An organic electroluminescent device comprising a boron-containing organic compound and a preparation method thereof

Abstract

This invention discloses a boron-containing organic compound and an organic electroluminescent device prepared therefrom, belonging to the field of semiconductor technology. The structure of the organic compound of this invention is shown in general formula (1). The compound of this invention has a narrow half-width at half-maximum and can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the purity of the emitted color and the lifetime of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of semiconductor technology, in particular to a boron-containing organic compound and an organic electroluminescent device comprising the same. BACKGROUND

[0002] Traditional fluorescent dopant materials are limited by early technology, and can only utilize 25% singlet excitons formed by electric excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%), and the external quantum efficiency is generally less than 5%, which is far from the efficiency of phosphorescent devices. The strong spin-orbit coupling of heavy atom centers in phosphorescent materials enhances intersystem crossing, which can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, the application of most phosphorescent materials in OLEDs is limited by problems such as high price, poor material stability, poor color purity, and serious device efficiency roll-off.

[0003] With the advent of the 5G era, higher requirements are put forward for color rendering standards. In addition to high efficiency and stability, luminescent materials also need narrower half-peak width to improve the color purity of device light emission. Fluorescent dopant materials can achieve high fluorescence quantum and narrow half-peak width through molecular engineering. Blue fluorescent dopant materials have achieved a phased breakthrough, and the half-peak width of boron-based materials can be reduced to below 30 nm. However, the green light region, which is more sensitive to the human eye, mainly focuses on phosphorescent dopant materials, but it is difficult to narrow the emission peak shape through simple methods. Therefore, in order to meet higher color rendering standards, it is of great significance to study high-efficiency green fluorescent dopant materials with narrow half-peak width.

[0004] In addition, sensitization technology combines triplet exciton sensitization materials with fluorescent dopant materials, uses triplet exciton sensitization materials as exciton sensitization media, fully utilizes triplet excitons, and transfers energy to fluorescent dopant materials through energy transfer, which can also achieve 100% internal quantum efficiency of the device. This technology can make up for the shortcomings of insufficient utilization of excitons of fluorescent dopant materials, effectively utilize the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent dopant materials, and has broad prospects in the application of OLEDs.

[0005] The boron-based compound with a resonance structure is easier to realize narrow full width at half maximum light emission. The application of such materials in sensitization technology can realize the preparation of devices with high efficiency and narrow full width at half maximum emission. In CN 107507921 A and CN 110492006 A, a combination technology of a light-emitting layer containing a boron-based material as a dopant and a TADF material as a host is disclosed, wherein the energy level difference between the lowest singlet state and the lowest triplet state is less than or equal to 0.2 eV; in CN 110492005 A and CN 110492009 A, a combination scheme of a light-emitting layer containing a boron-based material as a dopant and a ground-state complex as a host is disclosed; both of which can realize an efficiency comparable to phosphor and a relatively narrow full width at half maximum. Therefore, the development of a sensitization technology based on a narrow full width at half maximum boron-based light-emitting material has unique advantages and strong potential in the face of BT.2020 display indicators. SUMMARY

[0006] In view of the above problems existing in the prior art, the present application provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present application has a narrow full width at half maximum and can be used as a green light-emitting layer dopant material for an organic electroluminescent device, thereby improving the color purity and service life of the device.

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

[0008]

[0009] In general formula (1), “------” represents a single bond or a double bond;

[0010] M represents a substituted or unsubstituted C6-C 30 aromatic ring, a substituted or unsubstituted C2-C 30 heteroaromatic ring;

[0011] R1, R2 independently represent a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 20 cycloalkyl group;

[0012] wherein R1, R2 can also be bonded to form a ring structure formula a as follows:

[0013]

[0014] In formula a, the asterisk represents the position of the ring with c1 and c2, and M1 represents a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted C 6-20cycloalkyl;

[0015] M2is one of unsubstituted or substituted C6-C 30 aryl, unsubstituted or substituted C2-C 30 heteroaryl, unsubstituted or substituted C3-C 10 cycloalkyl;

[0016] X1, X2are one of a single bond, O, S, C(R3)(R4), N(R5) or Si(R6)(R7);

[0017] i is 0 or 1;

[0018] Ar1is one of unsubstituted or substituted C1-C 10 alkyl, unsubstituted or substituted C3-C 10 cycloalkyl, unsubstituted or substituted C6-C 30 aryl, unsubstituted or substituted C2-C 30 heteroaryl;

[0019] Z, Z1, Z2, Z3, Z4, Z5, Z6are each the same or different at each occurrence one of C-H, C-R or N, adjacent R can be connected to each other to form a ring;

[0020] R is at each occurrence independently the same or different one of a deuterium atom, a tritium atom, a halogen atom, unsubstituted or substituted C1-C 10 alkyl, unsubstituted or substituted C3-C 10 cycloalkyl, unsubstituted or substituted C1-C 10 alkoxy, unsubstituted or substituted C6-C 10 aryloxy, unsubstituted or substituted arylamine, unsubstituted or substituted C6-C 30 aryl, unsubstituted or substituted C2-C 30 heteroaryl;

[0021] R3, R4, R5, R6, R7are at each occurrence independently the same or different one of a hydrogen atom, unsubstituted or substituted C1-C 10 alkyl, unsubstituted or substituted C6-C 30 aryl, unsubstituted or substituted C2-C 30 heteroaryl;

[0022] substituents for substituents are optionally one or more of a deuterium atom, a halogen atom, a cyano group, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 heteroaryl, C6-C 30 arylamine;

[0023] The heteroatom in the heteroaryl group is optionally one or more of oxygen, sulfur, nitrogen, silicon atom.

[0024] Preferably, M1 represents a substituted or unsubstituted C6 aryl group, a substituted or unsubstituted C6 cycloalkyl group;

[0025] The substituent for the substituent group is optionally one or more of a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group, a C6-C 30 arylamino group;

[0026] The heteroatom in the heteroaryl group is optionally one or more of oxygen, sulfur, nitrogen, silicon atom.

[0027] Preferably, the structure of the organic compound is represented by General Formula (1-1) to General Formula (1-4):

[0028]

[0029]

[0030] In General Formula (1-1) to General Formula (1-4), M, Ar1, R1, R2, Z, Z1, Z2, Z3, Z4, Z5, Z6 have the same meanings as defined above;

[0031] Y1, Y2, Y3, Y4, Y5, Y6 each independently represents C-R;

[0032] Y7, Y8, Y9, Y 10 each independently represents C(R3)(R4);

[0033] R, R3, R4 have the same meanings as defined above.

[0034] Preferably, M represents:

[0035]

[0036] any one of the above;

[0037] Z has the same meaning as defined above.

[0038] Preferably, the structure of the organic compound is represented by General Formula (II-1):

[0039]

[0040] In general formula (II-1), formula a represents any one of the following ring structures:

[0041]

[0042] In general formula (II-1), Ar1, Z, Z1, Z2, Z3, Z4, Z5, Z6 have the same meanings as defined above;

[0043] Z7, Z8, Z9, the same or different at each occurrence, represent C-H, C-R or N, and adjacent R can be connected to each other to form a ring;

[0044] R has the same meaning as defined above.

[0045] Preferably, the organic compound has a structure represented by general formula (II-2):

[0046]

[0047] In general formula (II-2), Ar1, Z, Z1, Z2, Z3, Z4, Z5, Z6, X1, X2, i have the same meanings as defined above;

[0048] Z7, Z8, Z9, the same or different at each occurrence, represent C-H, C-R or N, and adjacent R can be connected to each other to form a ring;

[0049] R has the same meaning as defined above.

[0050] represents a single bond, O, S, C(R3)(R4), N(R5) or Si(R6)(R7);

[0051] M2 represents a structure as shown below:

[0052]

[0053] Preferably, the organic compound has a structure represented by any one of general formula (III-1) to general formula (III-20):

[0054]

[0055]

[0056] In general formula (III-1) to general formula (III-20), Z, Z1, Z2, Z3, Z4, Z5, Z6, X1, Ar1 have the same meanings as defined above;

[0057] Z7, Z8, Z9 each occurrence, identically or differently, denote C-H, C-R or N, adjacent R's can be connected to each other to form a ring;

[0058] R has the previously defined meaning;

[0059] X denotes O, S, C(R3)(R4), N(R5) or Si(R6)(R7);

[0060] R3, R4, R5, R6, R7 have the previously defined meaning;

[0061] Ar2, Ar3 denote one of the following: substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0062] The substituents for the substituents are optionally one or more of the following: deuterium atom, halogen atom, cyano group, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 heteroaryl, C6-C 30 aromatic amine group;

[0063] The heteroatom in the heteroaryl group is optionally one or more of the following: oxygen, sulfur, nitrogen, silicon atom.

[0064] Preferably, the organic compound has a structure according to any one of the following general formulae (IV-1) to (IV-8):

[0065]

[0066]

[0067] In the general formulae (IV-1) to (IV-8), the formula a denotes any one of the following ring structures:

[0068]

[0069] The Z, Z1, Z2, Z3, Z4, Z5, Z6, Ar1 have the previously defined meaning;

[0070] Z7, Z8, Z9 each occurrence, identically or differently, denote C-H, C-R or N, adjacent R's can be connected to each other to form a ring;

[0071] R has the previously defined meaning.

[0072] Preferably, R represents one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylphenyl-substituted amino group, a tert-butyl-substituted dibenzofuranyl group, a phenyl-substituted tert-butyl group, a xanthone group, a phenyl-substituted triazinyl group, a phenyl-substituted borane group, a methoxy group, a tert-butoxy group;

[0073] R1 and R2 represent, respectively, 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, and biphenyl. alkyl, deuterated diphenyl, tritriphenyl, deuterated terphenyl, tritriphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyrene, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethyl Fluorenyl, 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 boroalkyl, methoxy, tert-butoxy;

[0074] R3, R4, R5, R6, R7, respectively, represent one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylphenyl-substituted amino group, a tert-butyl-substituted dibenzofuranyl group, a phenyl-substituted tert-butyl group, a xanthone group, a phenyl-substituted triazinyl group, a phenyl-substituted borane group, a methoxy group, a tert-butoxy group;

[0075] Ar1, Ar2, and Ar3 represent adamantyl, methyl, deuterated methyl, tritrimethyl, 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, and tritium. Phenyl, diphenyl, deuterated diphenyl, tritriphenyl, deuterated terphenyl, tritriphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyrene, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenyl Carbazolyl, 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, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazine, phenyl-substituted boronyl, methoxy, tert-butoxy.

[0076] In a preferred embodiment, Ar1, Ar2, and Ar3 are represented by the following structure:

[0077]

[0078] In a preferred embodiment, R is represented by the following structure:

[0079]

[0080] In a preferred embodiment, the organic compound has a specific structural formula that is any one of the following:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] The application also provides an organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer between the cathode and the anode, wherein the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer comprises the boron-containing organic compound.

[0093] Preferably, the light-emitting layer comprises a host material and a dopant material, and the dopant material comprises the boron-containing organic compound.

[0094] Preferably, the light-emitting layer comprises a first host material, a second host material and a dopant material, and at least one of the first host material and the second host material is a TADF material, and the dopant material comprises the boron-containing organic compound.

[0095] Preferably, the light-emitting layer comprises a host material, an exciton sensitization material and a dopant material, and the exciton sensitization material is a metal element-containing complex, and the dopant material comprises the boron-containing organic compound.

[0096] The application has the beneficial technical effects of:

[0097] (1) The compound of the application can be used as a dopant material of a light-emitting layer material in an OLED device, can emit green fluorescence under the action of an electric field, and can be applied in the fields of OLED lighting or OLED display.

[0098] (2) The compound of the application can effectively improve the service life of a device when used as a dopant material and introducing a phosphorescent material as an exciton sensitization agent.

[0099] (3) The spectral FWHM of the compound of the application is relatively narrow, which can effectively improve the color gamut of a device and improve the light-emitting efficiency of the device. BRIEF DESCRIPTION OF DRAWINGS

[0100] Figure 1 The application lists the materials used in the structure of an OLED device.

[0101] In the figure, 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 DESCRIPTION

[0102] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings of the embodiments of the present application. In the case of no conflict, the embodiments in the present application and the features in the embodiments can be combined with each other. The present application will be further described below in conjunction with the drawings and specific embodiments, but not as a limitation of the present application.

[0103] In the present application, the words indicating orientation such as "upper", "lower", "top" and "bottom" used when describing electrodes and organic electroluminescent devices, and other structures, only indicate the orientation in a certain specific state, and do not mean that the relevant structure can only exist in the described orientation; on the contrary, if the structure can be transformed in position, for example, inverted, the orientation of the structure is changed accordingly. Specifically, in the present application, the "bottom" and "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" side.

[0104] In the present application, substituted or unsubstituted C6-C 30 Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted tetracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted substituted or unsubstituted indenyl, but not limited thereto.

[0105] In the present application, substituted or unsubstituted C2-C 30Heteroaryl means substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, 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 triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthylidinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxathiinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, combinations thereof, or fused rings of the foregoing, but are not limited thereto.

[0106] C1-C 10 Alkyl (including linear alkyl and branched alkyl) means methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, and the like, but is not limited thereto.

[0107] Halogen atom according to the present application means a chlorine atom, a fluorine atom, a bromine atom, and the like, but is not limited thereto.

[0108] C3-C 10 Cycloalkyl means a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as a ring-forming atom. In the present specification, C4-C9 cycloalkyl is preferably used, C5-C8 cycloalkyl is more preferably used, and C5-C7 cycloalkyl is particularly preferably used. Non-limiting examples thereof can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, and the like, but are not limited thereto.

[0109] As a substrate of the organic electroluminescent device according to the present application, any substrate commonly used for organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; non-transparent substrates such as silicon substrates. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. Depending on the properties of the substrate, the direction of use is different. In the present application, transparent PI film substrates are preferably used. The thickness of the substrate is not particularly limited.

[0110] A first electrode is formed on a substrate, and the first electrode and a second electrode can be opposite to each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it can 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), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can 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, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0111] 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.

[0112] In this context, the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0113] As a material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be used from among known materials related to OLED devices.

[0114] Examples of the above-described material can be a phthalocyanine derivative, a triazole derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, an oxadiazole derivative, a hydrazone derivative, a stilbene derivative, a pyridinoline derivative, a polysilane derivative, an imidazole derivative, a phenylenediamine derivative, an amino-substituted quinone derivative, a styryl anthracene derivative, a styryl amine derivative, etc. styrenic compounds, a fluorene derivative, a spirofluorene derivative, a silazane derivative, an aniline-based copolymer, a porphyrin compound, a carbazole derivative, a polyarylalkane derivative, a polyphenylenevinylene and a derivative thereof, a polythiophene and a derivative thereof, a poly-N-vinylcarbazole derivative, a conductive polymer oligomer such as a thiophene oligomer, an aromatic tertiary amine compound, a styryl amine compound, a triamine, a tetraamine, a benzidine, a propargyl diamine derivative, a p-phenylenediamine derivative, a m-phenylenediamine derivative, 1,1'-bis(4-diarylamino phenyl)cyclohexane, 4,4'-bis(diarylamine-based) biphenyl, bis[4-(diarylamine) phenyl] methane, 4,4'-bis(diarylamine) terphenyl, 4,4'-bis(diarylamine) quaterphenyl, 4,4'-bis(diarylamine) diphenyl ether, 4,4'-bis(diarylamine) diphenyl sulfane, bis[4-(diarylamine) phenyl] dimethyl methane, bis[4-(diarylamine) phenyl]-di(trifluoromethyl) methane, or a 2,2-diphenylethene compound, etc.

[0115] Further, according to the needs of device matching, the hole transport film layer between the electron blocking layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a superimposed structure of multiple hole transport materials. In this context, the film thickness of the various hole carrier conductive film layers described above is not particularly limited.

[0116] The hole injection layer comprises a hole-conducting host organic material and a P-doped material having a deep HOMO level (and a deep LUMO level). Based on the empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO level of the hole-conducting host organic material used in the anode interface buffer layer must have certain characteristics with the P-doped material, so as to enable the occurrence of charge transfer state between the host material and the doped material, to achieve ohmic contact between the buffer layer and the anode, and to achieve efficient injection of holes from the electrode to the hole injection layer.

[0117] In view of the above empirical summary, for different hole-conducting host materials with different HOMO levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0118] Therefore, in one embodiment of the present application, in order to better inject holes, the hole injection layer further comprises a P-doped material having charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylene tris(cyanocarbonyl)) tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0119] In the hole injection layer of the present application, the ratio of the hole transport material to the P-doped material used is 99:1 to 95:5, preferably 99:1 to 97:3, based on mass.

[0120] The thickness of the hole injection layer of the present application can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0121] The thickness of the hole transport layer of the present application can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0122] The thickness of the electron blocking layer of the present application can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0123] After the hole injection layer, the hole transport layer and the electron blocking layer are formed, the corresponding light emitting layer is formed on the electron blocking layer.

[0124] The light emitting layer can comprise a host material and a dopant material, the host material can use the green light host material common in the art, and the dopant material uses the boron-containing organic compound represented by the general formula (1) of the present application.

[0125] The light emitting layer can comprise a single host material or a double host material;

[0126] The double host material comprises a first host material and a second host material, and at least one of the first host material and the second host material is preferably a TADF material;

[0127] The TADF material refers to a material with the property of thermally activated delayed fluorescence, characterized by having a small energy level difference between the first excited singlet state and the first excited triplet state, so that both singlet and triplet excitons generated in the device can be utilized simultaneously, making the utilization rate of excitons generated inside the device as close to 100% as possible. Compared with traditional fluorescent materials, TADF materials have higher exciton utilization rate.

[0128] The light emitting layer can comprise a host material, an exciton sensitization material and a dopant material;

[0129] The exciton sensitization material refers to a material that can make the light emitting material in the light emitting layer fully utilize the electrically generated excitons, so that the light emitting layer finally produces the emission spectrum of the sensitized material. The exciton sensitization agent may have the functions of exciton trapping, exciton conversion, exciton transfer, etc. in the electroluminescent device. The boron-containing organic compound represented by the general formula (1) of the present application and the exciton sensitization material are used together, which has obvious improvement effect on the problems of device efficiency improvement, exciton annihilation in the device, efficiency reduction, etc.

[0130] In the light emitting layer of the present application, the ratio of the host material to the dopant material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0131] The thickness of the light emitting layer can be adjusted to optimize the light emitting efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10-50 nm, more preferably 15-40 nm, but the thickness is not limited to this range.

[0132] In the present application, the electron transport region can comprise, 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.

[0133] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light emitting layer to the cathode, thereby prolonging the lifetime of the device and improving the efficiency of the device. The hole blocking layer of the present application can be provided on the light emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present application, a compound having a hole blocking effect known in the art can be used, for example, a phenanthroline derivative such as bathocuproin (referred to as BCP), a metal complex of a hydroxyquinoline derivative such as aluminum (III) bis(2-methyl-8-quinolinolato)-4-phenylphenolate (BAlq), various rare earth metal complexes, an oxazole derivative, a triazole derivative, a triazine derivative, a pyrimidine derivative such as 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), and the like. The thickness of the hole blocking layer of the present application can be 2 to 200 nm, preferably 5 to 150 nm, but the thickness is not limited to this range.

[0134] The electron transport layer can be provided on the light emitting layer or the hole blocking layer, if present. The electron transport layer material is a material that readily receives electrons from the cathode and transfers the received electrons to the light emitting layer. A material having a high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present application, an electron transport layer material for an organic electroluminescent device known in the art can be used, for example, a metal complex of a hydroxyquinoline derivative represented by Alq3, BAlq, and Liq, various rare earth metal complexes, a triazole derivative, a triazine derivative such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), an imidazole derivative such as 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), an oxadiazole derivative, a thiadiazole derivative, a carbodiimide derivative, a quinoxaline derivative, a phenanthroline derivative, a silicon-based compound derivative, and the like. The thickness of the electron transport layer of the present application can be 10 to 80 nm, preferably 20 to 60 nm, and more preferably 25 to 45 nm, but the thickness is not limited to this range.

[0135] An electron injection layer can be provided on the electron transport layer. The electron injection layer material is generally a material having a low work function, preferably, so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present application, an electron injection layer material for an organic electroluminescent device known in the art can be used, for example, lithium; a lithium salt such as lithium 8-hydroxyquinolinate, lithium fluoride, lithium carbonate or lithium azide; or a cesium salt, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present application can be 0.1 to 5 nm, preferably 0.5 to 3 nm and more preferably 0.8 to 1.5 nm, but the thickness is not limited to this range.

[0136] A second electrode can be provided on the electron transport region. The second electrode can be a cathode. The second electrode can be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode can include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0137] The organic electroluminescent device of the present application can further include an encapsulation structure. The encapsulation structure can be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure can be, for example, a can such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0138] A method of manufacturing the organic electroluminescent device of the present application 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 on a substrate, and optionally a cover layer. In this regard, a method such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI can be used, but is not limited thereto. In the present application, it is preferable to use a vacuum evaporation method to form the respective layers. The respective process conditions in the vacuum evaporation method can be routinely selected by those skilled in the art as necessary.

[0139] The starting materials involved in the synthesis examples of the present application can be commercially available or prepared by conventional preparation methods in the art;

[0140] Synthesis of compound 7 of Example 1:

[0141]

[0142]

[0143] Under nitrogen protection, 10 mmol of starting material A-1, 10 mmol of NaH, 10 mL of anhydrous DMF were added to a three-necked flask, stirred at room temperature for 0.5 hours, then 10 mmol of starting material B-1 was added, and the reaction was carried out at room temperature for 2 hours. After the reaction was completed, 30 mL of deionized water was added, the white precipitate was filtered, the precipitate was dissolved with dichloromethane, dried with anhydrous sodium sulfate, filtered and concentrated, and column chromatography was used to separate to obtain intermediate a-1. LC-MS: measured value: 339.10 ([M+H] + ), theoretical value: 338.18.

[0144] Under nitrogen protection, 10 mmol of intermediate a-1, 11 mmol of starting material C-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butyl phosphine and 40 mL of anhydrous toluene were added to a three-necked flask, and the reaction was carried out at reflux for 30 hours. After the reaction was completed, 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: 583.29 ([M+H] + ), theoretical value: 582.14.

[0145] Under nitrogen protection, 10 mmol of intermediate b-1, 12 mmol of starting material D-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butyl phosphine and 50 mL of anhydrous toluene were added to a three-necked flask, and the reaction was carried out at reflux for 20 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain intermediate c-1. LC-MS: measured value: 770.36 ([M+H] + ), theoretical value: 769.32.

[0146] Under nitrogen protection, 10 mmol of intermediate c-1, 5 mL of o-dichlorobenzene were added to a sealed pressure tube. 12 mmol of n-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 5 hours, then 20 mmol of N, N-diisopropyl ethylamine was added at 0°C, heated to 200°C and reacted for 10 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain compound 7. 1H NMR (400 MHz, Chloroform-d) δ 9.08-8.98 (m, 1H), 8.79-8.67 (m, 2H), 8.35-8.22 (m, 1H), 8.09-6.96 (m, 20H), 1.36-1.28 (d, 18H). FWHM (measured by Fluorolog-3 series fluorescence spectrometer of Horiba under thin film state): 28 nm.

[0147] Synthesis of compound 31 of Example 2:

[0148]

[0149] A mixture solution of 11 mmol of starting material E-2, 10 mmol of starting material F-2, 1 mmol of X-phos, 20 mmol of Cs2CO3 and toluene / EtOH / H2O (80 ml / 40 ml / 40 ml) was added into a three-necked flask under nitrogen protection, then 0.5 mmol of Pd(OAc)2 was added, and the reaction was stirred at 110°C for 12 hours. After the reaction was completed, dichloromethane was used for extraction, and then the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed, and starting material B-2 was obtained by purification through a silica gel column. LC-MS: measured value: 285.08 ([M+H] + ), the theoretical value: 284.19.

[0150] The preparation method of intermediate a-2 was the same as that of intermediate a-1, except that starting material B-2 was used to replace starting material B-1, and intermediate a-2 was obtained. LC-MS: measured value: 471.35 ([M+H] + ), the theoretical value: 470.27.

[0151] The preparation method of intermediate b-2 was the same as that of intermediate b-1, except that intermediate a-2 was used to replace intermediate a-1, and intermediate b-2 was obtained. LC-MS: measured value: 715.33 ([M+H] + ), the theoretical value: 714.24.

[0152] The preparation method of intermediate c-2 was the same as that of intermediate c-1, except that intermediate b-2 was used to replace intermediate b-1, and starting material D-2 was used to replace starting material D-1, and intermediate c-2 was obtained. LC-MS: measured value: 967.18 ([M+H] + ), the theoretical value: 966.44.

[0153] The preparation method of compound 31 was the same as that of compound 7, except that intermediate c-2 was used to replace intermediate c-1, and compound 31 was obtained. FWHM (measured by Fluorolog-3 series fluorescence spectrometer of Horiba under thin film state): 26 am.

[0154] Synthesis of compound 41 of Example 3:

[0155]

[0156] The preparation method of intermediate b-3 is the same as that of intermediate b-1, except that raw material C-3 is used to replace raw material C-1 to obtain intermediate b-3. LC-MS: [M+H] measured value: 527.16, theoretical value: 526.08. +

[0157] The preparation method of intermediate c-3 is the same as that of intermediate c-1, except that intermediate b-3 is used to replace intermediate b-1, and raw material D-3 is used to replace raw material D-1 to obtain intermediate c-3. LC-MS: [M+H] measured value: 779.34, theoretical value: 778.29. +

[0158] The preparation method of compound 41 is the same as that of compound 7, except that intermediate c-3 is used to replace intermediate c-1 to obtain compound 41. FWHM (tested by Fluorolog-3 series fluorescence spectrometer of Horiba in a thin film state): 26 nm.

[0159] Synthesis of compound 51 of Example 4:

[0160]

[0161] The preparation method of intermediate c-4 is the same as that of intermediate c-2, except that raw material D-4 is used to replace raw material D-2 to obtain intermediate c-4. LC-MS: [M+H] measured value: 1023.34, theoretical value: 1022.51. +

[0162] The preparation method of compound 51 is the same as that of compound 7, except that intermediate c-4 is used to replace intermediate c-1 to obtain compound 51. FWHM (tested by Fluorolog-3 series fluorescence spectrometer of Horiba in a thin film state): 25 nm.

[0163] Synthesis of compound 182 of Example 5:

[0164]

[0165] The preparation method of intermediate b-5 is the same as that of intermediate b-1, except that raw material C-5 is used to replace raw material C-1 to obtain intermediate b-5. LC-MS: [M+H] measured value: 603.34, theoretical value: 602.11. +

[0166] ​​​​The preparation method of intermediate c-5 is the same as that of intermediate c-1, except that intermediate b-5 is used to replace intermediate b-1, and raw material D-5 is used to replace raw material D-1, to obtain intermediate c-5, LC-MS: measured value: 842.38 ([M+H] + ), the theoretical value is 841.32.

[0167] The preparation method of compound 182 is the same as that of compound 7, except that intermediate c-5 is used to replace intermediate c-1, to obtain compound 182. FWHM (tested by Fluorolog-3 series fluorescence spectrometer of Horiba in a thin film state): 26 nm.

[0168] Synthesis of compound 186 of Example 6:

[0169]

[0170] The preparation method of intermediate c-6 is the same as that of intermediate c-1, except that raw material D-6 is used to replace raw material D-1, to obtain intermediate c-6, LC-MS: measured value: 835.49 ([M+H] + ), the theoretical value is 834.35.

[0171] The preparation method of compound 186 is the same as that of compound 7, except that intermediate c-6 is used to replace intermediate c-1, to obtain compound 186. 1 H NMR (400 MHz, Chloroform-d) δ 8.83-8.66 (m, 2H), 8.26-8.13 (m, 2H), 7.99-7.90 (m, 1H), 7.77-7.56 (m, 5H), 7.48-7.01 (m, 17H), 1.35-1.26 (d, 18H). FWHM (tested by Fluorolog-3 series fluorescence spectrometer of Horiba in a thin film state): 27 nm.

[0172] The structural characterization of the compounds obtained in each example is shown in Table 1

[0173] Table 1

[0174]

[0175] The application effect of the OLED materials synthesized in the application in devices is illustrated in detail below through device examples 1-6 and device comparison examples 1-3. The device manufacturing processes of device examples 2-6 and device comparison examples 1-3 are completely the same as that of device example 1, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also consistent. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device example are shown in Table 2 and Table 3, respectively.

[0176] Device Example 1

[0177] like Figure 1 As 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 (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, 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 7 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 7 of 69:30:1. The light-emitting layer film thickness is 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.

[0178] The application effects of the OLED materials synthesized in this invention in devices are described in detail below through device examples 7-12 and device comparative examples 4-6. The fabrication processes of device examples 8-12 and device comparative examples 4-6 are completely identical to those of device example 7, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2 and 3, respectively.

[0179] Device Example 7

[0180] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness: 150 nm) is washed, i.e. sequentially washed with a cleaning agent (Semiclean M-L20), pure water, and dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. After the above washing, the ITO anode layer 2 is vacuum evaporated with a vacuum evaporation device to form a hole injection layer 3 having a film thickness of 10 nm of HT-1 and HI-1, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 having a film thickness of 60 nm is evaporated to form a hole transport layer 4. Subsequently, EB-1 having a film thickness of 30 nm is evaporated to form an electron blocking layer 5. After the above electron blocking material is evaporated, a light emitting layer 6 of an OLED light emitting device is formed using GH-1 and GH-2 as host materials, GD-1 as a first dopant material, and compound 7 as a second dopant material, and the mass ratio of GH-1, GH-2, GD-1, and compound 7 is 66:30:3:1, and the film thickness of the light emitting layer is 30 nm. After the above light emitting layer 6, HB-1 is continuously vacuum evaporated to form a hole blocking layer 7 having a film thickness of 5 nm. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum evaporated to form an electron transport layer 8 having a film thickness of 30 nm, and the mass ratio of ET-1 and Liq is 1:1. On the electron transport layer 8, a LiF layer having a film thickness of 1 nm is formed by a vacuum evaporation device, and this layer is an electron injection layer 9. On the electron injection layer 9, an Mg:Ag electrode layer having a film thickness of 80 nm is formed by a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is a cathode layer 10.

[0181] The molecular structures of the relevant materials are shown below:

[0182]

[0183] After the OLED light emitting device is completed as described above, the anode and the cathode are connected by a known driving circuit, and the voltage, current efficiency, and the lifetime of the device are measured. The devices of the examples and the comparison are prepared in the same manner, and the results are shown in Table 2, and the test results of the voltage, current efficiency, and the lifetime of the obtained devices are shown in Table 3.

[0184] Table 2

[0185]

[0186]

[0187] Table 3

[0188]

[0189] Note: The voltage, current efficiency, and emission peak were measured by IVL (current-voltage-luminance) test system (Suzhou Fudashan Scientific Instruments Co., Ltd.); the lifetime test system was EAS-62C OLED device lifetime tester from Japan System Techno Co., Ltd.; LT95 refers to the time taken for the device luminance to decay to 95%; all data were measured at 10 mA / cm 2 The following test.

[0190] As can be seen from the device data results in Table 3, compared with device comparative examples 1-3, the device lifetime of the compound of the present application in the single-doped system device is higher than that of the comparative examples; in the single-doped system device, the device efficiency also shows a better effect, which is due to the boron-nitrogen fused ring mother nucleus of this kind, which can adjust the light color, enhance the resonance strength, and improve the device efficiency; compared with device comparative examples 4-6, the compound of the present application in the double-doped system device using exciton sensitization material as the first doping has a greater improvement in the current efficiency and device lifetime of the device relative to the known material OLED device, and in the double-doped device, the device efficiency is also significantly improved compared with the single-doped device.

[0191] In summary, the above is only a preferred embodiment of the present application, and is not intended to limit the present application, and any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. A boron-containing organic compound, characterized by, The structure of the organic compound is shown in general formula (1-2): In general formula (1-2), M is represented as: R1 and R2 represent, independently, the substituted or unsubstituted C6-C6 segments. 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 20 cycloalkyl; Ar1represents one of substituted or unsubstituted C3-C10cycloalkyl, substituted or unsubstituted C6-C10aryl, substituted or unsubstituted C2-C10heteroaryl, and 10 substituted or unsubstituted C6-C10aryl, substituted or unsubstituted C2-C10heteroaryl, and 30 substituted or unsubstituted C6-C10aryl, substituted or unsubstituted C2-C10heteroaryl, and 30 substituted or unsubstituted C6-C10aryl, substituted or unsubstituted C2-C Z, Z1, Z2, Z3, Z4, Z5, Z6 represent C-H, C-R, the same or different at each occurrence; Each occurrence of R, whether identical or different, represents a deuterium atom, a 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 C6-C 10 Aryloxy groups, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C... 10 Alkyl, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from oxygen, sulfur, nitrogen, silicon atom.

2. A boron-containing organic compound, characterized by, The structure of the organic compound is any one of general formula (III-1), general formula (III-3), general formula (III-4), general formula (III-20): In General Formula (III-1), General Formula (III-3), General Formula (III-4), and General Formula (III-20), Ar1represents one of a substituted or unsubstituted C3to C 10 cycloalkyl group, a substituted or unsubstituted C6to C 30 aryl group, a substituted or unsubstituted C2to C 30 heteroaryl group. Z, Z1, Z2, Z3, Z4, Z5, Z6 represent C-H, C-R, the same or different at each occurrence; Z7, Z8, Z9 represent C-H, C-R, the same or different at each occurrence; Each occurrence of R, whether identical or different, represents a deuterium atom, a 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 C6-C 10 Aryloxy groups, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; X is represented as N(R5); R5 indicates substituted or unsubstituted C6-C6. 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C... 10 Alkyl, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is optionally one or more selected from oxygen, sulfur, nitrogen, silicon atom.

3. The boron-containing organic compound according to claim 1, wherein The R is represented as one of deuterium atom, halogen atom, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, pyridyl group, phenyl-substituted pyridyl group, quinolyl group, furanyl group, thienyl group, benzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, phenyl-substituted amino group, tert-butylphenyl-substituted amino group, tert-butyl-substituted dibenzofuranyl group, phenyl-substituted tert-butyl group, xanthenyl group, phenyl-substituted triazinyl group, methoxy group, tert-butoxy group; R1, R2 are each one of 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, anthryl, phenanthryl, pyrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, tert-butoxy; Ar1 is one of adamantyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, xanthone, phenyl-substituted triazinyl.

4. The boron-containing organic compound according to claim 2, wherein R represents one of a deuterium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylphenyl-substituted amino group, a tert-butyl-substituted dibenzofuranyl group, a phenyl-substituted tert-butyl group, a xanthone group, a phenyl-substituted triazinyl group, a methoxy group, a tert-butoxy group; R5 represents one of a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuranyl group, a phenyl-substituted tert-butyl group, a xanthone group, a phenyl-substituted triazinyl group. Ar1is one of adamantyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, t-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, t-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated t-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated t-butyl-substituted biphenyl, t-butyl-substituted dibenzofuranyl, xanthonyl, phenyl-substituted triazinyl.

5. A boron-containing organic compound, characterized by, The organic compound has a specific structure represented by any one of the following structures:

6. An organic electroluminescent device comprising a cathode and an anode, and an organic light-emitting functional layer between them, the organic light-emitting functional layer comprising a light-emitting layer, characterized in that, The light-emitting layer contains the boron-containing organic compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that The light-emitting layer contains a host material and a dopant material, and the dopant material contains the boron-containing organic compound according to any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 6, 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 host material and the second host material is a TADF material, and the dopant material contains the boron-containing organic compound according to any one of claims 1 to 5.

9. The organic electroluminescent device according to claim 6, which comprises a host material, an exciton-sensitizing material and a dopant material in the light-emitting layer, characterized in that, The exciton-sensitizing material is a complex containing a metal element, and the dopant material contains the boron-containing organic compound according to any one of claims 1 to 5.

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