A compound containing a triazine and phenanthroline structure, an organic electroluminescence device, and a laminated organic electroluminescence device

Abstract

The application discloses a compound containing triazine and phenanthroline structures, an organic electroluminescent device and a laminated organic electroluminescent device, and belongs to the technical field of semiconductor materials. The structure of the compound is shown in general formula (1), general formula (2) or general formula (3). The compound has good stability and electron resistance, and has good electron injection and electron transmission capacity. When the compound is used as a material of the organic electroluminescent device, the driving voltage, the device efficiency and the device life of the device are significantly improved.

Description

Technical Field

[0001] This invention relates to the field of semiconductor materials technology, and in particular to a compound containing triazine and phenanthroline structures and its application in organic electroluminescent devices. Background Technology

[0002] Organic Light Emission Diodes (OLEDs) technology can be used to manufacture novel display products and lighting products, and is expected to replace existing liquid crystal displays and fluorescent lighting, with a very wide range of applications. OLED devices have a sandwich-like structure, including electrode material layers and organic functional materials sandwiched between different electrode material layers. Various organic functional materials are stacked together according to their intended use to form the OLED light-emitting device. As a current-emitting device, when a voltage is applied to its two electrodes, and an electric field is applied to the positive and negative charges in the organic functional material layers, the positive and negative charges recombine in the light-emitting layer, thus generating OLED electroluminescence.

[0003] Currently, OLED display technology has been applied in smartphones, tablets, and other fields, and will further expand into large-screen applications such as televisions. However, compared with the requirements of actual product applications, the luminous efficiency and lifespan of OLED devices still need further improvement. In order to continuously improve the performance of OLED devices, continuous research and innovation in OLED optoelectronic functional materials are needed to create higher-performance OLED functional materials.

[0004] OLED optoelectronic functional materials used in OLED devices can be broadly categorized into two types based on their applications: charge injection transport materials and luminescent materials. Further, charge injection transport materials can be classified into electron injection transport materials, electron blocking materials, hole injection transport materials, and hole blocking materials. As charge transport materials, they require excellent carrier mobility and high glass transition temperature. In OLED devices, electrons are injected from the cathode and then transported through the electron transport layer to the host material, where they recombine with holes to generate excitons. Therefore, improving the injection and transport capabilities of the electron transport layer helps reduce the device driving voltage while achieving high electron-hole recombination efficiency. Thus, the electron transport layer is crucial, requiring high electron injection and transport capabilities as well as high electron durability.

[0005] Especially in the development of multilayer devices, the electronic charge generation layer consists of electron transport materials and metals. Electrons are generated through charge transfer complexes formed by the metal and electron transport materials. The electron transport material plays a crucial role, possessing not only excellent electron injection and transport characteristics and electron tolerance, but also the ability to coordinate with the metal to improve electron generation stability. Traditional charge generation materials are bisphenanthrene-line structures, which are formed by linking two phenanthrene-line substituent groups with aryl or heteroaryl groups. The two nitrogen atoms of phenanthrene can form stable complexes with metals, such as CN101010404A and CN101872844A in the prior art. However, when used as charge generation layer materials based on bisphenanthrene-line groups, insufficient electron injection and transport capabilities lead to increased device voltage and low device efficiency. Furthermore, due to the unsatisfactory electron tolerance and stability of phenanthrene, the material becomes unstable under negative charges and decomposes, resulting in a significant decrease in device lifetime. However, aryl-substituted phenanthroline groups, such as Bphen, have insufficient electronic tolerance and film stability. When used as electron transport materials or charge generation layers, phase separation occurs at the organic layer interface due to film crystallization, resulting in a significant decrease in device lifetime.

[0006] Compared to traditional molecules composed of triazine and phenanthrene groups, phenanthrene groups lack heteroatomic groups, thus they cannot form electron-withdrawing capabilities or coordinate with metals. As a result, when such materials are used as charge generation layer materials, they cannot form metal-organic complexes due to their inability to effectively coordinate with metals, thus failing to generate and inject charges. This leads to high device voltage and significantly reduced device efficiency.

[0007] With the significant advancements in OLED devices, the performance requirements for materials have also increased. These materials must not only possess excellent stability but also achieve good efficiency and lifespan at low driving voltages. However, current electron transport materials suffer from insufficient electron injection and transport capabilities, as well as inadequate thermal stability. Furthermore, defects in the electronic tolerance of these materials lead to phase separation or decomposition during device operation, resulting in poor device lifespan. Summary of the Invention

[0008] To address the aforementioned problems in the existing technology, this invention provides a compound containing triazine and phenanthroline. The compound of this invention bridges the triazine and phenanthroline groups through a specific terphenyl or biphenyl structure, thereby giving the compound excellent electron injection and transport capabilities, significantly enhancing its electron tolerance and stability. When applied to organic electroluminescent devices, it can effectively reduce the device's operating voltage and improve its luminous efficiency and lifespan.

[0009] The technical solution of the present invention is as follows: a compound containing triazine and phenanthroline structures, the structure of which is shown in general formula (1), general formula (2), or general formula (3):

[0010] In general formula (1), L1 represents a single bond or a phenylene; R1 and R3 are independently represented by any one of the structures shown in general formula a-1 to general formula a-7, and there is only one structure shown in general formula a-7;

[0011] In general formula (2), L2 represents a single bond or a phenylene; R2 and R4 are independently represented by any one of the structures shown in general formula a-1 to general formula a-7, and there is only one structure shown in general formula a-7;

[0012] In general formula (3), L3 and L4 are each independently represented as single bonds or phenylene; R5 and R6 are each independently represented as any one of the structures shown in general formulas a-1 to a-7, and there is only one structure represented as the structure shown in general formula a-7.

[0013] L3 and L4 can be the same or different;

[0014] In general formula a-7, Ar1 represents phenyl, biphenyl, or naphthyl.

[0015] In a preferred embodiment, the structure of the compound is shown in any one of general formulas (2-1) to (2-6):

[0016]

[0017]

[0018] In general formulas (2-1) to (2-6), the meanings of Ar1, L1, L2, L3, and L4 are the same as those defined above;

[0019] R1, R2, R3, R4, R5, and R6 can be independently represented by the structures shown in general formulas a-1, a-2, a-3, a-4, a-5, or a-6.

[0020] In a preferred embodiment, the structure of the compound is shown in any one of general formulas (3-1) to (3-36):

[0021]

[0022]

[0023]

[0024] In general formulas (3-1) to (3-36), the meanings of L1, L2, Ar1, L3, and L4 are the same as those defined above.

[0025] Preferably, L1, L2, L3, and L4 represent any of the following structures: single bond,

[0026] Preferably, Ar1 is represented by any of the following structures:

[0027] Preferably, the general formula a-2 is represented by any of the following structures:

[0028] Preferably, the general formula a-6 is represented by any of the following structures:

[0029] Preferably, R1, R2, R3, R4, R5, and R6 represent any of the following structures: general formula a-1, formula a-2-1, formula a-2-2, formula a-2-3, formula a-2-4, general formula a-3, general formula a-4, general formula a-5, formula a-6-1, formula a-6-2, formula a-6-3, and general formula a-7.

[0030] In a preferred embodiment, the compound containing triazine and phenanthroline structures has any one of the following structures:

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] An organic electroluminescent device includes a first electrode, a second electrode, and an organic functional layer located between the first and second electrodes. The organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the hole transport region and the electron transport region. The electron transport region contains the compound containing triazine and phenanthroline structures.

[0049] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region includes an electro-hole blocking layer, an electron transport layer, and an electron injection layer.

[0050] Preferably, the hole transport region includes a hole transport layer, the electron transport region includes an electron transport layer, and the electron transport layer includes the compound containing the triazine and phenanthroline structures.

[0051] Preferably, the electron transport region comprises an electron transport layer, which contains the compound containing the triazine and phenanthroline structures.

[0052] A stacked organic electroluminescent device includes a first electrode, a second electrode, a first light-emitting unit, a second light-emitting unit, and a charge-generating layer. The first light-emitting unit, the second light-emitting unit, and the charge-generating layer are located between the first electrode and the second electrode. The charge-generating layer is located between the first light-emitting unit and the second light-emitting unit, and the charge-generating layer contains the compound containing triazine and phenanthroline structures.

[0053] Preferably, the first light-emitting unit includes a hole transport region, a light-emitting layer, and an electron transport region, and the second light-emitting unit includes a hole transport region, a light-emitting layer, and an electron transport region. Preferably, the charge-generating layer further comprises a metallic material.

[0054] More preferably, the metallic material is Li, Ca, Ag, Cs, or Yb. More preferably, the metallic material is Yb.

[0055] The beneficial technical effects of this invention are as follows:

[0056] (1) The compounds of this invention are based on triazine and phenanthroline structures, with the triazine and phenanthroline groups connected by biphenyl or terphenyl bridging through specific linking sites. These compounds exhibit good electronic tolerance and stability, as well as excellent electron injection and transport capabilities. Therefore, when used as electron transport materials in OLED functional layers or charge generation layer materials in stacked devices, they can effectively reduce device driving voltage and improve the photoelectric efficiency and lifetime of OLED devices.

[0057] (2) The compounds of the present invention contain triazine and phenanthroline groups. Through a specific combination, the LUMO electron cloud distribution of the material can be further delocalized, improving the electronic tolerance and electronic stability of the material, forming weak bond interactions within and between molecules, improving the molecular planar arrangement, and significantly improving the electron mobility.

[0058] (3) Furthermore, since the compound of the present invention has good electron-withdrawing ability, film stability and electronic tolerance, it can be used as an n-type material of CGL layer. In particular, the phenanthroline group can form stable N-metal coordination bonds with metals such as Yb to form a stable and flat organic-metal doped film, which inhibits the oxidation of metals and is beneficial to improving charge generation efficiency and device stability.

[0059] (4) Specific bridging groups enable triazine and phenanthroline groups to produce a steric hindrance effect, which avoids excessive molecular stacking and the formation of local microcrystals, thereby improving the stability of the film phase.

[0060] (5) The compounds of the present invention can effectively increase the charge generation capability and the stability of the charge generation layer, which is beneficial to reduce the device driving voltage and improve device efficiency and service life.

[0061] Therefore, when the compound described in this invention is applied as an organic electroluminescent functional layer material to OLED devices, whether as an electron transport material or a charge generation layer material (CGL), it can effectively reduce the device driving voltage and improve the device lifespan. It has good application effects in OLED light-emitting devices and has good industrialization prospects. Attached Figure Description

[0062] Figure 1 This is a schematic diagram of the structure of a single-layer OLED device using the materials listed in this invention;

[0063] In the figure: 1. Substrate; 2. Anode; 3. Hole injection layer; 4. Hole transport layer; 5. Electron blocking layer; 6. Light emitting layer; 7. Hole blocking layer; 8. Electron transport layer; 9. Electron injection layer; 10. Cathode; 11. Capping layer.

[0064] Figure 2This is a schematic diagram of the structure of the materials listed in this invention applied to a multilayer OLED device;

[0065] In the figure: 1. Substrate; 2. First electrode layer; 3. Hole injection layer; 4. Hole transport layer; 5. Electron blocking layer; 6. Light emitting layer; 7. Hole blocking layer; 8. Electron transport layer; 9. Charge generation layer (CGL layer); 10. Hole transport layer; 11. Electron blocking layer; 12. Light emitting layer; 13. Hole blocking layer; 14. Electron transport layer; 15. Electron injection layer; 16. Second electrode layer; 17. Cover layer.

[0066] Figure 3 This is the 1H NMR spectrum of compound 106 of the present invention in deuterated chloroform.

[0067] Figure 4 This is the 1H NMR spectrum of compound 87 of the present invention in deuterated chloroform. Detailed Implementation

[0068] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Unless otherwise specified, the embodiments and features in the embodiments of the present invention can be combined with each other. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but this is not intended to limit the present invention.

[0069] In this invention, unless otherwise stated, HOMO refers to the highest occupied orbital of a molecule, and LUMO refers to the lowest empty orbital of a molecule. Furthermore, in this invention, HOMO and LUMO energy levels are represented by absolute values, and comparisons between energy levels are made by comparing their absolute values. Those skilled in the art know that the larger the absolute value of an energy level, the lower its energy.

[0070] In the accompanying drawings, for clarity, the dimensions of layers and regions may be exaggerated. It will also be understood that when a layer or element is referred to as being "above" another layer or substrate, the layer or element may be directly above that other layer or substrate, or intermediate layers may be present. Furthermore, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intermediate layers may be present. The same reference numerals throughout the drawings denote the same elements.

[0071] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0072] Organic light-emitting devices and multilayer organic light-emitting devices

[0073] The present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and an organic functional layer, wherein the organic functional layer is located between the first electrode and the second electrode, and the organic functional layer comprises a hole transport layer, a light-emitting layer and an electron transport layer, wherein the light-emitting layer is located between the hole transport layer and the electron transport layer, and the electron transport layer comprises the compound of general formula (1).

[0074] The present invention provides a stacked organic electroluminescent device, comprising a first electrode, a second electrode, a first light-emitting unit, a second light-emitting unit, and a charge-generating layer, wherein the first light-emitting unit, the second light-emitting unit, and the charge-generating layer are located between the first electrode and the second electrode, and the charge-generating layer is located between the first light-emitting unit and the second light-emitting unit, and the charge-generating layer comprises the compound of general formula (1).

[0075] In a preferred embodiment, the first light-emitting unit includes a hole transport region, a light-emitting layer, and an electron transport region, and the second light-emitting unit includes a hole transport region, a light-emitting layer, and an electron transport region. In a preferred embodiment, the charge-generating layer further comprises a metallic material. In a preferred embodiment, the metallic material is Li, Ca, Ag, Cs, or Yb.

[0076] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; and flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent substrate is preferred. There are no particular limitations on the thickness of the substrate.

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

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

[0079] In this paper, the hole transport region constituting an organic electroluminescent device can be listed as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

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

[0081] Examples of the aforementioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4”-bis(diarylamino)terphenyls, 4,4”'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

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

[0083] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

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

[0085] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

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

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

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

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

[0090] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0091] The light-emitting layer may comprise a host material and a dopant material. The host material may be any material selected from known materials used in OLED devices, and the dopant material may be any material selected from known materials used in OLED devices.

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

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

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

[0095] A hole-blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its efficiency. The hole-blocking layer of this invention can be disposed above the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives like aluminum(III)bis(2-methyl-8-quinoline)-4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and pyrimidine derivatives such as 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole) (CAS No.: 1345338-69-3), etc. The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm and more preferably 10-100 nm, but the thickness is not limited to this range.

[0096] An electron transport layer may be disposed above a light-emitting layer or (if present) a hole-blocking layer.

[0097] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0098] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0099] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used, typically 10-50 nm, preferably 15-20 nm.

[0100] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0101] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0102] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or prepared by conventional preparation methods in the art;

[0103] Preparation of intermediate C1:

[0104]

[0105]

[0106] Under nitrogen protection, in a 500 mL round-bottom flask, raw material A1 (20 mmol), raw material B1 (22 mmol), KOAC (60 mmol), and dioxane (150 mL) were added sequentially. Nitrogen was purged for 30 min to replace the air. Pd(PPh3)4 (0.4 mmol) was then added, and the mixture was heated under reflux for 15 h under nitrogen protection. TCL analysis of the reaction solution showed that raw material A1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, poured into a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted with dichloromethane (60 mL * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane, yielding intermediate C1. LC-MS: Measured value: 307.31 ([M+H) + Precision quality: 306.15.

[0107] Intermediate C was prepared using a synthetic method similar to that of intermediate C1. The raw materials A and B used are shown in Table 1.

[0108] Table 1

[0109]

[0110]

[0111] Preparation of intermediates D1, E1, and F1:

[0112]

[0113] Under nitrogen protection, in a 500 mL round-bottom flask, raw material C1 (30 mmol), raw material D1 (30 mmol), K2CO3 (90 mmol), tetrahydrofuran (180 mL), and water (60 mL) were added sequentially. Nitrogen gas was purged for 30 min to replace the air. Pd(PPh3)4 (0.6 mmol) was added, and the mixture was heated under reflux for 10 h under nitrogen protection. TCL analysis of the reaction solution showed that raw material C1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in 150 mL of dichloromethane, washed with 100 mL of water, poured into a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted with dichloromethane (50 mL * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain intermediate D1. LC-MS: Measured value: 266.91 ([M+H)+ ); Precision quality: 265.95.

[0114] Under nitrogen protection, in a 500 mL round-bottom flask, raw material E1 (30 mmol) and diethyl ether (150 mL) were added sequentially. The mixture was cooled to -78 °C, and nitrogen was purged for 30 min to replace the air. A 1.6 mol / L hexane solution of n-butyllithium (40 mmol) was slowly added, and the reaction was maintained at -78 °C for 3 h. Then, trimethyl borate (40 mmol) was added, and the reaction was maintained at -78 °C for 1 h. The mixture was then allowed to react at room temperature for 16 h. TCL analysis of the reaction solution showed that raw material E1 had reacted completely. After the reaction was complete, a dilute hydrochloric acid solution (50 mL) was added to the reaction system, and the organic solvent was removed by rotary evaporation. The residue was filtered to obtain a white solid intermediate, E1. LC-MS: Measured value: 278.21 ([M+H)). + ); Precision quality: 277.10.

[0115] Under nitrogen protection, intermediates D1 (15 mmol), E1 (15 mmol), K2CO3 (45 mmol), tetrahydrofuran (180 mL), and water (60 mL) were added sequentially to a 500 mL round-bottom flask. Nitrogen gas was purged for 30 min to replace the air. Pd(PPh3)4 (0.3 mmol) was added, and the mixture was heated under reflux for 12 h under nitrogen protection. TCL analysis of the reaction solution showed that intermediate D1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in 150 mL of dichloromethane, washed with 100 mL of water, poured into a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted with dichloromethane (50 mL * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain intermediate F1. LC-MS: Measured value: 420.27 ([M+H) + ); Precision quality: 419.12.

[0116] Intermediate D was prepared using a synthetic method similar to that of intermediate D1, and the raw materials C and D used are shown in Table 2; Intermediate E was prepared using a synthetic method similar to that of intermediate E1, and the raw material E used is shown in Table 2; Intermediate F was prepared using a synthetic method similar to that of intermediate F1, and the intermediates D and E used are shown in Table 2.

[0117] Table 2

[0118]

[0119]

[0120] Example 1: Synthesis of Compound 4

[0121]

[0122] Under nitrogen protection, intermediate F8 (20 mmol), intermediate C1 (22 mmol), K2CO3 (60 mmol), tetrahydrofuran (100 mL), and water (50 mL) were added sequentially to a 250 mL round-bottom flask. Nitrogen gas was purged for 30 min to replace the air. Palladium acetate (0.30 mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.50 mmol) were then added. The mixture was heated under nitrogen protection and refluxed for 14 h. TCL analysis of the reaction solution revealed that intermediate F8 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in 200 ml of dichloromethane, washed with 120 ml of water, poured into a separatory funnel, shaken, and allowed to stand for phase separation. The aqueous phase was extracted with dichloromethane (70 ml * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain compound 4. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.37; H, 4.68; N, 10.99. LC-MS: Measured value: 640.28 ([M+H]) + ), Precision quality: 639.24.

[0123] Example 2: Synthesis of Compound 21

[0124]

[0125] Compound 21 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F7 was used instead of intermediate F8, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.45; H, 4.61; N, 11.03. LC-MS: Measured value: 640.39 ([M+H]) + ), Precision quality: 639.24.

[0126] Example 3: Synthesis of Compound 27

[0127]

[0128] Compound 27 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F7 was used instead of intermediate F8, and intermediate C3 was used instead of intermediate C1. Elemental analysis: C 45 H 29N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.36; H, 4.65; N, 11.06. LC-MS: Measured value: 640.18 ([M+H]) + ), Precision quality: 639.24.

[0129] Example 4: Synthesis of Compound 44

[0130]

[0131] Compound 44 was prepared according to the synthetic method of Compound 4 in Example 1, except that intermediate F7 was used instead of intermediate F8, and intermediate C4 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.57; H, 4.52; N, 11.01. LC-MS: Measured value: 640.34 ([M+H]) + ), Precision quality: 639.24.

[0132] Example 5: Synthesis of Compound 71

[0133]

[0134] Compound 71 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F7 was used instead of intermediate F8, and intermediate C5 was used instead of intermediate C1. Elemental analysis: C 51 H 33 N5; Theoretical values: C, 85.57; H, 4.65; N, 9.78; Measured values: C, 85.60; H, 4.61; N, 9.80. LC-MS: Measured value: 716.41 ([M+H]) + Precision quality: 715.27.

[0135] Example 6: Synthesis of Compound 89

[0136]

[0137] Compound 89 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F4 was used instead of intermediate F8. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.40; H, 4.63; N, 10.97. LC-MS: Measured value: 640.65 ([M+H]+), Precise mass: 639.24.

[0138] Example 7: Synthesis of Compound 92

[0139]

[0140] Compound 92 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F3 was used instead of intermediate F8, and intermediate C6 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.56; H, 4.59; N, 10.83. LC-MS: Measured value: 640.56 ([M+H]) + ), Precision quality: 639.24.

[0141] Example 8: Synthesis of Compound 98

[0142]

[0143] Compound 98 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F2 was used instead of intermediate F8, and intermediate C7 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.44; H, 4.49; N, 11.05. LC-MS: Measured value: 640.57 ([M+H]) + ), Precision quality: 639.24.

[0144] Example 9: Synthesis of Compound 106

[0145]

[0146] Compound 106 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.37; H, 4.61; N, 11.03. LC-MS: Measured value: 640.34 ([M+H]) + ), Precision quality: 639.24.

[0147] Example 10: Synthesis of Compound 112

[0148]

[0149] Compound 112 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C3 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.51; H, 4.64; N, 10.88. LC-MS: Measured value: 640.22 ([M+H]) + ), Precision quality: 639.24.

[0150] Example 11: Synthesis of Compound 120

[0151]

[0152] Compound 120 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F5 was used instead of intermediate F8, and intermediate C8 was used instead of intermediate C1. Elemental analysis: C 49 H 31 N5; Theoretical values: C, 85.32; H, 4.53; N, 10.15; Measured values: C, 85.36; H, 4.47; N, 10.10. LC-MS: Measured value: 690.43 ([M+H]) + Precision quality: 689.26.

[0153] Example 12: Synthesis of Compound 126

[0154]

[0155] Compound 126 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F6 was used instead of intermediate F8, and intermediate C9 was used instead of intermediate C1. Elemental analysis: C 49 H 31 N5; Theoretical values: C, 85.32; H, 4.53; N, 10.15; Measured values: C, 85.39; H, 4.41; N, 10.18. LC-MS: Measured value: 690.70 ([M+H]) + Precision quality: 689.26.

[0156] Example 13: Synthesis of Compound 127

[0157]

[0158] Compound 127 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C4 was used instead of intermediate C1. Elemental analysis: C 45 H 29N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.45; H, 4.61; N, 10.93. LC-MS: Measured value: 640.47 ([M+H]) + ), Precision quality: 639.24.

[0159] Example 14: Synthesis of Compound 132

[0160]

[0161] Compound 132 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C5 was used instead of intermediate C1. Elemental analysis: C 51 H 33 N5; Theoretical values: C, 85.57; H, 4.65; N, 9.78; Measured values: C, 85.59; H, 4.59; N, 9.83. LC-MS: Measured value: 716.44 ([M+H]) + Precision quality: 715.27.

[0162] Example 15: Synthesis of Compound 168

[0163]

[0164] Compound 168 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F10 was used instead of intermediate F8, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 51 H 33 N5; Theoretical values: C, 85.57; H, 4.65; N, 9.78; Measured values: C, 85.52; H, 4.71; N, 9.81. LC-MS: Measured value: 716.35 ([M+H]) + Precision quality: 715.27.

[0165] Example 16: Synthesis of Compound 169

[0166]

[0167] Compound 169 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F10 was used instead of intermediate F8, and intermediate C3 was used instead of intermediate C1. Elemental analysis: C 51 H 33 N5; Theoretical values: C, 85.57; H, 4.65; N, 9.78; Measured values: C, 85.53; H, 4.67; N, 9.74. LC-MS: Measured value: 716.20 ([M+H]) +Precision quality: 715.27.

[0168] Example 17: Synthesis of Compound 212

[0169]

[0170] Compound 212 was prepared using the same synthetic method as compound 4 in Example 1, except that intermediate F8 was replaced by intermediate F9. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.40; H, 4.61; N, 10.99. LC-MS: Measured value: 640.32 ([M+H]) + ), Precision quality: 639.24.

[0171] Example 18: Synthesis of Compound 242

[0172]

[0173] Compound 242 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F9 was used instead of intermediate F8, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 51 H 33 N5; Theoretical values: C, 85.57; H, 4.65; N, 9.78; Measured values: C, 85.49; H, 4.63; N, 9.86. LC-MS: Measured value: 716.53 ([M+H]) + Precision quality: 715.27.

[0174] Example 19: Synthesis of Compound 248

[0175]

[0176] Compound 248 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F9 was used instead of intermediate F8, and intermediate C3 was used instead of intermediate C1. Elemental analysis: C 51 H 33 N5; Theoretical values: C, 85.57; H, 4.65; N, 9.78; Measured values: C, 85.59; H, 4.70; N, 9.70. LC-MS: Measured value: 716.35 ([M+H]) + Precision quality: 715.27.

[0177] Example 20: Synthesis of Compound 275

[0178]

[0179] Compound 275 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C10 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.38; H, 4.52; N, 11.03. LC-MS: Measured value: 640.62 ([M+H]) + ), Precision quality: 639.24.

[0180] Example 21: Synthesis of Compound 1

[0181]

[0182] Compound 1 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F7 was used instead of intermediate F8. Elemental analysis C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.04; H, 4.35; N, 12.59. LC-MS: Measured value: 564.01 ([M+H]+), Precise mass: 563.21.

[0183] Example 22: Synthesis of Compound 17

[0184]

[0185] Compound 17 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F7 was used instead of intermediate F8, and intermediate C11 was used instead of intermediate C1. Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.13; H, 4.45; N, 12.43. LC-MS: Measured value: 564.34 ([M+H]+), Precise mass: 563.21.

[0186] Example 23: Synthesis of Compound 87

[0187]

[0188] Compound 87 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8. Elemental analysis C 39 H 25N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.17; H, 4.49; N, 12.33. LC-MS: Measured value: 564.39 ([M+H]+), Precise mass: 563.21.

[0189] Example 24: Synthesis of Compound 91

[0190]

[0191] Compound 91 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C6 was used instead of intermediate C1. Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.08; H, 4.48; N, 12.44. LC-MS: Measured value: 564.16 ([M+H]+), Precise mass: 563.21.

[0192] Example 25: Synthesis of Compound 96

[0193]

[0194] Compound 96 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C7 was used instead of intermediate C1. Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.24; H, 4.28; N, 12.53. LC-MS: Measured value: 564.23 ([M+H]+), Precise mass: 563.21.

[0195] Example 26: Synthesis of Compound 101

[0196]

[0197] Compound 101 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F1 was used instead of intermediate F8, and intermediate C11 was used instead of intermediate C1. Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.09; H, 4.60; N, 12.29. LC-MS: Measured value: 564.25 ([M+H]+), Precise mass: 563.21.

[0198] Example 27: Synthesis of Compound 282

[0199]

[0200] Compound 282 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F11 was used instead of intermediate F8; Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.14; H, 4.49; N, 12.43. LC-MS: Measured value: 564.16 ([M+H]) + Precision quality: 563.21.

[0201] Example 28: Synthesis of Compound 283

[0202]

[0203] Compound 283 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F11 was used instead of intermediate F8, and intermediate C6 was used instead of intermediate C1; Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.11; H, 4.43; N, 12.40. LC-MS: Measured value: 564.19 ([M+H]) + Precision quality: 563.21.

[0204] Example 29: Synthesis of Compound 285

[0205]

[0206] Compound 285 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F11 was used instead of intermediate F8, and intermediate C11 was used instead of intermediate C1; Elemental analysis: C 39 H 25 N5; Theoretical value: C, 83.10; H, 4.47; N, 12.42; Measured value: C, 83.21; H, 4.40; N, 12.41. LC-MS: Measured value: 564.40 ([M+H]) + Precision quality: 563.21.

[0207] Example 30: Synthesis of Compound 286

[0208]

[0209] Compound 286 was prepared using the same synthetic method as compound 4 in Example 1, except that intermediate F12 was used instead of intermediate F8. Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.09; H, 4.51; N, 12.45. LC-MS: Measured value: 564.06 ([M+H]) + Precision quality: 563.21.

[0210] Example 31: Synthesis of Compound 289

[0211]

[0212] Compound 289 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F12 was used instead of intermediate F8, and intermediate C11 was used instead of intermediate C1. Elemental analysis: C 39 H 25 N5; Theoretical values: C, 83.10; H, 4.47; N, 12.42; Measured values: C, 83.13; H, 4.43; N, 12.39. LC-MS: Measured value: 564.68 ([M+H]+), Precise mass: 563.21.

[0213] Example 32: Synthesis of Compound 323

[0214]

[0215] Compound 323 was prepared using the same synthetic method as compound 4 in Example 1, except that intermediate F11 was used instead of intermediate F8; and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.44; H, 4.59; N, 10.97. LC-MS: Measured value: 640.12 ([M+H]) + ), Precision quality: 639.24.

[0216] Example 33: Synthesis of Compound 324

[0217]

[0218] Compound 324 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F12 was used instead of intermediate F8, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 45 H 29N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.37; H, 4.54; N, 10.97. LC-MS: Measured value: 640.07 ([M+H]) + ), Precision quality: 639.24.

[0219] Example 34: Synthesis of Compound 375

[0220]

[0221] Compound 375 was prepared using the same synthetic method as Compound 4 in Example 1, except that intermediate F13 was used instead of intermediate F8; and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 45 H 29 N5; Theoretical values: C, 84.48; H, 4.57; N, 10.95; Measured values: C, 84.74; H, 4.39; N, 10.84. LC-MS: Measured value: 640.17 ([M+H]) + ), Precision quality: 639.24.

[0222] The following details the application effects of the compound synthesized according to the present invention as an electron transport layer in devices through device Examples 1-20, 45-58, and comparative examples 1-9 and 30-40. Compared with device Example 1, device Examples 2-20, 45-58, and comparative examples 1-9 and 30-40 have the same fabrication process, use the same substrate and electrode materials, and maintain the same electrode film thickness. The only difference is the change in the electron transport material. The device structures are shown in Table 3, and the performance test results of each device are shown in Table 4.

[0223] The molecular structural formulas of the relevant materials are shown below:

[0224]

[0225]

[0226] The structures of compounds ET-1, ET-2, ET-3, ET-4, ET-5, ET-6, ET-7, ET-8, ET-9, ET-10, ET-11, ET-12, ET-13, ET-14, ET-15, ET-16, ET-17, ET-18, ET-19, and ET-20 are shown above. All of the above materials were commercially available.

[0227] Device Example 1

[0228] The specific preparation process is as follows:

[0229] like Figure 1 As shown, the transparent substrate layer 1 is transparent glass, and the anode layer 2 is Ag (100nm). On the anode layer 2, HT-1 and P-1 with a thickness of 10nm are deposited using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to P-1 of 97:3. Next, HT-1 with a thickness of 117nm is deposited as a hole transport layer 4. Subsequently, EB-1 with a thickness of 10nm is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes BH-1 as the host material and BD-1 as the dopant material, with a doping ratio of 3% by weight, and a light-emitting layer thickness of 20nm. After the light-emitting layer 6, HB-1 is deposited with a thickness of 8nm as a hole blocking layer 7. On top of the hole-blocking layer 7, compound 4 and Liq are further vapor-deposited at a mass ratio of 1:1. The vacuum-deposited film thickness of this material is 30 nm, and this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 16 nm is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10. On the cathode layer 10, CP-1 with a thickness of 65 nm is vacuum-deposited as a capping layer 11.

[0230] Device Examples 2-20, Examples 45-58, and Comparative Examples 1-9 and 30-40 were prepared in a similar manner to Device Example 1, and all used transparent glass as the substrate and Ag (100nm) as the anode. The difference was that the parameters in Table 3 below were used.

[0231] Table 3

[0232]

[0233]

[0234]

[0235]

[0236] The device was tested to measure its drive voltage, current efficiency, and LT95 lifetime. Drive voltage and current efficiency were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.), with a current density of 10 mA / cm² during testing. 2 LT95 refers to the time it takes for the device's brightness to decay to 95% of its initial brightness, measured at a current density of 50 mA / cm². 2The lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan. Efficiency and lifetime data for each device embodiment and comparative example are shown in Table 4.

[0237] Table 4

[0238]

[0239] As can be seen from the device data results in Table 4, the organic light-emitting device of the present invention has achieved significant improvements in both driving voltage and lifetime compared to the OLED device of the comparative material.

[0240] Furthermore, to illustrate the application of the compound of the present invention as a charge-generating layer in organic electroluminescent devices, the properties of the material of the present invention were studied by constructing a stacked device (a two-layer blue light-emitting device). It should be noted that, since the optical design of the stacked device needs to be taken into account, the film thickness and structure of the device need to be redesigned and adjusted compared to the single-layer device structure; it is not simply a matter of stacking single-layer devices.

[0241] The following details the application of the compounds synthesized in this invention as charge generation layer (CGL) materials in multilayer OLED devices through device examples 21-40, 60-73, and comparative examples 10-29. Device examples 22-40, 60-73, and comparative examples 10-29 are identical to device example 21 in terms of fabrication process, substrate material, electrode material, and electrode film thickness. The only difference is the change in the CGL material. Specific device structures are shown in Table 5. For ease of presentation, only the material structure of the CGL layer is listed in Table 5; other layer structures and film thicknesses are omitted as they are consistent.

[0242] Table 5

[0243] Device Examples CGL layer / film thickness Device Examples CGL layer / film thickness Device Comparison Example 10 ET-1:Yb=95:5 10nm Device Example 28 Compound 98:Yb = 95:5 10nm Device Comparison Example 11 ET-2:Yb=95:5 10nm Device Example 29 Compound 106:Yb = 95:5 10nm Device Comparison Example 12 ET-3:Yb=95:5 10nm Device Example 30 Compound 112:Yb = 95:5 10nm Device Comparison Example 13 ET-4:Yb=95:5 10nm Device Example 31 Compound 120:Yb = 95:5 10nm Device Comparison Example 14 ET-5:Yb=95:5 10nm Device Example 32 Compound 126:Yb = 95:5 10nm Device Comparison Example 15 ET-6:Yb=95:5 10nm Device Example 33 Compound 127:Yb = 95:5 10nm Device Comparison Example 16 ET-7:Yb=95:5 10nm Device Example 34 Compound 132:Yb = 95:5 10nm Device Comparison Example 17 ET-8:Yb=95:5 10nm Device Example 35 Compound 168:Yb = 95:5 10nm Device Comparison Example 18 ET-9:Yb=95:5 10nm Device Example 36 Compound 169:Yb = 95:5 10nm Device Comparison Example 19 ET-10:Yb=95:5 10nm Device Example 37 Compound 212: Yb = 95:5 10nm Device Comparison Example 20 ET-11:Yb=95:5 10nm Device Example 38 Compound 242:Yb = 95:5 10nm Device Comparison Example 21 ET-12:Yb=95:5 10nm Device Example 39 Compound 248:Yb = 95:5 10nm Device Comparison Example 22 ET-13:Yb=95:5 10nm Device Example 40 Compound 275:Yb = 95:5 10nm Device Comparison Example 23 ET-14:Yb=95:5 10nm Device Example 60 Compound 1: Yb = 95:5 10nm Device Comparison Example 24 ET-15:Yb=95:5 10nm Device Example 61 Compound 17: Yb = 95:5 10nm Device Comparison Example 25 ET-16:Yb=95:5 10nm Device Example 62 Compound 87:Yb = 95:5 10nm Device Comparison Example 26 ET-17:Yb=95:5 10nm Device Example 63 Compound 91:Yb = 95:5 10nm Device Comparison Example 27 ET-18:Yb=95:5 10nm Device Example 64 Compound 96:Yb = 95:5 10nm Device Comparison Example 28 ET-19:Yb=95:5 10nm Device Example 65 Compound 101:Yb = 95:5 10nm Device Comparison Example 29 ET-20:Yb=95:5 10nm Device Example 66 Compound 282: Yb = 95:5 10nm Device Example 21 Compound 4: Yb = 95:5 10nm Device Example 67 Compound 283:Yb = 95:5 10nm Device Example 22 Compound 21: Yb = 95:5 10nm Device Example 68 Compound 285:Yb = 95:5 10nm Device Example 23 Compound 27: Yb = 95:5 10nm Device Example 69 Compound 286:Yb = 95:5 10nm Device Example 24 Compound 44:Yb = 95:5 10nm Device Example 70 Compound 289:Yb = 95:5 10nm Device Example 25 Compound 71: Yb = 95:5 10nm Device Example 71 Compound 323:Yb = 95:5 10nm Device Example 26 Compound 89: Yb = 95:5 10nm Device Example 72 Compound 324:Yb = 95:5 10nm Device Example 27 Compound 92:Yb = 95:5 10nm Device Example 73 Compound 375:Yb = 95:5 10nm

[0244] Device Example 21

[0245] The specific preparation process is as follows:

[0246] like Figure 2As shown, the transparent substrate layer 1 is transparent glass, and the anode layer 2 is Ag (100nm). On the anode layer 2, HT-1 and P-1 with a thickness of 10nm are deposited using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to P-1 of 97:3. Next, HT-1 with a thickness of 117nm is deposited as a hole transport layer 4. Subsequently, EB-1 with a thickness of 10nm is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes BH-1 as the host material and BD-1 as the dopant material, with a doping ratio of 3% by weight, and a light-emitting layer thickness of 20nm. After the light-emitting layer 6, HB-1 is deposited with a thickness of 8nm as a hole blocking layer 7. On top of the hole blocking layer 7, ET-A and Liq are deposited with a mass ratio of ET-A to Liq of 1:1. The vacuum-deposited film of this material has a thickness of 20 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a charge generation layer 9 (CGL layer) is deposited using a vacuum evaporation apparatus. Its structure is Yb:compound 4 (Yb doping ratio is 5% by weight), and the film thickness is 10 nm. Next, HT-1 and P-1 with a thickness of 10 nm are deposited as hole injection layer 3, with a mass ratio of HT-1 to P-1 of 97:3. Then, HT-1 with a thickness of 117 nm is deposited as hole transport layer 10. Subsequently, EB-1 with a thickness of 10 nm is deposited as electron blocking layer 11. After the above electron blocking materials are deposited, the light-emitting layer 12 of the OLED light-emitting device is fabricated. Its structure includes BH-1 used in the OLED light-emitting layer 6 as the host material and BD-1 as the dopant material, with a doping ratio of 3% by weight, and the light-emitting layer film thickness is 20 nm. Following the aforementioned light-emitting layer 12, HB-1 is deposited by evaporation to a thickness of 8 nm, serving as a hole-blocking layer 13. Above the hole-blocking layer 13, ET-A and Liq are deposited by evaporation at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 14. On the electron transport layer 14, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 15. On the electron injection layer 15, a 16 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 16. On the cathode layer 16, a 65 nm thick CP-1 layer is vacuum-deposited as a capping layer 17.

[0247] After completing the fabrication of the electroluminescent device according to the above steps, the device's efficiency and optical lifetime were measured, and the results are shown in Table 6. The molecular structural formulas of the relevant materials are shown below:

[0248]

[0249]

[0250] The device was tested to measure its drive voltage, current efficiency, and LT95 lifetime. Drive voltage and current efficiency were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.), with a current density of 10 mA / cm² during testing. 2 LT95 refers to the time it takes for the device's brightness to decay to 95% of its initial brightness, measured at a current density of 50 mA / cm². 2 The lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan. Efficiency and lifetime data for each device embodiment and comparative example are shown in Table 6.

[0251] Table 6

[0252]

[0253]

[0254] As can be seen from Tables 4 and 6 above, when the compounds of the present invention are used as electron transport materials in single-layer devices, compared with comparative materials, the device voltage is reduced, and the device efficiency and device lifetime are significantly improved. This indicates that the compounds of the present invention have good technical effects when used as electron transport materials in single-layer OLEDs. Furthermore, when the compounds of the present invention are used as CGL materials in multilayer devices, compared with comparative materials, the device voltage is reduced, and the device efficiency and device lifetime are improved. This further demonstrates that the compounds of the present invention have good technical effects when used as CGL materials in multilayer OLED devices.

[0255] Therefore, it can be seen that the compounds formed by linking triazine and phenanthroline groups through biphenyl or terphenyl linking groups at specific sites have achieved good technical effects. The main reasons are as follows: the compounds are based on triazine and phenanthroline structures, with the triazine and phenanthroline groups linked by biphenyl or terphenyl bridges at specific linking sites. These compounds exhibit good electronic tolerance and stability, as well as good electron injection and transport capabilities. The specific structure of the compounds allows for further delocalization of the LUMO electron cloud distribution of the material, improving its electronic tolerance and stability, forming weak intramolecular and intermolecular bond interactions, enhancing molecular planar arrangement, significantly improving electron mobility, and improving electron generation capacity and stability. Therefore, the compounds of this invention possess good electron-withdrawing ability, film stability, and electronic tolerance. When used as n-type materials in the CGL layer, they can form stable N-metal coordination bonds with metals such as Yb, forming stable and flat organometallic doped films, suppressing metal oxidation, and improving charge generation efficiency and device stability.

[0256] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A compound containing a triazine and phenanthroline structure, characterized in that, The structure of the compound is shown in general formula (1), general formula (2), or general formula (3): In general formula (1), L1 represents a single bond or a phenylene; R1 and R3 are independently represented by any one of the structures shown in general formula a-1 to general formula a-7, and there is only one structure shown in general formula a-7; In general formula (2), L2 represents a single bond or a phenylene; R2 and R4 are independently represented by any one of the structures shown in general formula a-1 to general formula a-7, and there is only one structure shown in general formula a-7; In general formula (3), L3 and L4 are each independently represented as single bonds or phenylene; R5 and R6 are each independently represented as any one of the structures shown in general formulas a-1 to a-7, and there is only one structure represented as the structure shown in general formula a-7. L3 and L4 can be the same or different; In general formula a-7, Ar1 represents phenyl, biphenyl, or naphthyl.

2. The compound containing triazine and phenanthroline structures according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (2-1) to (2-6): In general formulas (2-1) to (2-6), Ar1, L1, L2, L3, and L4 have the same meanings as defined in claim 1; R1, R2, R3, R4, R5, and R6 can be independently represented by the structures shown in general formulas a-1, a-2, a-3, a-4, a-5, or a-6.

3. The compound containing triazine and phenanthroline structures according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (3-1) to (3-36): In general formulas (3-1) to (3-36), the meanings of L1, L2, Ar1, L3, and L4 are the same as those defined in claim 1.

4. The compound containing triazine and phenanthroline structures according to claim 1, characterized in that, The specific structure of the compound is any one of the following structures:

5. An organic electroluminescent device, comprising a first electrode, a second electrode, and an organic functional layer, wherein the organic functional layer is located between the first electrode and the second electrode, the organic functional layer comprising a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer is located between the hole transport region and the electron transport region, characterized in that, The electron transport region comprises the compound containing a triazine and phenanthroline structure as described in any one of claims 1-4.

6. The organic electroluminescent device according to claim 5, characterized in that, The electron transport region includes an electron transport layer, which contains the triazine and phenanthroline structure as described in any one of claims 1-4.

7. A stacked organic electroluminescent device, comprising a first electrode, a second electrode, a first light-emitting unit, a second light-emitting unit, and a charge-generating layer, wherein the first light-emitting unit, the second light-emitting unit, and the charge-generating layer are located between the first electrode and the second electrode, and the charge-generating layer is located between the first light-emitting unit and the second light-emitting unit, characterized in that, The charge-generating layer comprises the compound containing a triazine and phenanthroline structure as described in any one of claims 1-4.

8. The stacked organic electroluminescent device according to claim 7, characterized in that, The first light-emitting unit includes a hole transport region, a light-emitting layer, and an electron transport region, and the second light-emitting unit includes a hole transport region, a light-emitting layer, and an electron transport region.

9. The stacked organic electroluminescent device according to claim 7, characterized in that, The charge-generating layer also contains a metallic material.

10. The stacked organic electroluminescent device according to claim 9, characterized in that, The metallic material is Li, Ca, Ag, Cs, or Yb.

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