A boron-containing organic compound as an OLED doping material and an organic electroluminescent device prepared therefrom

Abstract

The present invention discloses a boron-containing organic compound, belonging to the field of semiconductor technology; the structure of the organic compound is shown in general formula (1). The compound of the present invention has a narrow half-width, high fluorescence quantum yield, a high glass transition temperature and molecular thermal stability, and suitable HOMO and LUMO energy levels. It can be used as a green light doping material in the light-emitting layer of an organic electroluminescent device, thereby improving the luminescent color purity and lifespan of the device.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and in particular to a boron-containing organic compound as an OLED doping material and an organic electroluminescent device containing the same. Background Art

[0002] Traditional fluorescent doping materials, limited by early technology, can only utilize the 25% of singlet excitons formed by electrical excitation to emit light. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lagging behind the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom center that enhances intersystem crossing, can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light, achieving a device internal quantum efficiency of 100%. However, the high cost of most phosphorescent materials, poor material stability, low color purity, and severe device efficiency roll-off have limited their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are being placed on color rendering standards. In addition to being efficient and stable, luminescent materials also need to have a narrower half-width to improve the color purity of the device's luminescent color. Fluorescent doping materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doping materials have achieved a phased breakthrough, and the half-width of boron-based materials can be reduced to below 30nm. However, research in the green light region, to which the human eye is more sensitive, has mainly focused on phosphorescent doping materials. However, their luminescent peak shape is difficult to narrow through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doping materials with narrow half-width.

[0004] In addition, TADF-sensitized fluorescence technology (TSF) combines TADF materials with fluorescent doping materials, using TADF materials as exciton-sensitizing media to convert triplet excitons formed by electrical excitation into singlet excitons, and transfers energy to fluorescent doping materials through long-range energy transfer of singlet excitons, which can also achieve 100% device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width luminescence. Such materials are used in TADF-sensitized fluorescence technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN110492006 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 110492005A and CN 110492009A 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 TADF-sensitized fluorescence technology based on narrow half-width boron-containing 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 with the prior art, the applicants have provided a boron-containing organic compound as a dopant material for OLEDs, and an organic electroluminescent device prepared therefrom. The compound exhibits a narrow half-width (FWHM), high fluorescence quantum yield, a high glass transition temperature (GST), molecular thermal stability, and suitable HOMO and LUMO energy levels. It 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 lifetime.

[0007] The technical solutions of the present invention are as follows:

[0008] A boron-containing organic compound, the structure of which is shown in general formula (1):

[0009]

[0010] In the general formula (1), R1-R3 are independently H, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, C6-C 30 aryloxy, substituted amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 The number of H in R1-R3 is 0 or 1;

[0011] R4 represents a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 R4 can also be connected to the A1 ring through a single bond; the A1 ring is represented by a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C30 One of the heteroaryl groups, at least one of the R4 and A1 rings represents a substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C 10 -One of C30 aryl groups;

[0012] X1-X3 are independently represented by C-R5, and each occurrence of R5 is the same or different and represents H, deuterium atom, cyano group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R5 is connected to the adjacent structure in the general formula (1) by a single bond or forming a ring;

[0013] The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups;

[0014] The heteroatoms in the heteroaryl group are selected from one or more of oxygen, sulfur and nitrogen.

[0015] In a preferred embodiment, the structure of the organic compound is as shown in any one of the general formulas (2) to (6):

[0016]

[0017]

[0018] In the general formula (2), Z1 represents O, S or NR a ; R a Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0019] In the general formula (3), Z2 represents O, S or NR b ; Each occurrence of Y1 is represented independently as CR c ;

[0020] R b Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Rc Each occurrence is represented identically or differently by H, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R c The connection mode with the adjacent structure in general formula (3) is single bond substitution or forming a ring;

[0021] In the general formula (4), Z3 represents O, S or NR d ; Each occurrence of Y2 is represented independently as CR e , R d Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R e Each occurrence is represented identically or differently by H, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R e The connection mode with the adjacent structure in general formula (4) is single bond substitution or forming a ring; the dotted line indicates connection or non-connection;

[0022] In the general formula (5), W ring, R A Respectively represent substituted or unsubstituted C6-C 30 Aryl; R A At least one of the W rings represents a substituted or unsubstituted C 10 -C 30 Aryl; R A It can also be connected to the W ring via a single bond;

[0023] In the general formula (6), Z4 represents O, S or NR f ; R f Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 R4 can also be connected to the benzene ring represented by Q through a single bond;

[0024] In general formulae (2) to (6), R1 to R3, X1 to X3, and R4 have the same meanings as defined above.

[0025] In a preferred embodiment, the structure of the organic compound is as shown in any one of the general formulas (1-1) to (1-18):

[0026]

[0027]

[0028]

[0029] In general formula (1-1) to general formula (1-10), X4 represents S, O or NR Z , R Z Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R x Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 Y1, Y2 are the same or different each time and represent N or C-Ro, Ro represents H, deuterium atom, cyano group, halogen atom, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, C6-C 30 aryloxy, substituted amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 Any adjacent Ro can also be connected to form a ring; Y1 and Y2 at the connection are represented by C;

[0030] In general formula (1-11) to general formula (1-16), X5 represents S, O or NR S , R S Expressed as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0031] In general formula (1-17) to general formula (1-18), each occurrence of V1 is the same or different and represents N or C-Rt, and Rt represents H, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, C6-C 30 aryloxy, substituted amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C 30 Any adjacent Rt can also be connected to form a ring; V1 at the connection point is represented by C;

[0032] In the general formula (1-17), V1 can also be connected with A1 to form a ring; in the general formula (1-18), V1 can also be connected with R4 to form a ring;

[0033] In general formulas (1-3) to (1-14), the dotted lines represent connection or non-connection;

[0034] In general formulae (1-1) to (1-18), R1-R3, X1-X3, and R4 have the same meanings as defined above.

[0035] In a preferred embodiment, R1-R3 and R5 are independently H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, a phenoxy group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a 1,3-dioxolane group, a benzodioxin group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a phenyl-substituted pyridyl group, a phenyl-substituted pyrimidinyl group, a quinolyl group, a furyl group, a thienyl group, a benzimidazolyl group, a phenyl-substituted benzimidazolyl group, a phenyl one of furanyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, tert-butyl-substituted tert-butyl-substituted phenyl, xanthone, and phenyl-substituted triazinyl; R5 is connected to the adjacent structure in the general formula (1) by single bond substitution to form a ring;

[0036] The substituents for the substituent group are optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, -CF3, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthrenyl group.

[0037] In a preferred embodiment, Ra, Rb, and Rd are independently represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, and xanthone;

[0038] Said Rc and Re are independently represented by H, deuterium atom, cyano group, adamantyl group, fluorine atom, methyl group, trifluoromethyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, cyclopentyl group, methyl substituted cyclopentyl group, cyclohexyl group, methoxy group, ethoxy group, phenoxy group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, 1,3-dioxolane, benzodioxin, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, phenyl substituted pyridyl group, phenyl substituted pyrimidinyl group, quinolyl group, furyl group, thienyl group, benzimidazolyl group, phenyl group R is one of a benzimidazolyl group substituted with benzofuranyl, dibenzofuranyl, dibenzothiophenyl group, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino group, tert-butylbenzene-substituted amino group, tert-butyl-substituted dibenzofuranyl 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, tert-butyl-substituted biphenyl group, phenyl-substituted tert-butyl group, xanthone group, and phenyl-substituted triazinyl group; R c The connection mode with the adjacent structure in general formula (3) is single bond substitution or forming a ring; R e The connection mode with the adjacent structure in the general formula (4) is in the form of single bond substitution or formation of a ring.

[0039] In a preferred embodiment, Rz and Rs are independently represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, or xanthone;

[0040] Ro and Rt represent H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, a phenoxy group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 1,3-dioxolane group, a benzodioxin group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a phenyl-substituted pyridyl group, a phenyl-substituted pyrimidinyl group, a quinolyl group, a furyl group, a thienyl group, a benzimidazolyl group, a phenyl-substituted benzimidazolyl group, a benzofuranyl group, a diphenyl group The present invention further comprises one of furanyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, 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, tert-butyl-substituted phenyl, tert-butyl-substituted phenyl, xanthone, and phenyl-substituted triazinyl; any adjacent Rt can also be connected to form a ring; any adjacent Ro can also be connected to form a ring.

[0041] More preferably, R1 and R2 are independently methyl, isopropyl, tert-butyl, phenyl or naphthyl; and R3 is phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano.

[0042] In a preferred embodiment, R1 and R2 are identical and represent tert-butyl or phenyl, R3 represents phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano, preferably methyl; X1 and X3 are each CH; X2 is C-R5; R5 is H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl, a trifluoromethyl, an ethyl, isopropyl, isobutyl, tert-butyl, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, a phenoxy group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a 1,3-dioxolane group, a benzodioxin group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a phenyl-substituted pyridyl group, a phenyl-substituted pyrimidinyl group, One of quinolyl, furyl, thienyl, benzimidazolyl, phenyl-substituted benzimidazolyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, 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, tert-butyl-substituted tert-butyl, xanthone, and phenyl-substituted triazinyl; the connection mode of R5 and the adjacent structure in the general formula (1) is a single bond substitution to form a ring.

[0043] More preferably, R1 and R2 are identically represented by tert-butyl, R3 is represented by phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl, or cyano, preferably methyl; and X1, X2, and X3 are all represented by CH.

[0044] More preferably, W ring, R A Each independently represents phenyl, terphenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene, pyrenyl, and at least one of ring W and RA represents naphthyl; R A It can be connected to the W ring through a single bond.

[0045] The specific structure of the boron-containing organic compound is any one of the following structures:

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] An organic light-emitting device comprises a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, and the functional layer of the organic light-emitting device comprises the boron-containing organic compound.

[0061] In a preferred embodiment, the functional layer comprises a light-emitting layer, and the doping material of the light-emitting layer is the boron-containing organic compound.

[0062] Further preferably, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound.

[0063] The beneficial technical effects of the present invention are:

[0064] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields.

[0065] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0066] (3) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

[0067] (4) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and enhance the luminous efficiency of the device;

[0068] (5) The vapor deposition decomposition temperature of the compound of the present invention is relatively high, which can inhibit the vapor deposition decomposition of the material and effectively improve the life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0069] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0070] 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 DESCRIPTION

[0071] The present invention will be described in detail below with reference to the accompanying drawings and embodiments.

[0072] In the present invention, unless otherwise specified, HOMO means the highest occupied molecular orbital of a molecule, and LUMO means the lowest unoccupied molecular orbital of a molecule. In addition, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and comparison between energy levels also refers to comparison of their absolute values. Those skilled in the art will appreciate that the larger the absolute value of an energy level, the lower the energy of that energy level.

[0073] Any numerical range listed herein is intended to include all subranges with the same numerical precision within the listed range. For example, "1.0 to 10.0" means all subranges (including 1.0 and 10.0) included between the listed minimum value 1.0 and the listed maximum value 10.0, that is, all subranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limit listed herein is intended to include all smaller numerical limits included herein, and any minimum numerical limit listed herein is intended to include all larger numerical limits included herein. Therefore, the applicant reserves the right to amend this specification, including the claims, to clearly describe any subranges falling within the scope clearly described herein.

[0074] In the drawings, the dimensions of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, the layer or element may be directly on the other layer or substrate, or intervening layers may be present. Furthermore, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intervening layers may be present. Like reference numerals refer to like elements throughout.

[0075] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms such as "upper," "lower," "top," and "bottom" that indicate orientation refer only to a particular state and do not imply that the structure can exist only in the described orientation. Conversely, if the structure can be repositioned, such as inverted, the orientation of the structure will change accordingly. Specifically, in the present invention, the "bottom" or "lower" side of an electrode refers to the side of the electrode closest to the substrate during fabrication, while the opposite side, farther from the substrate, is the "top" or "upper" side.

[0076] As the substrate for the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples include transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates; and flexible PI film substrates. Different substrates have varying mechanical strength, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use varies. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.

[0077] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a metal mixture. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0078] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light emitting layer and an electron transport region.

[0079] Herein, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0080] As materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.

[0081] Examples of the above materials 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 quilone derivatives, styrylanthracene 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, styrene amination compounds, compounds, triamines, tetraamines, benzidines, propargyl diamine 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)quaterphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds.

[0082] Furthermore, depending on the device configuration requirements, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this article, the thickness of the various hole carrier conductive film layers with different functions described above is not particularly limited.

[0083] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summary, in order to achieve smooth hole injection from the anode to the organic film layer, the HOMO energy level of the host organic material used in the anode interface buffer layer must have certain characteristics with the P-doped material. Only then can the charge transfer state between the host material and the dopant material be achieved, and ohmic contact between the buffer layer and the anode can be achieved, achieving efficient injection and conduction of holes from the electrode.

[0084] In view of the above empirical summary, for hole-type host materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0085] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further includes a P-type dopant 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(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0086] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0087] The thickness of the hole injection layer of the present invention may be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0088] The thickness of the hole transport layer of the present invention may be 5 to 200 nm, preferably 10 to 150 nm, and more preferably 20 to 100 nm, but the thickness is not limited to this range.

[0089] The thickness of the electron blocking layer of the present invention may be 1-20 nm, preferably 5-10 nm, but the thickness is not limited to this range.

[0090] 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.

[0091] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of the present invention.

[0092] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0093] The thickness of the light-emitting layer can be adjusted to optimize the luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-30 nm, but the thickness is not limited to this range.

[0094] In the present invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light emitting layer, but is not limited thereto.

[0095] 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 extending the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, for example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinolinol) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene) bis (9H-carbazole) (CAS No.: 1345338-69-3) and other pyrimidine derivatives. The thickness of the hole blocking layer of the present invention may be 2-200 nm, preferably 5-150 nm, and more preferably 10-100 nm, but the thickness is not limited to this range.

[0096] The electron transport layer can be disposed on the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that readily accepts electrons from the cathode and transfers the received electrons to the light-emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials for organic electroluminescent devices known in the prior art 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-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-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 may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0097] The electron injection layer may be provided above the electron transport layer. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer materials for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; or cesium salts such as cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0098] 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, but is not limited to, 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. The thickness of the cathode depends on the material used and is typically 10-50 nm, preferably 15-20 nm.

[0099] 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.

[0100] 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.

[0101] 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;

[0102] Example 1 Synthesis of Compound 2:

[0103]

[0104] Preparation of intermediate a1:

[0105] To a single-necked flask, raw material A1 (50.0 mmol), raw material B1 (55.0 mmol), potassium carbonate (150.0 mmol), and DMF (250 mL) were added sequentially. The mixture was then stirred at 110°C for 5 hours under nitrogen protection. After the reaction was completed, the mixture was cooled to room temperature and ethyl acetate (500 mL) was added. The mixture was then washed with saturated brine (50 mL x 5), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified on a silica gel column to obtain intermediate a1. LC-MS: Measured: 482.10 ([M+H]+), theoretical: 481.12.

[0106] Preparation of intermediate m1:

[0107] To a single-necked flask, intermediate a1 (10.0 mmol), starting material C1 (10.0 mmol), toluene (50 mL), potassium tert-butoxide (50 mmol), X-Phos (1.0 mmol), and Pd2(dba)3 (0.5 mmol) were added sequentially. The mixture was then stirred at 110°C for 5 hours under nitrogen. After cooling, the reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was separated by silica gel column, slurried, and filtered to obtain intermediate m1. LC-MS: Measured: 611.23 ([M+H]+), Required: 610.28.

[0108] Preparation of compound 2:

[0109] Intermediate m1 (5.0 mmol) and tert-butyltoluene (50 mL) were added sequentially to a single-necked flask. The temperature was lowered to -40°C, and tert-butyllithium (5.5 mmol) was slowly added. The mixture was stirred and warmed to room temperature. The n-hexane was then removed under reduced pressure at 60°C. Nitrogen was then applied, and BBr3 (10.0 mmol) and N,N-diisopropylethylamine (10 mmol) were added. The mixture was refluxed at 150°C for 36 hours. After the reaction, the temperature was lowered to 80°C, and the solvent was evaporated under reduced pressure. A buffer solution of sodium hydrogen phosphate and sodium dihydrogen phosphate was added, and the mixture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The organic phases were purified by silica gel column chromatography and slurried to obtain compound 2. LC-MS: Measured value: 585.43 ([M+H]+), theoretical value: 584.30.

[0110] Example 2 Synthesis of Compound 10:

[0111]

[0112] The preparation of intermediate m2 was based on intermediate m1. LC-MS: Found: 655.33 ([M+H]+), Required: 654.26.

[0113] The preparation of compound 10 was based on compound 2; LC-MS: found: 595.53 ([M+H]+), theoretical: 594.32.

[0114] Example 3 Synthesis of Compound 67:

[0115]

[0116] The preparation method of intermediate a3 refers to intermediate a1; LC-MS: measured value: 364.15 ([M+H]+), theoretical value: 363.03.

[0117] The preparation method of intermediate m3 refers to intermediate m1. LC-MS: Found: 703.31 ([M+H]+), Required: 702.27.

[0118] Preparation of compound 67:

[0119] To a single-necked flask, intermediate m3 (0.5 mmol) and tert-butylbenzene (30 mL) were added in sequence. Under nitrogen protection, a tert-butylbenzene solution of BI3 (1.0 mmol) was added and refluxed at 180°C for 48 hours. The mixture was cooled and directly spin-dried. Buffer solution was then added and extracted with ethyl acetate (300 mL). The mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The organic phase was concentrated and purified by silica gel column, followed by slurry filtration to obtain compound 67. LC-MS: Measured value: 711.62 ([M+H] + ), theoretical value: 710.25.

[0120] Example 4 Synthesis of Compound 126:

[0121]

[0122] The preparation of intermediate a4 was based on intermediate a1. LC-MS: Found: 508.11 ([M+H]+), Required: 507.04.

[0123] The preparation of intermediate b4 refers to intermediate a1. LC-MS: Measured value: 713.43 ([M+H]+), Calculated value: 712.23

[0124] Preparation of intermediate C4:

[0125] To a single-necked flask were added intermediate b4 (0.8 mmol), starting material D4 (1.0 mmol), dioxane (50 mL), potassium carbonate (8 mmol), X-Phos (0.1 mmol), and Pd2(dba)3 (0.05 mmol). The mixture was then stirred at 80°C overnight under nitrogen protection. After cooling, the reaction mixture was quenched with saturated brine (30 mL) and extracted three times with ethyl acetate (100 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated, and the intermediate compound c4 was isolated on a silica gel column. LC-MS: Measured value: 805.25 ([M+H]+), theoretical value: 804.35.

[0126] Preparation of intermediate m4:

[0127] To a single-necked flask were added intermediate c4 (0.5 mmol), starting material E4 (0.5 mmol), Pd(PPh3)4 (0.05 mmol), K2CO3 (3.0 mmol), toluene (20 mL), ethanol (10 mL), and water (2 mL). The mixture was then stirred at 80°C overnight under nitrogen protection. After cooling, saturated brine (10 mL) was added to quench the reaction solution, which was then extracted three times with ethyl acetate (50 mL). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated, and separated on a silica gel column to obtain intermediate m4. LC-MS: Measured value: 910.33 ([M+H]+), theoretical value: 909.35.

[0128] The preparation of compound 126 was based on compound 67. LC-MS: found: 918.55 ([M+H]+), theoretical: 917.33.

[0129] Example 5 Synthesis of Compound 131:

[0130]

[0131] The preparation of intermediate m5 was based on intermediate m1. LC-MS: found: 625.50 ([M+H]+), theoretical: 624.31.

[0132] The preparation of compound 131 was based on compound 67. LC-MS: found: 633.42 ([M+H]+), theoretical: 632.30.

[0133] Example 6 Synthesis of Compound 149:

[0134]

[0135] The preparation of intermediate m6 refers to m1. LC-MS: Found: 575.52 ([M+H]+), Required: 574.30.

[0136] The preparation of compound 149 was based on compound 67. LC-MS: found: 583.35 ([M+H]+), required: 582.28.

[0137] Example 7 Synthesis of Compound 188:

[0138]

[0139]

[0140] Preparation of intermediate a7:

[0141] To a single-necked flask, raw material A7 (10.0 mmol), DMF (50 mL), and NBS (11.1 mmol) were added in sequence. The mixture was protected from light and stirred at 80°C overnight. After cooling, saturated brine (50 mL) was added to quench the reaction solution. The mixture was extracted with ethyl acetate (300 mL), concentrated, and recrystallized to obtain intermediate a7. LC-MS: Measured value: 330.33 ([M+H] + ), theoretical value: 329.08.

[0142] The preparation of intermediate b7 was based on intermediate m4. LC-MS: found: 328.33 ([M+H]+), theoretical: 327.20.

[0143] The preparation of intermediate c7 was based on intermediate ml. LC-MS: found: 516.23 ([M+H]+), theoretical: 515.10.

[0144] The preparation of intermediate m7 was based on intermediate m1. LC-MS: found: 687.21 ([M+H]+), theoretical: 686.23.

[0145] The preparation of compound 188 was based on compound 2. LC-MS: found: 627.26 ([M+H]+), calculated: 626.29.

[0146] Example 8 Synthesis of Compound 246:

[0147]

[0148]

[0149] Preparation of intermediate a8: Reference compound b1. LC-MS: Found: 550.18 ([M+H]+), Required: 549.11.

[0150] Preparation of intermediate m8: Reference compound m1. LC-MS: Found: 687.41 ([M+H]+), Required: 686.27.

[0151] The preparation of compound 246 was referenced to compound 67. LC-MS: found: 695.52 ([M+H]+), required: 694.26.

[0152] Example 9 Synthesis of Compound 291:

[0153]

[0154]

[0155] Intermediate a9 was prepared from reference intermediate b1. LC-MS: found: 508.11 ([M+H]+), required: 507.04.

[0156] Intermediate b9 was prepared as reference intermediate ml. LC-MS: found: 645.20 ([M+H]+), required: 644.20.

[0157] Intermediate c9 was prepared with reference to intermediate c4. LC-MS: found: 737.44 ([M+H]+), required: 736.33.

[0158] Intermediate m9 was prepared with reference to intermediate m4. LC-MS: found: 842.36 ([M+H]+), required: 841.32.

[0159] The preparation of compound 291 was based on compound 126. LC-MS: found: 850.47 ([M+H]+), theoretical: 849.31.

[0160] Example 10 Synthesis of Compound 303:

[0161]

[0162] Intermediate m10 was prepared using reference intermediate m1. LC-MS: found: 771.24 ([M+H]+), required: 770.21.

[0163] The preparation of compound 303 was based on compound 2. LC-MS: found: 667.41 ([M+H]+), theoretical: 666.32.

[0164] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0165] Table 1

[0166]

[0167]

[0168] 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 embodiments of the present invention were tested, and the test results are shown in Table 2:

[0169] Table 2

[0170]

[0171] Note: Glass transition temperature (Tg) was determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter from NETZSCH, Germany) at a heating rate of 10°C / min. The thermal gravimetric temperature (Td) is the temperature at which the weight loss reaches 1% in a nitrogen atmosphere, measured on a TGA-50H thermogravimetric analyzer from Shimadzu Corporation, Japan, with a nitrogen flow rate of 20 mL / min. The highest occupied molecular orbital (HOMO) energy level was determined using an ionization energy measurement system (IPS-3) in a nitrogen environment. Eg was determined using a dual-beam UV-visible spectrophotometer (Model: TU-1901), where LUMO = HOMO + Eg. PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were measured in thin films using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0172] As can be seen from the data in the table above, the compounds of the present invention have high glass transition temperatures and decomposition temperatures. When used as dopants in the light-emitting layer, they can inhibit the crystallization and film phase separation of the material; they can also inhibit the decomposition of the material at high brightness, thereby improving the device's operating life. Furthermore, the compounds of the present application have shallow HOMO energy levels. When added as dopants to the host material, they can help suppress the generation of carrier traps, improve the host-guest energy transfer efficiency, and thus enhance the device's luminous efficiency.

[0173] The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; at the same time, the spectral FWHM of the material is narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device; finally, the evaporation decomposition temperature of the material is high, which can inhibit the evaporation decomposition of the material and effectively improve the life of the device.

[0174] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 1-10 and Comparative Example 1. Device Examples 2-10 and Comparative Examples 1-2 utilize identical fabrication processes to those of Device Example 1, using the same substrate and electrode materials, with the same electrode thickness. The only difference is the material used in the light-emitting layer. The layer structures and test results for each device example are shown in Tables 3 and 4, respectively.

[0175] Device Example 1

[0176] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a detergent (Semiclean M-L20), washed with pure water, 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, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm 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 60nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is made, using CBP as the main material and compound 2 as the doping material. The mass ratio of CBP and compound 2 is 97:3, and the light-emitting layer thickness is 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick film. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0177] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 11-20 and Comparative Examples 3-4. The device fabrication processes for Device Examples 12-20 and Comparative Examples 3-4 are identical to those for Device Example 11, utilizing the same substrate and electrode materials, with the same electrode thickness. The only difference is the material used in the light-emitting layer. The layer structures and test results for each device example are shown in Tables 3 and 4, respectively.

[0178] Device Example 11

[0179] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed, i.e., washed with a detergent (Semiclean M-L20), washed with pure water, dried, and then subjected to ultraviolet-ozone cleaning to remove organic residues on the transparent ITO surface. On the washed ITO anode layer 2, a vacuum evaporation device is used to deposit HT-1 and HI-1 with a thickness of 10nm as the hole injection layer 3. The mass ratio of HT-1 to HI-1 is 97:3. HT-1 is then evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 is then evaporated to a thickness of 30nm as the electron blocking layer 5. After the above electron blocking material evaporation is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared. CBP and DMAC-BP are used as the dual host materials, and Compound 2 is used as the dopant material. The mass ratio of CBP, DMAC-BP, and Compound 2 is 67:30:3, and the light-emitting layer thickness is 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick film. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0180] The molecular structure formula of the relevant materials is shown below:

[0181]

[0182] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known drive circuit, and the device's current efficiency, external quantum efficiency, and lifetime were measured. Examples and comparative examples of devices prepared using the same method are shown in Table 3; the test results for the current efficiency, external quantum efficiency, and lifetime of the resulting devices are shown in Table 4.

[0183] Table 3

[0184]

[0185]

[0186] Table 4

[0187]

[0188] Note: Voltage, current efficiency, and luminescence peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the lifespan test system was an EAS-62C OLED device lifespan tester from Japan System Giken Co., Ltd.; LT95 refers to the time it takes for the device's luminance to decay to 95%; all data are measured at 10 mA / cm 2 Next test.

[0189] It can be seen from the device data results in Table 4 that, compared with device comparison examples 1-4, the current efficiency, external quantum efficiency and device life of the organic light-emitting device of the present invention are greatly improved compared with OLED devices made of known materials.

[0190] In summary, the above are only 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 should be included in the scope of protection of the present invention.

Claims

1. A boron-containing organic compound, characterized in that The structure of the organic compound is shown in any one of the general formulas (3) to (5): In the general formula (3), Z2 represents O or S; Each occurrence of Y1 is represented independently as CR c ; The R c Each occurrence is represented identically or differently by H, a deuterium atom, a cyano group, a fluorine atom, a substituted or unsubstituted C1-C 10 alkyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, 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, phenyl-substituted tert-butyl; In the general formula (4), Z3 represents O, S; Each occurrence of Y2 is represented independently as CR e , R e Each occurrence is represented identically or differently by H, a deuterium atom, a cyano group, a fluorine atom, a substituted or unsubstituted C1-C 10 alkyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, 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, phenyl-substituted tert-butyl; Dashed lines indicate connections; In the general formula (5), W ring, R A Each independently represents phenyl, biphenyl, or naphthyl, and at least one of W ring and RA represents naphthyl; R A Connected to the W ring via a single bond; In general formula (3) to general formula (5), R1 to R3 are independently H, deuterium atom, cyano group, fluorine atom, substituted or unsubstituted C1-C 10 alkyl, adamantyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, 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, tert-butyl-substituted phenyl; the number of H in R1-R3 is 0 or 1; X1-X3 are independently represented by C-R5, and each occurrence of R5 is the same or different and represents H, deuterium atom, cyano group, substituted or unsubstituted C1-C 10 alkyl, adamantyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, fluorine atom, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, phenyl-substituted pyridyl, phenyl-substituted pyrimidinyl, quinolyl, benzimidazolyl, phenyl-substituted benzimidazolyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, 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, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl; The substituent for the substituent group may be selected from one or more of a fluorine atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, and a butyl group.

2. The boron-containing organic compound according to claim 1, characterized in that The structure of the organic compound is shown in any one of the general formulas (1-3), (1-10), (1-17), and (1-18): In the general formula (1-3) and the general formula (1-10), X4 represents S, O, R x It is represented by phenyl; Y1 and Y2 are the same or different when they appear each time, and Ro is H, a deuterium atom, a cyano group, a fluorine atom, a substituted or unsubstituted C1-C 10 alkyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, 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, phenyl-substituted tert-butyl; In general formula (1-17) to general formula (1-18), each occurrence of V1, which is the same or different, is represented by C-Rt, and Rt is represented by H; R4 represents a phenyl group; In the general formula (1-17), the A1 ring is a phenyl group, and V1 and A1 are connected to form a ring; in the general formula (1-18), V1 and R4 are connected to form a ring; In general formula (1-3) and general formula (1-10), the dotted line indicates a connection; In general formula (1-3), general formula (1-10), general formula (1-17), and general formula (1-18), R1-R3 and X1-X3 have the same meanings as defined in claim 1; The substituent for the substituent group may be selected from one or more of a fluorine atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, and a butyl group.

3. The boron-containing organic compound according to claim 1, characterized in that R1-R3 are each independently H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a 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 tert-phenyl group, a naphthyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino 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, or a phenyl-substituted tert-butyl group; R5 is H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a 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 naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a phenyl-substituted pyridyl group, a phenyl-substituted pyrimidyl group, a quinolyl group, a benzimidazolyl group, a phenyl-substituted benzimidazolyl group, a benzofuranyl group, a dibenzofuranyl group , dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, 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, tert-butyl-substituted phenyl, xanthone, phenyl-substituted triazinyl.

4. The boron-containing organic compound according to claim 2, characterized in that Ro represents one of H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a 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 tert-phenyl group, a naphthyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino 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, and a phenyl-substituted tert-butyl group.

5. The boron-containing organic compound according to claim 1, characterized in that R1 and R2 are independently methyl, isopropyl, tert-butyl, phenyl or naphthyl; R3 is phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano.

6. The boron-containing organic compound according to claim 1, characterized in that R1 and R2 are identical and represent tert-butyl or phenyl; R3 represents phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano; X1 and X3 are each CH; X2 is C-R5; R5 is H, a deuterium atom, a cyano group, an adamantyl group, a fluorine atom, a methyl, a trifluoromethyl, an ethyl, isopropyl, isobutyl, tert-butyl, a 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 naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a phenyl-substituted pyridyl group, a phenyl-substituted pyrimidyl group, a quinoline group The present invention further comprises one of the following: a phenyl group, a benzimidazolyl group, a phenyl-substituted benzimidazolyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuranyl 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 phenyl-substituted tert-butyl group, a xanthone group, and a phenyl-substituted triazinyl group.

7. The boron-containing organic compound according to claim 1, characterized in that R1 and R2 are identical and represent tert-butyl; R3 is phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl, or cyano; and X1, X2, and X3 are all CH.

8. The boron-containing organic compound according to claim 1, characterized in that R3 represents a methyl group.

9. The boron-containing organic compound according to claim 1, characterized in that The specific structure of the organic compound is any one of the following structures:

10. An organic light-emitting device comprising a cathode, an anode, and a functional layer, wherein the functional layer is located between the cathode and the anode, characterized in that: The functional layer of the organic light-emitting device comprises the boron-containing organic compound according to any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10, wherein the functional layer comprises a light-emitting layer, The doping material of the light-emitting layer is the boron-containing organic compound according to any one of claims 1 to 9.

12. The organic light-emitting device according to claim 11, wherein the light-emitting layer comprises a first host material, a second host material and a dopant material, wherein: At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1 to 9.

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