A boron-containing organic compound containing an indolocarbazole ring and an organic electroluminescent device for the preparation thereof

Abstract

The application discloses a boron-containing organic compound containing an indole carbazole ring and an organic electroluminescent device prepared from the same, and belongs to the technical field of semiconductors. The structure of the organic compound is shown in general formula (1). When the compound of the application is used as a doping material in a light-emitting layer material of an OLED light-emitting device, the compound can be used as a green light-emitting layer doping material of an organic electroluminescent device, so that the light-emitting color purity and efficiency of the device are improved.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and more particularly to a boron-containing organic compound containing an indolecarbazole ring and an organic electroluminescent device prepared therefrom. Background Technology

[0002] Traditional fluorescent doped materials, limited by early technologies, can only emit light using 25% of singlet excitons generated by electrical excitation. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lower than that of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at their heavy atom centers, enhance intersystem crossing and can effectively utilize both singlet and triplet excitons generated by electrical excitation, achieving an internal quantum efficiency of 100%. However, most phosphorescent materials are expensive, have poor material stability, low color purity, and suffer from severe efficiency roll-off, limiting their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements have been placed on color rendering standards. In addition to high efficiency and stability, luminescent materials also need narrower half-widths (HWHMs) to improve the purity of the emitted color in devices. Fluorescent dopants can achieve high fluorescence quantum density and narrow HWHM through molecular engineering. Significant breakthroughs have been achieved in blue fluorescent dopants, with the HWHM of boron-based materials reduced to below 30 nm. However, research on the green light region, which is more sensitive to the human eye, has mainly focused on phosphorescent dopants. However, the peak shape of these dopants is difficult to narrow using simple methods. Therefore, researching efficient green fluorescent dopants with narrow HWHMs is of great significance in meeting higher color rendering standards.

[0004] In addition, sensitization technology combines triplet exciton sensitizing materials with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it makes full use of triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization in fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in OLED applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width emission (HWHM). When applied to sensitization techniques, these materials can enable the fabrication of devices with high efficiency and narrow HWHM emission. For example, CN 107507921 A and CN 110492006 A disclose a light-emitting layer combination technique using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005 A and CN 110492009 A disclose a light-emitting layer combination scheme using excitocomplexes as the main body and boron-containing materials as dopants; both achieve efficiencies comparable to phosphorescence and relatively narrow HWHM. Therefore, developing sensitization techniques based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for improving BT.2020 display performance. Summary of the Invention

[0006] To address the aforementioned problems in the prior art, this invention provides a boron-containing organic compound with an indole-carbazole cyclic ring and an organic electroluminescent device prepared therefrom. The compound of this invention, by introducing an indole-carbazole cyclic ring structure at a specific position in the boron-nitrogen fused ring core, can be used as a green light doping material for the emitting layer of an organic electroluminescent device, thereby improving the purity and lifetime of the emitted light color.

[0007] The technical solution of the present invention is as follows: a boron-containing organic compound containing an indolecarbazole ring, wherein the structure of the boron-containing organic compound is shown in general formula (1):

[0008]

[0009] In general formula (1), each occurrence of Z, whether the same or different, is represented by CR;

[0010] Each occurrence of R, whether the same or different, represents a hydrogen atom, deuterium atom, tritium atom, halogen atom, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0011] Z1, Z2, and Z3 are each independently represented as CR a CR b CR c ;

[0012] R a R b Rc Each can be independently represented as a hydrogen atom, deuterium atom, tritium atom, halogen atom, or substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0013] M1 represents substituted or unsubstituted C6-C6. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0014] Ar1 represents C6-C6 with or without substitution. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0015] X represents one of O and S;

[0016] The substituents used for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, and C1-C2 atoms. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0017] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0018] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (1-1) to (1-7):

[0019]

[0020] In general formulas (1-1) to (1-7), Z, Z1, Z2, Z3, X, Ar1, R a R b R c The meaning is the same as the limitation mentioned above;

[0021] Y1, Y2, and Y3 represent one of O and S;

[0022] Z4, Z5, Z6, and Z7 are each independently represented as CR d CR e CR f CRg ;

[0023] R d R e R f R g Each can be independently represented as a hydrogen atom, deuterium atom, tritium atom, halogen atom, or substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0024] The substituents used for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, and C1-C2 atoms. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0025] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0026] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (4) to (26):

[0027]

[0028]

[0029] In general formulas (4) to (26), the meanings of Ar1, Z, Z1, Z2, and Z3 are the same as those in the above description.

[0030] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (27) to (37):

[0031]

[0032] In general formulas (27) to (37), the R b The definition is the same as the limitation mentioned above;

[0033] R1-R 97 Each can be independently represented as a hydrogen atom, deuterium atom, tritium atom, halogen atom, or substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0034] The substituents used for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, and C1-C2 atoms. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0035] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0036] In the preferred embodiment, R, R a R b R c R d R e R f R g R1-R 97 It can be represented as the structure shown below:

[0037] hydrogen atom,

[0038] Any one of them;

[0039] The Ar1 is represented by the following structure:

[0040]

[0041] Any one of them.

[0042] In a preferred embodiment, M1 is represented by any of the following ring structures:

[0043]

[0044] The definition of Z is the same as the limitation mentioned above.

[0045] In the preferred embodiment, R, R a R b R c R d R e R f R g R1-R97 Each of these can be independently represented as a hydrogen atom, deuterium atom, tritium atom, halogen atom, adamantyl, methyl, deuterated methyl, tritated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritated ethyl, isopropyl, deuterated isopropyl, tritated isopropyl, tert-butyl, deuterated tert-butyl, tritated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated benzene. alkyl, triphenyl, diphenyl, deuterated diphenyl, triphenyl, deuterated terphenyl, deuterated terphenyl, triphenyl terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthranilyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9, 9-Dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy;

[0046] The Ar1 is represented as adamantyl, methyl, deuterated methyl, tritriated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritriated ethyl, isopropyl, deuterated isopropyl, tritriated isopropyl, tert-butyl, deuterated tert-butyl, tritriated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritriated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritriated phenyl, diphenyl, deuterium Diphenyl, tritriphenyl, triphenyl, deuterated triphenyl, tritriphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spiro The following is a list of fluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boroalkyl, methoxy, and tert-butoxy.

[0047] M1 represents one of the following: phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, and xanthone.

[0048] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthreneyl.

[0049] In a preferred embodiment, the boron-containing organic compound has any one of the following structures:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer including a light-emitting layer containing the boron-containing organic compound.

[0063] In a preferred embodiment, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains the boron-containing organic compound containing an indolecarbazole ring.

[0064] In a preferred embodiment, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is a boron-containing organic compound containing an indolecarbazole ring.

[0065] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the aforementioned boron-containing organic compound containing an indole-carbazole ring.

[0066] The beneficial technical effects of this invention are as follows:

[0067] (1) The compound of the present invention can be used as a dopant material for OLED devices, and can emit green fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0068] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0069] (3) The compound of the present invention is used as a doping material, and TADF sensitizer is introduced as a second host, which can effectively improve device efficiency;

[0070] (4) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device.

[0071] The compounds of this invention have narrow half-width and high fluorescence quantum yield, and can be used as green light doping materials for the emitting layer of organic electroluminescent devices, thereby improving the emission color purity and lifetime of the devices. Attached Figure Description

[0072] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0073] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation

[0074] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0075] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0076] In this invention, C6-C is substituted or unsubstituted. 30Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. The compounds may be substituted, substituted or unsubstituted triphenyl, substituted or unsubstituted peryl, substituted or unsubstituted indole, but are not limited thereto.

[0077] In this invention, substituted or unsubstituted C2-C 30 Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted... The fused ring of substituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0078] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but are not limited to these.

[0079] The C3-C of this invention 10Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0080] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its application direction varies. In this invention, a transparent PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0081] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. The thickness of the first electrode layer depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0082] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light-emitting layer, and an electron transport region.

[0083] In this paper, the hole transport region constituting an organic electroluminescent device can be listed as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0084] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in OLED devices.

[0085] Examples of the aforementioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0086] Furthermore, depending on the device configuration requirements, the hole transport film layer between the electron blocking and hole injection layers of an organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this paper, the film thickness of the various hole carrier conduction films with different functions is not particularly limited.

[0087] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0088] Based on the above empirical summary, different P-doped materials need to be selected to match the hole-based host materials of different HOMO energy levels in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0089] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0090] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass meter.

[0091] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0092] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0093] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0094] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0095] The light-emitting layer may comprise a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a boron-containing organic compound containing an indolecarbazole ring as shown in the general formula (1) of this invention.

[0096] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0097] The dual-body material comprises a first body material and a second body material, wherein preferably at least one of the first body material and the second body material is a TADF material;

[0098] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0099] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0100] Exciton sensitizing materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing organic compound containing the carbazole-fluorene structure shown in the general formula (1) of this invention, when used in combination with the exciton sensitizing material, has a significant improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0101] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0102] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0103] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0104] A hole-blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its efficiency. The hole-blocking layer of this invention can be disposed above the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives like aluminum(III)bis(2-methyl-8-quinoline)-4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives like 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole-blocking layer of this invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0105] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthyl-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0106] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0107] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0108] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0109] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0110] Synthesis Examples

[0111] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0112] Example 1: Synthesis of Compound 63:

[0113]

[0114] Preparation of intermediate a-1:

[0115] Under nitrogen protection, 10 mmol of starting material A-1, 10 mmol of starting material B-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-1. LC-MS: Measured value: 389.22 ([M+H) + Theoretical value: 388.19.

[0116] Preparation of intermediate b-1:

[0117] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of starting material C-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 573.20 ([M+H) + Theoretical value: 572.24.

[0118] Preparation of intermediate c-1:

[0119] In a three-necked flask under nitrogen protection, 10 mmol of intermediate b-1, 13 mmol of starting material D-1, 15 mmol of cesium carbonate, and 20 mL of anhydrous DMF were added. The mixture was heated to 120 °C in the dark and reacted for 20 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-1. LC-MS: Measured value: 759.37 ([M+H)) + Theoretical value: 758.31.

[0120] Preparation of compound 63:

[0121] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate c-1 and 15 mL of anhydrous o-dichlorobenzene were added. After cooling to -78°C, 12 mmol of 2.5 M tert-butyllithium-n-hexane solution was added dropwise. The mixture was transferred to 60°C for a 4-hour reverse reaction. The reaction was then cooled to -42°C, and 15 mmol of boron tribromide was added dropwise. After slowly restoring to room temperature, the reaction was allowed to proceed for 8 hours. At 0°C, ultra-dry N,N-diisopropylaminolithium was added dropwise. The reaction mixture was heated to 180°C and reacted for 48 hours. After cooling to room temperature, the low-boiling solvent was removed by vacuum distillation. The product was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate, and the filtrate was collected. The filtrate was concentrated and purified by column chromatography to give compound 63. Compound 63 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer. 1 ¹H NMR (400 MHz, deuterated chloroform): δ 1.25–1.43 (27H, m), 6.51–6.70 (3H, m), 6.82 (1H, d), 7.11 (2H, m), 7.30–7.55 (5H, m), 7.62–7.83 (2H, dd), 7.95–8.14 (3H, m), 8.19–8.27 (2H, m).

[0122] Example 2: Synthesis of Compound 69:

[0123]

[0124] Preparation of intermediate c-2:

[0125] In a three-necked flask under nitrogen protection, 10 mmol of intermediate b-1, 13 mmol of starting material D-2, 15 mmol of cesium carbonate, and 20 mL of anhydrous DMF were added. The mixture was heated to 120 °C and reacted for 12 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-2. LC-MS: Measured value: 814.44 ([M+H)) + Theoretical value: 813.35.

[0126] Preparation of compound 69:

[0127] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-2 and 15 mL of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0 °C, and the mixture was heated to 60 °C and reacted for 4 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 8 hours. Next, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the mixture was heated to 200 °C and reacted for 22 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 69. Compound 69 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 21 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer. 1 ¹H NMR (400 MHz, deuterated chloroform): δ 1.25–1.36 (¹⁸H, d), 6.58–6.66 (³H, m), 6.77–6.89 (²H, m), 6.94–7.21 (⁸H, m), 7.28–7.69 (¹⁰H, m), 7.82–8.01 (³H, m), 8.05–8.19 (²H, m).

[0128] Example 3: Synthesis of Compound 71:

[0129]

[0130] Preparation of intermediate d-1:

[0131] Under nitrogen protection, 10 mmol of starting material A-2 and 20 mL of ultra-dry tetrahydrofuran were added to a three-necked flask. 12 mmol of 2.5 M n-butyllithium solution was added dropwise at -78 °C, and the mixture was stirred at -78 °C for 2 hours. Then, 15 mmol of triisopropyl borate dissolved in 5 mL of ultra-dry tetrahydrofuran was added dropwise, and the mixture was stirred at -78 °C for another 2 hours. The reaction was then slowly brought to room temperature and continued for 10 hours. The reaction was quenched by adding 2 mL of ethanol to the reaction mixture, and 20% hydrochloric acid was added until the pH was adjusted to 6-7. The organic phase was collected by separation, and the aqueous phase was extracted with 3 × 10 mL dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting solution was separated by column chromatography to obtain intermediate d-1. LC-MS: Measured value: 361.10 ([M+H) + Theoretical value: 360.13.

[0132] Preparation of intermediate e-1:

[0133] Add 10 mmol of intermediate d-1 and 150 mL of water to a three-necked flask, then add 0.5 mmol of Cu. 0.05 Ti 0.95 O 1.95 The catalyst, 20 mmol of hydrogen peroxide aqueous solution, and the mixture were stirred at room temperature for 12 hours. After the reaction, the precipitate was filtered, extracted with 2 × 40 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered again, and the organic phase was concentrated. Intermediate e-1 was obtained by column chromatography. LC-MS: Measured value: 333.19 ([M+H)). + Theoretical value: 332.12.

[0134] Preparation of intermediate c-3:

[0135] In a three-necked flask under nitrogen protection, 10 mmol of intermediate e-1, 13 mmol of intermediate b-1, 15 mmol of cesium carbonate, and 20 mL of anhydrous DMF were added. The mixture was heated to 120 °C and reacted for 16 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-3. LC-MS: Measured value: 885.49 ([M+H)) + Theoretical value: 884.35.

[0136] Preparation of compound 71:

[0137] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-3 and 15 mL of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0 °C, the system was heated to 60 °C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 5 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0 °C, the system was heated to 200 °C and reacted for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 71. Compound 71 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 21 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0138] Example 4: Synthesis of Compound 80:

[0139]

[0140] Preparation of intermediate c-4:

[0141] In a three-necked flask under nitrogen protection, 10 mmol of intermediate b-1, 13 mmol of starting material D-3, 15 mmol of cesium carbonate, and 20 mL of anhydrous DMF were added. The mixture was heated to 120 °C and reacted for 18 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-4. LC-MS: Measured value: 737.33 ([M+H)) + Theoretical value: 736.29.

[0142] Preparation of compound 80:

[0143] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-4 and 15 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 3 hours. Then, 15 mmol of boron tribromide was added at 0°C, and the mixture was transferred to room temperature and reacted for another 3 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0°C, the system was heated to 200°C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 80. Compound 80 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the peak (M) was 20 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0144] Example 5: Synthesis of Compound 96:

[0145]

[0146] Preparation of intermediate b-2:

[0147] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of starting material C-2, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-2. LC-MS: Measured value: 856.42 ([M+H) + Theoretical value: 855.30.

[0148] Preparation of intermediate c-5:

[0149] In a three-necked flask under nitrogen protection, 10 mmol of intermediate b-2, 13 mmol of starting material D-4, 15 mmol of cesium carbonate, and 20 mL of anhydrous NMP were added. The mixture was heated to 150 °C and reacted for 12 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-5. LC-MS: Measured value: 920.50 ([M+H) + Theoretical value: 919.43.

[0150] Preparation of compound 96:

[0151] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-5 and 15 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0°C, and the mixture was transferred to room temperature and reacted for another 2 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0°C, the system was heated to 200°C and reacted for 6 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 96. Compound 96 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 21 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer. 1 ¹H NMR (400 MHz, deuterated chloroform): δ 1.25–1.37 (27H, m), 6.39 (1H, d), 6.51–6.71 (6H, m), 6.77 (1H, d), 6.99–7.20 (6H, m), 7.37–7.72 (7H, m), 7.89–8.11 (5H, m), 8.19–8.28 (2H, m), 8.35 (1H, m).

[0152] Example 6: Synthesis of Compound 132:

[0153]

[0154] Preparation of raw material C-4:

[0155] Under nitrogen protection, 10 mmol of starting material C-3, 10 mmol of starting material E-1, 15 mmol of potassium carbonate, 0.5 mmol of Pd(PPh3)4, 20 mL of anhydrous toluene, and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain starting material C-4. LC-MS: Measured value: 284.99 ([M+H)) + Theoretical value: 283.94.

[0156] Preparation of intermediate b-3:

[0157] Under nitrogen protection, 10 mmol of starting material B-2, 10 mmol of starting material C-4, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 15 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-3. LC-MS: Measured value: 486.27 ([M+H)) + Theoretical value: 485.23.

[0158] Preparation of intermediate b-4:

[0159] Under nitrogen protection, 10 mmol of intermediate b-3, 10 mmol of starting material A-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-4. LC-MS: Measured value: 725.39 ([M+H)) + Theoretical value: 724.30.

[0160] Preparation of intermediate c-6:

[0161] In a three-necked flask under nitrogen protection, 10 mmol of intermediate b-4, 13 mmol of starting material D-5, 15 mmol of cesium carbonate, and 20 mL of anhydrous NMP were added. The mixture was heated to 150 °C and reacted for 17 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-6. LC-MS: Measured value: 855.41 ([M+H)) + Theoretical value: 854.40.

[0162] Preparation of compound 132:

[0163] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-6 and 15 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0°C, and the mixture was transferred to room temperature and reacted for another 2 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0°C, the system was heated to 200°C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 132. Compound 132 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 19 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0164] Example 7: Synthesis of Compound 137:

[0165]

[0166] Preparation of intermediate c-7:

[0167] In a three-necked flask under nitrogen protection, 10 mmol of intermediate b-4, 13 mmol of intermediate e-1, 15 mmol of cesium carbonate, and 20 mL of anhydrous NMP were added. The mixture was heated to 150 °C and reacted for 14 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate c-7. LC-MS: Measured value: 1037.55 ([M+H)). + Theoretical value: 1036.42.

[0168] Preparation of compound 137:

[0169] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-7 and 15 mL of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0 °C, the system was heated to 60 °C and reacted for 4 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 2 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 137. Compound 137 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 21 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0170] Example 8: Synthesis of Compound 254:

[0171]

[0172] Preparation of intermediate f-1:

[0173] Under nitrogen protection, 10 mmol of starting material C-3, 10 mmol of starting material E-1, 15 mmol of potassium carbonate, 0.5 mmol of Pd(PPh3)4, 20 mL of anhydrous toluene, and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-1. GC-MS: Measured value: 397.11 ([M+H) + Theoretical value: 396.07.

[0174] Preparation of intermediate b-5:

[0175] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of intermediate f-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 22 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 705.40 ([M+H) + Theoretical value: 704.33.

[0176] Preparation of intermediate c-8:

[0177] Under nitrogen protection, 10 mmol of intermediate b-5, 10 mmol of starting material D-4, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine, and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 17 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-8. LC-MS: Measured value: 829.34 ([M+H)) + Theoretical value: 828.38.

[0178] Preparation of compound 254:

[0179] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-8 and 15 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 3 hours. Then, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 4 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0°C, the system was heated to 200°C and reacted for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 254. Compound 254 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 21 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0180] Example 9: Synthesis of Compound 258:

[0181]

[0182] Preparation of intermediate c-9:

[0183] Under nitrogen protection, 10 mmol of intermediate b-5, 10 mmol of starting material D-5, 15 mmol of potassium carbonate, 0.5 mmol of Pd(PPh3)4, 20 mL of anhydrous toluene, and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 14 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-9. LC-MS: Measured value: 1017.53 ([M+H) + Theoretical value: 1016.45.

[0184] Preparation of compound 258:

[0185] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate C-9 and 15 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 3 hours. Then, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 4 hours. Next, 20 mmol of N,N-diisopropylethylamine was added at 0°C, the system was heated to 200°C and reacted for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 258. Compound 258 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer. 1 ¹H NMR (400 MHz, deuterated chloroform): δ 1.29–1.43 (27H, d), 6.59 (2H, m), 6.97 (1H, d), 7.11 (2H, m), 7.15–7.33 (2H, m), 7.38–8.12 (23H, m), 8.26–8.33 (2H, m).

[0186] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0187] Table 1

[0188]

[0189] The following details the application effects of the OLED materials synthesized in this invention in devices through device examples 1-9 and device comparative examples 1-3. Device examples 2-9 and device comparative examples 1-3 of this invention have the same fabrication process as device example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0190] Device Example 1

[0191] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (SemicleanM-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 63 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 63 of 69:30:1. The light-emitting layer has a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0192] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 10-18 and device comparative examples 4-6. Device examples 11-18 and device comparative examples 4-6 of this invention have the same fabrication process as device example 10, and use the same substrate material and electrode material, with the same electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0193] Device Example 11

[0194] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 63 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 63 is 66:30:3:1, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1; the thickness of this layer is 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0195] The molecular structural formulas of the relevant materials are shown below:

[0196]

[0197] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, external quantum efficiency, and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results for the current efficiency, external quantum efficiency, and lifetime of the obtained devices are shown in Table 3.

[0198] Table 2-1

[0199]

[0200]

[0201] Table 2-2

[0202]

[0203]

[0204] Table 3

[0205]

[0206] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0207] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1, ref-2, and ref-3, the emission peak of the compound of the present invention is between 510 and 550 nm, which can achieve the effect of green light emission very well. Compared with the devices of Comparative Examples 1-6, the organic light-emitting device of the present invention has achieved a significant improvement in current efficiency and lifetime compared with OLED devices of known materials, whether in a single-doped system or a double-doped system. When using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with the single-doped system.

[0208] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound containing an indole-carbazole ring, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (1-3) to (1-7): In general formulas (1-3) to (1-7), the recurrence of Z, whether the same or different, is represented by CR. Each occurrence of R, whether the same or different, represents a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 One of the following: cycloalkyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; Z1, Z2, and Z3 are each independently represented as CR a CR b CR c ; R a R b R c Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Ar1 represents C6 to C6 with or without substitution. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; X represents one of O and S; Y2 and Y3 represent one of O and S; Z4, Z5, Z6, and Z7 are each independently represented as CR d CR e CR f CR g ; R d R e R f R g Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 One of the following: cycloalkyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, C1 to C2 atoms. 10 Alkyl groups, C3-C 10 One or more of the cycloalkyl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

2. The boron-containing organic compound containing indolecarbazole ring according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (10) to (15), (18) to (19), and (22) to (23): In general formulas (10) to (15), (18) to (19), and (22) to (23), Ar1, Z, Z1, Z2, and Z3 have the same meanings as defined in claim 1.

3. The boron-containing organic compound containing indolecarbazole ring according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (28), (31) to (32), (34), (36) to (37): In general formulas (28), (31) to (32), (34), (36) to (37), the R b The definition is the same as that in claim 1; R7-R 10 R 30 -R 33 R 37 -R 39 R 57 -R 60 R 78 -R 81 R 89 -R 92 Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1 to C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 One of the following: cycloalkyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; R 11 -R 13 R 34 -R 36 R 40 -R 42 R 61 -R 63 R 82 -R 84 R 93 -R 95 Each can be independently represented as a hydrogen atom, deuterium atom, halogen atom, or C1 to C1 atom. 10 Alkyl, C3-C 10 One of the cycloalkyl groups; R 55 -R 56 R 64 -R 65 R 76 -R 77 R 85 -R 88 R 96 -R 97 They are represented independently as hydrogen atoms and tert-butyl groups, respectively. The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, C1 to C2 atoms. 10 Alkyl groups, C3-C 10 One or more of the cycloalkyl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

4. The boron-containing organic compound containing an indolecarbazole ring according to any one of claims 1 or 2, characterized in that, The R is represented by the following structure: hydrogen atom, Any one of them; The R a R b R c It can be represented as the structure shown below: hydrogen atom, Any one of them; The Ar1 is represented by the following structure: Any one of them.

5. The boron-containing organic compound containing indolecarbazole ring according to claim 1, characterized in that, The R, R d R e R f R g It can be represented as the structure shown below: hydrogen atom, Any one of them; The R a R b R c It can be represented as the structure shown below: hydrogen atom, Any one of them; the Ar1 is represented by the following structure: Any one of them.

6. The boron-containing organic compound containing indolecarbazole ring according to claim 3, characterized in that, The R b It can be represented as the structure shown below: hydrogen atom, Any one of them; The R7-R 10 R 30 -R 33 R 37 -R 39 R 57 -R 60 R 78 -R 81 R 89 -R 92 It can be represented as the structure shown below: hydrogen atom, Any one of them; The R 11 -R 13 R 34 -R 36 R 40 -R 42 R 61 -R 63 R 82 -R 84 R 93 -R 95 It can be represented as the structure shown below: hydrogen atom, Any one of them.

7. The boron-containing organic compound containing indolecarbazole ring according to claim 1 or 2, characterized in that, The R represents hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, naphthyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted... One of the following: diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, and tert-butylbenzene-substituted amino. The R a R b R c Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted One of the following: phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl; The Ar1 is represented as phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, oxanthoneyl, and phenyl-substituted triazineyl.

8. The boron-containing organic compound containing indolecarbazole ring according to claim 1, characterized in that, The R, R d R e R f R g Represented as hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, naphthyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: phenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, and tert-butylbenzene-substituted amino. The R a R b R c Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted One of the following: phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl; The Ar1 is represented as phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, oxanthoneyl, and phenyl-substituted triazineyl.

9. The boron-containing organic compound containing indolecarbazole ring according to claim 3, characterized in that, The R b Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl... One of the following: propyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, methoxy, and tert-butoxy. The R7-R 10 R 30 -R 33 R 37 -R 39 R 57 -R 60 R 78 -R 81 R 89 -R 92 Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, and methyl-substituted... One of the following: diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, and tert-butylbenzene-substituted amino. The R 11 -R 13 R 34 -R 36 R 40 -R 42 R 61 -R 63 R 82 -R 84 R 93 -R 95 Each of the following can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, or xanthoneyl.

10. The boron-containing organic compound containing an indolecarbazole ring according to claim 1, characterized in that, The boron-containing organic compound has any of the following structures:

11. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, said organic light-emitting functional layer comprising a light-emitting layer, characterized in that, The light-emitting layer contains a boron-containing organic compound as described in any one of claims 1-10.

12. The organic electroluminescent device according to claim 11, characterized in that, The light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains a boron-containing organic compound containing an indolecarbazole ring as described in any one of claims 1-10.

13. The organic electroluminescent device according to claim 11, wherein the light-emitting layer comprises a first host material, a second host material, and a dopant material, characterized in that, At least one of the first and second main materials is a TADF material, and the doped material is a boron-containing organic compound containing indolecarbazole ring as described in any one of claims 1-10.

14. The organic electroluminescent device according to claim 11, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing organic compound containing an indolecarbazole ring as described in any one of claims 1-10.

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