Boron compound for organic electroluminescence, luminescent material, and organic electroluminescence device

Abstract

The present application relates to a kind of boron compounds for organic electroluminescence, light emitting material and organic electroluminescence device, belong to organic electroluminescence device technical field, the boron compounds for organic electroluminescence satisfy any one of the following two conditions: (a) the boron element contained in the boron compounds for organic electroluminescence 10 The atomic abundance of B is 25 atom% or more;(b) the boron element contained in the boron compounds for organic electroluminescence 11 The atomic abundance of B is 83 atom% or more.The present application is by making 10 The atomic abundance of B is 25 atom% or more, can effectively improve the luminous intensity of the organic electroluminescence device subsequently prepared;Or by making 11 The atomic abundance of B is 83 atom% or more, so that the organic electroluminescence device decreases less with driving luminous intensity, i.e. prolong the service life of organic electroluminescence device.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence, specifically to a boron compound for organic electroluminescence, a luminescent material, and an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are self-emissive devices in which electrons injected from the electron injection electrode (cathode) recombine with holes injected from the hole injection electrode (anode) in the emissive layer to form excitons, which emit light while releasing energy. Such OLEDs offer advantages such as low driving voltage, high brightness, wide viewing angle, and short response time, and can be applied to full-color flat panel displays. Due to these advantages, OLEDs have attracted attention as a next-generation light source.

[0003] The emitting layer of an OLED is composed of a host / doped substrate containing a light-emitting material. In such an emitting layer, excitons can be efficiently generated from the charge injected into the host. The energy of the generated excitons can then be transferred to the dopant, resulting in efficient light emission from the dopant.

[0004] Researchers have previously conducted various studies on luminescent layers and continue to search for suitable luminescent materials. For example, in polycyclic aromatic hydrocarbons (PAHs) with multiple aromatic rings linked by boron or oxygen, due to the low aromaticity of the six-membered ring containing heteroatoms, the decrease in the HOMO-LUMO gap is small with the expansion of the conjugated system, resulting in a large band gap Eg. It has been reported that because SOMO1 and SOMO2 are located in the triplet excited state (T1), the exchange interaction between the two orbitals is reduced, leading to a small energy difference between the triplet excited state (T1) and the singlet excited state (S1). PAHs containing heteroatoms exhibit thermally active delayed fluorescence, thereby improving luminescence efficiency. However, existing improvements to luminescent materials are limited, resulting in a small variety of luminescent materials, and further improvements are needed in luminescence brightness or lifespan. Summary of the Invention

[0005] The purpose of this invention is to provide a boron compound for organic electroluminescence, a luminescent material, and an organic electroluminescent device to solve the problems mentioned in the background art.

[0006] To achieve the above objectives, the present invention provides the following technical solution:

[0007] An organic electroluminescent boron compound, wherein the organic electroluminescent boron compound satisfies either of the following two conditions:

[0008] (a) The boron element contained in the organic electroluminescent boron compound. 10The atomic abundance of B is 25 atom% or more, preferably 0 atom% or more, and more preferably 85 atom% or more.

[0009] (b) The boron element contained in the organic electroluminescent boron compound. 11 The atomic abundance of B is 83 atom% or more, preferably 90 atom% or more, and more preferably 95 atom% or more.

[0010] Atomic abundance refers to the ratio of the number of atoms of a specific isotope to the total number of atoms of that element in a mixture of isotopes, expressed as an atomic percentage (atom%). Naturally occurring boron compounds typically contain 19.9% ​​atomic abundance. 10 B, the inventor discovered through research that... 10 The atomic abundance of B makes 10 An atomic abundance of B of 25 atom% or higher can effectively improve the luminous brightness of the subsequently fabricated organic electroluminescent devices; or improve... 11 The abundance of B atoms makes 11 A boron atom abundance of 83% or higher can reduce the decrease in luminous intensity of organic electroluminescent devices as the driving force decreases, thus extending the lifespan of organic electroluminescent devices.

[0011] A luminescent material includes a host material and an organic electroluminescent boron compound as described above. Preferably, the organic electroluminescent boron compound has a mass content of 0.1-20% in the luminescent material.

[0012] As a further technical solution of the present invention, the main material includes anthracene derivatives, and the general structural formula of the anthracene derivatives is shown below:

[0013]

[0014] in,

[0015] Y is an aromatic substituent or a non-aromatic cyclic substituent;

[0016] Cy 2 It is an aryl group having 6 to 12 nuclear carbons, preferably

[0017] An organic electroluminescent device, said organic electroluminescent device being prepared by means of a boron compound for organic electroluminescence as described above or a luminescent material as described above.

[0018] Compared with the prior art, the beneficial effects of the present invention are: by improving... 10 The atomic abundance of B makes 10With an atomic abundance of over 25 atom%, boron can effectively improve the luminous brightness of subsequently fabricated organic electroluminescent devices; or by increasing... 11 The atomic abundance of B makes 11 The atomic abundance of boron is above 83%, which makes the decrease in luminous intensity of organic electroluminescent devices less as the driving force decreases, thus extending the lifespan of organic electroluminescent devices. Attached Figure Description

[0019] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device.

[0020] In the diagram: 1-Anode, 2-Hole injection layer, 3-Hole transport layer, 4-Electron blocking layer, 5-Light emitting layer, 6-Hole blocking layer, 7-Electron transport layer, 8-Electron injection layer, 9-Cathode. Detailed Implementation

[0021] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Where specific conditions are not specified in the embodiments, conventional conditions or conditions recommended by the manufacturer shall apply. Reagents or instruments whose manufacturers are not specified are all conventional products that can be purchased commercially.

[0022] Boron compounds for organic electroluminescence that satisfy either of the following two conditions:

[0023] (1) The boron element contained in the organic electroluminescent boron compound. 10 The atomic abundance of B is 25 atom% or higher; for example, 10 The atomic abundance of B is any value of 25 atom% or higher, such as 25 atom%, 30 atom%, 35 atom%, 40 atom%, 45 atom%, 50 atom%, 55 atom%, 60 atom%, 65 atom%, 70 atom%, 75 atom%, 80 atom%, 85 atom%, 80 atom%, 95 atom%, and 98 atom%, preferably 50 atom% or higher, more preferably 70 atom% or higher, and most preferably 85 atom% or higher;

[0024] (2) The boron element contained in the organic electroluminescent boron compound. 11The atomic abundance of B is 83 atom% or more; the selectable atomic abundances are 83 atom%, 84 atom%, 85 atom%, 86 atom%, 87 atom%, 88 atom%, 89 atom%, 90 atom%, 91 atom%, 92 atom%, 93 atom%, 94 atom%, 95 atom%, 96 atom%, 97 atom%, and 98 atom%, preferably 90 atom% or more, and more preferably 95 atom% or more.

[0025] It should be noted that naturally occurring boron compounds typically contain 19.9% ​​boron. 10 B. However, methods such as chromatography using ion exchange resins can be used to... 10 B and 11 B was separated and concentrated to obtain high atomic abundance. 10 B and 11 B. Alternatively, you can directly purchase existing high atomic abundance products. 10 B element, 10 BF3 or 11 BF3 10 BBr3 or 11 BBr3, for example, Merck's Sigma-Aldrich trading company, product number 601551, with an atomic abundance of 90 atom%. 10 Element B; catalog number 601357, atomic abundance 95%. 10 BF3, catalog number 610011, atomic abundance ≥95%. 11 BF3; catalog number 610038, atomic abundance 98.8%. 11 BF3; CAS number 20654-87-9 11 BBr3; CAS number 28098-24-0 10 BBr3. Alternatively, it can be prepared using the methods described in existing technologies CN109942005, CN109195910A, or CN103950947. 10 BF3 11 BF3 and 11 BCl3, with purities reaching 95.5%, 99.95%, and 99.999%, respectively. Alternatively, B isotopes and BBr3 isotopes can be prepared from elemental B and BF3 using methods described in existing technologies CN103950947 and CN103950949A, such as those described in CN103950947 and CN103950949A.

[0026] Furthermore, the structural formula of the boron compound for organic electroluminescence is either one of the following formulas (1) and (2):

[0027]

[0028] In general formulas (1) and (2),

[0029] X is selected from 10 B or 11 B;

[0030] Y may be the same or different from each other, and each is independently N-R1, CR2R3, O, S, Se or SiR4R5;

[0031] M is CR6R7, N-R8, O, or S;

[0032] Z is CR9 or NR 10 ;

[0033] R1-R 10 They may be identical or different from each other, and each independently comprises any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C5-C30 arylthio, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C5-C30 arylamino, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, nitro, cyano, and halogen; The R1-R 10 Adjacent groups can be linked together in a chemically feasible manner, such as by bonding or fusion, to form a ring.

[0034] Preferably, R1-R 10They may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C28 heteroaryl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C6-C25 aryloxy, substituted or unsubstituted C1-C26 alkylthio, substituted or unsubstituted C5-C25 arylthio, substituted or unsubstituted C1-C25 alkylamino, substituted or unsubstituted C5-C26 arylamino, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C5-C25 arylsilyl, nitro, cyano, and halogen; more preferably, the R1-R 10 Each of the following can be independently substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenanthryl, pyrene, fluorene, pyridyl, pyrimidinyl, pyrimidinyl, triazine, pyrroleyl, indoleyl, carbazolyl, furfural, etc. Any one of the following: alkyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted triazolyl.

[0035] In the above terms, "substitution" means that the hydrogen atom bonded to the carbon atom of the compound becomes another substituent, and there is no restriction on the position of substitution, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same or different from each other; for example, 3-10-membered heteroaryl groups, wherein the heteroatom in the heteroaryl group is selected from one or more of N, S, O, Si, P, Se, C1-C10 alkoxy, and C6-C20 arylamino.

[0036] Furthermore, the structural formula of the boron compound for organic electroluminescence is any one of the following general formulas (1)-1 to (2)-4:

[0037]

[0038] Wherein, Z and R1 are as defined in general formula (1) and general formula (2).

[0039] Furthermore, the structural formula of the boron compound for organic electroluminescence is any one of the following general formulas (1)-1-1 to (2)-4-4:

[0040]

[0041] Wherein, R1 and R8 are as defined in general formula (1) and general formula (2);

[0042] R 11 -R 21 They may be the same as or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthio, substituted or The following groups are included: unsubstituted C5-C30 arylthio groups, substituted or unsubstituted C1-C30 alkylamine groups, substituted or unsubstituted C5-C30 arylamine groups, substituted or unsubstituted C1-C30 alkylsilyl groups, substituted or unsubstituted C5-C30 arylsilyl groups, nitro groups, cyano groups, and halogen groups; adjacent groups in R11-R21 can be linked by chemically feasible bonding or fusion to form a ring.

[0043] Preferably, the R 11 -R 21 Each is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C28 heteroaryl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C6-C25 aryloxy, substituted or unsubstituted C1-C26 alkylthio, substituted or unsubstituted C5-C25 arylthio, substituted or unsubstituted C1-C25 alkylamino, substituted or unsubstituted C5-C26 arylamino, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C5-C25 arylsilyl, nitro, cyano, and halogen; more preferably, the R 11 -R 21Each of the following can be independently substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, anthraquinone, phenanthryl, pyrene, adamantyl, fluorene, pyridyl, pyrimidinyl, pyrimidinyl, triazine, pyrroleyl, indoleyl, carbazolyl, and substituted... Or any one of the following: unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted triazolyl.

[0044] The boron compound for organic electroluminescence is any one of the following compounds 1-216:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051] Wherein, B is 10 B or 11 B.

[0052] In addition, the present invention also provides a luminescent material, which includes a host material and the aforementioned organic electroluminescent boron compound as a dopant, wherein the organic electroluminescent boron compound has a mass content of 0.1-20% in the luminescent material.

[0053] Furthermore, the host material can be any existing host material. As long as the host material minimizes the charge injection barrier from the hole transport layer or electron transport layer, confines the charge to the light-emitting layer, and prevents the quenching of emitted excitons, various known materials can be used as the host material. Preferably, anthracene derivatives are used as the host material in this invention, which can better interact with the boron compound for organic electroluminescence of this invention, thereby improving the performance of the OLED device. The general structural formula of the anthracene derivative is shown below:

[0054]

[0055] in,

[0056] Y is an aromatic substituent or a non-aromatic cyclic substituent;

[0057] Cy 2 It is an aryl group having 6 to 12 nuclear carbons, preferably

[0058] Furthermore, the anthracene derivative is at least one of the following compounds H-1 to H-8:

[0059]

[0060] Furthermore, the mass content of the host material in the luminescent material is 50-99.9 wt%, preferably 80-95 wt%.

[0061] In addition, the present invention also provides an organic electroluminescent device, wherein one or more organic layers are disposed between the electrodes of the organic electroluminescent device. For example, the structure of the organic electroluminescent device is: "anode 1 / hole injection layer 2 / hole transport layer 3 / light emission layer 5 / electron transport layer 7 / electron injection layer 8 / cathode 9", "anode 1 / hole transport layer 3 / light emission layer 5 / electron transport layer 7 / electron injection layer 8 / cathode 9", "anode 1 / hole injection layer 2", "anode 1 / hole injection layer 2 / emitting layer 5 / electron transport layer 7 / electron injection layer 8 / cathode 9", "anode 1 / hole injection layer 2 / hole transport layer 3 / emitting layer 2 / emitting layer 5 / electron transport layer 7 / electron injection layer 8 / cathode 9", "anode 1 / hole injection layer 2 / hole transport layer 3 / emitting layer 2 / emitting layer 2 / emitting layer 3 ... Layer 5 / Electron Injection Layer 8 / Cathode 9", "Anode 1 / Hole Injection Layer 2 / Hole Transport Layer 3 / Emitting Layer 5 / Electron Transport Layer 8 / Cathode 9", "Anode 1 / Light Emitting Layer 5 / Electron Transport Layer 7 / Electron Injection Layer 8 / Cathode 9", "Anode 1 / Transport Layer 3 / Light Emitting Layer 5 / Electron Injection Layer 8 / Cathode 9", "Anode 1 / Hole Transport Layer 3 / Light Emitting Layer 5 / Electron Transport Layer 7 / Cathode 9", "Anode 1 / Hole Injection Layer 2 / Light Emitting Layer 5 / Electron Injection Layer 8 / Cathode 9", "Anode 1 / Hole Injection Layer 2 / Light Emitting Layer 5 / Electron Transport Layer 7 / Cathode 9" or "Anode 1 / Light Emitting Layer 5 / Electron Injection Layer 8 / Cathode 9".

[0062] Furthermore, such as Figure 1 As shown, the organic electroluminescent device is formed by stacking layers in the following order: "Anode 1 / Hole injection layer 2 / Hole transport layer 3 / Electron blocking layer 4 / Light-emitting layer 5 / Hole blocking layer 6 / Electron transport layer 7 / Electron injection layer 8 / Cathode 9". Electron blocking layer 4 and hole blocking layer 6 are added to this structure. The organic layers refer to all layers other than electrodes 1 and 9, namely hole injection layer 2, hole transport layer 3, electron blocking layer 4, light-emitting layer 5, hole blocking layer 6, electron transport layer 7, and electron injection layer 8. The substrate forming the organic electroluminescent device should be transparent and smooth, with a total light transmittance of at least 70%. Specifically, flexible transparent substrates, glass substrates a few micrometers thick, or special transparent plastics are used.

[0063] Thin films, such as anode 1, hole injection layer 2, hole transport layer 3, electron blocking layer 4, light-emitting layer 5, hole blocking layer 6, electron transport layer 7, electron injection layer 8, and cathode 9, are formed on a substrate and stacked by vacuum evaporation or deposition. Vacuum evaporation is typically performed in a reduced pressure atmosphere, usually below 10°C. -3 Pa is used to heat and vaporize the material. The thickness of each layer depends on the type of layer and the material used, but it is usually around 100 nm for anode 1 and cathode 9, and less than 50 nm for other organic layers including light-emitting layer 5.

[0064] For anode 1, materials with high work function and total transmittance of over 80% are typically used. Specifically, to allow light emitted from anode 1 to pass through, transparent conductive ceramics such as indium tin oxide (ITO) and zinc oxide (ZnO), transparent conductive ceramics such as polythiophene-polystyrene sulfonic acid (PEDOT-PSS) and polyaniline, as well as other transparent conductive materials, are used.

[0065] There is a hole injection transport layer 2 or a hole transport layer 3 between the anode and the light-emitting layer 5, so as to effectively transport holes from the anode 1 to the light-emitting layer.

[0066] The hole injection materials forming the hole injection layer 2 include, for example, poly(propylene ether ketone)-containing triphenylamine (KLHIP: PPBI), 1,4,5,8,9,11-hexaazabenzanilic acid (HATCN), and PEDOT-PSS. The hole layer 2 made of these materials is also known as a polymer buffer layer, which can effectively reduce the driving voltage of OLED devices.

[0067] Hole transport layer 3 is disposed between anode 1 and light-emitting layer 5 to effectively transport holes from anode 1 to light-emitting layer. Hole transport materials have a small ionization potential, meaning that electrons are easily excited from HOMO, and holes are easily generated. Examples include: poly(9,9-dioctylfluorene-alt-N-(4-butylphenyl)diphenylamine) (TFB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-di(m-toluene)benzidine (TPD), N,N'-di(1-naphthyl)-N,N'-diphenyl-N,N'-diphenylbenzidine (NPD), 4DBFHPB (hexaphenyl derivative), 4,4',4”-tri-(N-carbazolyl)-triphenylamine (TCTA), and 4,4',4”-tri[phenyl(m-toluene)amino]triphenylamine, etc.

[0068] The light-emitting layer 5 is the same as other light-emitting layers used in OLED devices, but the light-emitting layer 5 in this embodiment of the invention is prepared using the light-emitting material provided in this embodiment of the invention.

[0069] An electron blocking layer 4 can be disposed between the light-emitting layer 5 and the hole transport layer 3. Through the electron blocking layer 4, electrons can be trapped within the light-emitting layer, increasing the probability of charge recombination within the light-emitting layer and improving luminous efficiency. The electron blocking material forming the electron blocking layer 4 can be a monoamine derivative.

[0070] To effectively transport electrons from the cathode 9 to the light-emitting layer 5, a hole-blocking layer 6 and an electron transport layer 7 are disposed between the cathode 9 and the light-emitting layer 5. Electron transport materials forming the electron transport layer 7 include, for example: 1,4-bis(1,10-phenanthroline-2-yl)benzene (DPB), 8-hydroxyquinoline-lithium (Liq), 4,6-bis(3,5-di(pyridin-3-yl)phenyl)-2-methylpyrimidine (B3PymPm), 4,6-bis(3,5-di(pyridin-4-phenyl)-2-phenylpyrimidine (B4PyPm), 2-(4-biphenyl)-5-(p-tert-butylphenyl)-1,3,4-oxadiazole (tBPyPm)-1,3-bis[5-(4-t-butylphenyl)-2]oxadiazole (tBu-BD)-oxadiazolyl]benzene (OXD-7).

[0071] 3-(4-biphenyl-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), basoproline (BCP), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPPi), (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TFBi), and 3-(4-biphenyl)-4-phenyl-phenyl)-1,2,4-triazole (TAZ). Among these, a mixture of DPB and Liq is preferred.

[0072] Hole blocking layer 6 is a layer that confines holes in the light-emitting layer 5 to increase the probability of charge recombination in the light-emitting layer 5 and improve luminous efficiency. DBT-TRZ and other materials are used as hole blocking materials to form hole blocking layer 6. The thickness of hole blocking layer 6 and electron transport layer 7 is typically 3-50 nm and can be varied according to the required design.

[0073] The electron injection materials forming the electron injection layer 8 include, for example, lithium fluoride (LiF) and 2-hydroxy-(2,2')-bispyridyl-6-yl-phenolatrichium (Libpp).

[0074] The cathode 9 should be made of a material with a low work function (less than 4 eV) and stable chemical properties. Specifically, alloys of Al and alkali metals, such as Al-MgAg alloys, or alloys of Al and alkali metals like AlLi and AlCa, can be used. These cathode materials can be deposited by, for example, resistance heating evaporation, electron beam evaporation, sputtering, or ion plating.

[0075] The features and performance of the present invention will be further described in detail below with reference to specific embodiments.

[0076] Example 1

[0077] An organic electroluminescent boron compound, the structural formula of which is shown in Compound 1 below:

[0078]

[0079] In compound 1, B represents atoms with different atomic abundances. 10 B;

[0080] Its preparation method is as follows:

[0081] S1: BF3 and BBr3 with abundances of natural values ​​were purchased from Sigma-Aldrich for future use; and other purchased... 10 BBr3 (CAS number 28098-24-0), 11BBr3 (CAS number 20654-87-9) was used to adjust the atomic abundance to 25 atom%, 40 atom%, 60 atom%, 80 atom%, and 95 atom% respectively through sizing.

[0082] S2: Different Synthetic Methods 10 B atomic abundance and different 11 Boron compounds for organic electroluminescence with B atomic abundance;

[0083] See the following synthesis path:

[0084]

[0085] In a 100 mL reactor, starting material A-1 (50 mmol) and dichloromethane (50 mL) were stirred. The mixture was cooled to -10 °C and a dilute solution of bromine (50 mmol) in dichloromethane (70 mL) was added dropwise. The resulting mixture was stirred at 0 °C for 2 hours. After the reaction was complete, an aqueous solution of sodium thiosulfate was added to the reaction mixture, stirred, and extracted with ethyl acetate and H2O. The organic layer was concentrated under reduced pressure and recrystallized from ethanol to give intermediate 1 (12.63 g, yield 90.87%).

[0086]

[0087] Potassium hydroxide (86.34 mmol) and ethanol (60.00 mL) were dissolved in a 100 mL reactor, and intermediate 1 (43.17 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was refluxed with stirring for 2 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to remove ethanol and extracted with ethyl acetate and water. The organic layer was concentrated and purified by column chromatography to give intermediate 2 (4.22 g, yield 49.63%).

[0088]

[0089] Starting materials B-1 (32.00 mmol), C-1 (32.00 mmol), palladium acetate (2.00 mmol), sodium tert-butoxide (64.00 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (2.00 mmol), and toluene (80.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 3 (5.46 g, yield 83.79%).

[0090]

[0091] Intermediate 3 (20.30 mmol), intermediate 2 (20.30 mmol), palladium acetate (0.20 mmol), sodium tert-butoxide (40.60 mmol), tri-tert-butylphosphine (1.02 mmol), and toluene (80.00 mL) were placed in a 250 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was complete, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 4 (5.63 g, yield 73.66%).

[0092]

[0093] Intermediate 4 (15.64 mmol), starting material C-1 (15.64 mmol), palladium acetate (0.16 mmol), sodium tert-butoxide (31.28 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (0.78 mmol), and toluene (70.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 5 (4.43 g, yield 75.21%).

[0094]

[0095] Intermediate 5 (10.63 mmol), starting material D-1 (10.63 mmol), palladium acetate (0.11 mmol), sodium tert-butoxide (21.26 mmol), tri-tert-butylphosphine (0.53 mmol), and toluene (70 mL) were placed in a 100.00 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 6 (4.74 g, yield 83.94%).

[0096]

[0097] Intermediate 6 (7.53 mmol) and tert-butylbenzene (75.00 mL) were placed in a 100.00 mL reactor, and n-butyllithium (22.59 mmol) was added dropwise at -78 °C. After the addition was complete, the mixture was stirred at 60 °C for 3 hours. The reactor was then purged with nitrogen at 60 °C to remove heptane. Boron tribromide (15.06 mmol) was added dropwise at -78 °C. 10The boron atom abundances were 25, 40, 60, 80, and 95 atom%, respectively. The resulting mixture was stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (15.06 mmol) was added dropwise at 0°C. After the addition was complete, the mixture was stirred at 120°C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added to the reaction mixture at room temperature, stirred, and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography to obtain compound 1. 10 The yields and production volumes of boron compounds for organic electroluminescence with different boron atom abundances are shown in Table 1 below:

[0098] Table 1

[0099] <![CDATA[ 10 B atomic abundance (atom%) 25 40 60 80 95 Yield (%) 15.44 15.51 15.46 15.55 15.40 Yield (g) 0.54 0.50 0.52 0.56 0.53

[0100] Comparative Example 1

[0101] Using naturally abundant BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in Example 1.

[0102] Comparative Example 2

[0103] use 11 The abundance of boron atoms is 95%. 11 BBr3, i.e. 10 The abundance of boron atoms is 5%. 10 Using BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in Example 1.

[0104] Example 2

[0105] An organic electroluminescent boron compound, the structural formula of which is shown in compound 96 below:

[0106]

[0107] In compound 96, B represents atoms with varying atomic abundances. 10 B;

[0108] Its preparation method is as follows:

[0109] S1: BF3 and BBr3 with abundances of natural values ​​were purchased from Sigma-Aldrich for future use; and other purchased... 10 BBr3 (CAS number 28098-24-0), 11 BBr3 (CAS number 20654-87-9) was used to adjust the atomic abundance to 25 atom%, 40 atom%, 60 atom%, 80 atom%, and 95 atom% respectively through sizing.

[0110] S2: Different Synthetic Methods 10 B atomic abundance and different 11 Boron compounds for organic electroluminescence with B atomic abundance;

[0111] See the following synthesis path:

[0112]

[0113] The starting material A-96 (50 mmol) and dichloromethane (60 mL) were stirred in a 1 L reactor; the mixture was cooled to -10 °C and a dilute solution of bromine (50 mmol) in dichloromethane (70 mL) was added dropwise; the resulting mixture was stirred at 0 °C for 2 hours; after the reaction was complete, an aqueous solution of sodium thiosulfate was added to the reaction mixture, stirred, and extracted with ethyl acetate and H2O; the organic layer was concentrated under reduced pressure and recrystallized from ethanol to give intermediate 1 (12.60 g, yield 90.66%).

[0114]

[0115] Potassium hydroxide (86.34 mmol) and ethanol (60.00 mL) were dissolved in a 1 L reactor, and intermediate 1 (43.17 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was refluxed with stirring for 2 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to remove ethanol and extracted with ethyl acetate and water. The organic layer was concentrated and purified by column chromatography to give intermediate 2 (4.22 g, yield 49.59%).

[0116]

[0117] The starting materials B-96 (18.22 mmol), C-96 (18.22 mmol), palladium acetate (1.14 mmol), sodium tert-butoxide (36.44 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (1.14 mmol), and toluene (60.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 3 (4.18 g, yield 83.54%).

[0118]

[0119] Intermediate 3 (14.61 mmol), intermediate 2 (14.61 mmol), palladium acetate (0.15 mmol), sodium tert-butoxide (29.22 mmol), tri-tert-butylphosphine (0.73 mmol), and toluene (70.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was complete, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 4 (4.20 g, yield 73.71%).

[0120]

[0121] Intermediate 4 (10.26 mmol), starting material C-96 (10.26 mmol), palladium acetate (0.10 mmol), sodium tert-butoxide (20.52 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (0.10 mmol), and toluene (60.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 5 (3.76 g, yield 75.11%).

[0122]

[0123] Intermediate 5 (6.14 mmol), starting material D-96 (6.14 mmol), palladium acetate (0.06 mmol), sodium tert-butoxide (12.28 mmol), tri-tert-butylphosphine (0.31 mmol), and toluene (50 mL) were placed in a 100.00 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 6 (3.55 g, yield 83.41%).

[0124]

[0125] Intermediate 6 (4.32 mmol) and tert-butylbenzene (45.00 mL) were placed in a 70.00 mL reactor, and n-butyllithium (12.96 mmol) was added dropwise at -78 °C. After the addition was complete, the mixture was stirred at 60 °C for 3 hours. The reactor was then purged with nitrogen at 60 °C to remove heptane. Boron tribromide (8.64 mmol) was added dropwise at -78 °C. 10After the boron atom abundances were 25, 40, 60, 80, and 95%, the resulting mixture was stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (8.64 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added to the reaction mixture at room temperature, stirred, and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography to give compound 96. 10 The yields and production volumes of boron compounds for organic electroluminescence with different boron atom abundances are shown in Table 2 below:

[0126] Table 2

[0127] <![CDATA[ 10 B atomic abundance (atom%) 25 40 60 80 95 Yield (%) 15.33 15.40 15.30 15.47 15.39 Yield (g) 0.41 0.43 0.40 0.45 0.42

[0128] Comparative Example 3

[0129] Using naturally abundant BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in Example 1.

[0130] Comparative Example 4

[0131] use 11 The boron atom abundance is 95%. 11 BBr3, i.e. 10 The abundance of boron atoms is 5%. 10 Using BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in Example 1.

[0132] Other contents 10 The synthesis of boron compounds is similar to the synthesis methods, processes, and conditions in the above embodiments, and will not be described in detail in the embodiments of the present invention. The synthesis methods of the comparative examples are the same as those of the comparative examples above, and will not be described in detail here.

[0133] Example 3

[0134] An organic electroluminescent boron compound, the structural formula of which is shown in compound 150 below:

[0135]

[0136] In compound 150, B represents atoms of varying abundance. 11 B;

[0137] Its preparation method is as follows:

[0138] S1: BF3 and BBr3 with abundances of natural values ​​were purchased from Sigma-Aldrich for future use; and other purchased... 10 BBr3 (CAS number 28098-24-0),11 BBr3 (CAS No. 20654-87-9), and through proportioning... 11 The abundance of B atoms was adjusted to 83 atom%, 85 atom%, 90 atom%, and 93 atom%, respectively.

[0139] S2: Different Synthetic Methods 10 B atomic abundance and different 11 Boron compounds for organic electroluminescence with B atomic abundance;

[0140] See the following synthesis path:

[0141]

[0142] The starting material A-150 (50 mmol) and dichloromethane (50 mL) were stirred in a 100 mL reactor. The mixture was cooled to -10 °C, and a dilute solution of bromine (50 mmol) in dichloromethane (70 mL) was added dropwise. The resulting mixture was stirred at 0 °C for 2 hours. After the reaction was complete, an aqueous solution of sodium thiosulfate was added to the reaction mixture, stirred, and extracted with ethyl acetate and H2O. The organic layer was concentrated under reduced pressure and recrystallized from ethanol to give intermediate 1 (13.33 g, yield 90.67%).

[0143]

[0144] Potassium hydroxide (88.44 mmol) and ethanol (65.00 mL) were dissolved in a 100 mL reactor, and intermediate 1 (44.22 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was refluxed with stirring for 2 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to remove ethanol and extracted with ethyl acetate and water. The organic layer was concentrated and purified by column chromatography to give intermediate 2 (4.69 g, yield 49.78%).

[0145]

[0146] Starting materials B-150 (17.54 mmol), C-150 (17.54 mmol), palladium acetate (1.10 mmol), sodium tert-butoxide (35.08 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (1.10 mmol), and toluene (60.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 3 (4.97 g, yield 83.55%).

[0147]

[0148] Intermediate 3 (13.28 mmol), intermediate 2 (13.28 mmol), palladium acetate (0.13 mmol), sodium tert-butoxide (26.56 mmol), tri-tert-butylphosphine (0.66 mmol), and toluene (70.00 mL) were placed in a 250 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was complete, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 4 (4.57 g, yield 72.95%).

[0149]

[0150] Intermediate 4 (8.49 mmol), starting material C-150 (8.49 mmol), palladium acetate (0.08 mmol), sodium tert-butoxide (16.98 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (0.08 mmol), and toluene (45.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 5 (3.81 g, yield 74.90%).

[0151]

[0152] Intermediate 5 (5.00 mmol), starting material D-150 (5.00 mmol), palladium acetate (0.05 mmol), sodium tert-butoxide (10.00 mmol), tri-tert-butylphosphine (0.25 mmol), and toluene (40 mL) were placed in a 60.00 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 6 (3.16 g, yield 83.77%).

[0153]

[0154] Intermediate 6 (3.97 mmol) and tert-butylbenzene (40.00 mL) were placed in a 70.00 mL reactor, and n-butyllithium (7.94 mmol) was added dropwise at -78 °C. After the addition was complete, the mixture was stirred at 60 °C for 3 hours. The reactor was then purged with nitrogen at 60 °C to remove heptane. Boron tribromide (7.94 mmol) was added dropwise at -78 °C. 11After the boron atom abundances were 83, 85, 90, and 93%, respectively, the resulting mixture was stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (7.94 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added to the reaction mixture at room temperature, stirred, and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography to give compound 150. 11 The yields and production volumes of boron compounds for organic electroluminescence with different boron atom abundances are shown in Table 3 below.

[0155] Table 3

[0156] <![CDATA[ 11 B atomic abundance (atom%) 83 85 90 93 Yield (%) 15.37 15.28 14.99 15.20 Yield (g) 0.42 0.45 0.41 0.43

[0157] Comparative Example 5

[0158] use 10 The boron atom abundance is 50%. 11 BBr3, i.e. 11 The abundance of boron atoms is 50%. 11 Using BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in the above embodiments.

[0159] Comparative Example 6

[0160] Using naturally abundant BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in Example 3.

[0161] Example 4

[0162] An organic electroluminescent boron compound, the structural formula of which is shown in compound 206 below:

[0163]

[0164] In compound 150, B represents atoms of varying abundance. 11 B;

[0165] Its preparation method is as follows:

[0166] S1: BF3 and BBr3 with abundances of natural values ​​were purchased from Sigma-Aldrich for future use; and other purchased... 10 BBr3 (CAS number 28098-24-0), 11 BBr3 (CAS number 20654-87-9) was used to adjust the atomic abundance to 83 atom%, 85 atom%, 90 atom%, and 93 atom, respectively, through sizing.

[0167] S2: Different Synthetic Methods10 B atomic abundance and different 11 Boron compounds for organic electroluminescence with B atomic abundance;

[0168] See the following synthesis path:

[0169]

[0170] The starting material A-206 (50 mmol) and dichloromethane (100 mL) were stirred in a 200 mL reactor; the mixture was cooled to -10 °C and a dilute solution of bromine (50 mmol) in dichloromethane (80 mL) was added dropwise; the resulting mixture was stirred at 0 °C for 2 hours; after the reaction was complete, an aqueous solution of sodium thiosulfate was added to the reaction mixture, stirred, and extracted with ethyl acetate and H2O; the organic layer was concentrated under reduced pressure and recrystallized from ethanol to give intermediate 1 (15.87 g, yield 89.93%).

[0171]

[0172] Potassium hydroxide (84.98 mmol) and ethanol (60.00 mL) were dissolved in a 100 mL reactor, and intermediate 1 (42.49 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was refluxed with stirring for 2 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to remove ethanol and extracted with ethyl acetate and water. The organic layer was concentrated and purified by column chromatography to give intermediate 2 (5.80 g, yield 50.14%).

[0173]

[0174] The starting materials B-206 (22.78 mmol), C-206 (22.78 mmol), palladium acetate (1.42 mmol), sodium tert-butoxide (45.56 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (1.42 mmol), and toluene (80.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 3 (5.20 g, yield 83.32%).

[0175]

[0176] Intermediate 3 (18.26 mmol), intermediate 2 (18.26 mmol), palladium acetate (0.18 mmol), sodium tert-butoxide (36.52 mmol), tri-tert-butylphosphine (0.91 mmol), and toluene (70.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was complete, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 4 (6.07 g, yield 71.54%).

[0177]

[0178] Intermediate 4 (12.90 mmol), starting material C-206 (12.90 mmol), palladium acetate (0.13 mmol), sodium tert-butoxide (25.80 mmol), bis(diphenylphosphino)-1,1'-binaphthyl (0.13 mmol), and toluene (80.00 mL) were placed in a 100 mL reactor; the mixture was refluxed with stirring for 24 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 5 (5.41 g, yield 74.36%).

[0179]

[0180] Intermediate 5 (8.87 mmol), starting material D-206 (8.87 mmol), palladium acetate (0.09 mmol), sodium tert-butoxide (17.74 mmol), tri-tert-butylphosphine (0.44 mmol), and toluene (70 mL) were placed in a 100.00 mL reactor; the mixture was refluxed with stirring for 5 hours; after the reaction was completed, the reaction mixture was filtered; the filtrate was concentrated and purified by column chromatography to give intermediate 6 (5.15 g, yield 80.76%).

[0181]

[0182] Intermediate 6 (7.00 mmol) and tert-butylbenzene (70.00 mL) were placed in a 100.00 mL reactor, and n-butyllithium (14.00 mmol) was added dropwise at -78 °C. After the addition was complete, the mixture was stirred at 60 °C for 3 hours. The reactor was then purged with nitrogen at 60 °C to remove heptane. Boron tribromide (14.00 mmol) was added dropwise at -78 °C. 11After the boron atom abundances were 83, 85, 90, and 93%, respectively, the resulting mixture was stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (14.00 mmol) was added dropwise at 0 °C. After the addition was complete, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added to the reaction mixture at room temperature, stirred, and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography to give compound 206. 11 The yields and production volumes of boron compounds for organic electroluminescence with different boron atom abundances are shown in Table 4 below.

[0183] Table 4

[0184] <![CDATA[ 11 B atomic abundance (atom%) 83 85 90 93 Yield (%) 14.88 15.00 14.32 14.61 Yield (g) 0.75 0.76 0.73 0.74

[0185] Comparative Example 7

[0186] use 10 The boron atom abundance is 50%. 11 BBr3, i.e. 11 The abundance of boron atoms is 50%. 11 Using BBr3 as a raw material, the same material with the same structural formula as described above was synthesized following the same steps as in Example 4.

[0187] Comparative Example 8

[0188] Using naturally abundant BBr3 as a raw material, substances with the same structural formula were synthesized following the same steps as in Example 4.

[0189] Other contents 10 B. 11 The synthesis of boron compounds B is the same as that in the above embodiments in terms of synthesis method, process and conditions, and will not be described in detail in the embodiments of the present invention; the corresponding comparative examples are also synthesized in the same way as those in the above comparative examples, and will not be described in detail here.

[0190] Application Example 1

[0191] An organic electroluminescent device, the structure of which is: ITO anode / HIL / HTL / EML / ETL / EIL / cathode / light extraction layer; includes the following steps:

[0192] a. ITO anode: The coating thickness is... The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate was cleaned twice in distilled water, ultrasonically washed for 30 minutes, then repeatedly cleaned twice in distilled water, ultrasonically washed for 10 minutes. After washing, it was ultrasonically washed sequentially with methanol, acetone and isopropanol (5 minutes each time), dried, and then transferred to a plasma cleaner for 5 minutes. It was then sent to a vapor deposition machine, where other functional layers were sequentially vapor deposited on the substrate as the anode.

[0193] b. HIL (Hole Injection Layer): The evaporation rate of the vacuum evaporation hole injection layer material HT-1 and P-dopant is as follows; the evaporation rate ratio of HT-1 and P-dopant is 97:3, and the thickness is 10nm.

[0194] c. HTL (Hole Transport Layer): At the evaporation rate, HT-1 of 130 nm was vacuum-deposited on the hole injection layer as a hole transport layer.

[0195] d. EML (Emitting Layer): The evaporation rate, the vacuum evaporation thickness of the host material (H-3) and the doped material (prepared in Example 1) with a thickness of 20 nm. 10 Compound 1) with a boron atom abundance of 25% is used as the luminescent layer, and the chemical formula of its H-3 is shown below; wherein the evaporation rate ratio of H-3 to the dopant material is 98:2;

[0196] e. HB (hole blocking layer): with The evaporation rate was such that HB with a thickness of 5.0 nm was vacuum-deposited as a hole-blocking layer.

[0197] f. ETL (Electron Transport Layer): The evaporation rate was determined by vacuum evaporation of ET-1 and Liq with a thickness of 35 nm as electron transport layers. The chemical formula of ET-1 is shown below. The evaporation rate ratio of ET-1 to Liq is 50:50.

[0198] g. EIL (Electron Injection Layer): with The evaporation rate was such that a Yb film layer of 1.0 nm was deposited to form an electron injection layer;

[0199] h, Cathode: with The evaporation rate ratio of magnesium and silver at 18nm was 1:9, resulting in an OLED device.

[0200] i. Optical extraction layer: with The evaporation rate was used to vacuum evaporate a 70 nm thick CPL-1 layer on the cathode as a light extraction layer.

[0201] j. Subsequently, the substrate after vapor deposition is packaged. First, the cleaned cover plate is coated with UV adhesive using an adhesive coating equipment. Then, the coated cover plate is moved to the pressing section, the vapor-deposited substrate is placed on the top of the cover plate, and finally the substrate and cover plate are bonded together under the action of the bonding equipment, while the UV adhesive is cured by light.

[0202] The raw materials used in the above preparation method are as follows:

[0203]

[0204] The differences in Example 1 10 Organic electroluminescence with B atomic abundance was used to replace the components in Application Example 1 above with boron compounds. 10 A series of organic electroluminescent devices were obtained using a boron compound with a boron atom abundance of 25% for organic electroluminescence, under the same conditions as described above. 10 The organic electroluminescent devices prepared from boron compounds for organic electroluminescence in Example 1, with atomic abundances of 25 atom%, 40 atom%, 60 atom%, 80 atom%, and 95 atom%, are labeled as 1- 10 B-25, 1- 10 B-40, 1- 10 B-60, 1- 10 B-80, 1- 10 B-95.

[0205] Application Example 2

[0206] Using the same method and conditions as Application Example 1 above, except that the doped material (Example 1) is replaced with that of Example 2 above. 10 A series of organic electroluminescent devices were prepared using boron compounds of the B-series organic electroluminescence. 10 The organic electroluminescent devices prepared from boron compounds for organic electroluminescence in Examples 2, with atomic abundances of 25 atom%, 40 atom%, 60 atom%, 80 atom%, and 95 atom%, are labeled as 2- 10 B-25, 2- 10 B-40, 2- 10 B-60, 2- 10 B-80, 2- 10 B-95.

[0207] Application Example 3

[0208] Using the same method and conditions as Application Example 1 above, except that the doped material (Example 1) is replaced with that of Example 3 above. 11A series of organic electroluminescent devices were prepared using boron compounds of the B-series organic electroluminescence. 11 The organic electroluminescent devices prepared from boron compounds for organic electroluminescence in Examples 3, with atomic abundances of 83, 85, 90, and 93%, are labeled as 3- 11 B-83, 3- 11 B-85, 3- 11 B-90, 3- 11 B-93.

[0209] Application Example 4

[0210] Using the same method and conditions as Application Example 1 above, except that the doped material (Example 1) is replaced with that of Example 4 above. 11 A series of organic electroluminescent devices were prepared using boron compounds of the B-series organic electroluminescence. 11 The organic electroluminescent devices prepared from boron compounds in Examples 4, with atomic abundances of 83, 85, 90, and 93%, are labeled as 4- 11 B-83, 4- 11 B-85, 4- 11 B-90, 4- 11 B-93.

[0211] Compare with Example 1

[0212] Comparative Example 1 was used to prepare a naturally abundant organic electroluminescent boron compound instead of the one used in Example 1 above. 10 A boron compound with a boron atom abundance of 25% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 1- 10 B-nature, at this time, is also 11 Organic electroluminescent devices prepared from boron compounds with natural abundance of B.

[0213] Compare with Example 2

[0214] Prepared using Comparative Example 2 10 Organic electroluminescence with a boron atom abundance of 5% was used instead of the boron compound described in Example 1 above. 10 A boron compound with a boron atom abundance of 25% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 1- 10 B-5.

[0215] Compare with Example 3

[0216] Comparative Example 3 was used to prepare a naturally abundant organic electroluminescent boron compound instead of the one used in Example 2 above.10 A boron compound with a boron atom abundance of 25% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 2- 10 B-nature, at this time, is also 11 Organic electroluminescent devices prepared from boron compounds with natural abundance of B.

[0217] Compare with Example 4

[0218] Prepared using Comparative Example 4 10 Organic electroluminescence with a boron atom abundance of 5% was used instead of the boron compound described in Example 2 above. 10 A boron compound with a boron atom abundance of 25% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 2- 10 B-5.

[0219] Compare with Example 5

[0220] Prepared using Comparative Example 5 11 Organic electroluminescence with a boron atom abundance of 50% was used instead of the boron compound described in Example 3 above. 11 A boron compound with a boron atom abundance of 83% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 3- 11 B-50.

[0221] Compare with Example 6

[0222] Prepared using Comparative Example 6 11 Organic electroluminescence with a boron atom abundance of natural abundance was used instead of the boron compound described in Example 6 above. 11 A boron compound with a boron atom abundance of 83% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 3- 11 B-nature.

[0223] Compare with Example 7

[0224] Prepared using Comparative Example 7 11 Organic electroluminescence with a boron atom abundance of 50% was used instead of the boron compound described in Example 4 above. 11 A boron compound with a boron atom abundance of 83% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 4- 11 B-50.

[0225] Compare with Example 8

[0226] Prepared using Comparative Example 8 11 Organic electroluminescence with a boron atom abundance of natural abundance was used instead of the boron compound described in Example 4 above. 11A boron compound with a boron atom abundance of 83% was used, and an organic electroluminescent device was then prepared according to the same method and conditions described above; this device is labeled as 4- 11 B-nature.

[0227] The driving voltage, luminous efficiency, BI value and lifetime of the organic electroluminescent devices obtained in Application Examples 1-4 and Comparative Examples 1-8 were characterized at a brightness of 1000 nits. The test results are shown in Table 5 below.

[0228] Table 5

[0229]

[0230]

[0231] By comparing Application Examples 1 and 2 with Comparative Examples 1 to 4 in Table 5, it can be seen that the organic electroluminescent device prepared using the organic electroluminescent boron compound of the present invention as the blue light doping material, wherein... 10 The higher the abundance of boron atoms, the higher the luminous efficiency. A comparison of Application Examples 3 and 4 with Comparative Examples 5 to 8 in Table 5 shows that the organic electroluminescent devices prepared using the organic electroluminescent boron compound of this invention as the blue light doping material exhibit higher luminous efficiency. 11 The higher the abundance of boron atoms, the longer the lifespan of the corresponding device.

[0232] The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention. Therefore, the invention is not to be limited to the embodiments shown herein, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A boron compound for organic electroluminescence, characterized in that, The general structural formula of the boron compound for organic electroluminescence is either one of the following general formulas (1) and (2): ； In general formulas (1) and (2), X is selected from 10 B or 11 B; Y is N-R1; M is N-R8, O, or S; Z is CR9; R1, R8-R9 are each independently one of hydrogen, C1-C15 alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl. The boron compound for organic electroluminescence satisfies either of the following two conditions: (a) The boron element contained in the organic electroluminescent boron compound. 10 The atomic abundance of B is above 25 atom%. (b) The boron element contained in the organic electroluminescent boron compound. 11 The atomic abundance of B is above 83 atom%.

2. The boron compound for organic electroluminescence according to claim 1, characterized in that, The boron compound for organic electroluminescence satisfies either of the following two conditions: (a) The boron element contained in the organic electroluminescent boron compound. 10 The atomic abundance of B is above 50 atom%. (b) The boron element contained in the organic electroluminescent boron compound. 11 The atomic abundance of B is over 90%.

3. The boron compound for organic electroluminescence according to claim 1, characterized in that, The boron compound for organic electroluminescence satisfies either of the following two conditions: (a) The boron element contained in the organic electroluminescent boron compound. 10 The atomic abundance of B is above 85 atom%. (b) The boron element contained in the organic electroluminescent boron compound. 11 The atomic abundance of B is over 95%.

4. The boron compound for organic electroluminescence according to claim 1, characterized in that, The structural formulas of the boron compounds used for organic electroluminescence are as follows: general formulas (1)-1 to (1)-3, and any one of general formulas (2)-1 to (2)-3: ； Wherein, Z and R1 are defined as in general formula (1) and general formula (2).

5. A boron compound for organic electroluminescence, characterized in that, The boron compound for organic electroluminescence is any one of the following compounds: ； ； ； ； ； ； Wherein, B is 10 B or 11 B; and the boron element contained in the organic electroluminescent boron compound. 10 The atomic abundance of B is 25 atom% or higher, and the boron element contained in the organic electroluminescent boron compound is... 11 The atomic abundance of B is above 83 atom%.

6. A luminescent material, comprising a host material, characterized in that, The luminescent material further includes the boron compound for organic electroluminescence as described in claim 1 or 5.

7. The luminescent material according to claim 6, characterized in that, The boron compound used for organic electroluminescence has a mass content of 0.1-20% in the luminescent material.

8. The luminescent material according to claim 6, characterized in that, The main material includes anthracene derivatives, and the general structural formula of the anthracene derivatives is shown below: ； in, Y is an aromatic substituent or a non-aromatic cyclic substituent; Cy 2 It is an aryl group with 6 to 12 nuclear carbons.

9. The luminescent material according to claim 8, characterized in that, The Cy 2 for or Any one of them.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device is prepared using the organic electroluminescent boron compound as described in claim 1 or 5, or the luminescent material as described in any one of claims 6-9.

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