The third object of the present invention is to provide an organic electroluminescent device. Specifically, an embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer formed on the substrate in sequence; the light-emitting functional layers include 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; wherein, preferably, the light-emitting layer contains a general formula compound shown in any one of the above general formulas (1), (2-1), and (2-2), or the light-emitting layer contains at least one of the above specific compounds A1-A68, B1-B88, C1-C64, D1-D60, E1-E60, and F1-F60. Detailed Embodiments

[0092] Next, the specific preparation methods of the above new compounds of the present invention will be detailed with multiple synthesis examples, but the preparation methods of the present invention are not limited to these synthesis examples.

[0093] All kinds of chemical reagents used in the present invention, 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 all purchased from Shanghai Titan 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, UK).

[0094] The synthesis method of the compound of the present invention is briefly described below. First, nucleophilic substitution and Buchwald-Hartwig reaction are used to obtain intermediate I. Then, n-butyl lithium is used to undergo lithium halogen exchange, followed by nucleophilic addition with aromatic ketone, followed by acidification and ring closure to obtain intermediate II. Finally, under the action of tert-butyl lithium, electrophilic borylation is carried out with boron tribromide to obtain the target compound.

[0095] Synthesis Example 1 Synthesis of Compound A4

[0096]

[0097] In a two-necked flask, under nitrogen atmosphere, the compound 1-bromo-3-chloro-2-fluoro-4-iodobenzene (10 mmol), carbazole (10 mmol), and cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF), heated to 150°C, and reacted for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 100 mL of water, washed twice with 10 mL of methanol, and dried to obtain the target compound A4-1 as a light yellow solid.

[0098] In a double-necked flask, under a nitrogen atmosphere, compound A4-1 (10 mmol), intermediate I1 (10 mmol), tridibenzylideneacetone dipalladium (1 mmol), tri-tert-butylphosphine tetrafluoroborate (2 mmol), sodium tert-butoxide (12 mmol) were added in sequence, 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 over anhydrous sodium sulfate, then filtered and concentrated, and the compound was separated by a silica gel column with petroleum ether: dichloromethane = 10:1 as the developing solvent to obtain compound A4-2.

[0099] In a double-necked flask, under a nitrogen atmosphere, compound A4-2 (5mmol) was dissolved in 10ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyl lithium (1M, 6ml) was added, and the reaction was carried out at this temperature for 1 hour. 3,6-dimethyl-9-fluorenone was dissolved in 40ml of dry tetrahydrofuran cooled to -78°C in advance, and then the solution was slowly injected into the solution of A4-2 at -78°C, slowly warmed to room temperature, and reacted for 12 hours. After the reaction was completed, a small amount of methanol was added to quench, the solvent was evaporated under reduced pressure, 100ml of glacial acetic acid and 10ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with a saturated sodium carbonate aqueous solution, the liquid was extracted with dichloromethane and the organic phase was collected, the organic phase was dried with anhydrous sodium sulfate, and then the organic phase was filtered and concentrated, and the compound was separated by a silica gel column with petroleum ether: dichloromethane = 5:1 as the developing solvent to obtain compound A4-3.

[0100] In a sealed tube, dissolve compound A4-3 (1 mmol) in 20 mL of tert-butylbenzene. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then, warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, and pass the residue through a silica gel column using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A4 (purity by HPLC analysis: 99.24%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 931.4098; elemental analysis result: theoretical values: C, 88.921; H, 5.412; B, 1.163; N, 4.514 (%) ; experimental values: C, 88.926; H, 5.415; B, 1.165; N, 4.512 (%).

[0101] Synthesis Example 2 Synthesis of Compound A8

[0102]

[0103] The synthesis method of this compound is similar to that of Example 1. Only the intermediate I1 in the second step needs to be replaced with the corresponding indolocarbazole derivative to obtain the target compound A8 (purity by HPLC analysis: 99.04%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 953.3941; elemental analysis result: theoretical values: C, 89.391; H, 5.072; B, 1.133; N, 4.404 (%) ; experimental values: C, 89.389; H, 5.067; B, 1.123; N, 4.408 (%).

[0104] Synthesis Example 3 Synthesis of Compound A11

[0105]

[0106] The synthesis method of this compound is similar to that of Example 1. Only the first step needs to be replaced with the corresponding carbazole derivative to obtain the target compound A11 (purity by HPLC analysis: 99.22%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1125.4003; elemental analysis result: theoretical values: C, 88.521; H, 4.302; B, 0.963; N, 6.224 (%) ; experimental values: C, 88.552; H, 4.341; B, 0.982; N, 6.212 (%).

[0107] Synthesis Example 4 Synthesis of Compound A14

[0108]

[0109] The synthesis method of this compound is similar to that of Example 1. Only the first step needs to be replaced with the corresponding carbazole derivative to obtain the target compound A14 (purity analyzed by HPLC: 99.34%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 925.2723; elemental analysis result: theoretical values: C, 86.911; H, 3.922; B, 1.173; N, 4.546; S, 3.464 (%) ; experimental values: C, 86.921; H, 3.942; B, 1.162; N, 4.532; S, 3.472 (%).

[0110] Synthesis of Compound A19 in Synthesis Example 5

[0111]

[0112] The synthesis method of this compound is similar to that of Example 1. Only the first step needs to be replaced with the corresponding carbazole derivative to obtain the target compound A19 (purity analyzed by HPLC: 99.15%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1068.4363; elemental analysis result: theoretical values: C, 88.751; H, 5.002; B, 1.013; N, 5.244 (%) ; experimental values: C, 88.741; H, 5.021; B, 1.022; N, 5.231 (%).

[0113] Synthesis of Compound A27 in Synthesis Example 6

[0114]

[0115] The synthesis method of this compound is similar to that of Example 1. Only the first step needs to be replaced with the corresponding carbazole derivative to obtain the target compound A27 (purity analyzed by HPLC: 99.07%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1068.4363; elemental analysis result: theoretical values: C, 88.751; H, 5.002; B, 1.013; N, 5.244 (%) ; experimental values: C, 88.741; H, 5.011; B, 1.025; N, 5.231 (%).

[0116] Synthesis of Compound A39 in Synthesis Example 7

[0117]

[0118] The synthesis method of the compound is similar to that of Example 1, except that the first step is replaced with the corresponding carbazole derivative to obtain the target compound A39 (HPLC analysis purity 99.09%), a dark red solid. MALDI-TOF-MS results: molecular ion peak: 907.3159; elemental analysis results: theoretical value: C, 89.961; H, 4.222; B, 1.193; N, 4.634 (%); experimental value: C, 89.968; H, 4.222; B, 1.198; N, 4.639 (%).

[0119] Synthesis Example 8 Synthesis of Compound A43

[0120]

[0121] In a two-necked flask, under nitrogen atmosphere, the compound 1-bromo-3-chloro-4-fluoro-2-iodobenzene (10 mmol), I1 (10 mmol), and cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF), heated to 150°C, and reacted for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 100 mL of water, washed twice with 10 mL of methanol, and dried to obtain the target compound A43-1 as a light yellow solid.

[0122] In a double-necked flask, under a nitrogen atmosphere, compound A43-1 (10 mmol), diphenylamine (10 mmol), tridibenzylideneacetone dipalladium (1 mmol), tri-tert-butylphosphine tetrafluoroborate (2 mmol), sodium tert-butoxide (12 mmol) were added in sequence, 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 over anhydrous sodium sulfate, then filtered and concentrated, and the compound was separated by a silica gel column with petroleum ether: dichloromethane = 10:1 as the developing solvent to obtain compound A43-2.

[0123] In a two-necked flask, under a nitrogen atmosphere, dissolve compound A43-2 (5 mmol) in 10 ml of dry tetrahydrofuran, cool to -78 °C, add a pentane solution of n-butyllithium (1 M, 6 ml), and react at this temperature for 1 hour. Dissolve 9-fluorenone in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then slowly inject this solution into the solution of A43-2 at -78 °C, slowly warm to room temperature, and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, add 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid, and then heat to reflux. After reacting for 2 hours, neutralize with saturated aqueous sodium carbonate solution, extract and separate with dichloromethane and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase, and separate the compound by silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A43-3.

[0124] Dissolve compound A43-3 (1 mmol) in 20 mL of tert-butylbenzene in a sealed tube, cool to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL), and then warm to 30 °C and react for 1 hour. Cool to -78 °C again, slowly add boron tribromide (3 mmol), and then warm to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then warm to 160 °C and react for 12 hours. Evacuate the solvent under vacuum, pass through a silica gel column, with petroleum ether:dichloromethane = 10:1 as the eluent, to obtain the target compound A43 (HPLC analysis purity 99.11%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 933.4254; elemental analysis result: theoretical value: C, 88.731; H, 5.612; B, 1.163; N, 4.504 (%); experimental value: C, 88.736; H, 5.621; B, 1.165; N, 4.509 (%).

[0125] Synthesis Example 9 Synthesis of Compound A51

[0126]

[0127] The synthesis method of this compound is similar to that of Example 8, only the second step needs to be replaced with the corresponding diphenylamine derivative to obtain the target compound A51 (HPLC analysis purity 99.17%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 899.2566; elemental analysis result: theoretical value: C, 86.761; H, 3.812; B, 1.203; N, 4.674; S, 3.565 (%); experimental value: C, 86.755; H, 3.821; B, 1.206; N, 4.678; S, 3.551 (%).

[0128] Synthesis Example 10 Synthesis of Compound A59

[0129]

[0130] The synthesis method of this compound is similar to that of Example 8. Only the second step needs to be replaced with the corresponding diphenylamine derivative to obtain the target compound A59 (purity by HPLC analysis: 99.19%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 955.3159; elemental analysis result: theoretical values: C, 90.471; H, 4.012; B, 1.133; N, 4.404 (%) ; experimental values: C, 90.463; H, 4.021; B, 1.135; N, 4.408 (%).

[0131] Synthesis Example 11 Synthesis of Compound A64

[0132]

[0133] The synthesis method of this compound is similar to that of Example 8. Only the second step needs to be replaced with the corresponding diphenylamine derivative to obtain the target compound A64 (purity by HPLC analysis: 99.29%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1127.4159; elemental analysis result: theoretical values: C, 88.371; H, 4.472; B, 0.963; N, 6.214 (%) ; experimental values: C, 88.369; H, 4.471; B, 0.968; N, 6.219 (%).

[0134] Synthesis Example 12 Synthesis of Compound B1

[0135]

[0136] The synthesis method of this compound is similar to that of Example 1 to obtain the target compound B1 (purity by HPLC analysis: 99.12%), a dark red solid. MALDI-TOF-MS result: molecular ion peak: 841.2689; elemental analysis result: theoretical values: C, 89.891; H, 3.832; B, 1.283; N, 4.994 (%) ; experimental values: C, 89.888; H, 3.838; B, 1.276; N, 4.983 (%).

[0137] Synthesis Example 13 Synthesis of Compound B7

[0138]

[0139] The synthesis method of this compound is similar to that of Example 1, and the target compound B7 (purity by HPLC analysis: 99.19%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 1029.4254; Results of elemental analysis: theoretical values: C, 89.781; H, 5.092; B, 1.053; N, 4.084 (%) ; experimental values: C, 89.778; H, 5.089; B, 1.065; N, 4.078 (%).

[0140] Synthesis of Compound B16 in Synthesis Example 14

[0141]

[0142] The synthesis method of this compound is similar to that of Example 1, and the target compound B16 (purity by HPLC analysis: 99.12%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 993.3315; Results of elemental analysis: theoretical values: C, 90.631; H, 4.062; B, 1.093; N, 4.234 (%) ; experimental values: C, 90.621; H, 4.053; B, 1.078; N, 4.224 (%).

[0143] Synthesis of Compound B23 in Synthesis Example 15

[0144]

[0145] The synthesis method of this compound is similar to that of Example 1, and the target compound A11 (purity by HPLC analysis: 99.02%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 1006.3268; Results of elemental analysis: theoretical values: C, 89.461; H, 3.90; 2B, 1.073; N, 5.564 (%) ; experimental values: C, 89.452; H, 3.906; B, 1.074; N, 5.569 (%).

[0146] Synthesis of Compound B39 in Synthesis Example 16

[0147]

[0148] The synthesis method of this compound is similar to that of Example 1, and the target compound B39 (purity by HPLC analysis: 99.16%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 957.3315; Results of elemental analysis: theoretical values: C, 90.281; H, 4.212; B, 1.133; N, 4.394 (%) ; experimental values: C, 90.288; H, 4.218; B, 1.132; N, 4.395 (%).

[0149] Synthesis Example 17 Synthesis of Compound B42

[0150]

[0151] The synthesis method of this compound is similar to that of Example 8, and the target compound B42 (purity 99.21% by HPLC analysis) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 977.3941; elemental analysis result: theoretical values: C, 89.651; H, 4.952; B, 1.113; N, 4.304 (%); experimental values: C, 89.665; H, 4.985; B, 1.121; N, 4.303 (%).

[0152] Synthesis Example 18 Synthesis of Compound B53

[0153]

[0154] The synthesis method of this compound is similar to that of Example 8, and the target compound B53 (purity 99.22% by HPLC analysis) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 873.2410; elemental analysis result: theoretical values: C, 86.591; H, 3.692; B, 1.243; N, 4.814; S, 3.675 (%); experimental values: C, 86.583; H, 3.698; B, 1.246; N, 4.801; S, 3.679 (%).

[0155] Synthesis Example 19 Synthesis of Compound B65

[0156]

[0157] The synthesis method of this compound is similar to that of Example 1, and the target compound B65 (purity 99.09% by HPLC analysis) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 955.4098; elemental analysis result: theoretical values: C, 89.201; H, 5.272; B, 1.133; N, 4.404 (%); experimental values: C, 89.202; H, 5.275; B, 1.136; N, 4.401 (%).

[0158] Synthesis Example 20 Synthesis of Compound B67

[0159]

[0160] The synthesis method of this compound is similar to that of Example 1, and the target compound B67 (purity by HPLC analysis: 99.15%) is obtained, which is a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 1094.4520; Results of elemental analysis: theoretical values: C, 88.831; H, 5.062; B, 0.993; N, 5.124 (%); experimental values: C, 88.836; H, 5.068; B, 0.990; N, 5.128 (%).

[0161] Synthesis of Compound B75 in Synthesis Example 21

[0162]

[0163] The synthesis method of this compound is similar to that of Example 1, and the target compound B75 (purity by HPLC analysis: 99.17%) is obtained, which is a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 1097.5819; Results of elemental analysis: theoretical values: C, 88.581; H, 6.612; B, 0.983; N, 3.834 (%); experimental values: C, 88.578; H, 6.621; B, 0.978; N, 3.843 (%).

[0164] Synthesis of Compound B82 in Synthesis Example 22

[0165]

[0166] The synthesis method of this compound is similar to that of Example 8, and the target compound B82 (purity by HPLC analysis: 99.12%) is obtained, which is a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 847.3159; Results of elemental analysis: theoretical values: C, 89.251; H, 4.522; B, 1.283; N, 4.964 (%); experimental values: C, 89.254; H, 4.523; B, 1.278; N, 4.956 (%).

[0167] Synthesis of Compound B88 in Synthesis Example 23

[0168]

[0169] The synthesis method of this compound is similar to that of Example 8, and the target compound B88 (purity by HPLC analysis: 99.27%) is obtained, which is a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 859.3159; Results of elemental analysis: theoretical values: C, 89.401; H, 4.452; B, 1.263; N, 4.894 (%); experimental values: C, 89.407; H, 4.458; B, 1.264; N, 4.897 (%).

[0170] Synthesis Example 24 Synthesis of Compound C3

[0171]

[0172] The synthesis method of this compound is similar to that of Example 1, and the target compound C3 (purity 99.11% by HPLC analysis) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 953.3941; elemental analysis result: theoretical values: C, 89.391; H, 5.072; B, 1.133; N, 4.404 (%); experimental values: C, 89.398; H, 5.087; B, 1.133; N, 4.402 (%).

[0173] Synthesis Example 25 Synthesis of Compound C12

[0174]

[0175] The synthesis method of this compound is similar to that of Example 1, and the target compound C12 (purity 99.15% by HPLC analysis) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1091.5350; elemental analysis result: theoretical values: C, 89.071; H, 6.092; B, 0.993; N, 3.854 (%); experimental values: C, 89.067; H, 6.099; B, 0.995; N, 3.852 (%).

[0176] Synthesis Example 26 Synthesis of Compound C20

[0177]

[0178] The synthesis method of this compound is similar to that of Example 1, and the target compound B75 (purity 99.17% by HPLC analysis) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 993.3315; elemental analysis result: theoretical values: C, 90.631; H, 4.062; B, 1.093; N, 4.234 (%); experimental values: C, 90.633; H, 4.065; B, 1.097; N, 4.231 (%).

[0179] Synthesis Example 27 Synthesis of Compound C31

[0180]

[0181] The synthesis method of this compound is similar to that of Example 1, and the target compound C31 (HPLC analysis purity 99.35%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1138.4207; elemental analysis result: theoretical values: C, 89.621; H, 4.511; B, 0.952; N, 4.923 (%) ; experimental values: C, 89.632; H, 4.521; B, 0.955; N, 4.932 (%).

[0182] Synthesis of Compound C42 in Synthesis Example 28

[0183]

[0184] The synthesis method of this compound is similar to that of Example 8, and the target compound C42 (HPLC analysis purity 99.22%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 893.3002; elemental analysis result: theoretical values: C, 90.031; H, 4.062; B, 1.213; N, 4.704 (%) ; experimental values: C, 90.033; H, 4.056; B, 1.221; N, 4.701 (%).

[0185] Synthesis of Compound C49 in Synthesis Example 29

[0186]

[0187] The synthesis method of this compound is similar to that of Example 8, and the target compound C49 (HPLC analysis purity 99.21%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 873.2410; elemental analysis result: theoretical values: C, 86.591; H, 3.692; B, 1.243; N, 4.814; S, 3.675 (%) ; experimental values: C, 86.595; H, 3.689; B, 1.254; N, 4.821; S, 3.667 (%).

[0188] Synthesis of Compound C57 in Synthesis Example 30

[0189]

[0190] The synthetic method of this compound is similar to that of Example 8, and the target compound C57 (HPLC analysis purity 99.20%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1059.4032; elemental analysis result: theoretical values: C, 81.561; H, 5.512; B, 1.021; N, 3.962; Si, 7.951 (%) ; experimental values: C, 81.556; H, 5.521; B, 1.022; N, 3.966; Si, 7.965 (%).

[0191] Synthesis of Compound C60 in Synthesis Example 31

[0192]

[0193] The synthetic method of this compound is similar to that of Example 8, and the target compound C60 (HPLC analysis purity 99.12%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1177.4316; elemental analysis result: theoretical values: C, 88.691; H, 4.452; B, 0.92; 1N, 5.942 (%) ; experimental values: C, 88.679; H, 4.465; B, 0.932; N, 5.944 (%).

[0194] Synthesis of Compound D4 in Synthesis Example 32

[0195]

[0196] The synthetic method of this compound is similar to that of Example 1, and the target compound D3 (HPLC analysis purity 99.24%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1115.5350; elemental analysis result: theoretical values: C, 89.311; H, 5.962; B, 0.973; N, 3.764 (%) ; experimental values: C, 89.312; H, 5.956; B, 0.967; N, 3.766 (%).

[0197] Synthesis of Compound D12 in Synthesis Example 33

[0198]

[0199] The synthesis method of this compound is similar to that of Example 1, and the target compound D12 (HPLC analysis purity 99.12%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 891.2846; elemental analysis result: theoretical values: C, 90.231; H, 3.842; B, 1.211; N, 4.712 (%) ; experimental values: C, 90.233; H, 3.844; B, 1.212; N, 4.711 (%).

[0200] Synthesis of Compound D18 in Synthesis Example 34

[0201]

[0202] The synthesis method of this compound is similar to that of Example 1, and the target compound D16 (HPLC analysis purity 99.11%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 947.2566; elemental analysis result: theoretical values: C, 87.431; H, 3.622; B, 1.141; N, 4.432; S, 3.381 (%) ; experimental values: C, 87.433; H, 3.625; B, 1.144; N, 4.433; S, 3.381 (%).

[0203] Synthesis of Compound D34 in Synthesis Example 35

[0204]

[0205] The synthesis method of this compound is similar to that of Example 8, and the target compound D34 (HPLC analysis purity 99.02%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 843.2846; elemental analysis result: theoretical values: C, 89.681; H, 4.062; B, 1.281; N, 4.982 (%) ; experimental values: C, 89.686; H, 4.065; B, 1.278; N, 4.978 (%).

[0206] Synthesis of Compound D39 in Synthesis Example 36

[0207]

[0208] The synthesis method of this compound is similar to that of Example 8, and the target compound D39 (purity by HPLC analysis: 99.11%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 925.3628; elemental analysis result: theoretical values: C, 89.501; H, 4.792; B, 1.171; N, 4.542 (%); experimental values: C, 89.507; H, 4.779; B, 1.167; N, 4.564 (%).

[0209] Synthesis of Compound D48 in Synthesis Example 37

[0210]

[0211] The synthesis method of this compound is similar to that of Example 8, and the target compound D48 (purity by HPLC analysis: 99.15%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 949.2723; elemental analysis result: theoretical values: C, 87.241; H, 3.822; B, 1.141; N, 4.422; S, 3.371 (%); experimental values: C, 87.234; H, 3.832; B, 1.134; N, 4.432; S, 3.367 (%).

[0212] Synthesis of Compound D55 in Synthesis Example 38

[0213]

[0214] The synthesis method of this compound is similar to that of Example 8, and the target compound D55 (purity by HPLC analysis: 99.13%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1005.3315; elemental analysis result: theoretical values: C, 90.741; H, 4.011; B, 1.071; N, 4.181 (%); experimental values: C, 90.743; H, 4.014; B, 1.076; N, 4.185 (%).

[0215] Synthesis of Compound E1 in Synthesis Example 39

[0216]

[0217] The synthesis method of this compound is similar to that of Example 1, and the target compound E1 (purity by HPLC analysis: 99.04%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 930.2955; elemental analysis result: theoretical values: C, 89.031; H, 3.792; B, 1.161; N, 6.022 (%) ; experimental values: C, 89.023; H, 3.779; B, 1.166; N, 6.032 (%).

[0218] Synthesis Example 40 Synthesis of Compound E4

[0219]

[0220] The synthesis method of this compound is similar to that of Example 1, and the target compound E4 (purity by HPLC analysis: 99.04%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1130.5459; elemental analysis result: theoretical values: C, 88.121; H, 5.972; B, 0.961; N, 4.951 (%) ; experimental values: C, 88.132; H, 5.967; B, 0.966; N, 4.955 (%).

[0221] Synthesis Example 41 Synthesis of Compound E7

[0222]

[0223] The synthesis method of this compound is similar to that of Example 1, and the target compound E7 (purity by HPLC analysis: 99.04%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 992.4050; elemental analysis result: theoretical values: C, 88.301; H, 4.972; B, 1.091; N, 5.642 (%) ; experimental values: C, 88.310; H, 4.967; B, 1.089; N, 5.654 (%).

[0224] Synthesis Example 42 Synthesis of Compound E16

[0225]

[0226] The synthesis method of this compound is similar to that of Example 1, and the target compound E16 (purity by HPLC analysis: 99.16%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1032.3424; elemental analysis result: theoretical values: C, 89.532; H, 4.001; B, 1.052; N, 5.421 (%) ; experimental values: C, 89.535; H, 4.003; B, 1.055; N, 5.423 (%).

[0227] Synthesis Example 43: Synthesis of Compound E22

[0228]

[0229] The synthesis method of this compound is similar to that of Example 1, and the target compound E22 (purity by HPLC analysis: 99.11%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1045.3377; elemental analysis result: theoretical values: C, 88.421; H, 3.852; B, 1.031; N, 6.701 (%); experimental values: C, 88.424; H, 3.856; B, 1.035; N, 6.705 (%).

[0230] Synthesis Example 44: Synthesis of Compound E26

[0231]

[0232] The synthesis method of this compound is similar to that of Example 1, and the target compound E26 (purity by HPLC analysis: 99.15%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 996.3424; elemental analysis result: theoretical values: C, 89.151; H, 4.152; B, 1.081; N, 5.622 (%); experimental values: C, 89.155; H, 4.156; B, 1.084; N, 5.626 (%).

[0233] Synthesis Example 45: Synthesis of Compound E32

[0234]

[0235] The synthesis method of this compound is similar to that of Example 8, and the target compound E32 (purity by HPLC analysis: 99.12%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 912.2519; elemental analysis result: theoretical values: C, 85.521; H, 3.642; B, 1.181; N, 6.142; S, 3.511 (%); experimental values: C, 85.524; H, 3.645; B, 1.186; N, 6.147; S, 3.513 (%).

[0236] Synthesis Example 46: Synthesis of Compound E42

[0237]

[0238] The synthesis method of this compound is similar to that of Example 8, and the target compound E42 (purity by HPLC analysis: 99.17%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 896.2747; Results of elemental analysis: theoretical values: C, 87.051; H, 3.712; B, 1.211; N, 6.252; O, 1.781 (%) ; experimental values: C, 87.025; H, 3.721; B, 1.221; N, 6.255; O, 1.768 (%).

[0239] Synthesis of Compound E51 in Synthesis Example 47

[0240]

[0241] The synthesis method of this compound is similar to that of Example 8, and the target compound E51 (purity by HPLC analysis: 99.18%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 1264.4425; Results of elemental analysis: theoretical values: C, 88.282; H, 4.226; B, 0.851; N, 6.647 (%) ; experimental values: C, 88.282; H, 4.225; B, 0.858; N, 6.642 (%).

[0242] Synthesis of Compound E53 in Synthesis Example 48

[0243]

[0244] The synthesis method of this compound is similar to that of Example 8, and the target compound E53 (purity by HPLC analysis: 99.11%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 1084.3737; Results of elemental analysis: theoretical values: C, 89.661; H, 4.182; B, 1.001; N, 5.162 (%) ; experimental values: C, 89.667; H, 4.185; B, 1.006; N, 5.161 (%).

[0245] Synthesis of Compound E55 in Synthesis Example 49

[0246]

[0247] The synthesis method of this compound is similar to that of Example 8, and the target compound E55 (purity by HPLC analysis: 99.11%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 908.3111; elemental analysis result: theoretical values: C, 88.541; H, 4.102; B, 1.191; N, 6.162 (%); experimental values: C, 88.534; H, 4.110; B, 1.179; N, 6.166 (%).

[0248] Synthesis of Compound F2 in Synthesis Example 50

[0249]

[0250] The synthesis method of this compound is similar to that of Example 1, and the target compound F2 (purity by HPLC analysis: 99.14%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 901.2723; elemental analysis result: theoretical values: C, 86.561; H, 4.022; B, 1.201; N, 4.662; S, 3.551 (%); experimental values: C, 86.556; H, 4.012; B, 1.210; N, 4.656; S, 3.565 (%).

[0251] Synthesis of Compound F8 in Synthesis Example 51

[0252]

[0253] The synthesis method of this compound is similar to that of Example 1, and the target compound F8 (purity by HPLC analysis: 99.06%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1097.4914; elemental analysis result: theoretical values: C, 86.401; H, 5.872; B, 0.981; N, 3.832; S, 2.921 (%); experimental values: C, 86.406; H, 5.875; B, 0.978; N, 3.838; S, 2.926 (%).

[0254] Synthesis of Compound F18 in Synthesis Example 52

[0255]

[0256] The synthesis method of this compound is similar to that of Example 1, and the target compound F18 (purity by HPLC analysis: 99.12%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 995.3142; Results of elemental analysis: theoretical values: C, 85.621; H, 4.252; B, 1.091; N, 4.222; O, 1.611; S, 3.222 (%) ; experimental values: C, 85.622; H, 4.245; B, 1.079; N, 4.2232; O, 1.621; S, 3.232 (%).

[0257] Synthesis of Compound F23 in Synthesis Example 53

[0258]

[0259] The synthesis method of this compound is similar to that of Example 1, and the target compound F23 (purity by HPLC analysis: 99.17%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 972.3060; Results of elemental analysis: theoretical values: C, 87.651; H, 3.832; B, 1.112; N, 5.763; O, 1.644 (%) ; experimental values: C, 87.655; H, 3.836; B, 1.131; N, 5.776; O, 1.664 (%).

[0260] Synthesis of Compound F30 in Synthesis Example 54

[0261]

[0262] The synthesis method of this compound is similar to that of Example 8, and the target compound F30 (purity by HPLC analysis: 99.10%) is obtained as a dark red solid. Results of MALDI-TOF-MS: molecular ion peak: 921.3890; Results of elemental analysis: theoretical values: C, 87.291; H, 5.252; B, 1.171; N, 4.562; O, 1.741 (%) ; experimental values: C, 87.297; H, 5.265; B, 1.167; N, 4.556; O, 1.734 (%).

[0263] Synthesis of Compound F43 in Synthesis Example 55

[0264]

[0265] The synthesis method of this compound is similar to that of Example 8, and the target compound F43 (HPLC analysis purity: 99.14%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 987.2913; elemental analysis result: theoretical values: C, 83.881; H, 4.282; B, 1.093; N, 4.251; S, 6.492 (%) ; experimental values: C, 83.878; H, 4.268; B, 1.089; N, 4.235; S, 6.479 (%).

[0266] Synthesis of Compound F55 in Synthesis Example 56

[0267]

[0268] The synthesis method of this compound is similar to that of Example 8, and the target compound F55 (HPLC analysis purity: 99.10%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 987.2879; elemental analysis result: theoretical values: C, 87.531; H, 3.886; B, 1.093; N, 4.251; S, 3.242 (%) ; experimental values: C, 87.553; H, 3.888; B, 1.079; N, 4.255; S, 3.244 (%).

[0269] Synthesis of Compound A66 in Synthesis Example 57

[0270]

[0271] The synthesis method of this compound is similar to that of Example 1, and the target compound A66 (HPLC analysis purity: 99.20%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1191.5663; elemental analysis result: theoretical values: C, 89.651; H, 5.922; B, 0.911; N, 3.522 (%) ; experimental values: C, 89.655; H, 5.932; B, 0.921; N, 3.532 (%).

[0272] Synthesis of Compound C61 in Synthesis Example 58

[0273]

[0274] The synthesis method of this compound is similar to that of Example 1, and the target compound C61 (HPLC analysis purity 99.15%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1241.5819; elemental analysis result: theoretical values: C, 89.911; H, 5.842; B, 0.871; N, 3.382 (%) ; experimental values: C, 89.915; H, 5.845; B, 0.875; N, 3.389 (%).

[0275] Synthesis of Compound D57 in Synthesis Example 59

[0276]

[0277] The synthesis method of this compound is similar to that of Example 1, and the target compound D57 (HPLC analysis purity 99.10%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1129.4567; elemental analysis result: theoretical values: C, 90.331; H, 4.992; B, 0.961; N, 3.721 (%) ; experimental values: C, 90.333; H, 4.989; B, 0.965; N, 3.732 (%).

[0278] Synthesis of Compound E57 in Synthesis Example 60

[0279]

[0280] The synthesis method of this compound is similar to that of Example 1, and the target compound E57 (HPLC analysis purity 99.13%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1168.4676; elemental analysis result: theoretical values: C, 89.371; H, 4.912; B, 0.921; N, 4.792 (%) ; experimental values: C, 89.367; H, 4.921; B, 0.932; N, 4.789 (%).

[0281] Device Example

[0282] Next, the technical effects and advantages of the present invention are demonstrated and verified by specifically applying the compound of the present invention to an organic electroluminescent device to test its actual use performance.

[0283] The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. The organic material can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0284] The materials for the anode can be oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc., and any combination thereof. The materials for the cathode can be metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., and any combination thereof.

[0285] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0286] The materials for 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 poly(phenylene vinylene), 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, etc.

[0287] The light-emitting layer includes light-emitting dyes (i.e., dopants) that can emit spectra of different wavelengths, and can also include a host material at the same time. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or 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 simultaneously emit different colors such as red, green, and blue.

[0288] 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).

[0289] Specifically, the preparation method of the organic electroluminescent device of the present invention includes the following steps:

[0290] 1. Ultrasonically treat the glass plate coated with the anode material in a commercial cleaning agent, rinse it in deionized water, ultrasonically degrease it in an acetone:ethanol mixed solvent, bake it in a clean environment until all moisture is removed, clean it with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam;

[0291] 2. Place the glass plate with the anode described above in a vacuum chamber, evacuate to 1×10-5 to 9×10-3 Pa, and vacuum deposit a hole injection material on the above anode layer film to form a hole injection layer at a deposition rate of 0.1 - 0.5 nm / s;

[0292] 3. Vacuum deposit a hole transport material on the hole injection layer to form a hole transport layer at a deposition rate of 0.1 - 0.5 nm / s,

[0293] 4. Vacuum deposit an electron blocking layer on the hole transport layer at a deposition rate of 0.1 - 0.5 nm / s;

[0294] 5. Vacuum deposit the organic light-emitting layer of the device on the electron blocking layer. The organic light-emitting layer material includes a host material and a luminescent dye. Using the method of co-evaporation from multiple sources, adjust the deposition rate of the host material, the deposition rate of the sensitizer material, and the deposition rate of the dye so that the dye reaches the preset doping ratio;

[0295] 6. Vacuum deposit a hole blocking layer on the organic light-emitting layer at a deposition rate of 0.1 - 0.5 nm / s;

[0296] 7. Vacuum deposit the electron transport material of the device on the hole blocking layer to form an electron transport layer at a deposition rate of 0.1 - 0.5 nm / s;

[0297] 8. Vacuum deposit LiF as the electron injection layer at 0.1 - 0.5 nm / s on the electron transport layer, and vacuum deposit an Al layer as the cathode of the device at 0.1 - 0.5 nm / s.

[0298] The embodiment of the present invention also provides a display device, and the display device includes the organic electroluminescent device provided as above. The display device can specifically be a display device such as an OLED display, and any product or component with a display function including the display device, such as a TV, a digital camera, a mobile phone, a tablet computer, etc. The display device has the same advantages as the above organic electroluminescent device compared to the prior art, and will not be elaborated here.

[0299] The following further introduces the organic electroluminescent device of the present invention through specific embodiments.

[0300] Examples 1 - 56 of the present invention are organic light - emitting devices prepared using the compounds of the present invention. Comparative Examples 1 - 3 are parallel - comparison devices prepared using prior - art compounds P1, P2, and P3 according to the same preparation method as the compounds of the present invention. The structural schemes of all the prepared devices are shown in Table 1 below:

[0301] Table 1:

[0302]

[0303]

[0304]

[0305] Among them, the anode material is ITO; the hole - injection layer material is HI, generally with a total thickness of 5 - 30 nm, and 10 nm in this example; the hole - transport layer material is HT, with a total thickness generally of 5 - 500 nm, and 30 nm in this example; the Host of the organic light - emitting layer is a wide - bandgap host material, and the thickness of the organic light - emitting layer is generally 1 - 200 nm, and 30 nm in this example; the electron - transport layer material is ET, with a thickness generally of 5 - 300 nm, and 30 nm in this example; the electron - injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0306] The structural formulas of various organic materials used in the above - mentioned respective examples are as follows:

[0307]

[0308]

[0309] The device performances of Examples 1 - 56 and Comparative Examples 1 - 3 of the present invention are shown in Table 2 below:

[0310] Table 2:

[0311]

[0312]

[0313]

[0314] Compared with Comparative Example 1, a spiro atom is introduced on one side of the N-B-N structure in the parent nucleus of the compound in the present invention, connecting the two benzene rings on both sides, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the rigidity of the molecule, significantly narrowing the full width at half maximum (FWHM is 20 - 30 nm), and improving the luminescence efficiency (PLQY > 90%). Compared with Comparative Example 2, the compound in the present invention uses a single B atom to control the light color at about 625 nm, showing a pure red light emission. Compared with Comparative Example 3, the compound in the present invention adopts a spirofluorene structure, connecting diphenyls with a ring, protecting the easily broken phenyl through ring formation, and significantly improving the stability in the device. The compound in the present invention has the following characteristics: due to the spatial structure of the tetrahedron of the spiro atom, the introduction of the spiro atom forms two orthogonal planes at the spiro atom, significantly increasing the intermolecular distance and reducing the intermolecular interaction force, which can reduce the interaction between the host and the dye and between dyes in the device, thereby significantly improving the luminescence efficiency and the lifetime of the device, meeting the application standards. Moreover, the lifetimes of different spiro atom fragments in the device are different. Using an indolocarbazole group fused with a naphthalene ring or an anthracene ring can not only expand the π-conjugation of the whole molecule, shifting the light color to a pure red light emission with a standard of 620 - 630 nm, but also significantly narrowing the full width at half maximum of the emission due to the MR multiple resonance effect of indolocarbazole, achieving an ultra-narrowband pure red light emission.

[0315] The above experimental data show that after the organic electroluminescent device prepared by applying the novel MR-TADF material provided by the present invention, while achieving good performance of high color purity and high luminescence efficiency of the device, it also realizes a 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 invention in improving the device efficiency and stability. Given its excellent efficiency, color purity and stability, the above compound should have good application prospects.

[0316] Although the present invention has been described in conjunction with the embodiments, the present invention is not limited to the above embodiments. It should be understood that under the guidance of the inventive concept of the present invention, those skilled in the art can make various modifications and improvements, and the appended claims define the scope of the present invention.

[0317] Obviously, the above embodiments are merely examples for clear illustration and not limitations on the implementation manners. For those of ordinary skill in the art, other different forms of changes or alterations can be made based on the above description. It is not necessary and impossible to enumerate all the implementation manners here. And the obvious changes or alterations derived therefrom are still within the protection scope of the present invention.

Claims

1. An organic compound having a structure represented by the following formula (1): In formula (1), ring A, ring B, ring C, and ring I each independently represent a benzene ring, a naphthalene ring, or an anthracene ring; ring D, ring E, ring F, and ring G each independently represent one of an aromatic ring having 5 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms; ring Z and ring W each independently represent a benzene ring, a naphthalene ring, or an anthracene ring; X and Y each independently are selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; and when X is a single bond, Y is selected from CO, SO2, S, NR1, CR2R3, or SiR4R5; m and n each independently are 0 or 1; R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R z 、R w each independently represents a mono-substituent to a substituent group with the maximum allowable number; the a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i two adjacent ones among them are not connected or are connected by a chemical bond to form a ring; R z 、R w are not connected or are connected by a chemical bond to form a ring; Said R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R z 、R w are each independently connected to the connected ring structure by a chemical bond, or are fused through O, S, Se, NR1, CR2R3 or SiR4R5 to form a ring structure connection; R1, R2, R3, R4, and R5 are not connected to the adjacent group or are connected by a chemical bond 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, and R5 each independently are selected from one of the following groups which are unsubstituted or substituted with R': a linear alkyl group having 1 to 36 carbon atoms, a cycloalkyl group having 3 to 36 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms; R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R z 、R w each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino or one of the following groups which are unsubstituted or substituted with R': a linear alkyl group having 1 to 36 carbon atoms, a cycloalkyl group having 3 to 36 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a thioalkoxy group having 1 to 10 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms; Two adjacent R's are not connected or are connected by a chemical bond; R' is selected from deuterium, a halogen, a cyano group, an amino group, an alkenyl group having 2 to 20 carbon atoms, a linear alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 60 carbon atoms, a heteroarylamino group having 3 to 60 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 3 to 60 carbon atoms, or a combination of any one or two of them.

2. The organic compound according to claim 1, characterized in that, It has a structure represented by formula (2-1) or formula (2-2): Among them, the definitions of ring D, ring E, ring F, ring G, R a , R c , R d , R e , R f , R g , R i , R z , R w , m, and n are the same as those defined in formula (1); X is selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; Y is selected from a single bond, NR1, or CR2R3; and when X is a single bond, Y is selected from NR1 or CR2R3; Preferably, m is 0 or 1, X is selected from a single bond, NR1, or CR2R3; n is 1, and Y is selected from a single bond.

3. The organic compound according to claim 1 or 2, characterized in that, In formula (1), formula (2-1), and formula (2-2), ring D, ring E, ring F, and ring G each independently have a structure represented by formula (a) or formula (b), and the dashed line represents the fusion position of the following groups in formula (1), formula (2), and formula (2-2): 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 selected from hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R”-substituted C1-C20 linear 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), X 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 or is connected to R 4 to form a ring; R 2 、R 3 、R 4 are each independently selected from one of unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; R” is selected from deuterium, a halogen, a cyano group, an amino group, an alkenyl group having 2 to 20 carbon atoms, a linear alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 60 carbon atoms, a heteroarylamino group having 3 to 60 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 3 to 60 carbon atoms, or a combination of any one or two of them.

4. The organic compound according to claim 3, characterized in that In formula (a), U 1 , U 2 , U 3 , U 4 are each independently selected from CR 1 , and R 1 are each independently selected from hydrogen, deuterium, cyano, halogen, or a combination of one or two of the following substituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indeno[1,2-b]fluorene, trindene, isotrindene, spirotrindene, spiroisotrindene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, 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, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy, or silyl; In formula (b), R 2 , R 3 , R 4 are each independently selected from one or a combination of two of the following substituted groups: halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzoanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthrooxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, aza-carbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy.

5. The organic compound according to claim 1 or 2, characterized in that, Both ring Z and ring W are benzene rings; or one of ring Z and ring W is a naphthalene ring and the other is a benzene ring; Preferably, the R z , R w are each independently selected from hydrogen, deuterium, halogen, cyano, amino or one of the following groups which are unsubstituted or substituted with R': C1-C6 linear alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C1-C10 alkylsilyl, C2-C6 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl; R' is selected from deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl; More preferably, the R z , R w are each independently selected from hydrogen, deuterium, or a combination of one or two of the following substituted groups: cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, vinyl, propenyl, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, carbazolyl, pyridyl, quinolinyl, acridinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthrolinyl, 1,3,5-triazinyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, tert-butylphenyl, cyanophenyl, pyrrolidine, trimethylsilyl, triphenylsilyl, piperidine or methoxy; R z and R w are not connected or are connected by a chemical bond to form a ring.

6. The organic compound according to any one of claims 1-5, characterized in that, Said R a , R b , R c , R d , R e , R f , R g , R i are each independently selected from hydrogen, deuterium, halogen, cyano, amino, or one of the following groups that are unsubstituted or substituted with R': C1-C6 linear 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; R' is selected from any one of deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl; Preferably, the R a , R b , R c , R d , R e , R f , R g , R i are each independently selected from hydrogen, deuterium, or a combination of one or two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, aza-carbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy; R1, R2, R3, R4, and R5 are each independently selected from one or a combination of two of the following substituents: halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, biphenyl, azobenzene, terphenyl, triphenylbenzene, quaterphenyl, fluorenyl, spirobifluorenyl, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy.

7. The organic compound according to claim 1, characterized in that, Selected from the following specific structural compounds:

8. Use of the compound according to any one of claims 1-7 as a functional material in an organic electronic device, wherein the organic electronic device is an organic light-emitting device, an optical sensor, a solar cell, an organic thin-film transistor, or an organic field-effect transistor; Furthermore, the use of the compound is as a light-emitting layer material in an organic light-emitting device, specifically as a light-emitting material in the light-emitting layer.

9. An organic light-emitting device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1-7; Further, the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is formed on the first electrode, the second electrode is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region; wherein, The light-emitting layer contains the compound according to any one of claims 1-7.

10. A display device, comprising the organic light-emitting device according to claim 9.

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