Organic compound containing boron and nitrogen and organic electroluminescent device
By introducing boron-nitrogen fused ring groups into OLED materials, the problems of carrier balance and thermal stability have been solved, resulting in high-efficiency, long-life OLED devices suitable for high-end displays and smart lighting.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SHENZHEN INSTITUTE OF INFORMATION TECHNOLOGY
- Filing Date
- 2026-01-26
- Publication Date
- 2026-05-12
AI Technical Summary
Existing OLED materials have defects in carrier balance, luminous efficiency and thermal stability, especially blue OLED materials, which suffer from efficiency roll-off and insufficient device lifetime, and carrier transport imbalance leading to high driving voltage.
A boron-nitrogen-containing organic compound is designed to achieve synergistic transport of holes and electrons by introducing boron-nitrogen-fused-ring groups into the substituents of the nitrogen heterocyclic core and combining them with specific organic functional materials, thereby optimizing carrier balance and luminescence efficiency.
It has achieved high efficiency, long lifespan, and low driving voltage OLED devices, improving luminous efficiency and device lifespan, and is suitable for high-end display and smart lighting fields.
Smart Images
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Abstract
Description
Technical Field
[0001] This application belongs to the field of organic electroluminescence, and more specifically, relates to a boron-nitrogen-containing organic compound and an organic electroluminescent device. Background Technology
[0002] Organic light-emitting diode (OLED) technology, with its significant advantages such as self-illumination, high contrast, wide viewing angle, low power consumption, and flexible fabrication, has become a core technology in the fields of flat panel displays and next-generation lighting, and is widely used in terminal products such as smartphones, smart TVs, and wearable devices. The performance of OLED devices is highly dependent on organic functional materials, especially the molecular structure of the light-emitting layer (substrate and doped materials) and carrier transport layer materials, which directly determine key indicators such as luminous efficiency, lifetime, color purity, and driving voltage. Therefore, the research and development of new high-efficiency OLED materials has always been the core focus of industry competition.
[0003] However, existing OLED materials still face numerous technical bottlenecks. In terms of luminescence performance, blue OLED materials generally suffer from a rapid efficiency roll-off at high brightness due to the difficulty in controlling molecular energy levels, resulting in a device lifetime far shorter than that of red and green materials. Regarding carrier transport, most host materials (such as carbazole and triarylamines) exhibit strong hole transport capabilities but insufficient electron transport, causing the carrier recombination region to deviate from the center of the emissive layer, reducing luminescence efficiency and increasing driving voltage. Simultaneously, the materials lack sufficient thermal and chemical stability, making them prone to degradation and crystallization under long-term thermal or electrical stress conditions, severely limiting the lifespan of OLEDs. To address these issues, researchers have conducted studies on nitrogen-containing heterocyclic materials (such as indole-carbazole derivatives) and boron-containing organic materials. Nitrogen-containing heterocyclic materials possess rigid planar structures, high carrier mobility, and tunable energy level structures, but struggle to achieve balanced hole and electron transport simultaneously. Boron-containing materials can enhance electron transport capabilities and achieve efficient luminescence (especially blue light emission), but suffer from insufficient thermal stability and hole transport capabilities. Currently, the design of molecular integration of nitrogen-containing heterocyclic cores with boron-containing aryl substituents is still relatively limited, and the synergistic advantages of the two have not yet been fully utilized. Summary of the Invention
[0004] To address the shortcomings of existing technologies, the purpose of this application is to provide a boron-nitrogen-containing organic compound and an organic electroluminescent device, aiming to solve the technical problems that the design of molecular integration of nitrogen-containing heterocyclic cores and boron-containing aryl substituents in existing OLED materials is still relatively limited, and there are still defects in terms of carrier balance, luminous efficiency, and thermal stability.
[0005] To achieve the above objectives, in a first aspect, this application provides a boron-nitrogen-containing organic compound having a structure as shown in general formula (I): (I) in: Z is selected from CR4R5 or C=O; R4 and R5 are each independently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 cyclic atoms; R4 and R5 may be cyclic or non-cyclic with each other; R1, R2, and R3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or structural formula (A); and at least one of R1, R2, and R3 is selected from structural formula (A). (A) Ar1, Ar2, Ar3, and Ar4 are each independently selected from substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms. , Each is independently selected from non-existent, single key, or ; * indicates a connection point; The term "substituted or unsubstituted" indicates that the defined group is either unsubstituted or substituted by one or more substituents R. * Instead, the R * Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-20 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
[0006] In a second aspect, this application provides a mixture comprising a boron-nitrogen-containing organic compound as described in the first aspect, and further comprising at least another organic functional material; said other organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, or luminescent host materials.
[0007] Thirdly, this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and one or more organic functional layers located between the anode and the cathode, wherein the at least one organic functional layer comprises a boron-nitrogen-containing organic compound as described in the first aspect or a mixture as described in the second aspect.
[0008] This invention provides a novel type of OLED material comprising a specific nitrogen-containing heterocyclic core, with at least one boron-nitrogen fused-ring group introduced among the R1-R3 substituents of the core. Through this structural design, the hole transport characteristics of the nitrogen-containing heterocycle and the electron transport and luminescence modulation characteristics of the boron-nitrogen fused-ring group are synergistically utilized to overcome the shortcomings of existing materials in carrier balance, luminous efficiency, and thermal stability. Ultimately, this enables the fabrication of high-efficiency, long-lifetime, and low-driving-voltage OLED devices, providing crucial material support for the industrialization of OLED technology in high-end displays (such as 8K TVs and foldable phones) and smart lighting. Detailed Implementation
[0009] To make the objectives, technical solutions, and advantages of this application clearer, the following detailed description is provided in conjunction with embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the scope of this application.
[0010] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
[0011] The "halogen" mentioned in this invention includes fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.
[0012] In this invention, "ring atom number" refers to the number of atoms in the ring-forming structure of a compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the thiophene group has a ring atom number of 5, and carbazole has a ring atom number of 13.
[0013] In this invention, "number of carbon atoms" refers to the number of carbon atoms in the atoms constituting the ring of a structural compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by carbon atom bonding into a ring. When the ring is substituted by a substituent, the carbon atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of carbon atoms" described below unless otherwise specified. For example, phenyl has 6 carbon atoms, naphthyl has 10 carbon atoms, and phenanthrene has 14 carbon atoms.
[0014] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one or more hydrogen atoms. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 30 ring atoms" refers to an aryl containing 6 to 30 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 20 ring atoms; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives.
[0015] "Heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms" refers to a heteroaryl group having 5 to 30 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 20 ring atoms. Suitable examples include, but are not limited to: thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalyl, etc. Linyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthrynyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.
[0016] Alkyl groups include straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups, and combinations thereof; the number of carbon atoms in a "straight-chain alkyl group" is selected from 1 to 20, more preferably from 1 to 10. Non-limiting examples of straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, etc. The number of carbon atoms in a "branched alkyl group" is selected from 3 to 20, more preferably from 3 to 10. Non-limiting examples of branched alkyl groups include isopropyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, etc. The number of carbon atoms in a "cycloalkyl group" is selected from 3 to 20, more preferably from 3 to 10. Non-limiting examples of cyclic alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.
[0017] In this invention, when a single bond connecting groups penetrates the corresponding ring, it indicates that the single bond can be connected to any connectable site on the ring.
[0018] The terms “including,” “comprising,” “having,” “containing,” or “involving,” and their other variations herein, are inclusive or open-ended and do not exclude other unlisted elements or method steps.
[0019] In this specification, "independently selected" can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other.
[0020] 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.
[0021] This invention protects a boron-nitrogen-containing organic compound having a structure as shown in general formula (I): (I) in: Z is selected from CR4R5 or C=O; R4 and R5 are independently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 cyclic atoms; R4 and R5 may be cyclic or non-cyclic with each other; R1, R2, and R3 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or structural formula (A); and at least one of R1, R2, and R3 is selected from structural formula (A). (A) Ar1, Ar2, Ar3, and Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms. , Independent selection from non-existent, single key, or ; * indicates a connection point; The term "substituted or unsubstituted" indicates that the defined group is either unsubstituted or substituted by one or more substituents R. * Instead, the R * Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-20 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
[0022] Furthermore, the general formula (I) is selected from... or .
[0023] In an optional embodiment, R4 and R5 are independently selected from alkyl groups having 1-10 carbon atoms, substituted or unsubstituted aromatic groups having 6-10 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-10 cyclic atoms; R4 and R5 may be cyclic or non-cyclic with each other.
[0024] Furthermore, R4 and R5 are independently selected from alkyl, phenyl, or compounds having 1-6 carbon atoms, or compounds containing one or more R atoms. a Substituted phenyl, said R a Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-10 carbon atoms, and heteroaromatic group having 5-10 ring atoms.
[0025] In one embodiment, R4 and R5 are not in a loop with each other.
[0026] In another implementation, R4 and R5 form a ring around each other; further, the... Selected from Where n is selected from 0, 1, 2, 3 or 4.
[0027] In one specific embodiment, the Selected from, but not limited to, the following groups: .
[0028] In an optional embodiment, only one of R1, R2, and R3 is selected from structural formula (A).
[0029] Furthermore, the boron-nitrogen-containing organic compound is selected from any structure of general formulas (II-1)-(II-6):
[0030] .
[0031] In one embodiment, R1 in the general formulas (II-2), (II-3), (II-5), and (II-6) is independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1-20 carbon atoms, and is surrounded by one or more R groups. b Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, and surrounded by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; said R b Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
[0032] In one embodiment, R1 in the general formulas (II-2), (II-3), (II-5), and (II-6) is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and one or more R... b Substituted or unsubstituted phenyl, with one or more R b Substituted or unsubstituted naphthyl group, with one or more R b Substituted or unsubstituted pyridinyl group, with one or more R b Substituted or unsubstituted pyrimidine group, with one or more R b Substituted or unsubstituted triazine group, with one or more R b Substituted or unsubstituted quinolinyl group, with one or more R b Substituted or unsubstituted quinazolinyl group, with one or more R b Substituted or unsubstituted dibenzofuranyl, with one or more R b Substituted or unsubstituted dibenzothiophene group, or dibenzothiophene group with one or more R groups b Substituted or unsubstituted carbazole group. Further, the R... b Each occurrence is independently selected from one or at least two combinations of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, pyrimidinyl, triazinyl, quinolinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, and carbazoleyl.
[0033] In one embodiment, R2 in the general formulas (II-1), (II-3), (II-4), and (II-6) is independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1-20 carbon atoms, and is surrounded by one or more R groups. b Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, and surrounded by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; said R bEach occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
[0034] In one embodiment, R2 in the general formulas (II-1), (II-3), (II-4), and (II-6) is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and one or more R... b Substituted or unsubstituted phenyl, with one or more R b Substituted or unsubstituted naphthyl group, with one or more R b Substituted or unsubstituted pyridinyl group, with one or more R b Substituted or unsubstituted pyrimidine group, with one or more R b Substituted or unsubstituted triazine group, with one or more R b Substituted or unsubstituted quinolinyl group, with one or more R b Substituted or unsubstituted quinazolinyl group, with one or more R b Substituted or unsubstituted dibenzofuranyl, with one or more R b Substituted or unsubstituted dibenzothiophene group, or dibenzothiophene group with one or more R groups b Substituted or unsubstituted carbazole group. Further, the R... b Each occurrence is independently selected from one or at least two combinations of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, pyrimidinyl, triazinyl, quinolinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, and carbazoleyl.
[0035] In one embodiment, R3 in the general formulas (II-1), (II-2), (II-4), and (II-5) is independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1-20 carbon atoms, and is surrounded by one or more R groups. b Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, and surrounded by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; said R b Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
[0036] In one embodiment, R3 in the general formulas (II-1), (II-2), (II-4), and (II-5) is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and one or more R... bSubstituted or unsubstituted phenyl, with one or more R b Substituted or unsubstituted naphthyl group, with one or more R b Substituted or unsubstituted pyridinyl group, with one or more R b Substituted or unsubstituted pyrimidine group, with one or more R b Substituted or unsubstituted triazine group, with one or more R b Substituted or unsubstituted quinolinyl group, with one or more R b Substituted or unsubstituted quinazolinyl group, with one or more R b Substituted or unsubstituted dibenzofuranyl, with one or more R b Substituted or unsubstituted dibenzothiophene group, or dibenzothiophene group with one or more R groups b Substituted or unsubstituted carbazole group. Further, the R... b Each occurrence is independently selected from one or at least two combinations of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, pyrimidinyl, triazinyl, quinolinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, and carbazoleyl.
[0037] In an alternative embodiment, Ar1, Ar2, Ar3, and Ar4 are independently selected from one or more R c Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, or containing one or more R groups. c Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; said R c Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
[0038] In a particular embodiment, the structural formula (A) is selected from any of the following structures, but is not limited thereto:
[0039] ; in: Each time Z appears, it is independently selected from O, S, or Se; m1 is selected from 0, 1, 2, 3 or 4; m2 is selected from 0, 1, 2, 3, 4 or 5; m3 is selected from 0, 1, 2 or 3.
[0040] In a specific embodiment, the boron-nitrogen-containing organic compound described in this application is selected from, but not limited to, the following structures:
[0041] .
[0042] This application further provides a mixture comprising the boron-nitrogen-containing organic compound as described above, and also comprising at least another organic functional material; the other organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, or luminescent host materials.
[0043] This application further provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and one or more organic functional layers located between the anode and the cathode, wherein the at least one organic functional layer comprises a boron-nitrogen-containing organic compound as described above or a mixture thereof as described above.
[0044] Furthermore, the organic electroluminescent device of the present invention includes a substrate, and an anode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer sequentially stacked on the substrate; the light-emitting layer comprises a boron-nitrogen-containing organic compound or a mixture thereof as described above.
[0045] This invention also relates to the application of organic electroluminescent devices in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.
[0046] The present invention will be described below with reference to examples of compound preparation and device characterization. However, the present invention is not limited to the following examples. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that any changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.
[0047] Compound synthesis examples:
[0048]
[0049]
[0050] The above compounds were synthesized by purchasing the monohaloboron-azo heterocyclic compound from the market. The halocarbazole intermediate was synthesized according to the following literature (Org. Lett. 2025, 27, 25, 6593-6598). Then, Pd(OAc)₂ was reacted with pinacol diboronate to generate a carbazole pinacol borate intermediate for later use. The specific synthetic steps are as follows: Synthesis Example 1: Synthesis of Organic Compound (1)
[0051] Specific synthesis steps: The classic Suzuki reaction was adopted, and the specific process route is as follows: Equimolar amounts of the above reaction substrates 1-1 and 1-2 were mixed evenly. Toluene was used as the solvent, and 2M K2CO3 aqueous solution was added as the base. Under the action of catalyst Pd(PPh3)4, the mixture was heated and stirred under reflux overnight. The reaction was monitored by TLC thin-layer chromatography. After the reaction was complete, the heating was stopped. When the temperature of the reaction solution dropped to room temperature, dichloromethane and H2O were added for extraction. The organic phases were combined, and the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was recrystallized with a mixed solvent of dichloromethane and ethyl acetate to obtain the white product (1). The reaction yield was 85.1%, and MS (ASAP) = 771.5.
[0052] Synthesis Example 2: Synthesis of Organic Compound (2)
[0053] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 2-1 and 2-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (2). The reaction yield was 86.8% and MS (ASAP) = 982.2.
[0054] Synthesis Example 3: Synthesis of Organic Compound (3)
[0055] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 3-1 and 3-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (3). The reaction yield was 88.8% and MS (ASAP) = 683.5.
[0056] Synthesis Example 4: Synthesis of Organic Compound (4)
[0057] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 4-1 and 4-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (4). The reaction yield was 87.9% and MS (ASAP) = 911.5.
[0058] Synthesis Example 5: Synthesis of Organic Compound (5)
[0059] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 5-1 and 5-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (5). The reaction yield was 84.7% and MS (ASAP) = 747.2.
[0060] Synthesis Example 6: Synthesis of Organic Compound (6)
[0061] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 6-1 and 6-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (6). The reaction yield was 85.3% and MS (ASAP) = 977.2.
[0062] Synthesis Example 7: Synthesis of Organic Compound (7)
[0063] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 3-1 and 7-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (7). The reaction yield was 86.5% and MS (ASAP) = 697.3.
[0064] Synthesis Example 8: Synthesis of Organic Compound (8)
[0065] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 8-1 and 8-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (8). The reaction yield was 84.4% and MS (ASAP) = 863.3.
[0066] Synthesis Example 9: Synthesis of Organic Compound (9)
[0067] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 9-1 and 9-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (9). The reaction yield was 86.0% and MS (ASAP) = 757.4.
[0068] Synthesis Example 10: Synthesis of Organic Compound (10)
[0069] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 3-1 and 10-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (10). The reaction yield was 82.3% and MS (ASAP) = 896.3.
[0070] Synthesis Example 11: Synthesis of Organic Compound (11)
[0071] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 11-1 and 11-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (11). The reaction yield was 80.8% and MS (ASAP) = 881.4.
[0072] Synthesis Example 12: Synthesis of Organic Compound (12)
[0073] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 12-1 and 12-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (12). The reaction yield was 81.2% and MS (ASAP) = 1049.4.
[0074] Synthesis Example 13: Synthesis of Organic Compound (13)
[0075] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 13-1 and 13-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (13). The reaction yield was 85.1% and MS (ASAP) = 777.7.
[0076] Synthesis Example 14: Synthesis of Organic Compound (14)
[0077] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 12-1 and 14-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (14). The reaction yield was 87.2% and MS (ASAP) = 915.3.
[0078] Synthesis Example 15: Synthesis of Organic Compound (15)
[0079] Similar to the synthesis method in Example 1, the classic Suzuki reaction was used. The above reaction substrates 15-1 and 8-2 were heated and stirred under the action of a catalyst. The reaction solution was treated according to the post-treatment method of the classic Suzuki reaction to obtain product (15). The reaction yield was 88.1% and MS (ASAP) = 851.3.
[0080] Device Examples OLED device structure: ITO / HATCN (10nm) / NPB (35nm) / TCTA (5nm) / Host: 5wt% organic compound (1)-(15) / B3PYMPM (40nm) / LiF (1nm) / Al (150nm).
[0081] The fabrication steps of the OLED-1 device are as follows: a. Cleaning of conductive glass substrate: Clean with chloroform, ketone and isopropanol in sequence, and then perform ultraviolet ozone plasma treatment; b. Hole injection layer preparation: The cleaned conductive glass substrate is transferred to a nitrogen glove box and subjected to high vacuum (1×10⁻⁶). -6 Under millibar (mbar) conditions, HATCN was vacuum-deposited on an ITO substrate as a hole injection layer with a deposition thickness of 10 nm.
[0082] c. Hole transport layer preparation: NPB was vacuum-deposited on the hole injection layer as a hole transport layer with a deposition thickness of 35 nm.
[0083] d. Preparation of the light-emitting auxiliary layer: TCTA was vacuum-deposited on the hole transport layer as a light-emitting auxiliary layer with a deposition thickness of 5 nm.
[0084] e. Preparation of the light-emitting layer: Vacuum evaporation of the host organic compound (Host) on the light-emitting auxiliary layer: Organic compound (1) (weight doping ratio of 95:5)) as the light-emitting layer, with an evaporation thickness of 30nm.
[0085] f. Electron transport layer preparation: B3PYMPM was vacuum-deposited on the light-emitting layer as an electron transport layer with a deposition thickness of 40 nm.
[0086] g. Cathode layer preparation: LiF / Al (1nm / 150nm) was vacuum-deposited on the electron transport layer as the cathode layer; h. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.
[0087] The structure of Host is as follows:
[0088] OLED-(2-17) Device Fabrication Method: The fabrication method of OLED-(2-17) is the same as that of OLED-1, the difference being the selection of guest materials in the luminescent layer. Specifically, the guest luminescent material organic compound (1) in the luminescent layer is replaced with organic compound (2), organic compound (3), organic compound (4), organic compound (5), organic compound (6), organic compound (7), organic compound (8), organic compound (9), organic compound (10), organic compound (11), organic compound (12), organic compound (13), organic compound (14), and organic compound (15), respectively. The details are shown in Table 1.
[0089] OLED-Ref device fabrication method: The fabrication method of OLED-Ref device is the same as that of OLED-1. The difference lies in the selection of the guest light-emitting material in the light-emitting layer. Specifically, the organic compound (1) in the light-emitting layer is replaced with compound Ref. The structural formula of organic compound Ref is as follows:
[0090] Ref The current-voltage (JV) characteristics of each OLED device are characterized by a characterization device, while important parameters such as efficiency, lifetime and external quantum efficiency are recorded.
[0091] The specific photoelectric properties are shown in Table 1: Table 1
[0092] Testing revealed that the luminous efficiency and lifetime of the OLED-(1-15) devices prepared by this invention are significantly superior to those of OLED-Ref. For example, as blue light-emitting devices, OLED-2 (corresponding to organic compound (2)) has a luminous efficiency and lifetime approximately 2.6 times and 2.0 times that of OLED-Ref (corresponding to organic compound Ref), respectively. OLED-11 (corresponding to organic compound (11)) has a luminous efficiency 2.0 times that of OLED-Ref, while its lifetime is more than 1.9 times that of OLED-Ref. It is evident that the OLED devices prepared using the organic mixture of this invention exhibit significantly improved luminous efficiency and lifetime.
[0093] The above description is merely a specific embodiment of this application, but the scope of protection of this application is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the scope of the technology disclosed in this application should be included within the scope of protection of this application. Therefore, the scope of protection of this application should be determined by the scope of the claims.
Claims
1. A boron-nitrogen-containing organic compound, characterized in that, It has a structure as shown in general formula (I): （I） in: Z is selected from CR4R5 or C=O; R4 and R5 are independently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 cyclic atoms; R4 and R5 may be cyclic or non-cyclic with each other; R1, R2, and R3 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or structural formula (A); and at least one of R1, R2, and R3 is selected from structural formula (A). （A） Ar1, Ar2, Ar3, and Ar4 are independently selected from substituted or unsubstituted aromatic groups having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms. , Independent selection from non-existent, single key, or ; * indicates a connection point; The substitution or unsubstituted means that the defined group is not substituted or is substituted by one or more substituents R. * Instead, the R * Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-20 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
2. The boron-nitrogen-containing organic compound as described in claim 1, characterized in that, The general formula (I) is selected from or Furthermore, R4 and R5 are independently selected from alkyl groups having 1-10 carbon atoms, substituted or unsubstituted aromatic groups having 6-10 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-10 cyclic atoms; R4 and R5 may be cyclic or non-cyclic with each other.
3. The boron-nitrogen-containing organic compound as described in claim 2, characterized in that, R4 and R5 form a ring with each other; and the Selected from Where: n is selected from 0, 1, 2, 3 or 4; and R a Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-10 carbon atoms, and heteroaromatic group having 5-10 ring atoms.
4. The boron-nitrogen-containing organic compound as described in claim 2, characterized in that, The Selected from the following groups: 。 5. The boron-nitrogen-containing organic compound as described in claim 1, characterized in that, The boron-nitrogen-containing organic compounds are selected from any structure of general formulas (II-1)-(II-6): 。 6. The boron-nitrogen-containing organic compound as described in claim 5, characterized in that, In the general formulas (II-2), (II-3), (II-5), and (II-6), R1 is independently selected from hydrogen, deuterium, halogen, cyano, alkyl groups having 1-20 carbon atoms, and is surrounded by one or more R groups. b Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, and surrounded by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; In the general formulas (II-1), (II-3), (II-4), and (II-6), R2 is independently selected from hydrogen, deuterium, halogen, cyano, alkyl groups having 1-20 carbon atoms, and is surrounded by one or more R groups. b Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, and surrounded by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; In the general formulas (II-1), (II-2), (II-4), and (II-5), R3 is independently selected from hydrogen, deuterium, halogen, cyano, alkyl groups having 1-20 carbon atoms, and is surrounded by one or more R groups. b Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, and surrounded by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; The R b Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms.
7. The boron-nitrogen-containing organic compound as described in claim 5, characterized in that, Ar1, Ar2, Ar3, and Ar4 are independently selected from one or more R c Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted, or containing one or more R groups. c Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; The R c Each occurrence is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, alkyl group having 1-6 carbon atoms, aromatic group having 6-20 carbon atoms, and heteroaromatic group having 5-20 ring atoms; Preferably, the structural formula (A) is selected from any of the following structures: ； in: Each time Z appears, it is independently selected from O, S, or Se; m1 is selected from 0, 1, 2, 3 or 4; m2 is selected from 0, 1, 2, 3, 4 or 5; m3 is selected from 0, 1, 2 or 3.
8. The boron-nitrogen-containing organic compound according to claim 1, characterized in that, The boron-nitrogen-containing organic compound is selected from any of the following structures: 。 9. A mixture, characterized in that, The compound comprises a boron-nitrogen-containing organic compound as described in any one of claims 1 to 8, and further comprises at least one other organic functional material; said other organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, or luminescent host materials.
10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and at least one organic functional layer located between the anode and the cathode, wherein the at least one organic functional layer comprises a boron-nitrogen-containing organic compound as described in any one of claims 1 to 8 or a mixture as described in claim 9; Preferably, the organic electroluminescent device includes a substrate, and an anode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer sequentially stacked on the substrate; the light-emitting layer comprises a boron-nitrogen-containing organic compound as described in any one of claims 1 to 8 or a mixture as described in claim 9.