Boron-containing organic compound and organic electroluminescent device containing same

Abstract

The invention provides a boron-containing organic compound and an organic electroluminescent device containing the same, and the structural general formula of the boron-containing organic compound is a chemical formula I. The boron-containing organic compound provided by the invention is used as a doping material of a luminescent layer in the organic electroluminescent device, so that the device has low driving voltage and also has high luminous efficiency. And the light-emitting efficiency and the service life are excellent.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence, and relates to a boron-containing organic compound and an organic electroluminescent device containing the same. Background Technology

[0002] Organic Light Emission Diodes (OLEDs) technology can be used to manufacture novel display products and lighting products, and it holds promise as a replacement for existing liquid crystal displays and fluorescent lighting, with a wide range of applications. OLEDs have a sandwich-like structure, consisting of electrode material layers and organic functional materials sandwiched between them. These various functional materials are stacked together according to their intended use to form the OLED device. As a current-carrying device, when a voltage is applied to the two electrodes of the OLED, and an electric field is used to act on the positive and negative charges in the organic functional material layers, these charges recombine in the light-emitting layer, thus generating OLED electroluminescence.

[0003] As OLED technology continues to advance in both lighting and display fields, research into its core materials is receiving increasing attention. This is because a high-efficiency, long-life OLED device is typically the result of an optimized combination of device structure and various organic materials. This presents chemists with both significant opportunities and challenges in designing and developing functionalized materials with diverse structures. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and doped materials.

[0004] To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and fabrication process of OLED devices, but also to continuously research and innovate the optoelectronic functional materials in OLED devices to prepare functional materials with higher performance. Based on this, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve devices with low driving voltages, high luminous efficiency, and better lifespans. Summary of the Invention

[0005] In view of the shortcomings of the prior art, the purpose of this invention is to provide a boron-containing organic compound and an organic electroluminescent device containing the same.

[0006] To achieve this objective, the present invention adopts the following technical solution:

[0007] On one hand, the present invention provides a boron-containing organic compound, the general structural formula of which is chemical formula I:

[0008]

[0009] in,

[0010] The ring H represents a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl group, and the ring H is fused to the benzene ring.

[0011] Z1 and Z2 are each independently selected from direct bonding, BR1, CR2R3, NR4, O, PR5, SiR6R7, GeR8R9, S, CO, SO2 or represent non-existence, and at least one of Z1 and Z2 represents non-existence;

[0012] R1-R9 are independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, wherein the heteroatom contains at least one of O, S, N, Si, Se or B.

[0013] R2 and R3, R6 and R7, R8 and R9 can be connected to each other to form a loop;

[0014] Ra, Rb, Rc, and Rd are each independently selected from hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano, trifluoromethyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C2-C30 boraneyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, wherein the heteroatom contains at least one of O, S, N, Si, Se, and B;

[0015] Multiple Ra exist independently, or two adjacent Ra are connected to form a ring;

[0016] m and n are integers selected from 1, 2, and 3;

[0017] p is an integer selected from 1 and 2;

[0018] Re is independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C2-C30 boraneyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, wherein the heteroatom contains at least one of O, S, N, Si, Se, and B;

[0019] The substituent groups in the above-mentioned substituted or unsubstituted groups are selected from any one or a combination of at least two of the following: deuterium atom, tritium atom, halogen atom, cyano, TMS, trifluoromethyl, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, deuterated C6-C30 aryl, C2-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0020] In this invention, at least one of Z1 and Z2 indicates that it does not exist. When it does not exist, it means that there is no connection here.

[0021] Preferably, the boron-containing organic compound has the structure shown in any one of the following chemical formulas IA to IC:

[0022] .

[0023] More preferably, R1-R9 are independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, or substituted or unsubstituted quinolinyl. Substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazine.

[0024] Further preferably, Ra, Rb, Rc, and Rd are each independently selected from hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, and substituted or unsubstituted pyridine group. The group includes substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, and substituted or unsubstituted triazineyl.

[0025] More preferably, Re is independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted trimethylsilane, substituted or unsubstituted pyridyl, substituted or unsubstituted Quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazine.

[0026] More preferably, the substituent groups in the above-mentioned substituted or unsubstituted groups are selected from one or a combination of at least two of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, TMS (trimethylsilyl), adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azephenanthreneyl.

[0027] The aforementioned boron-containing organic compounds are further preferably those having the structure shown in any one of the following chemical formulas I-1 to I-24:

[0028] .

[0029] More preferably, Rd and Re are independently represented as one or a combination of at least two of the following groups:

[0030]

[0031] * Represents the linking site of a functional group.

[0032] In the above technical solution, it is further preferred that the boron-containing organic compound is any one of the following compounds, but not limited thereto:

[0033]

[0034] Where D represents deuterium.

[0035] The boron-containing organic compounds of the present invention can be prepared by synthetic methods known to those skilled in the art. Alternatively, the following reaction process is preferred for preparation.

[0036]

[0037] In the above formula, Ra - Re, m, n, p, Z1, Z2, and H are as defined in the above chemical formula I.

[0038] In contrast to the complex raw materials that are not publicly available, the synthesis will be carried out using classic Suzuki coupling reaction, Friedel-Crafts reaction, Ullmann-type amination reaction, substitution reaction, Kulinkovich reaction, etc., and will be applied in this invention.

[0039] Specific preparation method:

[0040] Step 1 specifically includes the following processes:

[0041] Add raw material A (1.0 eq), raw material B (1.5 eq), Ti(OiPr)4 (1.0 eq), c-C5H9MgCl (2.0 eq) and diethyl ether to a reaction flask, and carry out the reaction at -30℃ under nitrogen protection. Detect the reaction by thin-layer chromatography, then add hydrochloric acid to quench the reaction and stir for 0.5-1 hours to obtain intermediate 1.

[0042] Step 2 specifically includes the following processes:

[0043] Intermediate 1 (1.0 eq), KF (3.0 eq), 18-crown-6 (2.0 eq), and anhydrous acetonitrile were added to a reaction flask, followed by starting material C-1 (1.0 eq). The mixture was stirred at room temperature for 12 h (5-15 h) under nitrogen protection. The reaction was confirmed to be complete by thin-layer chromatography. Hydrochloric acid was then added to the reaction solution, and the mixture was stirred at room temperature for 3 hours. The solution was then neutralized with saturated dichloroethane and extracted with ethyl acetate. The combined organic phases were concentrated. Intermediate 2 was obtained by column chromatography using a mixed solution of petroleum ether and ethyl acetate (V:V = 100:1-150:1).

[0044] Step 4 specifically includes the following processes:

[0045] Intermediate 2 (1.0 eq) was dissolved in tert-butylbenzene and stirred at -40°C for 30 minutes under nitrogen protection. Tert-butyllithium (2.0 eq) was then injected, and the reaction was allowed to proceed for 1 hour. The temperature was then raised to 60°C and reacted for 2 hours. Vacuum was then applied to remove a small amount of n-pentane. The reaction mixture was then cooled to -40°C, and boron tribromide (2.0 eq) was added dropwise. The mixture was stirred at room temperature for 0.5 hours. The reaction mixture was then cooled to 0°C, and N,N-diisopropylethylamine (5.0 eq) was added and slowly restored to room temperature. The reaction mixture was then heated to 100°C and reacted for 2 hours, followed by cooling to room temperature. A saturated sodium carbonate aqueous solution was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated by vacuum distillation and purified by column chromatography using a mixture of dichloromethane and petroleum ether (V:V = 1:5-1:20) (simultaneously removing isomers generated during the reaction) to obtain chemical formula I.

[0046] Another object of the present invention is to provide an organic electroluminescent device, comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising a light-emitting layer, the light-emitting layer comprising a host material and a dopant material, the dopant material being a boron-containing organic compound as described above.

[0047] Preferably, the organic layer further includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, and a hole blocking layer.

[0048] The organic material layer of the organic light-emitting device of the present invention can be formed as a single-layer structure, but it can also be formed as a multilayer structure with one or more organic material layers. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, etc., as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it can include fewer or more organic material layers.

[0049] Except for the doped material layer containing chemical formula I, there are no special restrictions on other layer materials in OLED devices.

[0050] The devices described in this invention can be used in organic light-emitting devices, including but not limited to flat panel displays, computer monitors, medical monitors, televisions, billboards, lamps for internal or external lighting and / or signals, head-up displays, fully transparent or partially transparent displays, flexible displays, laser printers, telephones, mobile phones, photo albums, personal digital assistants (PDAs), wearable devices, laptops, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays tiled together, theater or stadium screens, phototherapy devices, and signs.

[0051] Compared with the prior art, the present invention has the following beneficial effects:

[0052] The boron-containing organic compound provided by this invention serves as a dopant material for the light-emitting layer in organic electroluminescent devices, enabling the devices to exhibit both low driving voltage and excellent luminous efficiency and lifespan. The compound is a novel structural compound formed by further fused aryl groups into a boron- and nitrogen-containing polycyclic structure. Firstly, the strong electron push-pull effect between the outer nitrogen (D) and boron-nitrogen core (A) results in the HOMO being distributed on the donor (nitrogen-containing five-membered ring), while the LUMO is mainly distributed on the acceptor (boron-nitrogen host core). This high spatial separation of the HOMO and LUMO significantly reduces ΔE. st This allows triplet excitons to efficiently return to the singlet state and emit light via reverse system-reverse crossover (RISC), effectively improving exciton utilization. Furthermore, this DA structure typically possesses a rigid fused-ring framework, which effectively suppresses non-radiative transitions caused by molecular vibrations and rotations, further enhancing luminescence efficiency. The presence of donor and acceptor units enables the molecule to simultaneously possess the ability to transport holes (contributed by the donor) and electrons (contributed by the acceptor). This bipolar characteristic facilitates a balance between hole and electron injection and transport in OLED devices, thereby improving device efficiency.

[0053] Secondly, in the compound of this invention, an additional phenyl or naphthyl group is fused to the phenyl group fused above the five-membered ring on the right side, which significantly expands the conjugated system, resulting in better charge transport capability and effectively improving the luminous efficiency of the device. At the same time, it enhances molecular rigidity, improves planarity, and enhances optical and thermal stability, which helps to improve the lifespan of the device. Attached Figure Description

[0054] Figure 1 This is the 1H NMR spectrum of compound 121 provided in Example 1 of this invention. Detailed Implementation

[0055] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0056] Additionally, it should be noted that the values ​​given in the following embodiments are as accurate as possible. However, those skilled in the art will understand that due to unavoidable measurement errors and experimental issues, each number should be understood as an approximation rather than an absolutely accurate value.

[0057] In the following sections, the synthetic methods of the above-described compounds will be described by representative examples. However, the synthetic methods of the compounds of the present invention are not limited to those illustrated below; the compounds of the present invention can be prepared by the illustrated methods and methods known in the art.

[0058] Example 1

[0059]

[0060] Since intermediate c-121 (corresponding to raw material A in the general formula) is not a prior art, it needs to be synthesized first, as shown in step 1 below.

[0061] Step 1 specifically includes the following processes:

[0062] In a reaction flask, starting material a-121 (1.0 eq, CAS No.: 1181972-60-0), starting material b-121 (1.0 eq, CAS No.: 425379-16-4), Cs2CO3 (2 eq), and DMF (N,N-dimethylformamide) were added, and the reaction was carried out at 150 °C for 5 h under nitrogen protection. After the reaction was completed by thin-layer chromatography, ethyl acetate and water were added for extraction and separation. The organic layer was concentrated, and purified by column chromatography using a mixed solution of ethyl acetate and cyclohexane (V:V=1:7) to obtain intermediate c-121 (yield: 69.7%).

[0063] Step 2 specifically includes the following processes:

[0064] In a reaction flask, starting material B-121 (1.0 eq, CAS No.: 1750-36-3), intermediate a-121 (1.5 eq), Ti(OiPr)4 (1.0 eq), c-C5H9MgCl (2.0 eq) and diethyl ether were added. The reaction was carried out at -30°C under nitrogen protection. The reaction was detected by thin-layer chromatography. Hydrochloric acid was added to quench the reaction and the mixture was stirred for 0.5 hours to obtain intermediate 1-121 (yield: 23.5%).

[0065] Step 3 specifically includes the following processes:

[0066] Intermediate 1-121 (1.0 eq), KF (3.0 eq), 18-crown-6 (2.0 eq), and anhydrous acetonitrile were added to a reaction flask, followed by starting material C-121 (1.0 eq, CAS No.: 780820-43-1). The reaction mixture was stirred at room temperature for 12 h (5-15 h) under nitrogen protection. The reaction was confirmed to be complete by thin-layer chromatography. Hydrochloric acid was then added to the reaction mixture, and after stirring at room temperature for 3 hours, the mixture was neutralized with saturated dichloroethane and extracted with ethyl acetate. The combined organic phases were concentrated. Intermediate 2-121 (yield: 52.4%) was purified by column chromatography using a mixed solution of petroleum ether and ethyl acetate (V:V = 100:1).

[0067] Step 4 specifically includes the following processes:

[0068] Intermediate 2-121 (1.0 eq) was dissolved in tert-butylbenzene and stirred at -40°C for 30 minutes under nitrogen protection. Tert-butyllithium (2.0 eq) was then injected, and the reaction was continued for 1 hour. The temperature was then raised to 60°C and reacted for 2 hours. Vacuum was then applied to remove a small amount of n-pentane, and the reaction mixture was lowered to -40°C. Boron tribromide (2.0 eq) was added dropwise, and the mixture was stirred at room temperature for 0.5 hours. The reaction mixture was then cooled to 0°C, N,N-diisopropylethylamine (5.0 eq) was added, and the mixture was slowly restored to room temperature. The reaction mixture was then heated to 100°C and reacted for 2 hours, followed by cooling to room temperature. A saturated sodium carbonate aqueous solution was added dropwise to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated by vacuum distillation and purified by column chromatography using a mixture of dichloromethane and petroleum ether (V:V = 1:7) (simultaneously removing isomers generated during the reaction) to give compound 121 (yield: 31.3%).

[0069] The obtained compound 121 was analyzed, and the results are as follows:

[0070] HPLC purity: >99.5%.

[0071] Mass spectrometry test: Waters XEVO TQD mass spectrometer with ESI source.

[0072] Test value MS(ESI, m / Z): [M+H] + =698.83

[0073] Elemental analysis:

[0074] The calculated values ​​are: C, 87.70; H, 5.20; B, 3.10; N, 4.01;

[0075] The test values ​​are: C, 87.34; H, 5.30; B, 3.19; N, 4.22.

[0076] The proton NMR spectrum of compound 121 is as follows: Figure 1 As shown.

[0077] In addition, it should be noted that other compounds of the present invention can be obtained by referring to the synthesis methods of the embodiments listed above, so they will not be listed one by one here.

[0078] The following detailed description, in conjunction with specific embodiments, illustrates an organic electroluminescent composition and an organic electroluminescent device provided by the present invention.

[0079] Device Example 1: Fabrication of Green Organic Light Emitting Device

[0080] The structure of the fabricated OLED device is: ITO anode / HIL / HTL / Prime / EML / HBL / ETL / EIL / cathode / CPL.

[0081] a. ITO anode: The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 1500 Å was cleaned three times in distilled water and ultrasonically washed for 40 min. Then it was cleaned three times in distilled water and ultrasonically washed for 20 min. After washing, it was ultrasonically washed sequentially with methanol, acetone and isopropanol (5 min each time). After drying, it was transferred to a plasma cleaner for 5 min and then sent to a vapor deposition machine. Using this substrate as the anode, other functional layers were sequentially vapor deposited on it.

[0082] b. HIL (Hole Injection Layer): Hole injection layer materials HT and P-dopant are vacuum-deposited at a deposition rate of 1 Å / s, wherein the deposition rate ratio of HT to P-dopant is 97:3, and the thickness is 10 nm.

[0083] c. HTL (Hole Transport Layer): A 130 nm thick HT layer is vacuum-deposited on top of the hole injection layer at a deposition rate of 1.5 Å / s as the hole transport layer.

[0084] d. Prime (light-emitting auxiliary layer): A 40 nm Prime layer was vacuum-deposited on the hole transport layer at a deposition rate of 1.0 Å / s as a light-emitting auxiliary layer.

[0085] e. EML (Emitting Layer): Then, on the above-mentioned emitting auxiliary layer, a emitting layer with a thickness of 30 nm is vacuum-deposited at a deposition rate of 1 Å / s. Host-1 and Host-2 are used as host materials, compound 121 provided in the above embodiment is used as a dopant, and GD-1 (Irppy) is used as a sensitizer. The mass ratio of host materials (Host-1 and Host-2), GD-1 and compound 121 is 89:10:1, wherein the deposition rate ratio of Host-1 and Host-2 is 50:50.

[0086] f. HBL (hole blocking layer): A hole blocking layer HB with a thickness of 5 nm is vacuum-deposited at a deposition rate of 0.5 Å / s.

[0087] g. ETL (Electron Transport Layer): ET and Liq layers with a thickness of 30 nm were vacuum-deposited at a deposition rate of 1 Å / s. The deposition rate ratio of ET to Liq was 50:50.

[0088] h. EIL (Electron Injection Layer): A 1 nm Yb film is deposited at a deposition rate of 0.5 Å / s to form the electron injection layer.

[0089] i. Cathode: Magnesium and silver are deposited at a deposition rate of 1 Å / s for 13 nm, with a deposition rate ratio of 1:9, to obtain the OLED device.

[0090] j. CPL (Optical Extraction Layer): A CPL with a thickness of 65 nm is vacuum-deposited on the cathode at a deposition rate of 1 Å / s as the optical extraction layer.

[0091] k. Subsequently, the vapor-deposited substrate is encapsulated. First, the cleaned cover plate is coated with UV adhesive using an adhesive coating equipment. Then, the coated cover plate is moved to the lamination section, and the vapor-deposited substrate is placed on the top of the cover plate. Finally, the substrate and cover plate are laminated under the action of the lamination equipment, while the UV adhesive is cured by light.

[0092] The structures of HT, P-dopant, Host-1, Host-2, GD-1, Prime, HB, ET, and CPL used in Embodiment 1 of the above device are shown below:

[0093] .

[0094] Referring to the method provided in Device Example 1 above, the corresponding compounds in Table 1 were selected to replace compound 121, and the doped material layer was deposited by vapor deposition to prepare the corresponding organic electroluminescent devices, which are respectively referred to as Device Examples 2-208.

[0095] Device Comparison Example 1-17:

[0096] This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses the existing comparative compound aq instead of the first dopant material (compound 121) in device example 1 for vapor deposition. The chemical structural formula of the comparative compound aq is as follows:

[0097]

[0098] At a brightness of 15000 nits, the driving voltage, luminous efficiency, and lifespan of the organic electroluminescent devices obtained in Device Examples 1-208 and Device Comparative Examples 1-17 were tested. The test results are shown below.

[0099] Table 1

[0100]

[0101] As can be seen from Table 1, the metal compounds in this invention have excellent light-emitting properties, and the organic electroluminescent devices prepared with them have better driving voltage, luminous efficiency and lifetime. Compared with the organic electroluminescent devices prepared with the comparative compounds, the performance is significantly improved.

[0102] Generally speaking, a 10% improvement in device lifetime is considered a significant performance improvement in the field, with an efficiency increase of more than 5%, which is considered a significant improvement in efficiency.

[0103] In the green light device of this invention, the luminous efficacy of the compound device is 156.6-164.5 cd / A, and the lifetime is 833-898 h. In contrast, the luminous efficacy of the comparative compound device is 138.7-148.4 cd / A, and the lifetime is 675-715 h. The efficiency improvement is at least 5.53%, and the lifetime improvement is at least 16.50%. Therefore, the compound device of this invention represents a significant advancement in luminous efficacy and lifetime compared to existing technologies.

[0104]

[0105] Comparative compounds a and b and compounds 122 and 1 are parallel comparative examples. The difference is that in comparative compounds a and b, only a phenyl group is fused above the five-membered ring on the right side of the parent nucleus, while in compounds 122 and 1 of this invention, a naphthyl group is fused above the five-membered ring on the right side of the parent nucleus. This significantly expands the conjugated system, resulting in better charge transport capability and effectively improving the luminous efficiency of the device. At the same time, it enhances molecular rigidity, improves planarity, and enhances optical and thermal stability, which helps to extend the lifespan of the device.

[0106]

[0107] Comparative examples e, g, h, i and compounds 81, 175, 128, 212 are parallel comparative examples. The difference lies in the location of the nitrogen on the right five-membered ring of the right parent nucleus in comparative compounds e, g, h, i, while in the compounds of this invention, the nitrogen on the right five-membered ring of the parent nucleus is on the outside. Due to the strong electron push-pull effect between the outer nitrogen (D) and the boron-nitrogen core (A), the HOMO is distributed on the donor (nitrogen-based five-membered ring), while the LUMO is mainly distributed on the acceptor (boron-nitrogen main nucleus). This high spatial separation of HOMO and LUMO significantly reduces ΔE. st This allows triplet excitons to efficiently return to the singlet state and emit light via reverse system-reverse crossover (RISC), effectively improving exciton utilization. Small ΔE st The efficient RISC process means that triplet excitons are not wasted and can be effectively recycled for luminescence, thus significantly improving the material's luminescence quantum yield. Furthermore, this DA structure typically has a rigid fused-ring framework, which effectively suppresses non-radiative transitions caused by molecular vibration and rotation, further improving luminescence efficiency. The stronger the electron-donating ability of the donor (outer nitrogen), the higher the HOMO level is raised, thereby narrowing the band gap between HOMO and LUMO. According to the formula E=hc / λ, the smaller the band gap, the lower the emitted photon energy and the longer the wavelength (redshift). The presence of donor and acceptor units allows the molecule to simultaneously possess the ability for hole transport (contributed by the donor) and electron transport (contributed by the acceptor). This bipolar characteristic is beneficial for balancing hole and electron injection and transport in OLED devices, thereby improving device efficiency.

[0108] The applicant declares that the present invention is illustrated by the above embodiments to illustrate the boron-containing organic compound and the organic electroluminescent device containing the same, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A boron-containing organic compound, characterized by, The boron-containing organic compound has a general structure of Formula I: ； wherein, Ring H represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and the ring H is connected to the phenyl ring in a fused manner; Z1, Z2 are each independently selected from a direct bond, BR1, CR2R3, NR4, O, PR5, SiR6R7, GeR8R9, S, CO, SO2, or represent the absence, and at least one of Z1, Z2 represents the absence; R1-R9 are independently selected from a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, wherein the heteroatom contains at least one of O, S, N, Si, Se, or B; R2 and R3, R6 and R7, R8 and R9 can be connected to each other to form a ring; Ra, Rb, Rc, Rd are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a trifluoromethyl group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C2-C30 borane group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, wherein the heteroatom contains at least one of O, S, N, Si, Se, B; a plurality of Ra are independently present or two adjacent Ra are connected to form a ring; m, n are selected from an integer of 1, 2, 3; p is selected from an integer of 1, 2; Re is independently selected from a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C2-C30 borane group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, wherein the heteroatom contains at least one of O, S, N, Si, Se, B; the substituent in the above-mentioned substituted or unsubstituted is selected from any one or a combination of at least two of a deuterium atom, a tritium atom, a halogen atom, a cyano group, TMS, a trifluoromethyl group, a C1-C10 alkyl group, a deuterium-substituted C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C6-C30 aryl group, a deuterium-substituted C6-C30 aryl group, a C2-C30 heteroaryl group, a deuterium-substituted C2-C30 heteroaryl group.

2. The boron-containing organic compound according to claim 1, characterized by The boron-containing organic compound has a structure represented by any one of Formula I-A to Formula I-C: 。 3. The boron-containing organic compound according to claim 1, wherein R1to R9each independently represent a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group.

4. The boron-containing organic compound according to claim 1 or 2, characterized by Ra, Rb, Rc, Rdare each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group.

5. The boron-containing organic compound according to claim 1 or 2, characterized by Reindependently represents a substituted or unsubstituted methyl, a substituted or unsubstituted ethyl, a substituted or unsubstituted isopropyl, a substituted or unsubstituted tert-butyl, a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted adamantyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted trimethylsilanyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted N-phenylcarbazolyl, a substituted or unsubstituted 9,9-dimethylfluorenyl, a substituted or unsubstituted 9,9-diphenylfluorenyl, a substituted or unsubstituted spirofluorenyl, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl.

6. The boron-containing organic compound of claim 1, wherein The substituent in the substituted or unsubstituted is selected from one or a combination of at least two of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, a trimethylsilanyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl 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 furanyl 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, a N-phenylcarbazolyl group, a carbazolinyl group, a phenanthrolinyl group.

7. The boron-containing organic compound of claim 1, wherein The boron-containing organic compound has a structure represented by any one of the following Chemical Formula I-1 to Chemical Formula I-24: 。 8. The boron-containing organic compound of claim 1, wherein Rd, Reindependently represent one or a combination of at least two of the following groups: ； The asterisk represents a bonding site of a group.

9. The boron-containing organic compound of claim 1, wherein The boron-containing organic compound is any one of the following compounds: ； wherein D represents a deuterium.

10. An organic electroluminescent device, characterized by The organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer including a light-emitting layer, the light-emitting layer including a host material, a dopant material, and a sensitizer, the dopant material being the boron-containing organic compound according to any one of claims 1 to 9; The organic layer further includes any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, a hole blocking layer.

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