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), #imgabs0# The compound of the present invention has a narrow full width at half maximum and a suitable emission color, and can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the color purity and lifetime 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] Traditional fluorescent doping materials are limited by early technologies and can only utilize 25% of the 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. Phosphorescent materials, due to the strong spin-orbit coupling of heavy atom centers that enhances intersystem crossing, can effectively utilize both singlet excitons and triplet excitons formed by electrical excitation for luminescence, enabling the internal quantum efficiency of the device to reach 100%. 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 being efficient and stable, the luminescent material also requires a narrower full width at half maximum to improve the color purity of the device luminescence. Fluorescent doping materials can achieve high fluorescence quantum and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum of boron-based materials can be reduced to below 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 a narrow full width at half maximum.

[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 sensitizing medium, it fully utilizes triplet excitons and transfers the energy to the fluorescent doping material through energy transfer, and can also achieve a 100% internal quantum efficiency of the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively exert 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-based compounds with resonance structures are more likely to achieve narrow full-width at half-maximum (FWHM) luminescence. When applied to sensitization technologies, such materials can be used to fabricate devices with high efficiency and narrow FWHM emission. For example, in CN 107507921 A and CN 110492006 A, a luminescent layer combination technology is disclosed, which uses a thermally activated delayed fluorescence (TADF) material with a singlet-triplet energy gap less than or equal to 0.2 eV as the host and a boron-based material as the dopant; in CN 110492005 A and CN 110492009 A, a luminescent layer combination scheme is disclosed, which uses an exciplex as the host and a boron-based material as the dopant. Both can achieve efficiency comparable to phosphorescence and a relatively narrow FWHM. Therefore, developing sensitization technologies based on narrow FWHM boron-based luminescent materials has unique advantages and strong potential in meeting the BT.2020 display standards. Summary of the Invention

[0006] In view of the above problems existing 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 has a specific boron-nitrogen fused ring structure, which endows the compound with a narrow FWHM and can be used as a green light-doping material for the luminescent layer of an organic electroluminescent device, thereby improving the color purity and lifespan of the device.

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

[0008]

[0009] In the general formula (1), the M ring represents a substituted or unsubstituted C6 - C 30 aryl ring, a substituted or unsubstituted C2 - C 30 heteroaryl ring;

[0010] Each occurrence of Z, which may be the same or different, represents C-R;

[0011] Each occurrence of Z1, which may be the same or different, represents C-R1;

[0012] Each occurrence of Z2, which may be the same or different, represents C-R2;

[0013] Each occurrence of Z3, which may be the same or different, represents C-R3;

[0014] The dashed line between Z1 indicates that Z1 is not connected or may be connected by a C-C bond;

[0015] R, R1, R2, and R3 each independently represent a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1 - C 10 alkyl group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C1 - C10 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;

[0016] Two adjacent Rs can bond to each other to form a ring;

[0017] R2 and R3 can be bonded to each other to form a ring;

[0018] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 One or more heteroaryl groups.

[0019] In a preferred embodiment, the structure of the organic compound is as shown in general formula (2) to general formula (9):

[0020]

[0021] In general formulae (2) to (9), Z, Z1, Z2, and Z3 have the same meanings as defined above.

[0022] In a preferred embodiment, the structure of the organic compound is as shown in general formula (10) to general formula (13):

[0023]

[0024] In general formula (10) to general formula (13), Z and Z1 have the same meanings as defined above;

[0025] Ra, R b 、R c 、R d 、R e are 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;

[0026] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, C1-C10 alkyl groups having from C3 to C 10 cycloalkyl groups having from C6 to C 30 aryl groups, C2 to C 30 one or more of heteroaryl groups.

[0027] In a preferred embodiment, the structure of the organic compound is represented by any one of the general formulas (14) to (32):

[0028]

[0029]

[0030]

[0031] In the general formulas (14) to (32), the meanings of Z and Z1 are the same as those defined above;

[0032] In a preferred embodiment, the R, R1, R2, R3, Ra, R b , R c , R d , R e are each 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 xanthenone group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group.

[0033] The M ring is represented as 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, a spirofluorene ring;

[0034] The substituents for the substitution groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a trideuteriomethyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a fluorine atom-substituted phenyl group, a methyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a biphenyl group, a 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 spirofluorenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a phenyl-substituted triazinyl group.

[0035] In a preferred embodiment, the R, R1, R2, R3, Ra, R b , R c , R d , R e are represented by the following structures:

[0036]

[0037]

[0038] In a preferred embodiment, the specific structure of the organic compound is any one of the following structures:

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052] 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 described above.

[0053] In a preferred embodiment, the light-emitting layer contains a host material and a dopant material, and the dopant material contains the boron-containing organic compound.

[0054] In a preferred embodiment, 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 described above.

[0055] In a preferred embodiment, the light-emitting layer contains a host material, an exciton sensitizing material and a dopant material. The exciton sensitizing material is a metal element-containing complex, and the dopant material is the boron-containing organic compound described above.

[0056] The beneficial technical effects of the present invention are as follows:

[0057] (1) The compound of the present invention is applied to an OLED device and can be used as a dopant material for a light-emitting layer material. It can emit green fluorescence under the action of an electric field and can be applied to the fields of OLED lighting or OLED display;

[0058] (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;

[0059] (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;

[0060] (4) The compound of the present invention can relatively easily achieve green light emission;

[0061] (5) The specific boron-nitrogen fused ring structure of the compound of the present invention can expand the molecular space volume, reduce the intermolecular interaction force, improve the device sensitization efficiency and reduce the device roll-off. Description of the Drawings

[0062] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0063] 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

[0064] Next, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present invention. Without conflict, the embodiments in the present invention and the features in the embodiments may be combined with each other. The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments, but it is not a limitation of the present invention.

[0065] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms indicating directions such as "upper", "lower", "top", and "bottom" only represent the directions in a specific state, and do not mean that the relevant structures can only exist in the described directions; on the contrary, if the structure can be transformed in position, for example, inverted, the direction of the structure 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.

[0066] In the present invention, substituted or unsubstituted C6-C 30 aryl and / or substituted or unsubstituted C2-C 30 heteroaryl refers 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 di(p - terphenyl) 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 dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a fused ring of a combination of the foregoing groups, but not limited thereto.

[0067] 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.

[0068] The halogen atom in the present invention refers to a chlorine atom, a fluorine atom, a bromine atom, etc., but not limited thereto.

[0069] 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 this article, 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.

[0070] 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.

[0071] 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 generally 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0072] The organic functional material layer disposed between the first electrode and the second electrode includes a hole transport region, a light-emitting layer, and an electron transport region in sequence from bottom to top.

[0073] 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.

[0074] 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.

[0075] 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, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinyl 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.

[0076] 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-mentioned hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0077] 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 very 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 expect 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 the hole injection conduction.

[0078] 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.

[0079] 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, or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0080] 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, by mass.

[0081] 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.

[0082] The thickness of the hole transport layer of the present invention can be 5 - 200 nm, preferably 10 - and more preferably 20 - 100 nm, but the thickness is not limited to this range.

[0083] 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.

[0084] After forming the hole injection layer, hole transport layer and electron blocking layer, a corresponding light-emitting layer is formed on the electron blocking layer.

[0085] The light-emitting layer can comprise a host material and a doping material. The host material can be a common green host material in the art, and the doping material is a resonance-type organic compound represented by the general formula (1) of the present invention.

[0086] The light-emitting layer can comprise a single host material or a dual host material;

[0087] The dual host material comprises a first host material and a second host material. At least one of the first host material and the second host material is preferably a TADF material;

[0088] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by 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 efficiency generated electrochemically inside the device to approach 100% as much as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization efficiency.

[0089] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0090] The exciton sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to fully utilize electrochemically generated 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.

[0091] 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.

[0092] 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, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0093] 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.

[0094] 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 may 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 may be 2 - 200 nm, preferably 5 - 150 nm, but the thickness is not limited to this range.

[0095] The electron transport layer may 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. Materials with high electron mobility are 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.

[0096] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is usually a material preferably having 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.

[0097] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may 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 may 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.

[0098] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances, such as moisture and oxygen, from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can, or a thin film covering the entire surface of the organic layer.

[0099] The method for preparing an organic electroluminescent device of the present invention comprises 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 cover layer, on a substrate. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI methods can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0100] The raw materials involved in the synthesis examples of the present invention can be purchased from the market or prepared by conventional preparation methods in the art;

[0101] Example 1 Synthesis of Compound 90:

[0102]

[0103] Under nitrogen, 10 mmol of raw material B-1 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A 12 mmol solution of n-butyllithium in n-hexane was added dropwise at 0°C. After 1 hour of reaction, raw material A-1 was added. The reaction was continued at 0°C for 2 hours. The reaction was then slowly returned to room temperature for 2 hours before quenching with 2 mL of water. The reaction solution was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate a-1. LC-MS: Measured value: 391.12 ([M+H] + ), theoretical value: 390.20.

[0104] Under nitrogen protection, 10 mmol of intermediate a-1, 11 mmol of raw material C-1, 10 ml of trifluoroacetic acid, and 5 ml of dichloromethane were added to a three-necked flask and reacted at room temperature for 2 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 568.19 ([M+H] + ), theoretical value: 567.16.

[0105] Under nitrogen, 10 mmol of intermediate b-1, 10 mmol of raw material D-1, 15 ml of DMF, 11 mmol of potassium carbonate, and 0.2 mmol of CuI 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 c-1. LC-MS: Measured value: 767.40 ([M+H]+ ), Theoretical value: 766.43.

[0106] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-1, 5 ml of o-xylene, and 30 mmol of boron tribromide were added. After reacting at 90 °C for 12 hours, 60 mmol of N,N-diisopropylethylamine was added and heated to 200 °C and reacted for 48 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 90. 1 H NMR (400 MHz, chloroform-d): δ 1.22 - 1.45 (27H, m), 7.11 - 7.52 (13H, m), 7.55 - 7.93 (8H, m), 8.02 - 8.16 (2H, dd), 8.33 (1H, ddd). In toluene solution (1×10 -5 M), the full width at half maximum is 28 nm (measured by a Horiba Fluorolog-3 series fluorescence spectrometer).

[0107] Synthesis of compound 97 in Example 2:

[0108]

[0109] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of raw material D-2, 15 ml of DMF, 11 mmol of potassium carbonate, and 0.2 mmol of CuI 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 c-2. LC-MS: Measured value: 807.33 ([M + H] + ), Theoretical value: 806.37.

[0110] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-2, 5 ml of o-xylene, and 30 mmol of boron tribromide were added. 60 mmol of N,N-diisopropylethylamine was added and heated to 200 °C and reacted for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 97. In toluene solution (1×10 -5 M), the full width at half maximum is 26 nm (measured by a Horiba Fluorolog-3 series fluorescence spectrometer).

[0111] Synthesis of compound 114 in Example 3:

[0112]

[0113] Under nitrogen protection, 10 mmol of raw material B-2, 10 mmol of raw material E-2, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask, and the mixture was 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 d-1. LC-MS: Measured value: 301.22 ([M+H] + ), theoretical value: 300.16.

[0114] Under nitrogen protection, 10 mmol of intermediate d-1, 12 mmol of bis(pinacolato)diboron, 12 mmol of sodium acetate, 0.5 mmol of Pd(dppf)Cl2, and 50 mL of 1,4-dioxane were added to a three-necked flask, and the mixture was refluxed for 15 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-1. LC-MS: Measured value: 311.30 ([M+H] + ), theoretical value: 310.21.

[0115] Under nitrogen protection, 10 mmol of intermediate e-1, 10 mmol of raw material B-3, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask, and the mixture was refluxed for 5 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: 421.17 ([M+H] + ), theoretical value: 420.15.

[0116] Under nitrogen protection, 10 mmol of intermediate d-2 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 12 mmol of n-butyllithium in n-hexane was added dropwise at 0 °C. After reacting for 1 hour, raw material A-1 was added, and the reaction continued at 0 °C for 3 hours. The reaction was quenched by adding 2 ml of water after slowly returning to room temperature and reacting for 3 hours. The reaction solution was concentrated, and intermediate a-2 was obtained by recrystallization with ethanol:dichloromethane. LC-MS: Measured value: 523.31 ([M+H] + ), theoretical value: 522.29.

[0117] Under nitrogen protection, 10 mmol of intermediate a-2, 11 mmol of raw material C-1, 10 ml of trifluoroacetic acid, and 5 ml of dichloromethane were added to a three-necked flask, and the mixture was 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 b-2. LC-MS: Measured value: 700.31 ([M+H] + ), theoretical value: 699.25.

[0118] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material D-2, 15 ml of DMF, 11 mmol of potassium carbonate and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-3. LC-MS: Measured value: 939.44 ([M+H] + ), theoretical value: 938.46.

[0119] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-3, 5 ml of o-xylene, and 30 mmol of boron tribromide were added. 60 mmol of N,N-diisopropylethylamine was added and heated to 200 °C and reacted for 17 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 114. Half-peak width in toluene solution (1×10 -5 M) is 26 nm (measured by a Fluorolog-3 series fluorescence spectrometer from Horiba).

[0120] Synthesis of compound 130 in Example 4:

[0121]

[0122] Under nitrogen protection, 10 mmol of raw material B-4, 10 mmol of raw material E-3, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask, and the mixture was 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 d-3. LC-MS: Measured value: 399.27 ([M+H] + ), theoretical value: 398.16.

[0123] Under nitrogen protection, 10 mmol of intermediate d-3, 12 mmol of bis(pinacolato)diboron, 12 mmol of sodium acetate, 0.5 mmol of Pd(dppf)Cl2, and 50 mL of 1,4-dioxane were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-2. LC-MS: Measured value: 365.33 ([M+H] + ), theoretical value: 364.26.

[0124] Under nitrogen protection, 10 mmol of intermediate e-2, 10 mmol of raw material B-3, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask, and the mixture was refluxed for 5 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: 475.23 ([M+H] + ), theoretical value: 474.19.

[0125] Under nitrogen protection, 10 mmol of intermediate d-3 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 12 mmol of n-butyllithium in n-hexane was added dropwise at 0 °C. After reacting for 2 hours, raw material A-1 was added, and the reaction was continued at 0 °C for 4 hours. After slowly returning to room temperature and reacting for 2 hours, 2 ml of water was added to quench the reaction. The reaction solution was concentrated, and recrystallization from ethanol:dichloromethane was used to obtain intermediate a-3. LC-MS: Measured value: 577.40 ([M+H] + ), theoretical value: 576.34.

[0126] Under nitrogen protection, 10 mmol of intermediate a-3, 11 mmol of raw material C-1, 10 ml of trifluoroacetic acid, and 5 ml of dichloromethane were added to a three-necked flask, and the mixture was 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 b-3. LC-MS: Measured value: 754.33 ([M+H] + ), theoretical value: 753.30.

[0127] Under nitrogen protection, 10 mmol of intermediate b-3, 10 mmol of raw material D-2, 15 ml of DMF, 11 mmol of potassium carbonate and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-4. LC-MS: Measured value: 993.43 ([M+H] + ), theoretical value: 992.51.

[0128] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-4, 5 ml of o-xylene, and 30 mmol of boron tribromide were added. 60 mmol of N,N-diisopropylethylamine was added, and the mixture was heated to 200 °C and reacted for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 130. The half-peak width in toluene solution (1×10 -5 M) was 26 nm (measured by a Horiba Fluorolog-3 series fluorescence spectrometer).

[0129] Synthesis of Compound 123 in Example 5:

[0130]

[0131] Under nitrogen protection, 10 mmol of intermediate b-3, 10 mmol of raw material D-3, 15 ml of DMF, 11 mmol of potassium carbonate and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 18 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-5. LC-MS: Measured value: 953.51 ([M+H] + ) and the theoretical value: 952.57.

[0132] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-5, 5 ml of o-xylene, and 30 mmol of boron tribromide were added. 60 mmol of N,N-diisopropylethylamine was added and heated to 200 °C and reacted for 19 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 123. Half-peak width in toluene solution (1×10 -5 M) is 27 nm.

[0133] Synthesis of compound 200 in Example 6:

[0134]

[0135] Under nitrogen protection, 10 mmol of intermediate d-4 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 12 mmol of n-butyllithium in n-hexane was added dropwise at 0 °C. After reacting for 3 hours, raw material A-2 was added, and the reaction was continued at 0 °C for 5 hours. After slowly returning to room temperature and reacting for 2 hours, 2 ml of water was added to quench the reaction. The reaction solution was concentrated, and recrystallized with ethanol:dichloromethane to obtain intermediate a-5. LC-MS: Measured value: 581.44 ([M+H] + ) and the theoretical value: 580.37.

[0136] Under nitrogen protection, 10 mmol of intermediate a-5, 11 mmol of raw material C-1, 10 ml of trifluoroacetic acid, and 5 ml of dichloromethane were added to a three-necked flask and reacted at room temperature for 2 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-5. LC-MS: Measured value: 758.39 ([M+H] + ) and the theoretical value: 757.33.

[0137] Under nitrogen protection, 10 mmol of intermediate b-5, 10 mmol of raw material D-2, 15 ml of DMF, 11 mmol of potassium carbonate and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 24 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-6. LC-MS: Measured value: 997.51 ([M+H] + ), theoretical value: 996.54.

[0138] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-6, 5 ml of o-xylene, and 30 mmol of boron tribromide were added, and 60 mmol of N,N-diisopropylethylamine was added and heated to 200 °C for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 200. The half-peak width in toluene solution (1×10 -5 M) is 25 nm (measured by a Fluorolog-3 series fluorescence spectrometer from Horiba).

[0139] Synthesis of compound 251 in Example 7:

[0140]

[0141] Under nitrogen protection, 10 mmol of intermediate d-3 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask, and a solution of 12 mmol of n-butyllithium in n-hexane was added dropwise at 0 °C. After reacting for 3 hours, raw material A-3 was added, and the reaction continued at 0 °C for 6 hours. After slowly returning to room temperature and reacting for 4 hours, 2 ml of water was added to quench the reaction. The reaction solution was concentrated, and recrystallization was carried out using ethanol:dichloromethane to obtain intermediate a-6. LC-MS: Measured value: 691.42 ([M+H] + ), theoretical value: 690.48.

[0142] Under nitrogen protection, 10 mmol of intermediate a-6, 11 mmol of raw material C-1, 10 ml of trifluoroacetic acid, and 5 ml of dichloromethane were added to a three-necked flask, and the reaction was carried out at room temperature for 1 hour. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-6. LC-MS: Measured value: 868.41 ([M+H] + ), theoretical value: 867.44.

[0143] Under nitrogen protection, 10 mmol of intermediate b-6, 10 mmol of raw material D-2, 15 ml of DMF, 11 mmol of potassium carbonate and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-7. LC-MS: Measured value: 1107.57 ([M+H]+ ), Theoretical value: 1106.65.

[0144] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-7, 5 ml of o-xylene, and 30 mmol of boron tribromide were added. 60 mmol of N,N-diisopropylethylamine was added and heated to 200 °C and reacted for 13 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 251. In a toluene solution (1×10 -5 M), the full width at half maximum is 28 nm (measured by a Horiba Fluorolog-3 series fluorescence spectrometer).

[0145] The structural characterization of the compounds obtained in each example is shown in Table 1 [[ID=Ill]]

[0146] Table 1

[0147]

[0148] The compounds of the present invention can be used in light-emitting devices and can be used as a dopant material for the light-emitting layer.

[0149] The application effects of the OLED materials synthesized by the present invention in devices are described in detail below through Device Examples 1-7 and Device Comparative Examples 1-3. Device Examples 2-7 and Device Comparative Examples 1-3 of the present invention have exactly the same device manufacturing process as Device Example 1, and the same substrate material and electrode material are used. The film thickness of the electrode material also remains the same. The difference is that the light-emitting layer material in the device is replaced. The layer structures and test results of each device example are shown in Tables 2-1 and 3 respectively:

[0150] Device Example 1

[0151] 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 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, and compound 90 is used as the doping material. The mass ratio of GH-1, GH-2, and compound 90 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 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 with a mass ratio of 1:1 and 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 application effects of the OLED materials synthesized by the present invention in the devices are described in detail below through device examples 8-14 and device comparative examples 4-6. The manufacturing processes of the devices in device examples 9-14 and device comparative examples 4-6 of the present invention are exactly the same as those in device example 8, 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. The layer structures and test results of each device example are shown in Tables 2-2 and 3 respectively:

[0153] Device Example 9

[0154] 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 90 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 90 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 with a mass ratio of 1:1 and 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.

[0155] The molecular structural formulas of the related materials are as follows:

[0156]

[0157] 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 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 2-1 and 2-2; the test results of the current efficiency, external quantum efficiency, and lifetime of the obtained devices are shown in Table 3.

[0158] Table 2-1

[0159]

[0160] Table 2-2

[0161]

[0162] Table 3

[0163]

[0164] Note: The voltage, current efficiency, and emission peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fosda Scientific Instruments Co., Ltd.); the lifetime test system was the EAS-62C OLED device lifetime tester from System Technology Research Co., Ltd. in 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.

[0165] From the device data results in Table 3, it can be seen that this framework compound has the characteristics of high efficiency and long lifetime on the basis of achieving green light emission, and the material has excellent stability. Compared with Comparative Examples 1-6 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 the OLED devices of known materials; when using an exciton-sensitizing material as the first dopant, the device efficiency has been significantly improved compared to single doping. 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 principle 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 in General Formula (3) to General Formula (4): In General Formula (3) - General Formula (4), each occurrence of Z, which may be the same or different, represents C-R; Each occurrence of Z1, which may be the same or different, represents C-R1; The dashed line between Z1 indicates that Z1 is not connected or may be connected by a C-C bond; R and R1 each independently represent 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-butylphenyl-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.

2. The boron-containing organic compound according to claim 1, wherein The structure of the organic compound is shown in General Formula (10) to General Formula (13): In General Formula (10) - General Formula (13), each occurrence of Z, which may be the same or different, represents C-R; Each occurrence of Z1, which may be the same or different, represents C-R1; R and R1 each independently represent one of a hydrogen atom and a deuterium atom; Ra, R b , R c , R d , R e 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.

3. The boron-containing organic compound according to claim 1, characterized in that, Each of R and R1 independently represents 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 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 oxanthrone group, and a phenyl-substituted triazinyl group.

4. The boron-containing organic compound according to claim 2, wherein The Ra, R b , R c , R d , R e are each independently represented by a hydrogen atom, 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, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene 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-butylbenzene-substituted amino group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl group, xanthone group, phenyl-substituted triazinyl group.

5. The boron-containing organic compound according to claim 2, wherein The Ra, R b , R c , R d , R e are represented in the following structure:

6. The boron-containing organic compound according to claim 1, wherein The specific structure of the organic compound is any one of the following structures:

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

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

9. The organic electroluminescent device according to claim 7, 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 1-6.

10. The organic electroluminescent device according to claim 7, 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 1-6.

Images