Novel compound for light-emitting device, and organic light-emitting device comprising same
A novel compound for OLEDs with high T1 value and HOMO level addresses the limitations of existing OLEDs by enhancing charge balance and thermal stability, resulting in improved efficiency and extended lifespan.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- DONGJIN SEMICHEM CO LTD
- Filing Date
- 2025-11-25
- Publication Date
- 2026-07-02
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Figure KR2025019666_02072026_PF_FP_ABST
Abstract
Description
Novel compound for light-emitting devices and organic light-emitting device including the same The present invention relates to a compound for a light-emitting device and an organic light-emitting device comprising the same. Materials used as organic layers in organic light-emitting devices can be broadly classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. Furthermore, the above-mentioned luminescent materials can be classified according to their luminescence mechanism into fluorescent materials derived from a singlet excited state of electrons, phosphorescent materials derived from a triplet excited state of electrons, and delayed fluorescent materials derived from the movement of electrons from a triplet excited state to a singlet excited state; they can also be classified according to their luminescence color into blue, green, and red luminescent materials, and yellow and orange luminescent materials necessary to achieve better natural colors. A typical organic light-emitting diode (OLED) may have a structure in which an anode is formed on a substrate, and a hole transport layer, an emissive layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transport layer, the emissive layer, and the electron transport layer are organic thin films composed of organic compounds. The driving principle of an organic light-emitting diode having the structure described above is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light-emitting layer via the hole transport layer, and electrons injected from the cathode move to the light-emitting layer via the electron transport layer. The holes and electrons recombine in the light-emitting layer to generate excitons. Light is generated as these excitons change from an excited state to a ground state. The efficiency of an organic light-emitting diode can generally be divided into internal luminescence efficiency and external luminescence efficiency. Internal luminescence efficiency is related to how efficiently excitons are generated and converted into light in organic layers interposed between the first electrode and the second electrode, such as the hole transport layer, the light-emitting layer, and the electron transport layer, and is theoretically known to be 25% for fluorescence and 100% for phosphorescence. Although various compounds have been known to date for use in such organic light-emitting diodes (OLEDs), the development of new materials is continuously required due to the high driving voltage, low efficiency, and short lifespan of OLEDs utilizing known materials. Therefore, efforts have been sustained to develop OLEDs with low-voltage operation, high brightness, and long lifespan by utilizing materials with superior properties. The present invention aims to provide a novel compound for a light-emitting device used in organic light-emitting devices such as fluorescence, phosphorescence, and delayed fluorescence, and an organic light-emitting device containing the same. In addition, the purpose is to provide a novel compound for a light-emitting device and an organic light-emitting device comprising the same, which can be used in one or more organic layers among the light-emitting layer, hole injection layer, hole transport layer, and light-emitting auxiliary layer of an organic light-emitting device to improve the lifespan, efficiency, driving voltage, color purity, electrochemical stability, and thermal stability of the organic light-emitting device. The above tasks and additional tasks are described in detail below. In order to solve the problem described above, the present invention, in one embodiment, A compound for a light-emitting device represented by the following chemical formula 1 is provided. <Chemical Formula 1> In the above chemical formula 1, X1 to X16 are each independently C, CR, or N, and L and L1 are each independently substituted or unsubstituted C5–C30 arylene groups, substituted or unsubstituted C2–C30 heteroarylene groups, or a combination thereof, and Ar1 is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkyleneoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 divalent alkylamine group, a substituted or unsubstituted C5-C30 divalent arylamine group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 heterocycloalkyl group, a substituted or unsubstituted C3-C50 cycloalkenyl group, a substituted or unsubstituted C2-C50 heterocycloalkenyl group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. Ar2 to Ar5 are each independently a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 dialkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 heterocycloalkyl group, a substituted or unsubstituted C3-C50 cycloalkenyl group, a substituted or unsubstituted C2-C50 heterocycloalkenyl group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 It is a heteroaryl group, and R is independently hydrogen or deuterium, and p, m, and n are each independently integers from 0 to 4, and The 1 and 2 indicated at the bottom of the carbazole represent the first carbazole and the second carbazole, respectively. In addition, in one embodiment of the present invention, An organic light-emitting device containing the above-described compound for a light-emitting device is provided. A compound for a light-emitting device according to one embodiment of the present invention has a high T1 value and an appropriate HOMO level, so that holes and electrons achieve charge balance and high efficiency can be obtained, and has a high glass transition temperature, so that thermal stability is excellent and the device lifespan can be significantly improved. In addition, by using a compound for a light-emitting device according to one embodiment of the present invention in one or more organic layers among the light-emitting layer, hole injection layer, hole transport layer, and light-emitting auxiliary layer of an organic light-emitting device, the lifespan, efficiency, driving voltage, color purity, electrochemical stability, and thermal stability of the organic light-emitting device can be improved. The above effects and additional effects are described in detail below. FIG. 1 is a schematic cross-sectional view showing the configuration of an organic light-emitting device according to one embodiment of the present invention. <Explanation of Symbols> 100: Substrate 200: Hole injection layer 300: Precision Transport Layer 400: Emitting layer 500: Electron transport layer 600: Electron injection layer 1000: First electrode 2000: Second electrode 3000: Capping layer Before describing the present invention in detail below, it should be understood that the terms used in this specification are intended only to describe specific embodiments and are not intended to limit the scope of the invention, which is defined solely by the appended claims. Unless otherwise stated, all technical and scientific terms used in this specification have the same meaning as generally understood by those skilled in the art. Throughout this specification and claims, the term “aryl” means comprising an aromatic hydrocarbon ring group having C5-50, e.g., phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perylenyl, crisenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocrisenyl, anthracenyl, stilbenyl, pyrenyl, etc., and “heteroaryl” means an aromatic ring having C2-50 comprising at least one heteroatom, e.g., pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, It may mean including heterocyclic rings formed from acrridinyl, phenanthrolinyl, thienyl, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acrridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzofuran ring, thiazole ring, thiadiazole ring, benzothiophene ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, etc. Additionally, the term "arylene" means that a hydrogen in the above aryl group is replaced by a direct bond to become a divalent substituent, and specific examples are not limited to cases where the above-described aryl structure becomes a divalent substituent. Likewise, the term "heteroarylene" means that a hydrogen in the above heteroaryl group is replaced by a direct bond to become a divalent substituent, and specific examples are not limited to cases where the above-described heteroaryl structure becomes a divalent substituent. Also, in the chemical formula, Ar x (where x is an integer) means, unless specifically defined, a substituted or unsubstituted C6–C50 aryl group, or a substituted or unsubstituted C2–C50 heteroaryl group, and Lx (where x is an integer) means a directly bonded, substituted, or unsubstituted C6–C50 arylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, unless specifically defined, and R x (where x is an integer) means, unless specifically defined, hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2-C50 heteroaryl group. Throughout this specification and claims, the term “substituted or unsubstituted” refers to a deuterium, halogen, amino group, cyano group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group, carboxyl group, carbonyl group, or a C1–C30 alkyl group, a C1–C30 alkylsulfinyl group, a C1–C30 alkylsulfonyl group, a C1–C30 alkylsulfanyl group, a C1–C12 fluoroalkyl group, a C2–C30 alkenyl group, a C1–C30 alkoxy group, a C1–C12 N-alkylamino group, a C2–C20 N,N-dialkylamino group, a substituted or unsubstituted C1–C30 sulfide group, a C1–C6 N-alkylsulfamoyl group, a C2–C12 N,N-dialkylsulfamoyl group, It may mean that it is substituted or not substituted with one or more groups selected from the group consisting of C0-C30 silyl groups, C3-C20 cycloalkyl groups, C3-C20 heterocycloalkyl groups, C6-C50 aryl groups, and C3-C50 heteroaryl groups. Additionally, throughout this specification, the same symbols may have the same meaning unless specifically stated otherwise. Meanwhile, matters described in the specification using the above-defined terms such as "aryl," "heteroaryl," "arylene," "heteroarylene," and "substitution" are deemed to include the examples listed above and their combinations; accordingly, the above-mentioned terms may be replaced by the examples listed above or subsequently modified. In addition, when ranges such as "C2 to C50" or "0 to 7" are described in this specification, they may be reduced to various ranges within the described ranges even without special description, and are deemed to be described in this specification. For example, C2 to C50 is deemed to describe various reduced ranges such as C5 to C50, C6 to C30, C6 to C20, C6 to C15, C6 to C10, and C12 to C30, in addition to C2 to C50. Accordingly, the description of numerical ranges in this specification may be reduced and corrected later. In addition, the numbering of carbazole in this specification is as follows. Meanwhile, various embodiments of the present invention may be combined with any other embodiments unless explicitly stated otherwise. Hereinafter, embodiments of the present invention and the effects thereof will be described. An organic light-emitting device according to one embodiment of the present invention may be an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode. A compound for a light-emitting device according to the present invention may be included in any one or more of the organic layers. Specifically, the compound for the light-emitting device may be included in one or more organic layers among a light-emitting layer, a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, and more specifically, may be included in the light-emitting layer. Meanwhile, the light-emitting layer may further include an electron-transporting host comprising an electron-transporting moiety, a cooling dopant, and a sensorizer. As a specific example of a compound for a light-emitting device according to the present invention, a compound for a light-emitting device represented by the following chemical formula 1 may be cited. <Chemical Formula 1> In the above chemical formula 1, X1 to X16 are each independently C, CR, or N, and L and L1 are each independently substituted or unsubstituted C5–C30 arylene groups, substituted or unsubstituted C2–C30 heteroarylene groups, or a combination thereof, and Ar1 is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkyleneoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 divalent alkylamine group, a substituted or unsubstituted C5-C30 divalent arylamine group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 heterocycloalkyl group, a substituted or unsubstituted C3-C50 cycloalkenyl group, a substituted or unsubstituted C2-C50 heterocycloalkenyl group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. Ar2 to Ar5 are each independently a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 dialkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 heterocycloalkyl group, a substituted or unsubstituted C3-C50 cycloalkenyl group, a substituted or unsubstituted C2-C50 heterocycloalkenyl group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 It is a heteroaryl group, and R is independently hydrogen or deuterium, and p, m, and n are each independently integers from 0 to 4, and The 1 and 2 indicated at the bottom of the carbazole represent the first carbazole and the second carbazole, respectively. Meanwhile, in the above Chemical Formula 1, Chemical Formula 2 and the following terms regarding substitution, the substituent in the case of substitution is deuterium, halogen, amino group, cyano group, hydroxyl group, thiol group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group, carboxyl group, carbonyl group, or C1-C30 alkyl group, C1-C30 alkylsulfinyl group, C1-C30 alkylsulfonyl group, C1-C30 alkylsulfanyl group, C1-C30 fluoroalkyl group, C2-C30 alkenyl group, C1-C30 alkoxy group, C0-C30 amino group, C1-C12 N-alkylamino group, C2-C20 N,N-dialkylamino group, substituted or unsubstituted C1-C30 sulfide group, C1-C6 Examples include N-alkylsulfamoyl groups, C2–C12 N,N-dialkylsulfamoyl groups, C0–C30 silyl groups, C3–C30 cycloalkyl groups, C1–C30 heterocycloalkyl groups, C6–C50 aryl groups, and C3–C50 heteroaryl groups. More specific substituents include deuterium, halogen, nitrile groups, C1–C10 alkyl groups, C1–C10 alkoxy groups, C1–C10 alkylthio groups, C1–C10 fluoroalkyl groups in which hydrogen is substituted with fluorine, C6–C20 aryl groups, and C3–C20 heteroaryl groups, and more specific substituents include deuterium. Meanwhile, if there is a separate definition of a substituent, it may be followed. In the above chemical formula 1, L1 may specifically be a substituted or unsubstituted C5–C30 arylene group, more specifically a C6–C18 arylene group, and Ar1 may specifically be a substituted or unsubstituted C5-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, or a combination thereof, and more specifically, may be a substituted or unsubstituted carbazole. In addition, as a specific example of a compound for a light-emitting device according to the present invention, the above chemical formula 1 may be a compound for a light-emitting device represented by the following chemical formula 2. <Chemical Formula 2> In the above chemical formula 2, The same symbol as Chemical Formula 1 above has the same definition, and X17 to X24 are each independently C, CR, or N, and L is a substituted or unsubstituted C5–C30 arylene group, and L1 is a substituted or unsubstituted C5–C30 arylene group, a substituted or unsubstituted C2–C30 heteroarylene group, or a combination thereof, and Ar5 is a substituted or unsubstituted C5–C50 aryl group or a substituted or unsubstituted C2–C50 heteroaryl group, and The numbers 1 to 3 indicated at the bottom of the carbazole represent the first carbazole, the second carbazole, and the third carbazole, respectively. The compounds for light-emitting devices of the present invention represented by the above chemical formulas 1 and 2 have a first carbazole and a second carbazole connected by a linker L, which can significantly improve efficiency and lifespan. In addition, an additional third carbazole is coupled through the L1 linker, which can lower the driving voltage and significantly improve efficiency and lifespan. Meanwhile, in the above Chemical Formula 1 and Chemical Formula 2, The above R may contain more deuterium than hydrogen among the total R. More specifically, the above R may be entirely deuterium. Lifespan can be significantly improved by introducing deuterium. Meanwhile, in the above Chemical Formula 1 and Chemical Formula 2, The CC bonding positions of the first carbazole and the second carbazole connected to the connector L may be X6 and X9, X6 and X10, X6 and X11, X6 and X12, X7 and X9, X7 and X10, X7 and X12, X8 and X9, X8 and X12, or X5 and X12. Specifically, the CC bonding positions between the two carbazoles may be X6 and X11. As shown in the embodiments described below, it can be confirmed that when the bonding positions are X6 and X11, device characteristics such as efficiency and lifespan are significantly superior. In addition, L connecting the first carbazole and the second carbazole may specifically be a C6 to C18 arylene group, and specifically may be a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, or a deuterium-substituted or unsubstituted terphenylene group. In addition, when L is a phenylene group, it may be a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group, and specifically, it may be a 1,3-phenylene group. As shown in the examples described below, it can be confirmed that when phenylene is a meta-bond, device characteristics such as efficiency and lifespan are significantly superior. Meanwhile, in the above Chemical Formula 1 and Chemical Formula 2, The above Ar2 to Ar4 may each be an independently substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 dialkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. Specifically, the Ar2 may be a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, or a terphenyl group substituted or unsubstituted with deuterium. Meanwhile, in the above Chemical Formulas 1 and 2, Ar5 can be bonded to X21 to X24, specifically to X22. When Ar5 is bonded to X22, the lifespan and device characteristics can be further improved. In addition, Ar5 may be a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted dibenzofuran, or a deuterium-substituted or unsubstituted dibenzothiophene, and specifically, may be a deuterium-substituted or unsubstituted phenyl group. By introducing a phenyl group, the device lifespan can be further improved. In addition, in the above Chemical Formula 1 and Chemical Formula 2, Specifically, p may be an integer from 1 to 4, from 1 to 3, or from 1 to 2. More specifically, p may be 1. Meanwhile, in the above Chemical Formulas 1 and 2, In the case where p is 1 and Ar5 is a phenylene group substituted or unsubstituted with deuterium, L1 may be a C5-C30 arylene group substituted or unsubstituted with deuterium, a C2-C30 heteroarylene group substituted or unsubstituted with deuterium, or a combination thereof. This allows for further improvement of device characteristics and lifespan. In addition, in the above Chemical Formula 1 and Chemical Formula 2, The above L1 may be a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, or a terphenylene group substituted or unsubstituted with deuterium, specifically a phenylene group substituted or unsubstituted with deuterium, and the phenylene group may be a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group, more specifically a 1,3-phenylene group. In addition, the above Chemical Formula 1 may be a compound for a light-emitting device represented by any one of the following compounds. The following compounds are merely examples for explaining the present invention, and the present invention is not limited thereto. Although not illustrated, compounds having a structure in which some or all of the hydrogen in the following compounds is substituted with deuterium are also considered to be examples and are included in the compounds of Chemical Formula 1. One embodiment of the compound of the present invention can be synthesized by the following schematic reaction scheme. As another embodiment, the present invention provides an organic light-emitting device containing a compound for a light-emitting device. Specifically, the organic light-emitting device comprises a first electrode and a second electrode; and one or more organic layers interposed between the first electrode and the second electrode, and a compound for the light-emitting device may be contained in one or more of the organic layers. The organic layer containing the above-mentioned compound for the light-emitting device may be one or more of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and an exciton blocking layer. Specifically, it may be a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, or a light-emitting layer, and more specifically, it may be a light-emitting layer. In this case, the compound for the light-emitting device of the present invention may be used alone or together with a known organic light-emitting compound. For example, when used in a light-emitting layer, an electron transport host including an electron transport moiety, a cooling dopant, and a sensorizer may be further included. In the present invention, the light-emitting auxiliary layer is a layer formed between the hole transport layer and the light-emitting layer, and may also be referred to as a second hole transport layer or a third hole transport layer depending on the number of hole transport layers. More specifically, an organic light-emitting device according to one embodiment of the present invention may include one or more organic layers constituting a light-emitting portion, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL), between a first electrode (anode) and a second electrode (cathode). Optionally, a hole blocking layer (HBL, not shown) or an electron transport assisting layer may be further included between the light-emitting layer (EML) and the electron transport layer (ETL), and an electron blocking layer (EBL, not shown) or a light-emitting assisting layer may be further included between the hole transport layer (HTL) and the light-emitting layer (EML). FIG. 1 is a cross-sectional view schematically showing the configuration of an organic light-emitting device according to an embodiment of the present invention. An organic light-emitting device according to one embodiment of the present invention can be manufactured as shown in the structure described in FIG. 1. As shown in FIG. 1, the organic light-emitting device may have a structure in which a substrate (100), a first electrode (1000), a hole injection layer (200), a hole transport layer (300), a light-emitting layer (400), an electron transport layer (500), an electron injection layer (600), a second electrode (2000), and a capping layer (3000) are sequentially stacked from the bottom. Here, although not shown, the capping layer (3000) may have a structure in which a first capping layer and a second capping layer are stacked. Additionally, it may have a structure in which a third capping layer with a different refractive index from the first capping layer and the second capping layer is added and stacked, but is not limited thereto. Furthermore, the capping layer may have a form in which a refractive index gradient exists. The refractive index gradient may gradually decrease as it extends outward, or it may gradually increase as it extends outward. Here, the substrate (100) may be a substrate commonly used in organic light-emitting devices, and may be a transparent glass substrate or a flexible plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Additionally, the first electrode (1000) is used as a hole injection electrode for hole injection in an organic light-emitting device. The first electrode (1000) is manufactured using a material having a low work function to enable hole injection and can be formed from a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene. In addition, the hole injection layer (200) may be formed by depositing a hole injection layer material on the upper part of the first electrode (1000) by a method such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett (LB) method. When forming the hole injection layer (200) by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material for the hole injection layer (200), the structure and thermal characteristics of the desired hole injection layer (200), but generally, a deposition temperature of 50-500°C, 10 -8 to 10-3 A vacuum level of torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness of 10 Å to 5 μm can be appropriately selected. Meanwhile, a charge generation layer may be additionally deposited on the surface of the hole injection layer (200) as needed. Conventional materials may be used as the charge generation layer material, and HATCN may be an example. Additionally, the hole transport layer (300) may be formed by depositing a hole transport layer material on top of the hole injection layer (200) by a method such as vacuum deposition, spin coating, casting, or LB method. When forming the hole transport layer (300) by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select conditions within a range that is almost identical to the formation of the hole injection layer (200). The hole transport layer (300) may be formed using a known compound. Such a hole transport layer (300) may be one or more layers, and although not shown in FIG. 1, it may be two layers: a first hole transport layer and a second hole transport layer (light-emitting auxiliary layer). At least one of the first hole transport layer and the second hole transport layer may include a compound for a light-emitting device according to the present invention. In addition, the light-emitting layer (400) may be formed by depositing a light-emitting layer material on top of the hole transport layer (300) or the light-emitting auxiliary layer by a method such as vacuum deposition, spin coating, casting, or LB method. When forming the light-emitting layer (400) by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select conditions within a range that is almost identical to the formation of the hole injection layer (200). The light-emitting layer material may use a compound for a light-emitting device according to the present invention or a known compound as a host or dopant. Furthermore, a compound for a light-emitting device according to the present invention may be used as a host and a known compound as a dopant, and although not limited to dopants, a phosphorescent or fluorescent dopant may be used together to form the light-emitting layer. For example, BD142 (N6,N12-bis(3,4-dimethylphenyl)-N6,N12-dimethylchrysene-6,12-diamine) can be used as the fluorescent dopant, and as the phosphorescent dopant, the green phosphorescent dopant Ir(ppy)3 (tris(2-phenylpyridine) iridium), the blue phosphorescent dopant F2Irpic (iridium(III) bis[4,6-difluorophenyl)-pyridinato-N,C2'] picolinate), and UDC's red phosphorescent dopant RD61 can be co-vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but it is preferable to dope the dopant at a concentration of 0.01 to 15 parts by weight relative to 100 parts by weight of the host. If the dopant content is less than 0.01 parts by weight, there is a problem that the color development is not properly achieved because the amount of dopant is insufficient, and if it exceeds 15 parts by weight, there is a problem that the efficiency decreases rapidly due to the concentration quenching phenomenon. Here, when a phosphorescent dopant is used together with the light-emitting layer material, a hole suppression material (HBL) may be additionally deposited on the upper part of the light-emitting layer (400) by vacuum deposition or spin coating to prevent the phenomenon of triplet excitons or holes diffusing into the electron transport layer (500). The hole suppression material that can be used is not particularly limited, and known materials may be arbitrarily selected and used. Examples include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or hole suppression materials described in Japanese Patent Publication No. 11-329734 (A1). Representative examples include Balq (bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide), phenanthroline-based compounds (e.g., UDC's BCP (vasocuproin)), etc. The light-emitting layer (400) of the present invention may include one or more or two or more blue light-emitting layers. Meanwhile, the light-emitting layer of the present invention includes a compound for a light-emitting device according to the present invention as a hole-transporting host, and may further include an electron-transporting host, a cooling dopant, and a sensorizer. The above electron-transporting host comprises an electron-transporting moiety, which may be selected from, for example, a cyano group, a π electron-deficient nitrogen-containing cyclic group, and a group represented by one of the following chemical formulas. In the above chemical formulas, *, *' and *" are each adjacent
[0149] It is a bonding site with any atom. The above "π electron-deficient nitrogen-containing cyclic group" is a cyclic group having at least one *-N=*' moiety, for example, an imidazole group, a pyrazol group, a thiazole group, an isothiaazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthiridine group, a quinoxaline group, a quinazolin group, a sinoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiaazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, It may be selected from the imidazopyrimidine group and the azacarbazole group; and the condensation ring of two or more of the above π electron-deficient nitrogen-containing cyclic groups. When the above host is a mixture of an electron transport host and a hole transport host, the weight ratio of the electron transport host and the hole transport host may be selected from a range of 1:9 to 9:1, for example, 2:8 to 8:2, as another example, 4:6 to 6:4, and as yet another example, 5:5. When the weight ratio of the electron transport host and the hole transport host satisfies the range described above, a balance of hole and electron transport into the light-emitting layer can be achieved. The cooling dopant may have a maximum emission wavelength of its emission spectrum of 400 nm or more and 550 nm or less. For example, the maximum emission wavelength of the emission spectrum of the cooling dopant may be 400 nm or more and 495 nm or less, or 450 nm or more and 495 nm or less, but is not limited thereto. That is, the cooling dopant may emit blue light. The "maximum emission wavelength" refers to the wavelength at which the emission intensity is maximum, and may also be referred to as the "peak emission wavelength." In one embodiment, the cooling dopant does not contain metal atoms. In one embodiment, the cooling dopant may be selected from condensed polycyclic compounds and styryl-based compounds. For example, the cooling dopant may include one of a naphthalene-containing core, a fluorene-containing core, a spiro-bifluorene-containing core, a benzofluorene-containing core, a dibenzofluorene-containing core, a phenanthrene-containing core, anthracene-containing core, a fluorantene-containing core, a triphenylene-containing core, a pyrene-containing core, a chrysene-containing core, a naphthacene-containing core, a fisene-containing core, a perylene-containing core, a pentafene-containing core, an indenoanthracene-containing core, a tetracene-containing core, and a bisanthracene-containing core, but is not limited thereto. For a detailed description of cooling dopants and specific examples of compounds, refer to Korean Published Patent No. 2010-0115134, the contents of which are deemed to be described in this specification. The above-mentioned sensorizer comprises Pt. Specifically, the above-mentioned sensorizer is an organometallic compound comprising Pt. In one embodiment, the above-mentioned sensorizer may comprise Pt and an organic ligand (L11), and L11 and Pt may form one, two, three, or four cyclometallated rings. For a detailed description of the sensorizer and specific examples of compounds, reference may be made to Korean Patent Publication No. 2010-0115134, the contents of which are deemed to be described in this specification. Additionally, the above-mentioned electron transport layer (500) is formed on the upper surface of the light-emitting layer (400) and may be formed by methods such as vacuum deposition, spin coating, or casting. Although the deposition conditions of the above-mentioned electron transport layer (500) vary depending on the compound used, it is generally preferable to select conditions within a range that is almost identical to the formation of the hole injection layer (200). The electron transport layer material may be optionally selected from the compounds for light-emitting devices according to the present invention or ordinary known materials. As for ordinary known materials, for example, quinoline derivatives, particularly tris(8-quinolinolato)aluminum (Alq3), or ET4 (6,6'-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl)di-2,2'-bipyridine) may be used. Furthermore, the electron injection layer (600) may be formed by depositing an electron injection layer material on top of the electron transport layer (500), and may be formed by methods such as vacuum deposition, spin coating, or casting. As the electron injection layer material, a compound for a light-emitting device according to the present invention or a known material such as LiF, NaCl, CsF, Li2O, BaO, etc. may be used. In addition, the second electrode (2000) is used as an electron injection electrode and can be formed on the upper surface of the electron injection layer (600) by a method such as vacuum deposition or sputtering. Various metals can be used as the material for the second electrode (2000). Specific examples include materials such as lithium (Li), aluminum (Al), gold (Au), silver (Ag), magnesium (Mg), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag), but are not limited thereto. Furthermore, a transmissive electron injection electrode using ITO or IZO may be used to obtain a front-emitting device. As shown in FIG. 1, the capping layer (3000) may be formed on the outer side of the first electrode (1000) where the hole injection layer (200) is not formed. Additionally, it may be formed on the outer side of the second electrode (2000) where the electron injection layer (600) is not formed, but is not limited thereto. Such a capping layer (3000) may be formed by a deposition process, and the thickness of the capping layer (3000) may be 100 to 3,000 Å, and more specifically, 300 to 2,000 Å. By controlling the thickness in this way, the transmittance of the capping layer (3000) may be prevented from decreasing. Additionally, although not illustrated in FIG. 1, according to one embodiment of the present invention, an organic layer having various functions may be additionally formed between the capping layer (3000) and the first electrode (1000) or between the capping layer (3000) and the second electrode (2000). Alternatively, an organic layer having various functions may be additionally formed on the upper surface (outer surface) of the capping layer (3000), and one or more separate functional layers may be inserted in the middle of the capping layer (3000), but are not limited thereto. The organic light-emitting device of the present invention may not only have a structure comprising a first electrode (1000), a hole injection layer (200), a hole transport layer (300), a light-emitting layer (400), an electron transport layer (500), an electron injection layer (600), a second electrode (2000), and a capping layer (3000), but may also have various structures of organic light-emitting devices, and may additionally include one or two intermediate layers as needed. Meanwhile, the thickness of each organic layer formed according to the present invention can be adjusted according to the required degree, specifically 1 to 1,000 nm, and more specifically 1 to 150 nm. The present invention will be explained in more detail below through examples of compound synthesis and organic light-emitting diodes according to an embodiment of the present invention. The following synthesis and examples are merely illustrative of the present invention and do not limit the scope of the present invention to the following examples. 10 g of SMA29, 8.2 g of SMB1, 6 g of t-BuONa, 0.57 g of Pd2(dba)3, and 0.3 g of (t-Bu)3P were dissolved in 100 ml of toluene in a round-bottom flask and stirred under reflux. The reaction was monitored by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then column purified and recrystallized to obtain 11 g of compound (yield 66%). m / z: 801.31 (100.0%), 802.32 (65.3%), 803.32 (21.0%), 804.32 (4.6%), 802.31 (1.1%) Synthesis Examples 2 to 46 and Comparative Synthesis Examples 1 to 11 Compounds 2 to 46 of Table 1 and Comparative Compounds 1 to 13 of Table 3 were synthesized, respectively, by using one of the following SMA1 to SMA55 instead of SMA29 and one of SMB1 to SMB23 instead of SMB1 in the same manner as in Synthesis Example 1. Manufacturing of organic light-emitting diodes FIG. 1 shows the structure of a general organic light-emitting device, and the present invention is manufactured to have the structure of the organic light-emitting device shown in FIG. 1 as an example. Specifically, the manufactured organic light-emitting device is stacked in the order from bottom to top: anode (hole injection electrode (1000)) / hole injection layer (200) / hole transport layer (300) / light-emitting layer (400) / electron transport layer (500) / electron injection layer (600) / cathode (electron injection electrode (2000)) / capping layer (1000). When fabricating an organic light-emitting device, the substrate (10) may be a transparent glass substrate or a flexible plastic substrate. The hole injection electrode (1000) is used as an anode for hole injection in an organic light-emitting device. It uses a material having a low work function to enable hole injection and can be formed from a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene. The materials listed in Table 2 below were used for the hole injection layer (200), hole transport layer (300), light-emitting layer (400), electron transport layer (500), electron injection layer (600), and capping layer. In addition, a cathode (2000) for electron injection was formed on the electron injection layer (600). Various metals can be used as the cathode. Specific examples include materials such as aluminum, gold, silver, magnesium, and magnesium-silver alloy. Example 1 An indium tin oxide (ITO) substrate having a silver (Ag) reflective layer formed thereon was cleaned with distilled water ultrasonics. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried. Subsequently, HT01 doped with NDP9 at 3 wt% was deposited as a hole injection layer of 100 Å and HT01 as a hole transport layer of 1000 Å were deposited on the ITO substrate. Then, a host P-Host (compound 1) [45 wt%]:N-Host [45 wt%] and a dopant Pt-Dopant [5 wt%]:MR-Dopant [5 wt%] were doped and deposited to a thickness of 350 Å as an emissive layer. Next, a mixture of ET01 and Liq (1:1, wt. / wt.) was deposited to a thickness of 300 Å as an electron transport layer, followed by the deposition of LiF to a thickness of 10 Å to form an electron injection layer. Next, MgAg was deposited to a thickness of 15 nm to form a cathode, and CPM01 was deposited as a capping layer to a thickness of 1000 Å on the cathode. An organic light-emitting diode was fabricated by encapsulating the device in a glove box. Examples 2 to 46 An organic light-emitting device was fabricated by preparing the light-emitting layer using the compounds prepared in Synthesis Examples 2 to 46, respectively, instead of P-Host (compound 1), in the same manner as in Example 1 above. Comparative Examples 1 to 13 An organic light-emitting device was fabricated by preparing it as a light-emitting layer using Comparative Compounds 1 to 13 shown in Table 3 below, respectively, instead of P-Host (Compound 1), in the same manner as in Example 1 above. <Experimental Example 1> Performance Evaluation of Organic Light Emitting Diodes The performance of organic light-emitting diodes was evaluated by applying voltage with a Keithley 2400 source measurement unit to inject electrons and holes and measuring the luminance when light is emitted using a Konica Minolta spectroradiometer (CS-2000), and measuring the current density and luminance with respect to the applied voltage of Examples 1 to 46 and Comparative Examples 1 to 13 under atmospheric pressure conditions, and the results are shown in Table 4 below. Device DataOp.Vcd / Alm / WCIE1931_xCIE1931_yLT95 Example 1 4.4725.420.650.1340.054127 Example 2 4.4526.721.70.1350.054137 Example 3 4.4525.920.820.1360.053130 Example 4 4.6724.720.10.1360.054107 Example 5 4.6825.720.90.1360.054108 Example 6 4.6524.9120.40.1370.055104 Example 7 4.6322.3417.080.1340.054109 Example 84.622.9218.120.1350.054118 Example 94.6122.8617.620.1340.053115 Example 104.6721.4617.240.1330.05491 Example 114.6821.8117.560.1340.05497 Example 124.6421.5517.440.1330.05597 Example 134.4822.4117.440.1340.055100 Example 144.524.1319.710.1340.054108 Example 154.4523.6118.20.1330.0551 02 Example 16 4.56 22.01 17.1 0.1 36 0.05 487 Example 17 4.57 23.75 19.16 0.1 33 0.05 490 Example 18 4.51 22.56 17.57 0.1 33 0.05 389 Example 19 4.52 20.15 16.04 0.1 36 0.05 4 98 Example 204.5 120.9 316.9 0.1 35 0.05 4104 Example 214.5 20.7 416.7 40.1 33 0.05 5100 Example 224.6 319.8 415.9 40.1 34 0.05 482 Example 234.6 420.2 716.7 10.1 34 0.05 386 Example 244.5920.1416.610.1350.05484 Example 254.5919.0114.30.1360.05498 Example 264.6518.9313.50.1360.055100 Example 274.6219.5713.940.1360.05 5104 Example 284.6919.0212.510.1370.05497 Example 294.6321.2115.050.1340.05480 Example 304.6219.5713.940.1350.05578 Example 314.6321.0714.940.1360.05485 Example 3 24.6519.813.690.1360.05581 Example 3 34.618.6512.960.1360.05595 Example 3 44.4318.2214.210.1370.054101 Example 3 54.418.414.740.1340.05594 Example 3 64.3818.715.010.1350.05484 Example 3 74.4426.921.80.1350.054182 Example 3 84.4326.621.120.1360.0 53174 Example 394.6123.4218.420.1350.054142 Example 404.4924.4119.910.1340.054140 Example 414.4419.215.210.1350.05489 Example 424.6719.714.170.1350.05490 Example 434.5421.714.010.1350.05492 Example 444.4725.920.940.1350.054109 Example 454.5425.720.810.13 50.054102 Example 4 64.5125.220.70.1350.054100 Comparative Example 1 4.3516.5212.80.1340.05458 Comparative Example 2 4.3512.278.480.1330.05353 Comparative Example 3 4.4615.4311.150.1340.05448 Comparative Example 4 4.4711.248.440.1330.05440 Comparative Example 5 4.4515.1210.680.1340.05545 Comparative Example 6 4.4711.998.230.1340.05 438 Comparative Example 74.59 14.88 10.33 0.133 0.05342 Comparative Example 84.53 14.38 10.97 0.136 0.05440 Comparative Example 94.57 11.067 87 0.133 0.05438 Comparative Example 104.59 11.017 82 0.133 0.05535 Comparative Example 114.48 11.277 86 0.133 0.05545 Comparative Example 124.5 11.097 57 0.133 0.05542 Comparative Example 135.17 14.428 77 0.136 0.05548. As shown in Table 2 above, compared to Comparative Examples 1 to 13, the embodiments of the present invention show improved efficiency and lifespan, and it can be confirmed that the physical properties are excellent in all aspects. In addition, when comparing the embodiments of the present invention (Examples 5 and 6 with Comparative Examples 1 and 2) and (Examples 29-32 with Comparative Examples 7-10), the case having a phenylene linker between the first carbazole and the second carbazole showed superior device performance compared to the case without such a linker and the general P-Host CBP. Specifically, it was confirmed that the efficiency and lifespan of the compounds of the present invention in the form of Cz-Ph-Cz-Ph-Cz, which additionally introduced a phenylene linker, were improved compared to the Cz-Cz-Ph-Cz compounds. Among these, Examples 1, 2, and 3, in which both the first carbazole and the second carbazole linked to phenylene were connected at the 3rd position, showed high device performance, and in particular, the compounds 37-40, in which the entire form was substituted with deuterium, showed a lifespan increase of about 20-30% compared to when it was hydrogen. When comparing cases where Ph-Cz and a heterocompound are directly bonded to a Cz-Ph-Cz compound (Examples 1-6 and Comparative Examples 11 and 12), it was shown that the lifespan and efficiency increased when Ph-Cz was bonded compared to when a heterocompound (dibenzofuran, dibenzothiophene) was directly bonded. In addition, it was confirmed that the overall device performance of compounds in which the phenylene between the first carbazole and the second carbazole is bonded at the meta position is improved compared to compounds in which it is not (Examples 25-26, 33-36). In addition, when comparing the performance between the examples, in (Examples 1-3 and 4-6), (Examples 7-9 and 10-12), (Examples 13-15 and 16-18), and (Examples 19-21 and 22-24), when a phenyl substituent is present in the third carbazole, the driving voltage is improved and the efficiency and lifespan are improved compared to when it is not. This research is funded by the Ministry of Trade, Industry and Energy and the Korea Institute of Industrial Technology Planning and Evaluation (KEIT) in 2025 (Project No.: 00423106, Project Title: Development of Long-Life Blue Photosensitive Organic Light-Emitting Material with EQE of Over 20% and Synthesis Manufacturing Process Technology Applying Intermolecular Exciton Interaction Control Technology). This work was supported by the Technology Innovation Program (Project No.: 00423106, Project Title: Development of long lifetime blue sensitized organic light-emitting material with EQE of over 20% and synthetic manufacturing process technology applying bimolecular exciton interaction control technology) through the Korea Planning & Evaluation Institute of Industrial Technology (KEIT) funded by the Ministry of Trade, Industry & Energy (MOTIE, Korea) This application was filed as a result of the following task. National R&D projects that supported this invention <Project ID> 2410000823 <Assignment No.> 00423106 <Ministry Name> Ministry of Trade, Industry and Energy <Name of Project Management (Specialized) Agency> Korea Institute of Industrial Technology Planning and Evaluation <Research Project Name> Electronic Components Industry Technology Development (R&D) - Establishment of Display Innovation Process Platform <Project Title> Development of Long-Life Blue Photosensitive Organic Light-Emitting Material with EQE Over 20% and Synthesis Manufacturing Process Technology Using Intermolecular Exciton Interaction Control Technology <Name of Project Performing Organization> Dongjin Semichem <Research Period> 2025.01.01 ~ 2025.12.31
Claims
1. Compound represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, X1 to X16 are each independently C, CR, or N, and L and L1 are each independently substituted or unsubstituted C5–C30 arylene groups, substituted or unsubstituted C2–C30 heteroarylene groups, or a combination thereof, and Ar1 is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkyloxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 divalent alkylamine group, a substituted or unsubstituted C5-C30 divalent arylamine group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 heterocycloalkyl group, a substituted or unsubstituted C3-C50 cycloalkenyl group, a substituted or unsubstituted C2-C50 heterocycloalkenyl group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. Ar2 to Ar5 are each independently a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 dialkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C1-C50 heterocycloalkyl group, a substituted or unsubstituted C3-C50 cycloalkenyl group, a substituted or unsubstituted C2-C50 heterocycloalkenyl group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 It is a heteroaryl group, where R is independently hydrogen or deuterium, p, m, and n are each independently integers from 0 to 4, and The 1 and 2 indicated at the bottom of the carbazole represent the first carbazole and the second carbazole, respectively.
2. In Paragraph 1, The above chemical formula 1 is a compound represented by the following chemical formula 2. <Chemical Formula 2> In the above chemical formula 2, The same symbol as Chemical Formula 1 above has the same definition, and X17 to X24 are each independently C, CR, or N, and L is a substituted or unsubstituted C5–C30 arylene group, and L1 is a substituted or unsubstituted C5–C30 arylene group, a substituted or unsubstituted C2–C30 heteroarylene group, or a combination thereof, and Ar5 is a substituted or unsubstituted C5–C50 aryl group or a substituted or unsubstituted C2–C50 heteroaryl group, and The numbers 1 to 3 indicated at the bottom of the carbazole represent the first carbazole, the second carbazole, and the third carbazole, respectively.
3. In Paragraph 1, The above R is a compound in which all of them are deuterium.
4. In Paragraph 1, Compounds in which the CC bonding positions of the first carbazole and the second carbazole connected to L are X6 and X9, X6 and X10, X6 and X11, X6 and X12, X7 and X9, X7 and X10, X7 and X12, X8 and X9, X8 and X12, or X5 and X12.
5. In Paragraph 1, A compound in which the CC bonding positions of the first carbazole and second carbazole connected to L are X6 and X11.
6. In Paragraph 1, The above L is a compound in which the phenylene group is substituted or unsubstituted with deuterium, the biphenylene group is substituted or unsubstituted with deuterium, or the terphenylene group is substituted or unsubstituted with deuterium.
7. In Paragraph 1, The above L is a compound in which a 1,3-phenylene group is substituted or unsubstituted with deuterium.
8. In Paragraph 1, Compounds in which Ar2 to Ar4 are each independently a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C2-C30 dialkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C5-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group.
9. In Paragraph 1, The above Ar2 is a compound in which a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, or a terphenyl group substituted or unsubstituted with deuterium.
10. In Paragraph 2, A compound in which Ar5 is a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted dibenzofuran, or a deuterium-substituted or unsubstituted dibenzothiophene.
11. In Paragraph 2, The above Ar5 is a compound of phenyl substituted or unsubstituted with deuterium.
12. In Paragraph 2, The above L1 is a compound in which the phenylene group is substituted or unsubstituted with deuterium, the biphenylene group is substituted or unsubstituted with deuterium, or the terphenylene group is substituted or unsubstituted with deuterium.
13. In Paragraph 2, The above L1 is a phenylene group substituted or unsubstituted with deuterium, and is a compound that is a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group.
14. In Paragraph 2, The above Ar5 is a compound that binds to X22.
15. In Paragraph 1, The above compound is selected from the following compounds and compounds in which some or all of the hydrogens are substituted with deuterium:
16. An organic light-emitting device comprising the compound of claim 1.
17. In Paragraph 16, The above organic light-emitting device is, First electrode; Second electrode; and It includes one or more organic layers interposed on the inner side of the first electrode and the second electrode, and One or more of the above organic layers are organic light-emitting diodes containing the above compound.
18. In Paragraph 17, The above compound is an organic light-emitting device included in one or more organic layers among a light-emitting layer, a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.
19. In Paragraph 17, The above compound is an organic light-emitting device included in a light-emitting layer.
20. In Paragraph 19, The above-described light-emitting layer is an organic light-emitting device further comprising an electron-transporting host including an electron-transporting moiety, a cooling dopant, and a sensorizer.