A boron-containing organic compound and an organic electroluminescent device prepared therefrom

Abstract

The present 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 the present invention is shown in general formula (1) to general formula (3). The compound of the present invention has a narrow full width at half maximum. When used as a doped material in the light-emitting layer material of an OLED light-emitting device, it can be used as a green light doped material for the light-emitting layer of an organic electroluminescent device, thereby improving the light emission color purity and efficiency of the device.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing organic compound and an organic electroluminescent device prepared therefrom. Background Art

[0002] Limited by early technologies, traditional fluorescent doping materials can only utilize 25% of singlet excitons formed by electrical excitation for luminescence. The internal quantum efficiency of the device is relatively low (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a significant gap compared with the efficiency of phosphorescent devices. Due to the strong spin-orbit coupling of heavy atom centers, phosphorescent materials enhance intersystem crossing, enabling effective utilization of both singlet excitons and triplet excitons formed by electrical excitation, thus achieving an internal quantum efficiency of 100% for the device. However, most phosphorescent materials are expensive, with poor material stability, poor color purity, and serious efficiency roll-off of the device, which limit their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are put forward for the color rendering standard. In addition to high efficiency and stability, luminescent materials also require a narrower full width at half maximum (FWHM) to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum yield and narrow FWHM through molecular engineering. Breakthroughs have been made in blue fluorescent doping materials, and the FWHM of boron-based materials can be reduced to less than 30 nm. In the green light region, to which the human eye is more sensitive, research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study highly efficient green fluorescent doping materials with narrow FWHM.

[0004] In addition, the sensitization technology combines a triplet exciton sensitizing material with a fluorescent doping material. Using the triplet exciton sensitizing material as an exciton sensitization medium, it makes full use of triplet excitons and transfers the energy to the fluorescent doping material through energy transfer, also achieving an internal quantum efficiency of 100% for the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively utilize the characteristics of high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width luminescence. Such materials are used in sensitization technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN 110492006 A disclose a TADF material with a difference between the lowest singlet state and the lowest triplet state energy level of less than or equal to 0.2eV as the main body, and a boron-containing material as the doping luminescent layer combination technology; CN 110492005 A and CN 110492009 A disclose a luminescent layer combination scheme with an exciplex as the main body and a boron-containing material as the doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the Invention

[0006] To address the aforementioned issues in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention can be used as a green light dopant in the emitting layer of an organic electroluminescent device, thereby improving the device's luminescent color purity and efficiency.

[0007] The technical solution of the present invention is as follows: a boron-containing organic compound, the structure of which is shown in any one of general formulas (1) to (3):

[0008]

[0009] In general formula (1) to general formula (3), each occurrence of Z that is the same or different is represented by C-R1;

[0010] R1 is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0011] M1 represents a substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0012] Ar1 and Ar2 are independently substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3~C10 A cycloalkyl group, a substituted or unsubstituted C2-C 10 An alkenyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 A heteroaryl group;

[0013] Ar1 and M1 can also form a ring by bonding;

[0014] The substituents for the substituents are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a C1-C 10 An alkyl group, a C3-C 10 A cycloalkyl group, a C6-C 30 An aryl group, a C2-C 30 One or more of a heteroaryl group.

[0015] In a preferred embodiment, the structure of the organic compound is represented by any one of general formulas (4) to (18):

[0016]

[0017] In general formulas (4) to (18), the meanings of Z, Ar1, and Ar2 are the same as defined above;

[0018] Y represents one of O or S.

[0019] In a preferred embodiment, the structure of the organic compound is represented by any one of general formulas (19) to (24):

[0020]

[0021] In general formulas (19) to (24), the meanings of Z and Ar2 are the same as defined above.

[0022] In a preferred embodiment, the structure of the organic compound is represented by any one of general formulas (25) to (38):

[0023]

[0024]

[0025] In general formulas (25) to (38), the meanings of Z, Ar1, and Ar2 are the same as defined above;

[0026] R a 、R b 、R c 、R d Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryls;

[0027] For the substituents of the substituting group, the substituents are each independently selected from a deuterium atom, a tritium atom, a halogen atom, an alkyl group of C1-C 10 An alkyl group of C3-C 10 A cycloalkyl group of C6-C 30 An aryl group of C6-C 30 One or more of heteroaryls.

[0028] In a preferred embodiment, Ar1 and Ar2 are represented by the following structures:

[0029]

[0030] The R1, R a R b R c R d Are represented by the following structures:

[0031]

[0032]

[0033] In a preferred embodiment, the R1, R a R b R c R dEach is independently represented by 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, a trifluoromethyl 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 anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene 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-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted boranyl group, a methoxy group, or a tert-butoxy group.

[0034] The M1 and M2 rings are represented by a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, an N-phenylcarbazole ring, a 9,9-dimethylfluorene ring, or a spirofluorene ring;

[0035] Ar1 and Ar2 are each independently selected from the group consisting of phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazine;

[0036] The substituents for the substituent groups are each independently selected from the group consisting of deuterium atom, tritium atom, halogen atom, adamantyl, methyl, tritiated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, fluorine atom-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, phenyl-substituted amino, tert-butylbenzene-substituted amino, phenyl-substituted triazine.

[0037] Preferably, the specific structure of the organic compound is any one of the following structures:

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0050] Preferably, the light-emitting layer contains a host material and a dopant material, and the dopant material contains the boron-containing organic compound.

[0051] Preferably, the light-emitting layer contains a first host material, a second host material and a dopant material. At least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound.

[0052] The beneficial technical effects of the present invention are as follows:

[0053] (1) The compound of the present invention can be used as a dopant material for the light-emitting layer material when applied to an OLED device, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

[0054] (2) As a dopant material, the compound of the present invention introduces a TADF sensitizer as the second host, which can effectively improve the device efficiency;

[0055] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the device color gamut and the light-emitting efficiency of the device;

[0056] (4) Due to the introduction of the cyclohexane structure, the compound of the present invention has higher solubility;

[0057] (5) By introducing a cyclohexane structure at a specific position, the compound of the present invention can reduce the intermolecular interaction and reduce the efficiency roll-off caused by molecular packing;

[0058] (6) There is no selectivity problem in the last step of closing the ring with B in the compound of the present invention, and the difficulty of large-scale synthesis of the material is lower. Description of the Drawings

[0059] Figure 1 It is a schematic structural diagram of the material listed in the present invention applied to an OLED device;

[0060] Among them, 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 manners

[0061] The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. Without conflict, the embodiments and features in the embodiments of the present invention may be combined with each other. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but it is not intended to limit the present invention.

[0062] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, the words indicating directions such as "upper", "lower", "top", and "bottom" only represent the directions in a certain specific state, and do not mean that the relevant structures can only exist in the described directions; on the contrary, if the structures can be transformed in position, for example, inverted, the directions of the structures will be changed accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer 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" sides.

[0063] In the present invention, substituted or unsubstituted C6-C 30 aryl and / or substituted or unsubstituted C2-C 30 heteroaryl refer to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted A base, a substituted or unsubstituted diaminotriphenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indene group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a fused ring of a combination of the aforementioned groups, but not limited thereto.

[0064] The C1-C 10 The alkyl group (including a linear alkyl group and a branched alkyl group) refers to a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an isobutyl group, a sec-butyl group, a neopentyl group, a n-pentyl group, an isopentyl group, an octyl group, a heptyl group, a n-decyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1-butylpentyl group, etc., but not limited thereto.

[0065] The halogen in the present invention refers to a chlorine atom, a fluorine atom, a bromine atom, etc., but not limited thereto.

[0066] The C3-C 10 The cycloalkyl group refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In the present text, a C4-C9 cycloalkyl group is preferably used, a C5-C8 cycloalkyl group is more preferably used, and a C5-C7 cycloalkyl group is particularly preferably used. Non-limiting examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4,4-dimethylcyclohexyl group, an adamantyl group, a cycloheptyl group, etc., but not limited thereto.

[0067] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothness, and water resistances. Depending on the nature of the substrate, its usage directions are different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0068] A first electrode is formed on the substrate, and the first electrode and the second electrode can face 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 metal mixture. The thickness of the first electrode layer depends on the material used and is usually 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0069] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0070] In this article, the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0071] As the materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials for OLED devices for use.

[0072] Examples of the above materials may include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinolone derivatives, styryl anthracene derivatives, styrylamine derivatives, and other styrene compounds such as fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinylene and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers, and other conductive polymer oligomers, aromatic tertiary amine compounds, styrylamine compounds, triamines, tetraamines, benzidine compounds, propynediamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamino)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)diphenyl sulfides, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0073] Furthermore, according to the device matching requirements, the hole transport film layer between the electron blocking layer and the hole injection layer that constitutes the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this article, for the above various hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0074] The hole injection layer contains a host organic material that can conduct holes and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material, so as to be expected to achieve the occurrence of the charge transfer state between the host material and the doping material, achieve Ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection conduction.

[0075] In view of the above empirical summaries, for hole-type host materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve Ohmic contact at the interface and improve the hole injection effect.

[0076] Thus, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further comprises a P-type doping material with charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (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-trimethylenetris(cyanomethanylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0077] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1 - 95:5, preferably 99:1 - 97:3, based on mass.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light-emitting layer is formed on the electron blocking layer.

[0082] The light-emitting layer may comprise a host material and a doping material. The host material may use a common green host material in the art, and the doping material uses the resonance-type organic compound represented by the general formula (1) of the present invention.

[0083] The light-emitting layer may comprise a single host material or a dual host material;

[0084] The dual 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;

[0085] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by having a small energy difference between the first singlet excited state and the first triplet excited state. Therefore, singlet excitons and triplet excitons generated can be utilized simultaneously in the device, enabling the exciton utilization rate of the electroluminescence in the device to approach 100% as much as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0086] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0087] The exciton sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to fully utilize electroluminescent excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may perform functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing organic compound shown in the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0088] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1 - 70:30, preferably 99:1 - 85:15, and more preferably 97:3 - 87:13, based on mass.

[0089] The thickness of the light-emitting layer can be adjusted to optimize the luminescence efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0090] In the present invention, the electron transport region may sequentially include a hole blocking layer, an electron transport layer, and an electron injection layer disposed above the light-emitting layer from bottom to top, but is not limited thereto.

[0091] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby prolonging the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be disposed above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art with hole blocking effects can be used, such as phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum(III) bis(2-methyl-8-quinolinolato)-4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives such as 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 the present invention can be 2 - 200 nm, preferably 5 - 150 nm, but the thickness is not limited to this range.

[0092] The electron transport layer can be disposed above the light-emitting layer or, if present, the hole-blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. A material with a high electron mobility is preferably used. 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. For example, metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq, and Liq, various rare earth metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-bis(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201) and other imidazole derivatives, 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.

[0093] The electron injection layer can be disposed above the electron transport layer. The electron injection layer material is generally preferably a material with a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials known in the prior art for organic electroluminescent devices can be used. For example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention can 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.

[0094] The second electrode can be disposed above 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 their compounds or mixtures; 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 their compounds or mixtures, but is not limited thereto. The thickness of the cathode depends on the material used.

[0095] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure may be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure may 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.

[0096] A 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 covering layer on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form each of the layers. Those skilled in the art can conventionally select each process condition in the vacuum evaporation method according to actual needs.

[0097] The raw materials involved in the synthesis examples of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0098] Synthesis of Compound 42 in Example 1:

[0099]

[0100]

[0101] Under the protection of nitrogen, 10 mmol of raw material A-1, 25 mmol of raw material B-1, 1 mmol of CuI, 15 mmol of cesium carbonate, 2 mmol of phenanthroline, and 10 mL of anhydrous DMF were added to a three-necked flask and reacted at room temperature for 4 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: 339.24 ([M+H] + )), theoretical value: 338.20.

[0102] 1 mmol of intermediate a-1, 1 mmol of raw material C-1, and 10 mmol of methanol were added to a sealed pressure-resistant tube, and 300 mg of concentrated sulfuric acid was added dropwise. The mixture was refluxed and stirred for 8 hours. The reaction solution was cooled to room temperature, diluted with 20 ml of dichloromethane, and separated by column chromatography to obtain intermediate b-1 and intermediate b-2. Intermediate b-1: LC-MS: Measured value: 293.23 ([M+H] + )), theoretical value: 292.19. 1 HNMR (400 MHz, chloroform-d): δ 1.41 - 1.79 (12H, m), 1.91 - 2.25 (6H, m), 2.29 - 2.58 (4H, m), 7.29 (2H, d); Intermediate b-2: LC-MS: Measured value: 293.34 ([M+H] +), theoretical value: 292.19. 1 H NMR (400 MHz, deuterated chloroform): δ 1.44-1.68 (10H, m), 1.73-2.25 (8H, m), 2.31-2.50 (4H, m), 6.76 (2H, d).

[0103] In a sealed pressure tube, under nitrogen protection, 10 mmol of intermediate b-1 was added to anhydrous o-dichlorobenzene. 22 mmol of methyllithium (n-hexane) solution was added dropwise at -40 degrees Celsius. After stirring for 3 hours, the mixture was returned to room temperature. The reaction solution was concentrated and separated by column chromatography to obtain intermediate c-1. LC-MS: Measured value: 325.33 ([M+H] + ), theoretical value: 324.26.

[0104] In a sealed pressure tube, under nitrogen protection, 10 mmol of intermediate b-2 was added to anhydrous o-dichlorobenzene. 22 mmol of methyllithium (n-hexane) solution was added dropwise at -40 degrees Celsius. After stirring for 3 hours, the mixture was returned to room temperature. The reaction solution was concentrated and separated by column chromatography to obtain intermediate c-2. LC-MS: Measured value: 325.29 ([M+H] + ), theoretical value: 324.26.

[0105] Under nitrogen protection, 10 mmol of intermediate c-2, 11 mmol of raw material D-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and 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 d-2. LC-MS: Measured value: 457.44 ([M+H] + ), theoretical value: 456.35.

[0106] Under nitrogen protection, 10 mmol of raw material D-2, 11 mmol of raw material E-2, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 13 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-2. LC-MS: Measured value: 524.30 ([M+H] + ), theoretical value: 523.16.

[0107] Under nitrogen protection, 10 mmol of intermediate e-2, 11 mmol of intermediate d-2, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 8 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-2. LC-MS: Measured value: 900.54 ([M+H] + ), theoretical value: 899.59.

[0108] In a sealed pressure tube, under nitrogen protection, 10 mmol of intermediate f-2 and 5 ml of o-xylene were added. A 12 mmol solution of tert-butyl lithium in n-hexane was added at 0°C, and the system was heated to 60°C and reacted for 2 hours. Subsequently, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 6 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added at 0°C, and 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 42. 1 HNMR (400 MHz, deuterated chloroform): δ 1.33 (9H, s), 1.35-1.86 (53H, m), 1.92 (1H, m), 2.17 (1H, ddd), 6.76 (2H, ddd), 6.82-6.91 (2H, d), 7.13-7.40 (5H, m), 7.53-7.71 (2H, m), 7.88 (1H, dd).

[0109] Example 2 Synthesis of Compound 43:

[0110]

[0111] Under nitrogen, 10 mmol of raw material D-2, 11 mmol of raw material E-3, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and 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 f-3. LC-MS: Measured value: 564.20 ([M+H] + ), theoretical value: 563.10.

[0112] Under nitrogen protection, 10 mmol of intermediate f-3, 11 mmol of intermediate d-2, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate g-3. LC-MS: Measured value: 940.51 ([M+H] + ), theoretical value: 939.53.

[0113] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate g-3 and 5 ml of o-dichlorobenzene were added. A 12 mmol solution of tert-butyl lithium in n-hexane was added at 0°C, and the system was heated to 60°C and allowed to react for 2 hours. Subsequently, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 2 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added at 0°C, and the system was heated to 200°C and allowed to react for 3 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 43.

[0114] Example 3 Synthesis of Compound 73:

[0115]

[0116] Under nitrogen protection, 10 mmol of intermediate c-1, 11 mmol of raw material D-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-1. LC-MS: Measured value: 457.41 ([M+H] + ), theoretical value: 456.35.

[0117] Under nitrogen, 10 mmol of raw material D-2, 11 mmol of raw material E-3, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 13 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-3. LC-MS: Measured value: 582.30 ([M+H] + ), theoretical value: 581.24.

[0118] Under nitrogen protection, 10 mmol of intermediate f-3, 11 mmol of raw material F-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and 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 g-4. LC-MS: Measured value: 770.35 ([M+H] + ), theoretical value: 769.31.

[0119] Under nitrogen protection, 10 mmol of intermediate g-4, 11 mmol of intermediate d-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 30 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate g-5. LC-MS: Measured value: 1146.72 ([M+H] + ), theoretical value: 1145.73.

[0120] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate g-5 and 5 ml of o-dichlorobenzene were added. A 12 mmol solution of tert-butyl lithium in n-hexane was added at 0°C, and the system was heated to 60°C and reacted for 3 hours. Subsequently, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 3 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added at 0°C, and the system was heated to 200°C and reacted for 7 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 73.

[0121] Example 4 Synthesis of Compound 82:

[0122]

[0123] Under nitrogen, 10 mmol of raw material D-3, 11 mmol of raw material E-4, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and 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-4. LC-MS: Measured value: 546.22 ([M+H] + ), theoretical value: 545.15.

[0124] Under nitrogen protection, 10 mmol of intermediate f-4, 11 mmol of raw material D-4, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 7 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate g-6. LC-MS: Measured value: 678.34 ([M+H] + ), theoretical value: 677.24.

[0125] Under nitrogen, 10 mmol of intermediate g-6, 11 mmol of intermediate d-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 11 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate g-7. LC-MS: Measured value: 1054.72 ([M+H] + ), theoretical value: 1053.67.

[0126] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate g-7 and 5 ml of o-dichlorobenzene were added. A 12 mmol solution of tert-butyl lithium in n-hexane was added at 0°C, and the system was heated to 60°C and reacted for 2 hours. Subsequently, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 2 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added at 0°C, and the system was heated to 200°C and reacted for 8 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 82.

[0127] Example 5 Synthesis of Compound 97:

[0128]

[0129]

[0130] Under nitrogen, 10 mmol of raw material E-2, 10 mmol of raw material D-5, 20 ml of DMF, 1 ml of water, 15 mmol of potassium carbonate, 0.2 mmol of CuI, 1.5 mmol of 18-crown ether-6, and 0.5 ml of DMPU were added to a three-necked flask and refluxed for 6 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-5. LC-MS: Measured value: 747.42 ([M+H] + ), theoretical value: 746.30.

[0131] Under nitrogen protection, 10 mmol of intermediate f-5, 10 mmol of intermediate d-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 o-dichlorobenzene were added to a three-necked flask and 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 g-8. LC-MS: Measured value: 1123.75 ([M+H] + ), theoretical value: 1122.72.

[0132] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate g-8 and 5 ml of o-dichlorobenzene were added. A 12 mmol solution of tert-butyl lithium in n-hexane was added at 0°C, and the system was heated to 60°C and allowed to react for 3 hours. Subsequently, 15 mmol of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 2 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added at 0°C, and the system was heated to 200°C and allowed to react for 5 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 97.

[0133] Example 6 Synthesis of Compound 125:

[0134]

[0135] Under nitrogen protection, 10 mmol of intermediate c-1, 10 mmol of raw material D-6, 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 refluxed for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-3. LC-MS: Measured value: 527.49 ([M+H] + ), theoretical value: 526.43.

[0136] Under nitrogen protection, 10 mmol of intermediate f-2, 10 mmol of intermediate d-3, 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 refluxed for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate g-9. LC-MS: Measured value: 970.71 ([M+H] + ), theoretical value: 969.67.

[0137] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate g-9 and 5 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0 °C, and 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 reaction was continued at room temperature for 3 hours. Subsequently, 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 2 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 125.

[0138] The structural characterizations of the compounds obtained in each example are shown in Table 1.

[0139] Table 1

[0140]

[0141] The compounds of the present invention can be used in light-emitting devices as doping materials for the light-emitting layer. The physical and chemical properties of the compounds prepared in the above examples of the present invention were tested. The FWHM (full width at half maximum) values of compounds 42, 43, 73, 82, 97, and 125 of the present invention were 25 nm, 24 nm, 25 nm, 29 nm, 28 nm, and 26 nm, respectively.

[0142] The FWHM (full width at half maximum) in the thin film state was measured by a Horiba Fluorolog-3 series fluorescence spectrometer.

[0143] As a doping material, the compounds of the present invention have a relatively narrow spectral FWHM, which can effectively improve the color gamut of the device and enhance the light-emitting efficiency of the device.

[0144] The application effects of the OLED materials synthesized in the present invention in devices are described in detail below through Device Examples 1-6 and Device Comparative Examples 1-4. The manufacturing processes of Device Examples 2-6 and Device Comparative Examples 1-4 of the present invention are exactly the same as that of Device Example 1, and the same substrate materials and electrode materials are used. The film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced.

[0145] The layer structures and test results of each device example are shown in Tables 3-1 and 4 respectively:

[0146] Device Example 1

[0147] As Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then ultraviolet-ozone washing is carried out to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED device is fabricated. GH-1 and GH-2 are used as host materials, and compound 42 is used as a doping material. The mass ratio of GH-1, GH-2, and compound 42 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm. This layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously evaporated by vacuum evaporation, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated by a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0148] The application effects of the OLED materials synthesized by the present invention in the device are described in detail below through device examples 7-12 and device comparative example 5. The fabrication processes of the devices in device examples 8-12 and device comparative example 5 of the present invention are exactly the same as those in device example 7, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced.

[0149] The layer structures and test results of each device example are shown in Tables 3-2 and 4 respectively:

[0150] Device Example 7

[0151] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-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 doping material, and compound 42 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 42 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 with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0152] The molecular structural formulas of the related materials are as follows:

[0153]

[0154] After completing the OLED light-emitting device as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency, external quantum efficiency, and the lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Tables 3-1 and 3-2; the test results of the current efficiency, external quantum efficiency, and lifetime of the obtained devices are shown in Table 4.

[0155] Table 3-1

[0156]

[0157] Table 3-2

[0158]

[0159] Table 4

[0160]

[0161] Note: The voltage, current efficiency, and emission peak were measured using an IVL (current-voltage-luminance) test system (Suzhou FushiDa Scientific Instrument Co., Ltd.); the lifetime test system was the EAS-62C OLED device lifetime tester from System Technology Research Co., Ltd. of Japan; LT95 refers to the time it takes for the device luminance to decay to 95%; all data were measured at 10 mA / cm 2 under the test.

[0162] From the device data results in Table 4, it can be seen that compared with Comparative Examples 1-5 of the device, both the current efficiency and device lifetime of the organic light-emitting device of the present invention have been significantly improved compared to OLED devices made of known materials; when using an exciton-sensitizing material as the first dopant, the device efficiency has been significantly improved compared to single-doping.

[0163] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, The structure of the organic compound is shown as any one of general formula (4) or general formula (13): In general formula (4) and general formula (13), Z, each occurrence being the same or different, represents C-R1; R1 independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Ar1 and Ar2 each independently represent a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, or a substituted or unsubstituted C2-C 30 heteroaryl group; The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms; Y represents one of O or S.

2. A boron-containing organic compound, characterized in that, The structure of the organic compound is shown as any one of general formula (22) or general formula (24): In general formula ( R1 independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Ar2 represents a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, or a substituted or unsubstituted C2-C 30 heteroaryl group; The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms.

3. A boron-containing organic compound, characterized in that, ​ ​ R1 is independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; Ar1 and Ar2 each independently represent a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; R a 、R b 、R c 、R d each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms.

4. The boron-containing organic compound according to claim 1, wherein ​ Ar1 and Ar2 represent phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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 dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl, one of them.

5. The boron-containing organic compound according to claim 2, wherein R1 is represented by one of a hydrogen atom, 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 pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene 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-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an oxanthrone group, a phenyl-substituted triazinyl group; Ar2 is represented as phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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 dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl, one of them.

6. The boron-containing organic compound according to claim 3, characterized in that, The R1, R a , R b , R c , R d are each independently represented by a hydrogen atom, 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 anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene 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-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl group, an oxanthrone group, a phenyl-substituted triazinyl group; Ar1 and Ar2 are represented as phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, 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 dibenzofuryl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl, one of which.

7. A boron-containing organic compound, characterized in that, The specific structure of the organic compound is any one of the following structures:

8. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer includes a light-emitting layer, characterized in that, The light-emitting layer contains the boron-containing organic compound according to any one of claims 1-7; The light-emitting layer comprises a host material and a dopant material, and the dopant material contains the boron-containing organic compound according to any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, wherein the light-emitting layer comprises a first host material, a second host material, and a doping 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 is the boron-containing organic compound according to any one of claims 1-7.

10. The organic electroluminescent device according to claim 8, wherein the light-emitting layer comprises a host material, an exciton sensitizing material, and a doping material, and is characterized in that: The exciton sensitizing material is a metal element-containing complex, and the dopant material is the boron-containing organic compound according to any one of claims 1-7.

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