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

Abstract

The present application relates to an organic compound, and also relates to an organic electroluminescent device using the same.The organic compound of the present application has a structure shown in the following formula.The compound of the present application has the characteristics of high luminous efficiency, narrow light spectrum emission and high stability, and the organic electroluminescent device using the compound of the present application has higher external quantum efficiency and longer device life.

Description

TECHNICAL FIELD

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

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

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

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

[0005] In recent years, new OLED materials based on multiple resonance (MR) have become a hot spot in the field of organic electroluminescence, which have the advantages of high efficiency and narrow spectrum. The light color of early multiple resonance light-emitting materials is usually limited in the deep blue and blue light region, and it is difficult to simply regulate the light color by changing the peripheral substituent group without changing the half peak width. Therefore, designing high-performance wide color gamut multiple resonance narrow spectrum dye is the future direction of OLED development, which is very important for the development of the industry. SUMMARY

[0006] An organic compound has the structure shown in the following formula (1):

[0007]

[0008] In formula (1),

[0009] Each of ring A, ring B, ring C, and ring D independently represents any one of a C5-C20 monocyclic aromatic ring or a fused aromatic ring, a C4-C20 monocyclic heterocyclic ring, or a fused heterocyclic ring; and ring E represents a C5-C20 aromatic ring.

[0010] The ring B and the ring C can be connected by a single bond, O, CO, SO2, S, NR2, CR3R4, SiR3R4, or BR5; and the ring C and the ring D can be connected by a single bond.

[0011] The X is NR2, O, or S.

[0012] R1is not connected or connected to form a ring with the adjacent R d ; R2, R3, and R4are each independently not connected or connected to form a ring with the adjacent R b , R c ; R6is not connected or connected to form a ring with the adjacent R c , R d ; and R7is not connected or connected to form a ring with the adjacent R

[0013] R6is each independently not connected or connected to the adjacent ring A or ring B by a single bond, O, CO, SO2, S, NR7, CR8R9, or BR 10 ;

[0014] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 are each independently selected from one of the following substituted or unsubstituted groups: a C1-C36 chain alkyl group, a C3-C36 cyclic alkyl group, a C6-C30 arylamino group, a C6-C60 monocyclic aryl group, a C6-C60 fused ring aryl group, a C6-C60 aryloxy group, a C5-C60 monocyclic heteroaryl group, or a C5-C60 fused ring heteroaryl group.

[0015] said R a , R b , R c , R d , R e each independently represents a single substituent to the maximum allowable number of substituent groups, R a , R b , R c , R d , R e each independently is selected from one of hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or a substituted or unsubstituted group selected from one of C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;

[0016] said R a , R b , R c , R d , R e are not connected or connected by a single bond between adjacent two of them;

[0017] when the above R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R a , R b , R c , R d , R e independently exist, the substituent groups are each independently selected from one of deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 fused ring heteroaryl.

[0018] Preferably, in formula (1), the ring A, ring B, ring C, ring D each independently represents one of C5-C10 aromatic ring, C4-C10 heteroaromatic ring, and the ring E represents C5-C10 aromatic ring; more preferably, the ring E is a benzene ring.

[0019] or preferably, in formula (1), each of the rings A, B, C, D independently represents a C5-C10 aromatic ring, and the ring E is a benzene ring; more preferably, each of the rings A, B, C, D is independently selected from any one of a benzene ring, a naphthalene ring or a fluorene ring; most preferably, each of the rings A, B, C, D is independently selected from a benzene ring.

[0020] Preferably, the ring C is not connected with the ring D; the ring B is not connected with the ring C or is connected with the ring C through a single bond, O, S, NR2, CR3R4, BR5; more preferably, the ring B is not connected with the ring C or is connected with the ring C through a single bond, NR2, BR5.

[0021] Further, the compound of the present application has a structure as shown in the following formula (2):

[0022]

[0023] In formula (2), m, n, p each independently represents 1 or 0;

[0024] Y1 represents a single bond, O, CO, SO2, S, NR2, CR3R4, SiR3R4 or BR5, Y2, Y3 each independently represents a single bond, O, CO, SO2, S, NR7, CR8R9 or BR 10 ;

[0025] R 6’ is selected from one of hydrogen, deuterium, halogen, a chain alkyl group of Cl-C30, a cyclic alkyl group of C3-C30, an alkoxy group of Cl-C10, a thioalkoxy group of Cl-C10, an arylamino group of C6-C30, a heteroarylamino group of C3-C30, a monocyclic aryl group of C6-C60, a fused ring aryl group of C6-C60, an aryloxy group of C6-C60, a monocyclic heteroaryl group of C5-C60, a fused ring heteroaryl group of C5-C60;

[0026] R1, R2, R3, R4, R5, R7, R8, R9, R 10 , R a , R b , R c , R d , R e are defined the same as in claim 1;

[0027] Preferably, n is 0, and p is 1;

[0028] or preferably, m is 1, n is 0, p is 1, Y1 is a single bond, NR2 or BR5, Y2 is H, Y3 is a single bond, NR7 or BR 10 ;

[0029] or preferably, m is 1, n is 0, p is 0, Y1is a single bond, NR2or BR5, Y2is H, and Y3is H.

[0030] or further, the compound of the present application has a structure as shown in formula (3) or formula (4) below:

[0031]

[0032] in formula (3) and formula (4), q represents 1 or 0; Y4represents a single bond, O, S, NR2, CR3R4or BR5; R1, R2, R3, R4, R5, R a , R b , R c , R d , R e are defined the same as in claim 1;

[0033] Preferably, q is 0, and Y4is H.

[0034] or preferably, q is 1, and Y4is a single bond, NR2or BR5.

[0035] Further, in formula (1), formula (2), formula (3) and formula (4), the R a , R b , R c , R d , R e are each independently selected from one of hydrogen, deuterium, halogen, C1-C6 linear alkyl, C3-C6 cyclic alkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, cyano, C6-C20 arylamino, C3-C20 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, and C5-C30 heteroaryl;

[0036] Preferably, the R a , R b , R c , R d , R eEach of the following substituents, independently selected from hydrogen, deuterium, or substituted or unsubstituted, is 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, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirodifluorene, dihydrogen phenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthreneimidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxalinimidazoleyl, oxazolyl Benzoxazolyl, naphthooxazolyl, anthraxoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2, 4-Omnidiazolyl, 1,2,5-Omnidiazolyl, 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, Tetraazolyl, 1,2,4,5-Tetraazinyl, 1,2,3,4-Tetraazinyl, 1,2,3,5-Tetraazinyl, Puryl, Pteridyl, Indazyl, Benzothiadiazolyl, 9,9-Dimethylacridyl, Triarylamine, Adamantane, Fluorophenyl, Methylphenyl, Trimethylphenyl, Cyanophenyl, Tetrahydropyrrole, Piperidine, Methoxy, Si, or a combination of the two substituents listed above;

[0037] More preferably, the R a R b R c R d R ehydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthryl, benzoanthryl, phenanthryl, benzophenanthryl, pyrenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydophenanthryl, dihydropyrenyl, tetrahydropyrenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzoimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-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, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, or silyl.

[0038] Still further, in formula (1), the R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthryl, benzoanthryl, phenanthryl, benzophenanthryl, pyrenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, biphenyl, terphenyl, triphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydophenanthryl, dihydropyrenyl, tetrahydropyrenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzoimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, pyrazinyl, phenoxazinyl, phenothiazinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, phenanthroline, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-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, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylaminyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, or silyl.

[0039] In the present application, the "substituted or unsubstituted" group / ring can be substituted with one substituent or can be substituted with multiple substituents, and when the substituents are multiple (at least two), the substituents can be the same or different. The same meaning is applied when the same expression is used below. If not specifically mentioned, the selection range of the substituent is as described above, and will not be repeated.

[0040] In the present application, the halogen can be fluorine, chlorine, bromine, or iodine. The same meaning is applied when the same expression is used below.

[0041] In the present application, the description of chemical elements includes the concept of isotopes having the same chemical properties unless otherwise specified. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0042] In the present application, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0043] In the present application, the expression of the ring structure with a dash through it indicates that the connection site is at any position on the ring structure that can form a bond.

[0044] In the present application, the expression of Ca-Cb represents that the number of carbon atoms of the group is a-b, and unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms of the substituent.

[0045] In the present application, "independently of each other" means that when the subject has multiple, they can be the same or different.

[0046] In the present application, 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.

[0047] The C3-C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56 or C58, etc.

[0048] The C6-C58 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.

[0049] The C3-C58 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56 or C58, etc.

[0050] The C1-C20 can each be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0051] The C3-C20 can each be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0052] The C6-C30 can each be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0053] The C3-C30 can each be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0054] The C6-C54 can each 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, or C54, etc.

[0055] The C3-C54 can each 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, or C54, etc.

[0056] The C1-C10 can each be C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10.

[0057] The C3-C10 can each be C3, C4, C5, C6, C7, C8, C9, or C10.

[0058] The C1-C36 chain alkyl includes C1-C36 straight chain alkyl, and also includes C1-C36 branched chain alkyl, preferably C1-C16 straight chain or branched chain alkyl, and more preferably C1-C10 straight chain or branched chain alkyl, and exemplarily includes, but is not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0059] Specific examples of the C1-C36 alkoxy groups can be exemplified by the monovalent groups obtained by attaching the above-mentioned straight-chain or branched alkyl groups to O. Specific examples of the C1-C30 alkylthio groups can be exemplified by the monovalent groups obtained by attaching the above-mentioned straight-chain or branched alkyl groups to S.

[0060] The C3-C36 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes monocycloalkyl or polycycloalkyl groups. Monocycloalkyl refers to an alkyl group containing a single ring structure, while polycycloalkyl refers to a structure formed by two or more cycloalkyl groups sharing one or more carbon atoms on a ring; exemplary examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0061] The C6-C60 aryl group, preferably C6-C30 aryl group, and more preferably C6-C20 aryl group, includes monocyclic aryl and fused-ring aryl groups; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, exemplarily including but not limited to: phenyl, biphenyl, terphenyl, etc.; the fused-ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent bonds. Groups in which carbon atoms are fused together include, but are not limited to: naphthyl, anthraceneyl, phenanthryl, indeneyl, fluorenyl and their derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranthyl, triphenylene, pyrene, perylene, Benzyl or tetraphenyl, etc.

[0062] The C3-C60 heteroaryl group, preferably C3-C30 heteroaryl group, and more preferably C3-C20 heteroaryl group, includes monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc.

[0063] In the present application, the C6-C60 aryloxy is a monovalent group that can be exemplified by the above-mentioned aryl group linked to O, and the C3-C60 heteroaryloxy is a monovalent group that can be exemplified by the above-mentioned heteroaryl group linked to O. The C6-C60 arylthio is a monovalent group that can be exemplified by the above-mentioned aryl group linked to S, and the C3-C60 heteroarylthio is a monovalent group that can be exemplified by the above-mentioned heteroaryl group linked to S.

[0064] In the present application, the C6-C60 arylamino is a monovalent group that can be exemplified by at least one hydrogen of -NH2 being substituted with the above-mentioned aryl group, and exemplarily includes, but is not limited to, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, and the like. The C3-C60 heteroarylamino is a monovalent group that can be exemplified by at least one hydrogen of -NH2 being substituted with the above-mentioned heteroaryl group, and exemplarily includes, but is not limited to, pyridylamino, pyrimidylamino, dibenzofuranylamino, and the like.

[0065] Further, the compounds of the general formula (1) of the present application can preferably be exemplified by the following specific compounds 1 to 304, which are merely representative:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] The structural design innovation point of the compound of the present application is that a single boron-nitrogen, boron-oxygen and boron-sulfur covalent bond is introduced on one side of the classic boron-nitrogen parent nucleus, which further reduces the half-peak width of the material, improves the color purity, and significantly improves the efficiency of the corresponding light-emitting device, thereby providing guidance for constructing new ultra-narrow spectral light-emitting materials. The specific content is as follows: the embedding of B-N bond maintains the planar structure of MR multiple resonance skeleton, while the structural conjugation is enhanced, the rigidity of the molecule is significantly enhanced, the half-peak width (FWHM is 16-26 nm) is obviously narrowed, and the light-emitting efficiency (PLQY>90%) is improved. In synthesis, the present application utilizes the guiding effect of N atom on B atom on the amine group to realize the formation of B-N covalent bond, and further guide the effective occurrence of electrophilic boronation reaction, so that the target material can be obtained in only three steps, the reaction condition is simple, and the yield is high. In addition, the B-O covalent bond and B-S covalent bond are designed to be introduced into the compound of the present application, the heavy atom effect of the heteroatom is utilized to improve the reverse inter-system crossing rate of the material, further reduce the efficiency roll-off of the device, and improve the stability thereof; at the same time, since the electron-donating ability of oxygen and sulfur is weaker than that of nitrogen, the obtained material can further make the light color blue shift, while the half-peak width is kept narrow. Further, the compound of the present application can adjust the light color in the range from blue light to green light by designing the change of the peripheral substituent group, while keeping the characteristic of narrow half-peak width, and the service life of the device is greatly improved.

[0078] Specifically, in the general formula (1) of the present application, ring A, B, C and D can each independently be selected from one of benzene ring, naphthalene ring and pyridine ring, although these groups have different electron-donating or electron-withdrawing abilities, when introduced into the general formula of the compound of the present application, the optical physical properties of the compound of the present application can be effectively adjusted, such as red shift and blue shift of absorption and emission. Since the molecular structure of the compound of the present application has a rigid π-conjugated plane, the light emission of the molecule mainly comes from short-range intramolecular charge transfer, therefore, the ring A-F has little effect on the half-peak width and photoluminescence quantum efficiency of the compound of the present application, and ideal optical physical properties can be obtained. In combination with a more preferred scheme, when X is NR2 and ring B and C are connected by a single bond, and the peripheral group is a carbazole group, due to the relatively weak electron-donating ability of the carbazole group, the excited state electrons of this series of compounds are delocalized on the entire conjugated plane, and the light-emitting performance and stability of the material are greatly improved. On the other hand, when X is O or S and ring B and C are connected by a single bond, the heavy atom effect is introduced by the bridging of O atom or S atom, the reverse inter-system crossing rate of the material is improved, the efficiency roll-off of the device is reduced, and the stability thereof is improved.

[0079] The electroluminescent spectrum of the OLED device prepared by using the compound has a relatively narrow half-peak width (<20 nm), and exhibits obvious multiple resonance thermally activated delayed fluorescence characteristics, thereby greatly enriching the skeleton system of multiple resonance narrow spectrum materials, greatly simplifying the synthesis process, and improving the reaction yield; the corresponding electroluminescent device has low starting voltage, high luminous efficiency and longer service life, can meet the requirements of current panel manufacturing enterprises for high-performance materials, and has good application prospect in industrialization.

[0080] The second object of the present application is to provide the use of the compound according to the first object 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.

[0081] The third object of the present application is to provide an organic electroluminescent device. Specifically, the embodiments of the present application provide an organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer formed in sequence on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is between the hole transport layer and the electron transport layer; preferably, the light-emitting layer contains the general compound of the present application represented by any one of the general formulae (1) to (4) or at least any one of the specific compounds 1 to 304. DETAILED DESCRIPTION

[0082] The specific preparation methods of the novel compounds of the present application will be described in detail below with a plurality of synthesis examples, but the preparation methods of the present application are not limited to these synthesis examples.

[0083] The various chemicals used in the present application, such as petroleum ether, tert-butylbenzene, ethylene glycol dimethyl ether, sodium sulfate, toluene, dichloromethane, cesium carbonate, sodium hydride, boron tribromide, tetrahydrofuran, N,N-dimethylformamide, n-butyllithium, reaction intermediates and other basic chemical raw materials are purchased from Shanghai Titan Science and Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds is a ZAB-HS type mass spectrometer (manufactured by Micromass Company, UK).

[0084] The synthesis of the compounds of the present application is briefly described as follows. First, intermediate I is obtained by nucleophilic substitution and Buchwald-Hartwig reaction. Then, Suzuki coupling with boronic ester is carried out to obtain intermediate II. Finally, electrophilic boronation with boron tribromide under the action of n-butyl lithium or tert-butyl lithium is carried out to obtain the target compound.

[0085] The general synthetic scheme is as follows:

[0086]

[0087] Synthetic examples

[0088] Synthesis of compound 1 of example 1

[0089]

[0090] In a two-necked flask, compound 1-1 (15.7 mmol), 3,6-di-tert-butylcarbazole (31.4 mmol), cesium carbonate (61 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under nitrogen atmosphere, and the reaction was carried out at 150°C for 12 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 10 mL of water, and then washed once with 10 mL of methanol, and dried to obtain the target compound 1-2 as a light yellow solid.

[0091] In a two-necked flask, compound 1-2 (5 mmol), compound 1-4 (5.5 mmol), tetrakis triphenylphosphine palladium (0.5 mmol), potassium carbonate (25 mmol), and a mixed solution of ethylene glycol dimethyl ether (DME): water = 4:1 (120 mL) were sequentially added, and the reaction was carried out at 80°C for 16 hours under nitrogen atmosphere. After cooling, the organic phase was separated and collected, and the organic phase was dried with anhydrous sodium sulfate, followed by filtration and concentration of the organic phase. The compound was separated by silica gel column with petroleum ether: dichloromethane = 10:1 as the developing agent to obtain compound 1-3.

[0092] Compound 1-3 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube, cooled to -78 °C, then added n-butyllithium in pentane (1 M, 2.5 mL), then warmed to 30 °C for 1 hour. Again cooled to -78 °C, slowly added boron tribromide (3 mmol), then warmed to 30 °C and continued stirring for 1 hour. After cooling to 0 °C, diisopropylethylamine (3 mmol) was added, then warmed to 160 °C and reacted for 12 hours. The solvent was removed by vacuum evaporation, and the target compound 1 (HPLC analysis purity 99.43%) was obtained as a yellow solid by silica gel column chromatography with petroleum ether: dichloromethane = 10: 1 as the developing agent. MALDI-TOF-MS results: molecular ion peak: 813.44; elemental analysis results: theoretical value: C, 85.61; H, 6.57; B, 2.66; N, 5.16 (%); experimental value: C, 85.51; H, 6.67; B, 2.76; N, 5.06 (%).

[0093] The following synthetic examples were synthesized in the same manner as Example 1, except that 1-4 was replaced with the boronate ester starting material corresponding to the segment in the examples.

[0094]

[0095] Target compound 2 (HPLC analysis purity 99.37%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 925.57; elemental analysis results: theoretical value: C, 85.62; H, 7.51; B, 2.33; N, 4.54 (%); experimental value: C, 85.72; H, 7.41; B, 2.43; N, 4.44 (%).

[0096] Target compound 3 (HPLC analysis purity 99.89%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 965.51; elemental analysis results: theoretical value: C, 87.05; H, 6.37; B, 2.24; N, 4.35 (%); experimental value: C, 87.15; H, 6.27; B, 2.34; N, 4.25 (%).

[0097] Target compound 7 (HPLC analysis purity 99.08%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 841.47; elemental analysis results: theoretical value: C, 85.61; H, 6.83; B, 2.57; N, 4.99 (%); experimental value: C, 85.71; H, 6.73; B, 2.67; N, 4.89 (%).

[0098] Target compound 8 (HPLC purity 99.87%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 978.5; elemental analysis result: Theoretical value: C, 85.89; H, 6.18; B, 2.21; N, 5.72 (%); Experimental value: C, 85.99; H, 6.08; B, 2.31; N, 5.62 (%).

[0099] Target compound 17 (HPLC purity 99.63%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 943.39; elemental analysis result: Theoretical value: C, 86.54; H, 5.02; B, 2.29; N, 4.45; O, 1.70 (%); Experimental value: C, 85.15; H, 6.23; B, 2.29; N, 4.75; O, 1.67 (%).

[0100] Target compound 18 (HPLC purity 99.37%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 959.37; elemental analysis result: Theoretical value: C, 85.09; H, 4.94; B, 2.25; N, 4.38; S, 3.34 (%); Experimental value: C, 83.67; H, 6.13; B, 2.25; N, 4.67; S, 3.39 (%).

[0101] Target compound 23 (HPLC purity 99.12%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 949.42; elemental analysis result: Theoretical value: C, 75.88; H, 5.41; B, 2.28; F, 12; N, 4.42 (%); Experimental value: C, 75.98; H, 5.51; B, 2.18; F, 12.1; N, 4.32 (%).

[0102] Target compound 34 (HPLC purity 99.31%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 949.42; elemental analysis result: Theoretical value: C, 75.88; H, 5.41; B, 2.28; F, 12 (%); Experimental value: C, 75.98; H, 5.31; B, 2.38; F, 11.9 (%).

[0103] Target compound 37 (HPLC purity 99.75%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 829.44; elemental analysis result: Theoretical value: C, 83.96; H, 6.44; B, 2.61; N, 5.06; O, 1.93 (%); Experimental value: C, 84.06; H, 6.54; B, 2.51; N, 5.16; O, 1.83 (%).

[0104] Target compound 46 (HPLC purity 99.26%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 949.42; elemental analysis result: the theoretical value: C, 75.88; H, 5.41; B, 2.28; F, 12 (%) ; the experimental value: C, 75.98; H, 5.31; B, 2.38; F, 11.9 (%).

[0105] Synthesis of compound 50 of example 2

[0106]

[0107] In a double-necked flask, compound 50-1 (15.7 mmol), 3,6-di-tert-butylcarbazole (15.7 mmol), cesium carbonate (30 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under nitrogen atmosphere, and the temperature was raised to 60°C, and the reaction was carried out for 4 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed twice with 10 mL of water, and then washed once with 10 mL of methanol, and dried to obtain the target compound 50-2, a light yellow solid.

[0108] In a double-necked flask, compound 50-3 (5 mmol), compound 50-2 (5 mmol), tris(dibenzylideneacetone)dipalladium (0.5 mmol), tri-tert-butylphosphonium tetrafluoroborate (1 mmol), sodium tert-butoxide (1 mmol) were sequentially added, 100 mL of dry toluene was added, and the temperature was raised to 110°C, and the reaction was carried out for 12 hours. After cooling, the organic phase was separated and collected, the organic phase was dried with anhydrous sodium sulfate, and then filtered and concentrated, and the compound was separated by silica gel column with petroleum ether: dichloromethane = 10:1 as developing agent to obtain compound 50-4.

[0109] The synthesis of compound 50-5 is similar to that of compound 1-3, except that the corresponding raw material is replaced by 50-4 to obtain compound 50-5.

[0110] The synthesis of compound 50 is similar to the last step of the synthesis of compound 1, except that the corresponding raw material is replaced by 50-5 to obtain compound 50 (HPLC purity 98.78%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 927.58; elemental analysis result: the theoretical value: C, 85.43; H, 7.71; B, 2.33; N, 4.53 (%) ; the experimental value: C, 85.34; H, 7.81; B, 2.42; N, 4.42 (%).

[0111] The synthesis of the following synthesis examples is similar to that of example 2, except that the corresponding secondary amine fragment and borate ester fragment are replaced.

[0112]

[0113]

[0114] Target compound 51 (HPLC purity 99.28%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 967.52; Elemental analysis result: Theoretical value: C, 86.86; H, 6.56; B, 2.23; N, 4.34 (%) ; Experimental value: C, 86.96; H, 6.46; B, 2.33; N, 4.24 (%).

[0115] Target compound 56 (HPLC purity 99.00%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 980.52; Elemental analysis result: Theoretical value: C, 85.71; H, 6.37; B, 2.2; N, 5.71 (%) ; Experimental value: C, 85.81; H, 6.27; B, 2.3; N, 5.61 (%).

[0116] Target compound 60 (HPLC purity 99.43%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 921.45; Elemental analysis result: Theoretical value: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%) ; Experimental value: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0117] Target compound 61 (HPLC purity 99.20%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 954.48; Elemental analysis result: Theoretical value: C, 83.02; H, 5.91; B, 2.26; N, 8.8 (%) ; Experimental value: C, 83.12; H, 5.81; B, 2.36; N, 8.7 (%).

[0118] Target compound 63 (HPLC purity 99.89%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 905.47; Elemental analysis result: Theoretical value: C, 84.86; H, 6.34; B, 2.39; N, 4.64; O, 1.77 (%) ; Experimental value: C, 84.96; H, 6.44; B, 2.29; N, 4.74; O, 1.67 (%).

[0119] Target compound 64 (HPLC purity 99.17%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 921.45; elemental analysis result: theory: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%); experiment: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0120] Target compound 65 (HPLC purity 99.74%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 853.36; elemental analysis result: theory: C, 81.61; H, 5.31; B, 2.53; N, 4.92; O, 5.62 (%); experiment: C, 81.71; H, 5.41; B, 2.43; N, 5.02; O, 5.52 (%).

[0121] Target compound 66 (HPLC purity 99.12%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 921.45; elemental analysis result: theory: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%); experiment: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0122] Target compound 67 (HPLC purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 843.33; elemental analysis result: theory: C, 82.58; H, 4.66; B, 2.56; N, 8.3; O, 1.9 (%); experiment: C, 82.68; H, 4.76; B, 2.46; N, 8.4; O, 1.8 (%).

[0123] Target compound 68 (HPLC purity 99.16%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 921.45; elemental analysis result: theory: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%); experiment: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0124] Target compound 69 (HPLC assay purity 99.15%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 928.41 ; Elemental analysis result: Theoretical value: C, 82.77; H, 5.43; B, 2.33; N, 6.03; O, 3.45 (%); Experimental value: C, 82.87; H, 5.53; B, 2.23; N, 6.13; O, 3.35 (%).

[0125] Target compound 75 (HPLC assay purity 99.11%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1031.65; Elemental analysis result: Theoretical value: C, 86.12; H, 7.72; B, 2.09; N, 4.07 (%); Experimental value: C, 86.22; H, 7.62; B, 2.19; N, 3.97 (%).

[0126] Target compound 77 (HPLC assay purity 99.52%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 754.32; Elemental analysis result: Theoretical value: C, 81.19; H, 4.81; B, 2.87; N, 11.14 (%); Experimental value: C, 81.29; H, 4.91; B, 2.77; N, 11.24 (%).

[0127] Target compound 82 (HPLC assay purity 99.58%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 929.6; Elemental analysis result: Theoretical value: C, 85.24; H, 7.91; B, 2.32; N, 4.52 (%); Experimental value: C, 85.34; H, 8.01; B, 2.22; N, 4.62 (%).

[0128] Target compound 85 (HPLC assay purity 99.08%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 845.43; Elemental analysis result: Theoretical value: C, 82.37; H, 6.32; B, 2.56; N, 4.97; O, 3.78 (%); Experimental value: C, 82.47; H, 6.42; B, 2.46; N, 5.07; O, 3.68 (%).

[0129] Target compound 86 (HPLC assay purity 99.13%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 847.43; Elemental analysis result: Theoretical value: C, 82.17; H, 6.54; B, 2.55; N, 4.96; S, 3.78 (%); Experimental value: C, 82.27; H, 6.64; B, 2.45; N, 5.06; S, 3.68 (%).

[0130] Target compound 89 (HPLC purity 99.24%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 865.45; Elemental analysis result: Theoretical value: C, 83.24; H, 6.17; B, 2.5; N, 8.09 (%); Experimental value: C, 83.34; H, 6.27; B, 2.4; N, 8.19 (%).

[0131] Target compound 93 (HPLC purity 99.25%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1145.57; Elemental analysis result: Theoretical value: C, 85.93; H, 6.07; B, 1.89; N, 6.11 (%); Experimental value: C, 86.03; H, 6.17; B, 1.79; N, 6.21 (%).

[0132] Target compound 133 (HPLC purity 99.48%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 855.49; Elemental analysis result: Theoretical value: C, 85.61; H, 6.95; B, 2.53; N, 4.91 (%); Experimental value: C, 85.71; H, 7.05; B, 2.43; N, 5.01 (%).

[0133] Target compound 146 (HPLC purity 99.19%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 844.48; Elemental analysis result: Theoretical value: C, 83.89; H, 6.92; B, 2.56; N, 6.63 (%); Experimental value: C, 83.99; H, 7.02; B, 2.46; N, 6.73 (%).

[0134] Target compound 149 (HPLC purity 99.22%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 918.38; Elemental analysis result: Theoretical value: C, 83.67; H, 4.83; B, 2.35; N, 9.15 (%); Experimental value: C, 83.77; H, 4.93; B, 2.25; N, 9.25 (%).

[0135] Target compound 151 (HPLC purity 99.41%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 905.47; Elemental analysis result: Theoretical value: C, 84.86; H, 6.34; B, 2.39; N, 4.64; O, 1.77 (%); Experimental value: C, 84.96; H, 6.44; B, 2.29; N, 4.74; O, 1.67 (%).

[0136] Target compound 152 (HPLC assay purity 99.82%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 921.45; elemental analysis result: theory: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%); experiment: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0137] Target compound 153 (HPLC assay purity 99.09%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 951.43; elemental analysis result: theory: C, 75.72; H, 5.61; B, 2.27; F, 11.98; N, 4.42 (%); experiment: C, 75.82; H, 5.71; B, 2.17; F, 12.08; N, 4.32 (%).

[0138] Target compound 156 (HPLC assay purity 99.63%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 921.45; elemental analysis result: theory: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%); experiment: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0139] Target compound 168 (HPLC assay purity 99.55%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 904.48; elemental analysis result: theory: C, 84.96; H, 6.46; B, 2.39; N, 6.19 (%); experiment: C, 85.06; H, 6.56; B, 2.29; N, 6.29 (%).

[0140] Target compound 171 (HPLC assay purity 99.55%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 816.45; elemental analysis result: theory: C, 83.83; H, 6.66; B, 2.65; N, 6.86 (%); experiment: C, 83.93; H, 6.76; B, 2.55; N, 6.96 (%).

[0141] Target compound 178 (HPLC assay purity 99.34%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 847.43; Elemental analysis result: Theoretical value: C, 82.17; H, 6.54; B, 2.55; N, 4.96; S, 3.78 (%); Experimental value: C, 82.27; H, 6.64; B, 2.45; N, 5.06; S, 3.68 (%).

[0142] Target compound 182 (HPLC assay purity 99.76%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 867.46; Elemental analysis result: Theoretical value: C, 83.05; H, 6.39; B, 2.49; N, 8.07 (%); Experimental value: C, 83.15; H, 6.49; B, 2.39; N, 8.17 (%).

[0143] Target compound 186 (HPLC assay purity 99.67%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1151.62; Elemental analysis result: Theoretical value: C, 85.48; H, 6.56; B, 1.88; N, 6.08 (%); Experimental value: C, 85.58; H, 6.66; B, 1.78; N, 6.18 (%).

[0144] Target compound 194 (HPLC assay purity 99.32%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 830.28; Elemental analysis result: Theoretical value: C, 86.77; H, 3.88; B, 2.6; N, 6.75 (%); Experimental value: C, 86.87; H, 3.98; B, 2.5; N, 6.85 (%).

[0145] Target compound 203 (HPLC assay purity 99.72%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 727.15; Elemental analysis result: Theoretical value: C, 79.25; H, 3.19; B, 2.97; N, 5.78; S, 8.81 (%); Experimental value: C, 79.35; H, 3.29; B, 2.87; N, 5.88; S, 8.71 (%).

[0146] Synthesis of compound 213 of example 3

[0147]

[0148] In a two-necked flask, compound 213-1 (15.7 mmol), 3,6-di-tert-butylcarbazole (15.7 mmol), cesium carbonate (30 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under nitrogen atmosphere, and the reaction was carried out at 60°C for 4 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed with 10 mL of water twice, and then washed with 10 mL of methanol once, and dried to obtain the target compound 213-2 as a light yellow solid.

[0149] In a two-necked flask, compound 213-2 (15.7 mmol), 213-3 (15.7 mmol), cesium carbonate (30 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF) under nitrogen atmosphere, and the reaction was carried out at 60°C for 4 hours. After the reaction was completed and cooled, it was poured into cold water, filtered, washed with 10 mL of water twice, and then washed with 10 mL of methanol once, and dried to obtain the target compound 213-4 as a light yellow solid.

[0150] The synthesis of compound 213-5 was similar to that of compound 1-3, except that the corresponding starting material was replaced by 213-4, to obtain compound 213-5.

[0151] The synthesis of compound 213 was similar to the last step of the synthesis of compound 1, except that the corresponding starting material was replaced by 213-5, to obtain compound 213 (HPLC analysis purity 98.78%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 978.5; elemental analysis results: theoretical value: C, 85.89; H, 6.18; B, 2.21; N, 5.72 (%); experimental value: C, 85.79; H, 6.28; B, 2.31; N, 5.62 (%).

[0152] The synthesis of the following compounds was similar to that in Example 3, except that the corresponding molecular fragments were replaced.

[0153]

[0154] The target compound 98 (HPLC analysis purity 99.29%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 949.49; elemental analysis results: theoretical value: C, 83.46; H, 6.47; B, 2.28; N, 4.42; O, 3.37 (%); experimental value: C, 83.56; H, 6.57; B, 2.18; N, 4.52; O, 3.27 (%).

[0155] Target compound 103 (HPLC assay purity 99.79%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1015.5; Elemental analysis result: Theoretical value: C, 85.12; H, 5.85; B, 2.13; N, 6.89 (%) ; Experimental value: C, 85.22; H, 5.95; B, 2.03; N, 6.99 (%).

[0156] Target compound 106 (HPLC assay purity 99.21%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 919.43; Elemental analysis result: Theoretical value: C, 83.57; H, 6.03; B, 2.35; N, 4.57; S, 3.49 (%) ; Experimental value: C, 83.67; H, 6.13; B, 2.25; N, 4.67; S, 3.39 (%).

[0157] Target compound 109 (HPLC assay purity 99.44%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 903.45; Elemental analysis result: Theoretical value: C, 85.05; H, 6.13; B, 2.39; N, 4.65; O, 1.77 (%) ; Experimental value: C, 85.15; H, 6.23; B, 2.29; N, 4.75; O, 1.67 (%).

[0158] Target compound 115 (HPLC assay purity 99.14%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 921.45; Elemental analysis result: Theoretical value: C, 83.39; H, 6.23; B, 2.35; N, 4.56; S, 3.48 (%) ; Experimental value: C, 83.49; H, 6.33; B, 2.25; N, 4.66; S, 3.38 (%).

[0159] Target compound 118 (HPLC assay purity 99.29%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1010.47; Elemental analysis result: Theoretical value: C, 83.17; H, 5.98; B, 2.14; N, 5.54; S, 3.17 (%) ; Experimental value: C, 83.27; H, 6.08; B, 2.04; N, 5.64; S, 3.07 (%).

[0160] Target compound 124 (HPLC assay purity 99.20%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 976.48; Elemental analysis result: Theoretical value: C, 86.07; H, 5.98; B, 2.21; N, 5.74 (%) ; Experimental value: C, 86.17; H, 6.08; B, 2.11; N, 5.84 (%).

[0161] Target compound 205 (HPLC assay purity 99.68%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 903.45; Elemental analysis result: Theoretical value: C, 85.05; H, 6.13; B, 2.39; N, 4.65; O, 1.77 (%) ; Experimental value: C, 85.15; H, 6.23; B, 2.29; N, 4.75; O, 1.67 (%).

[0162] Target compound 209 (HPLC assay purity 99.34%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 819.32; Elemental analysis result: Theoretical value: C, 83.53; H, 4.8; B, 2.64; N, 5.13; O, 3.9 (%) ; Experimental value: C, 83.63; H, 4.9; B, 2.54; N, 5.23; O, 3.8 (%).

[0163] Target compound 211 (HPLC assay purity 99.15%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 895.4; Elemental analysis result: Theoretical value: C, 84.48; H, 5.29; B, 2.41; N, 7.82 (%) ; Experimental value: C, 84.58; H, 5.39; B, 2.31; N, 7.92 (%).

[0164] Target compound 215 (HPLC assay purity 99.19%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1030.44; Elemental analysis result: Theoretical value: C, 87.38; H, 5.08; B, 2.1; N, 5.43 (%) ; Experimental value: C, 87.48; H, 5.18; B, 2; N, 5.53 (%).

[0165] Synthesis of compound 147 of example 4

[0166]

[0167] In a two-necked flask, compound 147-1 (5 mmol), compound 147-2 (5 mmol), tris-dibenzylideneacetone palladium (0.5 mmol), tri-tert-butylphosphonium tetrafluoroborate (1 mmol), sodium tert-butoxide (1 mmol) were added successively under nitrogen atmosphere, 100 ml dry toluene was added and the temperature was raised to 110°C, 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, the compound was separated by silica gel column with petroleum ether: dichloromethane = 10: 1 as developing agent to obtain compound 147-3.

[0168] In a two-necked flask, compound 147-3 (5 mmol), compound 147-4 (5 mmol), tris-dibenzylideneacetone palladium (0.5 mmol), tri-tert-butylphosphonium tetrafluoroborate (1 mmol), sodium tert-butoxide (1 mmol) were added successively under nitrogen atmosphere, 100 ml dry toluene was added and the temperature was raised to 110°C, 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, the compound was separated by silica gel column with petroleum ether: dichloromethane = 10: 1 as developing agent to obtain compound 147-5.

[0169] The synthesis of compound 147-6 was similar to that of compound 1-3, except that the corresponding starting material was replaced by 147-5 to obtain compound 147-6.

[0170] The synthesis of compound 147 was similar to the last step of the synthesis of compound 1, except that the corresponding starting material was replaced by 147-6 to obtain compound 147 (HPLC analysis purity 98.78%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 871.78; elemental analysis results: theoretical value: C, 84.04; H, 6.82; B, 2.48; N, 4.82; O, 1.84 (%); experimental value: C, 84.14; H, 6.72; B, 2.58; N, 4.77; O, 1.79 (%).

[0171] The synthesis of the following compounds was similar to that in Example 4, except that the corresponding molecular fragments were replaced.

[0172]

[0173] The target compound 59 (HPLC analysis purity 99.50%), yellow solid. MALDI-TOF-MS results: molecular ion peak: 881.36; elemental analysis results: theoretical value: C, 80.38; H, 5.14; B, 2.45; N, 4.77; O, 7.26 (%); experimental value: C, 80.48; H, 5.24; B, 2.35; N, 4.87; O, 7.16 (%).

[0174] Target compound 62 (HPLC purity 99.41%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 1009.54; Elemental analysis result: Theoretical value: C, 84.44; H, 6.49; B, 2.14; N, 6.93 (%) ; Experimental value: C, 84.54; H, 6.59; B, 2.04; N, 7.03 (%).

[0175] Target compound 67 (HPLC purity 99.67%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 885.38; Elemental analysis result: Theoretical value: C, 82.72; H, 5.12; B, 2.44; N, 7.91; O, 1.81 (%) ; Experimental value: C, 82.82; H, 5.22; B, 2.34; N, 8.01; O, 1.71 (%).

[0176] Target compound 95 (HPLC purity 99.64%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 996.58; Elemental analysis result: Theoretical value: C, 80.72; H, 7.08; B, 2.17; N, 8.43; O, 1.6 (%) ; Experimental value: C, 80.82; H, 7.18; B, 2.07; N, 8.53; O, 1.5 (%).

[0177] Target compound 134 (HPLC purity 99.27%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 806.34; Elemental analysis result: Theoretical value: C, 83.39; H, 5; B, 2.68; N, 6.95; O, 1.98 (%) ; Experimental value: C, 83.49; H, 5.1; B, 2.58; N, 7.05; O, 1.88 (%).

[0178] Target compound 135 (HPLC purity 99.74%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 765.26; Elemental analysis result: Theoretical value: C, 78.44; H, 4.87; B, 2.82; N, 5.49; S, 8.38 (%) ; Experimental value: C, 78.54; H, 4.97; B, 2.72; N, 5.59; S, 8.28 (%).

[0179] Target compound 142 (HPLC assay purity 99.52%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 761.41; elemental analysis result: theory: C, 85.16; H, 6.49; B, 2.84; N, 5.52 (%) ; experiment: C, 85.26; H, 6.59; B, 2.74; N, 5.62 (%).

[0180] Target compound 150 (HPLC assay purity 99.45%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 926.41; elemental analysis result: theory: C, 82.94; H, 5.66; B, 2.33; N, 6.04; Si, 3.03 (%) ; experiment: C, 83.04; H, 5.76; B, 2.23; N, 6.14; Si, 2.93 (%).

[0181] Target compound 155 (HPLC assay purity 99.66%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 821.34; elemental analysis result: theory: C, 83.33; H, 5.03; B, 2.63; N, 5.11; O, 3.89 (%) ; experiment: C, 83.43; H, 5.13; B, 2.53; N, 5.21; O, 3.79 (%).

[0182] Target compound 158 (HPLC assay purity 99.84%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 841.29; elemental analysis result: theory: C, 79.91; H, 4.91; B, 2.57; N, 4.99; S, 7.62 (%) ; experiment: C, 80.01; H, 5.01; B, 2.47; N, 5.09; S, 7.52 (%).

[0183] Target compound 169 (HPLC assay purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 732.32; elemental analysis result: theory: C, 81.99; H, 5.23; B, 2.95; N, 7.65; O, 2.18 (%) ; experiment: C, 82.09; H, 5.33; B, 2.85; N, 7.75; O, 2.08 (%).

[0184] Target compound 177 (HPLC assay purity 99.90%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 735.32; elemental analysis result: theory: C, 81.65; H, 5.34; B, 2.94; N, 5.71; O, 4.35 (%); experiment: C, 81.75; H, 5.44; B, 2.84; N, 5.81; O, 4.25 (%).

[0185] Target compound 191 (HPLC assay purity 99.39%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 637.16; elemental analysis result: theory: C, 79.15; H, 3.32; B, 3.39; N, 6.59; O, 2.51 (%); experiment: C, 79.25; H, 3.42; B, 3.29; N, 6.69; O, 2.41 (%).

[0186] Target compound 220 (HPLC assay purity 99.46%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 745.31; elemental analysis result: theory: C, 82.17; H, 5; B, 2.9; N, 5.64; O, 4.29 (%); experiment: C, 82.27; H, 5.1; B, 2.8; N, 5.74; O, 4.19 (%).

[0187] Target compound 221 (HPLC assay purity 99.70%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 749.28; elemental analysis result: theory: C, 80.12; H, 4.98; B, 2.88; N, 5.61; O, 2.13 (%); experiment: C, 80.22; H, 5.08; B, 2.78; N, 5.71; O, 2.03 (%).

[0188] Target compound 223 (HPLC assay purity 99.77%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 857.43; elemental analysis result: theory: C, 82.62; H, 6.23; B, 2.52; N, 4.9; O, 3.73 (%); experiment: C, 82.72; H, 6.33; B, 2.42; N, 5; O, 3.63 (%).

[0189] Synthesis of compound 226 of example 5

[0190]

[0191] The synthesis was similar to that of compound 1, except that compound 1-4 was replaced by compound 226-1 to give the target compound 226 (HPLC analytical purity 99.36%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 796.47; elemental analysis result: the theoretical value: C, 84.42; H, 7.34; B, 2.71; N, 3.52; O, 2.01 (%); the experimental value: C, 84.38; H, 6.76; B, 2.82; N, 3.83; O, 2.21 (%).

[0192] The following synthesis examples were synthesized in a similar manner to Example 3, except that the corresponding boronate fragment was replaced.

[0193]

[0194] The target compound 225 (HPLC analytical purity 99.10%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 740.41; elemental analysis result: the theoretical value: C, 84.33; H, 6.81; B, 2.92; N, 3.78; O, 2.16 (%); the experimental value: C, 84.43; H, 6.91; B, 2.82; N, 3.88; O, 2.06 (%).

[0195] The target compound 227 (HPLC analytical purity 99.23%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 734.34; elemental analysis result: the theoretical value: C, 81.76; H, 5.49; B, 2.94; N, 7.63; O, 2.18 (%); the experimental value: C, 81.86; H, 5.59; B, 2.84; N, 7.73; O, 2.08 (%).

[0196] The target compound 229 (HPLC analytical purity 99.84%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 765.41; elemental analysis result: the theoretical value: C, 83.15; H, 6.45; B, 2.82; N, 5.49; O, 2.09 (%); the experimental value: C, 83.25; H, 6.55; B, 2.72; N, 5.59; O, 1.99 (%).

[0197] Target compound 230 (HPLC assay purity 99.50%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 685.25; Elemental analysis result: Theoretical value: C, 78.85; H, 4.85; B, 3.15; N, 6.13; O, 2.33; S, 4.68 (%); Experimental value: C, 78.95; H, 4.95; B, 3.05; N, 6.23; O, 2.23; S, 4.58 (%).

[0198] Target compound 235 (HPLC assay purity 99.42%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 686.29; Elemental analysis result: Theoretical value: C, 80.49; H, 5.29; B, 3.15; N, 4.08; O, 6.99 (%); Experimental value: C, 80.59; H, 5.39; B, 3.05; N, 4.18; O, 6.89 (%).

[0199] Target compound 238 (HPLC assay purity 99.33%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 713.37; Elemental analysis result: Theoretical value: C, 82.48; H, 6.36; B, 3.03; N, 5.89; O, 2.24 (%); Experimental value: C, 82.58; H, 6.46; B, 2.93; N, 5.99; O, 2.14 (%).

[0200] Target compound 244 (HPLC assay purity 99.33%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 791.42; Elemental analysis result: Theoretical value: C, 83.45; H, 6.49; B, 2.73; N, 5.31; O, 2.02 (%); Experimental value: C, 83.55; H, 6.59; B, 2.63; N, 5.41; O, 1.92 (%).

[0201] Target compound 245 (HPLC assay purity 99.28%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 711.27; Elemental analysis result: Theoretical value: C, 79.34; H, 4.96; B, 3.04; N, 5.91; O, 2.25; S, 4.51 (%); Experimental value: C, 79.44; H, 5.06; B, 2.94; N, 6.01; O, 2.15; S, 4.41 (%).

[0202] Target compound 251 (HPLC assay purity 99.28%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 746.29; Elemental analysis result: Theoretical value: C, 82.06; H, 4.86; B, 2.9; N, 3.75; O, 6.43 (%); Experimental value: C, 82.16; H, 4.96; B, 2.8; N, 3.85; O, 6.33 (%).

[0203] Target compound 255 (HPLC assay purity 99.85%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 766.25; Elemental analysis result: Theoretical value: C, 78.34; H, 4.73; B, 2.82; N, 3.65; O, 2.09; S, 8.36 (%); Experimental value: C, 78.44; H, 4.83; B, 2.72; N, 3.75; O, 1.99; S, 8.46 (%).

[0204] Target compound 259 (HPLC assay purity 99.08%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 882.37; Elemental analysis result: Theoretical value: C, 84.37; H, 5.02; B, 2.45; N, 6.35; O, 1.81 (%); Experimental value: C, 84.47; H, 5.12; B, 2.35; N, 6.45; O, 1.71 (%).

[0205] Target compound 261 (HPLC assay purity 99.28%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 716.32;

[0206] Elemental analysis result: Theoretical value: C, 85.49; H, 5.35; B, 3.02; N, 3.91; O, 2.23 (%); Experimental value: C, 85.59; H, 5.45; B, 2.92; N, 4.01; O, 2.13 (%).

[0207] Target compound 266 (HPLC assay purity 99.09%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 812.45;

[0208] Elemental analysis result: Theoretical value: C, 82.76; H, 7.19; B, 2.66; N, 3.45; S, 3.94 (%); Experimental value: C, 82.86; H, 7.29; B, 2.56; N, 3.55; S, 3.84 (%).

[0209] Target compound 267 (HPLC assay purity 99.38%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 732.3; Elemental analysis result: Theoretical value: C, 78.69; H, 5.78; B, 2.95; N, 3.82; S, 8.75 (%); Experimental value: C, 78.79; H, 5.88; B, 2.85; N, 3.92; S, 8.65 (%).

[0210] Target compound 275 (HPLC assay purity 99.28%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 786.4; Elemental analysis result: Theoretical value: C, 80.92; H, 6.66; B, 2.75; N, 3.56; O, 2.03; S, 4.08 (%); Experimental value: C, 81.02; H, 6.76; B, 2.65; N, 3.66; O, 1.93; S, 4.28 (%).

[0211] Target compound 282 (HPLC assay purity 99.81%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 726.25;

[0212] Elemental analysis result: Theoretical value: C, 79.35; H, 4.99; B, 2.98; N, 3.86; S, 8.83 (%); Experimental value: C, 79.45; H, 5.09; B, 2.88; N, 3.96; S, 8.73 (%).

[0213] Target compound 288 (HPLC assay purity 99.81%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 808.39;

[0214] Elemental analysis result: Theoretical value: C, 80.2; H, 6.23; B, 2.67; N, 6.93; S, 3.96 (%); Experimental value: C, 80.3; H, 6.33; B, 2.57; N, 7.03; S, 3.86 (%).

[0215] Target compound 294 (HPLC assay purity 99.22%), yellow solid. MALDI-TOF-MS result: Molecular ion peak: 762.27;

[0216] Elemental analysis result: Theoretical value: C, 80.33; H, 4.76; B, 2.84; N, 3.67; O, 4.2; S, 4.2 (%); Experimental value: C, 80.43; H, 4.86; B, 2.74; N, 3.77; O, 4.1; S, 4.28 (%).

[0217] Target compound 296 (HPLC analytical purity 99.33%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 862.38;

[0218] Elemental analysis results: Theoretical value: C, 80.74; H, 6.08; B, 2.51; N, 3.25; S, 7.43 (%); Experimental value: C, 80.84; H, 6.18; B, 2.41; N, 3.35; S, 7.33 (%).

[0219] Target compound 302 (HPLC analytical purity 99.89%), yellow solid. MALDI-TOF-MS result: molecular ion peak: 774.27;

[0220] Elemental analysis results: Theoretical value: C, 80.64; H, 4.69; B, 2.79; N, 3.62; O, 4.13; S, 4.14 (%); Experimental value: C, 80.74; H, 4.79; B, 2.69; N, 3.72; O, 4.03; S, 4.28 (%).

[0221] The technical effects and advantages of the present application are demonstrated and verified by testing the actual use performance of the compounds of the present application applied to the organic electroluminescent device.

[0222] The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material can be further divided into multiple regions, for example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0223] The material of the anode can be an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof. The material of the cathode can be a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.

[0224] The hole transport region is between the anode and the light emitting layer. The hole transport region can be a single layer structure of a hole transport layer (HTL), including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0225] The material of the hole transport zone can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0226] The light-emitting layer includes light-emitting dyes (i.e. dopants) that can emit different wavelengths of light spectrum, and can also include host materials (Host). The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, blue, etc. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or can be stacked together to form a color light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can emit different colors such as red, green, blue, etc. at the same time.

[0227] The electron transport zone 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 zone 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).

[0228] Specifically, the method for preparing the organic electroluminescent device of the present application includes the following steps:

[0229] 1. The glass plate coated with an anode material is treated with ultrasonic waves in a commercial cleaning agent, washed in deionized water, treated with ultrasonic waves in a mixed solvent of acetone and ethanol to remove oil, baked in a clean environment until the water is completely removed, washed with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface;

[0230] 2. The glass plate with the anode is placed in a vacuum chamber, vacuumed to 1 x 10-5 to 9 x 10-3 Pa, and a hole injection layer is formed by vacuum evaporation of a hole injection material on the anode layer film at an evaporation rate of 0.1 to 0.5 nm / s;

[0231] 3. A hole transport layer is formed by vacuum evaporation of a hole transport material on the hole injection layer at an evaporation rate of 0.1 to 0.5 nm / s,

[0232] 4. An electron blocking layer is formed by vacuum evaporation on the hole transport layer at an evaporation rate of 0.1 to 0.5 nm / s;

[0233] 5. Vacuum depositing the organic light-emitting layer on the electron blocking layer, the organic light-emitting layer material comprising host material and light-emitting dye, using the method of multi-source co-deposition, adjusting the evaporation rate of the host material, the evaporation rate of the sensitizer material and the evaporation rate of the dye to make the dye reach the preset doping ratio;

[0234] 6. Vacuum depositing the hole blocking layer on the organic light-emitting layer, the evaporation rate being 0.1-0.5 nm / s;

[0235] 7. Vacuum depositing the electron transport material of the device on the hole blocking layer to form the electron transport layer, the evaporation rate being 0.1-0.5 nm / s;

[0236] 8. Vacuum depositing LiF on the electron transport layer as the electron injection layer at the evaporation rate of 0.1-0.5 nm / s, and vacuum depositing Al layer as the cathode of the device at the evaporation rate of 0.1-0.5 nm / s.

[0237] The embodiment of the present application also provides a display device, which comprises the organic electroluminescent device provided in the above. The display device can be specifically a display device such as OLED display, and a television, digital camera, mobile phone, tablet computer or any product or component having display function comprising the display device. The display device has the same advantages as the organic electroluminescent device relative to the prior art, and will not be described here.

[0238] The organic electroluminescent device of the present application will be further described below through specific embodiments.

[0239] Embodiments 1-50 of the present application are organic electroluminescent devices prepared by using the compound of the present application, and Comparative Examples 1-6 are parallel comparison devices prepared by using the compound P1, P2, P3 and P4 of the prior art according to the same preparation method as the compound of the present application. The structure scheme of all the prepared devices is shown in Table 1 below:

[0240] Table 1:

[0241]

[0242]

[0243]

[0244] Wherein, the anode material is ITO; the hole injection layer material is HI, and the total thickness is generally 5-30 nm, and in the embodiment, it is 10 nm; the hole transport layer material is HT, and the total thickness is generally 5-500 nm, and in the embodiment, it is 30 nm; the Host organic light-emitting layer wide-band-gap host material is TD, which is a TADF type host, and the thickness of the organic light-emitting layer is generally 1-200 nm, and in the embodiment, it is 30 nm; the electron transport layer material is ET, and the thickness is generally 5-300 nm, and in the embodiment, it is 30 nm; the electron injection layer and the cathode material are LiF (0.5 nm) and aluminum (150 nm).

[0245] The structural formula of each type of organic material used in each of the above embodiments is as follows:

[0246]

[0247]

[0248]

[0249] The performance of the devices prepared in Examples 1-50 and Comparative Examples 1-6 of the present application is shown in Table 2 below:

[0250] Table 2:

[0251]

[0252]

[0253]

[0254] Compared with the comparative examples, the compound in the present application connects the center with the surrounding benzene ring by introducing a single boron-nitrogen covalent bond, to construct a new type of organic narrow-spectrum light-emitting material. The embedding of the B-N bond maintains the planar structure of the MR multiple resonance skeleton. Compared with Comparative Examples 5 and 6, the design of the connecting peripheral benzene ring in the structure of the compound of the present application significantly enhances the rigidity of the molecule, significantly narrows the full width at half maximum (FWHM in 16-26 nm), and improves the light-emitting efficiency (PLQY > 90%). Since the peripheral groups are all carbazole groups, the carbazole group has relatively weak electron-donating ability, so the excited state electrons of this series of compounds are delocalized on the entire conjugated plane, and the light-emitting performance and stability of the material are greatly improved. By changing the peripheral substituent group, the light color can be adjusted in the blue to green range, while maintaining the characteristic of narrow light-emitting full width at half maximum, and the lifetime of the device is greatly improved. On the other hand, the compound of the present application also introduces heavy atom effect through B-O bond and B-S bond bridging, improves the reverse intersystem crossing rate of the material, reduces the efficiency roll-off of the device, improves its stability, and further blue-shifts the light color, while also maintaining the characteristic of narrow full width at half maximum.

[0255] The experimental data above show that the organic electroluminescent device prepared by using the novel MR-TADF material provided by the application has low efficiency roll-off and long device life while realizing high color purity and high luminous efficiency of the device. Therefore, the novel compound of the application is a good organic luminescent functional material, and is expected to be popularized and applied commercially.

[0256] Although the application is described in combination with the embodiments, the application is not limited to the above embodiments, and it should be understood that those skilled in the art can make various modifications and improvements under the guidance of the concept of the application, and the appended claims define the scope of the application.

[0257] Obviously, the above embodiments are only examples for clearly illustrating the application, and are not intended to limit the implementation modes. Based on the above description, other different forms of changes or variations can be made by those skilled in the art. Here, it is not necessary and also impossible to enumerate all the implementation modes. The obvious changes or variations derived therefrom are still within the protection scope of the application.

Claims

1. An organic compound having a structure according to formula (2), formula (3) or formula (4): ###0001### ###0002### ###0003### m, p are independently 1 or 0, n is 0, and m, n, p are not simultaneously 0; Y1 represents a single bond, CO, NR2 or BR5, Y3 represents independently a single bond, CO or CR8R9; q represents 1 or 0; Y4 represents a single bond or BR5; R2 is selected from methyl; R5 is selected from phenyl or methyl substituted phenyl; R8, R9 are each independently selected from phenyl. （2） （3） （4） 3. A compound selected from the following specific structures: ###0004### ###0005### ###0006### ###0007### ###0008### ###0009### ###0010### ###0011### ###0012### ###0013### ###0014### ###0015### ###0016### ###0017### ###0018### ###0019### ###0020### ###0021### ###0022### ###0023### ###0024### ###0025### ###0026### ###0027### ###0028### ###0029### ###0030### ###0031### ###0032### ###0033### ###0034### ###0035### ###0036### ###0037### ###0038### ###0039### ###0040### ###0041### ###0042### ###0043### ###0044### ###0045### ###0046### ###0047### ###0048### ###0049### ###0050### ###0051### ###0052### ###0053### ###0054### ###0055### ###0056### ###0057### ###0058### ###0059### ###0060### ###0061### ###0062### ###0063### ###0064### ###0065### ###0066### ###0067### ###0068### ###0069### ###0070### ###0071### ###0072### ###0073### ###0074### ###0075### ###0076### ###0077### ###0078### ###0079### ###0080### ###0081### ###0082### ###0083### ###0084### ###0085### ###0086### ###0087### ###0088### ###0089### ###0090### ###0091### ###0092### ###0093### ###0094### ###0095### ###0096### ###0097### ###0098### ###0099### ###0100### ###0101### ###0102### ###0103### ###0104### ###0105### ###0106### ###0107### ###0108### ###0109### ###0110### ###0111### ###0112### ###0113### ###0114### ###0115### ###0116### ###0117### ###0118### ###0119### ###0120### ###0121### ###0122### ###0123### ###0124### ### ​ ​ R1and the adjacent R a not connected or connected in a ring; ​ R 6’ one selected from the group consisting of hydrogen, a chain alkyl group of Cl~C30, an arylamino group of C6~C30, an aryl group of C6~C60, a heteroaryl group of C5~C60; R a , R b , R c , R d each independently represents a single substituent to the maximum permissible number of substituent groups, R a , R b , R c , R d each independently is selected from one or a combination of two substituent groups from the group consisting of hydrogen, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, cyano, C6-C20 arylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl; R e is hydrogen; R a , R b are not connected or are connected by a single bond.

2. The organic compound according to claim 1, characterized by said R a , R b , R c , R d are each independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, fluoranthenyl, xanthenyl, fluorxenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, methoxy, or a combination of two substituents from the above. ​ 。 ​ ​ 5. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first and second electrodes, the light-emitting functional layers comprising a hole-transporting zone, a light-emitting layer, an electron-transporting zone, the hole-transporting zone and the electron-transporting zone being separated by the light-emitting layer; wherein, ​

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