Low-voltage, highly efficient and long-life organic light-emitting devices
By integrating a pyrene-based compound and anthracene compound in the light-emitting layers, the OLEDs achieve low voltage, high efficiency, and long life characteristics, addressing the efficiency and lifetime challenges of existing devices.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2025-07-10
- Publication Date
- 2026-03-11
AI Technical Summary
Existing organic light-emitting devices (OLEDs) face challenges in achieving simultaneously high efficiency and long lifetime, particularly as they scale in size, with driving voltage and material crystallization issues affecting performance.
Incorporating a pyrene-based compound with a specific structure in at least one of the light-emitting layers, along with an anthracene compound in the remaining layers, to enhance the efficiency and stability of the OLEDs.
The OLEDs exhibit low voltage driving characteristics, high luminous efficiency, and extended lifespan due to the use of these compounds, optimizing energy levels and mobility within the layers.
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Figure 2026042720000001_ABST
Abstract
Description
[Technical Field]
[0001] The present invention relates to an organic light-emitting device with low voltage, high efficiency and long life, and more particularly to an organic light-emitting device that can exhibit low voltage, high efficiency and long life by using a compound with a specific structure as a light-emitting layer material in the organic light-emitting device. [Background technology]
[0002] Organic light emitting diodes (OLEDs) are displays that utilize the self-luminous phenomenon and have advantages such as a wide viewing angle, being lighter, thinner, and smaller than LCDs, and having a fast response time. As such, they are expected to be used in full-color displays and lighting.
[0003] Organic light-emitting devices generally refer to the conversion of electrical energy into light energy using organic materials. Organic light-emitting devices utilizing organic light-emitting technology typically have a structure comprising an anode, a cathode, and an organic layer between them. To enhance the efficiency and stability of the device, the organic layer often has a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an organic light-emitting device, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons combine, excitons are generated. Light is emitted when these excitons fall back to the ground state. Such organic light-emitting devices are known to have advantageous properties, such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and fast response.
[0004] Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions, and electron blocking layer materials or hole blocking layer materials can be added as needed.
[0005] The most important issues in organic light emitting devices are their lifetime and efficiency, and as displays become larger in area, these efficiency and lifetime issues must be addressed. Here, the efficiency, lifetime, and driving voltage are interrelated, and as efficiency increases, the driving voltage decreases relatively. When the driving voltage decreases, the crystallization of organic materials due to Joule heating generated during driving decreases, resulting in a tendency for the lifetime to be extended.
[0006] However, efficiency cannot be maximized by simply improving the organic layers, because long life and high efficiency can be achieved simultaneously when the energy levels and T1 values between each organic layer, and the inherent properties of the material (mobility, interface properties, etc.) are optimally combined.
[0007] In general, in an organic light emitting device, excitons are generated by recombination when electrons are transferred from an electron transport layer to an emission layer and holes are transferred from a hole transport layer to an emission layer.
[0008] In this regard, a technology for increasing the stability and luminous efficiency of an organic light-emitting device by forming the light-emitting layer in the organic light-emitting device with two or more layers has been realized as a product. For example, when two light-emitting layers are formed, one of the two light-emitting layers corresponds to the exciton recombination region and the other corresponds to the triplet-triplet fusion region, thereby providing a mechanism for energy transfer from the first light-emitting layer adjacent to the hole transport layer to the second light-emitting layer. In the case of a material used for the light-emitting layer, it is advantageous to have a relatively high triplet energy value and fast electron mobility.
[0009] As a conventional technology relating to an organic light-emitting element including two or more light-emitting layers, Korean Patent Publication No. 10-2021-0077686 (June 25, 2021) discloses technology relating to an organic electroluminescent element in which an emitting region includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer and the second light-emitting layer are adjacent to each other, the first light-emitting layer is located between the anode and the second light-emitting layer, and either the first light-emitting layer or the second light-emitting layer includes a compound having at least one deuterium atom.
[0010] However, although various methods for manufacturing organic light-emitting devices have been attempted in the prior art, including these prior art documents, there is a continuing need for the development of organic light-emitting devices that include multiple light-emitting layers and simultaneously have improved luminous efficiency and long life characteristics. [Prior art documents] [Patent documents]
[0011] [Patent Document 1] Korean Patent Publication No. 10-2021-0077686 (Publication Date: June 25, 2021) Summary of the Invention [Problem to be solved by the invention]
[0012] Therefore, a technical problem to be solved by the present invention is to provide an organic light emitting diode (OLED) having low voltage, high efficiency, and long life characteristics by including a plurality of light emitting layers in the organic light emitting diode, and including a pyrene-based compound with a specific structure in at least one of the plurality of light emitting layers. [Means for solving the problem]
[0013] In order to achieve the above object, the present invention provides a light-emitting device comprising: a first electrode; a second electrode facing the first electrode; a first emitting layer interposed between the first electrode and the second electrode, the first emitting layer including a first host and a first dopant; and a second emitting layer including a second host and a second dopant, At least one of the first host and the second host includes a compound represented by Chemical Formula 1.
[0014] [Chemical formula 1] TIFF2026042720000002.tif49170
[0015] In the above Chemical Formula 1, The substituents R may be the same or different and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted cycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The m is an integer of 1 to 9, and when the m is 2 or more, each R may be the same or different. In addition, when the m is 8 or less, each TIFF2026042720000003.tif32170 may be identical to or different from each other, Z is Si or Ge; The substituents R1 and R2 may be the same or different and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted Substituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, Heterocycloalkyl groups having a fused ring, substituted or unsubstituted aryl groups having 8 to 30 carbon atoms having a fused aliphatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms having a fused aliphatic hydrocarbon ring, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy groups having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy groups having 2 to 30 carbon atoms, substituted or any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The substituent R3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or any one selected from an unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; However, except when R1 to R3 are all substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, the linking groups L1 and L2 may be the same or different and each independently represent a linking group selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 24 carbon atoms and fused with an aliphatic hydrocarbon ring; The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 1 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
[0016] The present invention also provides a compound represented by Chemical Formula 1. [Effects of the Invention]
[0017] The organic light emitting diode (OLED) according to the present invention can have excellent device characteristics such as low voltage driving characteristics, high luminous efficiency, and long life.
[0018] In particular, when the compound represented by Chemical Formula 1 is used in at least one of the plurality of light-emitting layers in the organic light-emitting device according to the present invention and the anthracene compound represented by Chemical Formula 2 described below is used in at least one of the remaining light-emitting layers, the device can exhibit low-voltage operation, high light-emitting efficiency, and long life. [Brief explanation of the drawings]
[0019] [Figure 1] 1 is a schematic diagram of an organic light-emitting device according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION
[0020] The present invention will be described in more detail below. In each drawing of the present invention, the size or dimensions of structures are shown enlarged or reduced compared to the actual size for clarity of the present invention, and well-known structures are omitted so that characteristic structures can be seen, so that the present invention is not limited to the drawings.
[0021] Furthermore, the size and thickness of each component shown in the drawings are shown arbitrarily for the sake of convenience, and the present invention is not necessarily limited to the drawings. Furthermore, thicknesses are shown enlarged in the drawings to clearly depict multiple layers and regions. Furthermore, thicknesses of some layers and regions are shown exaggerated in the drawings for the sake of convenience. When a layer, film, region, plate, or other portion is described as being "on" another portion, this includes not only the case where the portion is "directly on" the other portion, but also the case where another portion is interposed therebetween.
[0022] Furthermore, throughout the specification, when a part "comprises" a certain element, this does not mean that it excludes other elements, but that it may further include other elements, unless otherwise specified. Furthermore, throughout the specification, "on" means that it is located above or below the target part, and does not necessarily mean that it is located above the direction of gravity.
[0023] The present invention provides a light-emitting device comprising: a first electrode; a second electrode facing the first electrode; a first emitting layer interposed between the first electrode and the second electrode, the first emitting layer including a first host and a first dopant; and a second emitting layer including a second host and a second dopant, At least one of the first host and the second host includes a compound represented by Chemical Formula 1.
[0024] [Chemical formula 1] TIFF2026042720000004.tif49170
[0025] In the above Chemical Formula 1, The substituents R may be the same or different and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted cycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The m is an integer of 1 to 9, and when the m is 2 or more, each R may be the same or different. In addition, when the m is 8 or less, each TIFF2026042720000005.tif32170 may be identical to or different from each other, Z is Si or Ge; The substituents R1 and R2 may be the same or different and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted Substituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, Heterocycloalkyl groups having a fused ring, substituted or unsubstituted aryl groups having 8 to 30 carbon atoms having a fused aliphatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms having a fused aliphatic hydrocarbon ring, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy groups having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy groups having 2 to 30 carbon atoms, substituted or any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The substituent R3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or any one selected from an unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; However, except when R1 to R3 are all substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, the linking groups L1 and L2 may be the same or different and each independently represent a linking group selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 24 carbon atoms and fused with an aliphatic hydrocarbon ring; The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 1 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
[0026] On the other hand, in the present invention, when considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and the "substituted or unsubstituted aryl group having 5 to 50 carbon atoms," the range of carbon atoms in the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when the group is regarded as unsubstituted, without taking into account the portion substituted with the substituent. For example, a phenyl group substituted with a butyl group at the para position should be regarded as an aryl group having 6 carbon atoms and substituted with a butyl group having 4 carbon atoms.
[0027] The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen atom. When the aryl group has a substituent, it may be fused with adjacent substituents to form an additional ring. The aryl group may also include an organic radical derived by removing one hydrogen atom from an arene ring formed by condensing two arene rings.
[0028] Specific examples of the aryl group include aromatic radical groups such as a phenyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, an o-terphenyl group, an m-terphenyl group, a p-terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyl group, a chrysenyl group, a naphthacenyl group, a fluoranthenyl group, and a triphenylenyl group, but are not limited thereto. The aryl group may also include an organic radical formed by removing one hydrogen atom from an arene ring formed by condensing two arene rings, such as an arene ring formed by condensing a fluorene ring with a phenylene ring, or an arene ring formed by condensing a fluorene ring with a phenanthrene ring.
[0029] Furthermore, one or more hydrogen atoms in the aryl group can be substituted with a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group, a germanium group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphate group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 3 to 24 carbon atoms, or an alkylheteroaryl group having 3 to 24 carbon atoms.
[0030] In the present invention, the aromatic hydrocarbon ring refers to an aromatic ring composed of carbon and hydrogen, and the aliphatic hydrocarbon ring refers to a hydrocarbon ring composed of carbon and hydrogen but not belonging to an aromatic hydrocarbon ring. In this case, the aliphatic hydrocarbon ring may preferably be a hydrocarbon ring in which at least 30% of the carbon atoms forming the ring are bonded via an sp3 orbital structure and the ring contains 0 to 3 double bonds and / or triple bonds, or more preferably a hydrocarbon ring in which at least 50% of the carbon atoms forming the ring are bonded via an sp3 orbital structure and the ring contains 0 to 2 double bonds and / or triple bonds.
[0031] Furthermore, the aryl group having an aliphatic hydrocarbon ring fused thereto in the present invention means a cyclic substituent in which two adjacent carbon atoms in an aliphatic hydrocarbon ring and two adjacent carbon atoms, excluding a carbon atom that has become an organic radical by removing hydrogen from one of the carbon atoms constituting the ring in the aryl group, are fused together to share one double bond, and which has non-aromaticity as a whole. Specific examples include, but are not limited to, a tetrahydronaphthyl group, tetrahydrobenzocycloheptene, tetrahydrophenanthrene group, tetrahydroanthracenyl group, and octahydrotriphenylene group.
[0032] The heteroaryl group, which is a substituent used in the compound of the present invention, refers to an aromatic aryl group having 2 to 24 carbon atoms and containing one, two, or three heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aromatic ring, with the remaining ring atoms being carbon, and the rings can be fused to form a ring. At least one hydrogen atom of the heteroaryl group can be substituted with the same substituent as in the aryl group.
[0033] Specific examples of the heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a carbolinyl group, an acenaphthoquinoxalinyl group, an indenoquinazolinyl group, an indenoisoquinolinyl group, an indenoquinolinyl group, a pyridoindolyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolin ... Examples of such an alkyl group include, but are not limited to, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoselenophene group, a dibenzothiophenyl group, a dibenzofuranyl group, a dibenzoselenophene group, a phenanthrolinyl group, a thiazolinyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group, a phenothiazinyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzoselenophene group, and an indolocarbazole group.
[0034] In the present invention, the aromatic heterocycle means an aromatic hydrocarbon ring in which one or more aromatic carbons are substituted with heteroatoms, and the aromatic heterocycle preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.
[0035] Furthermore, the heteroaryl group having an aliphatic hydrocarbon ring fused thereto is a substituent having a structure in which a heteroaryl group is substituted for the aryl group in the aryl group having an aliphatic hydrocarbon ring fused thereto. Specific examples include, but are not limited to, a tetrahydroindole group, a tetrahydrobenzofuranyl group, a tetrahydrobenzothiophene group, a tetrahydrocarbazole group, a tetrahydrodibenzofuranyl group, a tetrahydrobenzothiophene group, a tetrahydroquinoline group, and a tetrahydroquinoxaline group.
[0036] In the present invention, the "fused ring in which an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring are fused" means a fused ring in which two adjacent carbon atoms of the aromatic hydrocarbon ring and two adjacent carbon atoms of the aliphatic hydrocarbon ring are fused to each other so as to be shared with each other. Examples include tetrahydronaphthalene and dihydroindene rings in which two adjacent carbon atoms of a benzene ring and a cyclohexane ring are fused to each other so as to be shared with each other.
[0037] Furthermore, in the present invention, the "fused ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are fused" refers to a fused ring in which two adjacent carbon atoms in the aromatic heterocycle and two adjacent carbon atoms in the aliphatic hydrocarbon ring are fused to each other so as to be shared with each other, and an example thereof includes a hexahydrodibenzofuran ring in which a benzofuran ring and a cyclohexane ring are fused to each other so as to share with each other two adjacent carbon atoms in each ring.
[0038] The alkyl group, which is a substituent used in the present invention, is a substituent in which one hydrogen atom has been removed from an alkane, and may have a structure including a straight chain and a branched structure. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 2-methyl ... Examples of alkyl groups include, but are not limited to, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl groups, and one or more hydrogen atoms of the alkyl group may be substituted with the same substituents as in the aryl group.
[0039] The halogenated alkyl group as a substituent used in the present invention means a substituent in which at least one hydrogen atom in the alkyl group as a substituent is substituted with a halogen group, and preferably, the halogen group may be a fluorine atom.
[0040] The "cyclo" in the cycloalkyl group, cycloalkoxy group, etc., which are substituents used in the compounds of the present invention, means a substituent having a structure that can form a monocyclic or polycyclic saturated hydrocarbon within the alkyl or alkoxy group. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc. One or more hydrogen atoms in the cycloalkyl group can be substituted with the same substituents as in the aryl group, and this also applies to the cycloalkoxy.
[0041] In addition, in the present invention, the heterocycloalkyl group means a group in which one or more of the carbon atoms in the ring of a substituent forming a cycloalkyl structure are substituted with a heteroatom, and preferably, one to three carbon atoms can be substituted with one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te.
[0042] The cycloalkyl group fused with an aromatic hydrocarbon ring or an aromatic heterocycle means a cyclic substituent that shares one double bond and exhibits non-aromaticity as a whole, in which two adjacent carbon atoms in the aromatic hydrocarbon ring or aromatic heterocycle and two adjacent carbon atoms excluding the carbon atom that has become an organic radical by removing hydrogen from one of the carbon atoms constituting the ring in the cycloalkyl group are fused with each other, and the two adjacent carbon atoms share one double bond, and the cycloalkyl group exhibits non-aromaticity as a whole, and specific examples thereof include, but are not limited to, tetrahydronaphthyl, tetrahydrophenanthrene group, tetrahydroquinoline group, tetrahydroquinoxaline group, and cyclopentabenzofuran.
[0043] Furthermore, the heterocycloalkyl group having a fused aromatic hydrocarbon ring refers to a cycloalkyl group having a fused aromatic hydrocarbon ring in which one or more carbon atoms in the cycloalkyl ring are substituted with heteroatoms, and is preferably a substituent having a structure in which one to three carbon atoms in the cycloalkyl ring are substituted with one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te. Specific examples include, but are not limited to, a hexahydrodibenzofuranyl group, a hexahydrocarbazole group, a hexahydrodibenzothiophene group, and a dihydrobenzodioxin group, and the group as a whole exhibits non-aromaticity.
[0044] Furthermore, the aryl group or heteroaryl group fused with an aliphatic heterocycle is a substituent having a structure in which an aliphatic heterocycle is fused in place of the aliphatic hydrocarbon ring in the aryl group or heteroaryl group fused with an aliphatic hydrocarbon ring. Specific examples include, but are not limited to, a chroman group, a dihydropyranopyridine group, a thiochroman group, a dihydrobenzodioxin group, a dihydrothiopyranopyridine group, and a dihydropyranopyrimidine group, and the like, and the group as a whole exhibits non-aromaticity.
[0045] The aliphatic heterocycle means an aliphatic hydrocarbon ring in which one or more carbon atoms are substituted with heteroatoms, and the aliphatic heterocycle may preferably have 1 to 3 carbon atoms in the aliphatic hydrocarbon ring substituted with one or more heteroatoms selected from N, O, S, etc.
[0046] The alkoxy group, which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the terminal of an alkyl group or a cycloalkyl group, and specific examples thereof include, but are not limited to, methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantaneoxy, dicyclopentaneoxy, bornyloxy, and isobornyloxy. One or more hydrogen atoms in the alkoxy group can be substituted with the same substituents as in the aryl group.
[0047] Specific examples of the arylalkyl group, which is a substituent used in the compound of the present invention, include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc., and one or more hydrogen atoms in the arylalkyl group can be substituted with the same substituents as in the aryl group.
[0048] Specific examples of the alkylaryl group, which is a substituent used in the compound of the present invention, include, but are not limited to, tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, and t-butylphenanthryl, and one or more hydrogen atoms in the alkylaryl group can be substituted with the same substituents as in the aryl group.
[0049] In addition, in the present invention, an alkenyl group means an alkyl substituent containing one carbon-carbon double bond formed by two carbon atoms, and an alkynyl group means an alkyl substituent containing one carbon-carbon triple bond formed by two carbon atoms.
[0050] Furthermore, the alkylene group used in the present invention is an organic radical derived by removing two hydrogen atoms in an alkane molecule, which is a linear or branched saturated hydrocarbon. Specific examples of the alkylene group include, but are not limited to, a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group, an iso-amylene group, and a hexylene group. One or more hydrogen atoms in the alkylene group may be substituted with the same substituents as in the aryl group.
[0051] In the present invention, the amine group is a functional group containing -NH2, in which one or more of the two hydrogen atoms bonded to the nitrogen atom in -NH2 are substituted with any one selected from an alkyl group, a cycloalkyl group, an aryl group, an aryl group fused with an aliphatic hydrocarbon ring, an arylalkyl group, an alkylaryl group, a heteroaryl group, and a heteroaryl group fused with an aliphatic hydrocarbon ring, and when both of the two hydrogen atoms bonded to the nitrogen atom in -NH2 are substituted with the above-mentioned substituents, these respective substituents may be the same or different, and one or more hydrogen atoms in the alkyl group, cycloalkyl group, aryl group, aryl group fused with an aliphatic hydrocarbon ring, arylalkyl group, alkylaryl group, heteroaryl group, and heteroaryl group fused with an aliphatic hydrocarbon ring bonded to the nitrogen atom in the amine group can be substituted with the same substituents as in the case of the aryl group.
[0052] Here, each aryl group in the aryl group, arylheteroaryl group, aryl group fused with an aliphatic hydrocarbon ring, cycloalkylaryl group, etc. bonded to the nitrogen atom of the amine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the heteroaryl group, arylheteroaryl group, etc. may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
[0053] Examples of the amine group include an alkylamine group in which one or two alkyl groups, which may be the same or different, are bound to the nitrogen atom, an arylamine group in which one or two aryl groups, which may be the same or different, are bound to the nitrogen atom, and an alkylarylamine group in which one alkyl group and one aryl group are bound to the nitrogen atom.Other examples include heteroarylamine groups, arylheteroarylamine groups, alkyl (aryl with an aliphatic hydrocarbon ring fused) amine groups, aryl (aryl with an aliphatic hydrocarbon ring fused) amine groups, cycloalkyl (aryl with an aliphatic hydrocarbon ring fused) amine groups, cycloalkylarylamine groups, and heteroaryl (aryl with an aliphatic hydrocarbon ring fused) amine groups.
[0054] The silyl group, which is a substituent used in the compound of the present invention, is a functional group containing -SiH3, in which one or more of the three hydrogen atoms bonded to the silicon atom in -SiH3 are substituted with any one selected from the group consisting of an alkyl group, a cycloalkyl group, an aryl group, an aryl group fused with an aliphatic hydrocarbon ring, an arylalkyl group, an alkylaryl group, a heteroaryl group, and a heteroaryl group fused with an aliphatic hydrocarbon ring. When one, two, or three hydrogen atoms bonded to the silicon atom in -SiH3 are substituted with the above-mentioned substituents, these respective substituents may be the same or different, and one or more hydrogen atoms in the alkyl group, cycloalkyl group, aryl group, aryl group fused with an aliphatic hydrocarbon ring, arylalkyl group, alkylaryl group, heteroaryl group, and heteroaryl group fused with an aliphatic hydrocarbon ring that are bonded to the silicon atom in the silyl group can be substituted with the same substituents as in the case of the aryl group.
[0055] Here, each aryl group in the aryl group, arylheteroaryl group, aryl group fused with an aliphatic hydrocarbon ring, cycloalkylaryl group, etc. bonded to the silicon atom of the silyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the heteroaryl group, arylheteroaryl, etc. may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
[0056] Examples of the silyl group include an alkylsilyl group in which one, two, or three alkyl groups, which may be the same or different, are bonded to a silicon atom; an arylsilyl group in which one, two, or three aryl groups, which may be the same or different, are bonded to a silicon atom; an alkylarylsilyl group in which one alkyl group and one aryl group are bonded to a silicon atom; and an alkylarylheteroarylsilyl group in which one alkyl group, one aryl group, and one heteroaryl group are bonded to a silicon atom. Other examples include alkyl(heteroaryl)silyl groups, arylheteroarylsilyl groups, alkyl(aryl with an aliphatic hydrocarbon ring fused)silyl groups, alkyl(aryl)(aryl with an aliphatic hydrocarbon ring fused)silyl groups, cycloalkyl(aryl with an aliphatic hydrocarbon ring fused)silyl groups, cycloalkylarylheteroarylsilyl groups, and alkyl(heteroaryl)(aryl with an aliphatic hydrocarbon ring fused)silyl groups.
[0057] Specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl.
[0058] In the present invention, a germanium group (or a germyl group or a germane group) refers to a functional group in which a germanium (Ge) atom replaces a silicon (Si) atom in the silyl group, and the remaining portion is as described for the silyl group.
[0059] Specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, and dimethylfurylgermane.
[0060] In the present invention, the substituent (A) and the "adjacent substituent (B)" in the aromatic ring mean the substituent (B) bonded to an aromatic ring carbon atom adjacent to the aromatic ring carbon atom to which the substituent (A) in the aromatic ring is bonded; the "adjacent substituent (B)" to the substituent (A) in the alicyclic ring means the substituent (B) bonded to a ring carbon atom adjacent to the ring carbon atom to which the substituent A in the alicyclic ring is bonded; and the substituent (A) bonded to a specific carbon atom in the aliphatic chain structure and the "adjacent substituent (B)" mean the substituent (B) bonded to a carbon atom adjacent to the specific carbon atom to which the substituent A in the aliphatic chain structure is bonded.
[0061] In the present invention, an alkenyl group refers to an alkyl substituent containing one carbon-carbon double bond formed by two carbon atoms, and an alkynyl group refers to an alkyl substituent containing one carbon-carbon triple bond formed by two carbon atoms.
[0062] Furthermore, the alkylene group used in the present invention is an organic radical derived by removing two hydrogen atoms in an alkane molecule, which is a linear or branched saturated hydrocarbon. Specific examples of the alkylene group include, but are not limited to, a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group, an iso-amylene group, and a hexylene group. One or more hydrogen atoms in the alkylene group may be substituted with the same substituents as in the aryl group.
[0063] On the other hand, more preferred examples of the "substituted" in the "substituted or unsubstituted" in the chemical formula 1 in the present invention include deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 3 to 18 carbon atoms, an alkylheteroaryl group having 3 to 18 carbon atoms, an aromatic group having 9 to 20 carbon atoms, The aryl group may be substituted with one or more substituents selected from the group consisting of a cycloalkyl group fused with a hydrocarbon ring, a cycloalkyl group having 7 to 20 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having 9 to 20 carbon atoms fused with an aromatic heterocycle, an aryl group having 9 to 20 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having 7 to 20 carbon atoms fused with an aliphatic hydrocarbon ring, an alkoxy group having 1 to 12 carbon atoms, an amine group having 1 to 18 carbon atoms, a silyl group having 1 to 18 carbon atoms, a germanium group having 1 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms, and one or more hydrogen atoms in each of the substituents can be substituted with deuterium or tritium.
[0064] In the present invention, a more preferred example of the substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms and fused with an aromatic hydrocarbon ring may be a substituted or unsubstituted cycloalkyl group having 9 to 20 carbon atoms and fused with an aromatic hydrocarbon ring.
[0065] In the present invention, a more preferred example of the substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms and fused with an aromatic heterocycle may be a substituted or unsubstituted cycloalkyl group having 7 to 20 carbon atoms and fused with an aromatic heterocycle.
[0066] In the present invention, a more preferred example of the substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms and fused with an aromatic hydrocarbon ring may be a substituted or unsubstituted heterocycloalkyl group having 9 to 20 carbon atoms and fused with an aromatic hydrocarbon ring.
[0067] In the present invention, a more preferred example of the substituted or unsubstituted aryl group having 8 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring may be a substituted or unsubstituted aryl group having 9 to 20 carbon atoms and fused with an aliphatic hydrocarbon ring.
[0068] In the present invention, a more preferred example of the substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring may be a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms and fused with an aliphatic hydrocarbon ring.
[0069] In the present invention, a more preferred example of the substituted or unsubstituted aryl group having 6 to 30 carbon atoms and fused with an aliphatic heterocycle may be a substituted or unsubstituted aryl group having 7 to 20 carbon atoms and fused with an aliphatic heterocycle.
[0070] In the present invention, a more preferred example of the substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic heterocycle may be a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms and fused with an aliphatic heterocycle.
[0071] On the other hand, in the specification of the present invention, "the R 31 ~R 37 may be linked with the A1 to A3 rings to form an alicyclic or aromatic monocyclic or polycyclic ring, and in this case, R 31 ~R 37 Each substituent (R 31 ~R 37A further ring can be formed by removing one hydrogen radical from each of the A1 to A3 rings to form an alicyclic or aromatic monocyclic or polycyclic ring, and by connecting the rings together, which is referred to as "the R 32 and R 33 , R 34 and R 35 , and R 36 and R 37 can be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the same applies to the R 32 and R 33 When forms a ring, R 32 Remove one hydrogen radical from R 33 This means that a further ring can be formed by removing one hydrogen radical from each of the groups and linking them together.
[0072] The present invention uses the compound represented by Chemical Formula 1 as a material for at least one light-emitting layer in an organic light-emitting device including multiple light-emitting layers. In this case, the compound represented by Chemical Formula 1 is characterized by including at least one silane group or germanium group in a pyrene ring. Through the structure represented by Chemical Formula 1, when compared to when all the substituents of the silane group are phenyl, if one of the substituents is substituted with a structure such as naphthalene having 10 or more carbon atoms, the triplet value is lowered. This satisfies two requirements: a triplet value lower than that of a dopant in any one light-emitting layer in the organic light-emitting device and a triplet value higher than that of a host in the remaining light-emitting layer. As a result, an organic light-emitting device exhibiting higher efficiency and longer life than conventional organic light-emitting devices can be realized.
[0073] The compound represented by Chemical Formula 1 used as a light-emitting layer material in the organic light-emitting device according to the present invention may preferably be a compound represented by the following Chemical Formula 1-1 or 1-2.
[0074] [Chemical formula 1-1] TIFF2026042720000006.tif39170
[0075] [Chemical formula 1-2] TIFF2026042720000007.tif39170
[0076] In the above Chemical Formula 1-1 and Chemical Formula 1-2, The substituent R is the same as R defined above, Z1 and Z2 may be the same or different and are each independently Si or Ge; The substituents R4, R5, R7 and R8 may be the same or different from each other, and are each independently the same as R1 and R2 defined above; The substituents R6 and R9 may be the same or different from each other, and each independently represent the same as R3 defined above; However, except when R4 to R6 are all substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, The linking groups L3 to L6 may be the same as or different from each other and are each independently the same as the linking groups L1 and L2 defined above, m1 is 9, and each R may be the same or different. m2 is 8, and each R may be the same or different. The "substituted" in "substituted or unsubstituted" in Chemical Formula 1-1 and Chemical Formula 1-2 is the same as defined above for the "substituted" in "substituted or unsubstituted."
[0077] In one embodiment, R1 and R2 in Chemical Formula 1 may be the same or different and may each independently be any one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, and a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.
[0078] In one embodiment, R3 in Chemical Formula 1 may be any one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 10 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, and a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.
[0079] In one embodiment, R in Chemical Formula 1-1 and Chemical Formula 1-2 may be the same or different and is any one selected from hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and more preferably hydrogen or deuterium.
[0080] In one embodiment, R6 in Chemical Formula 1-1 and Chemical Formula 1-2 can be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
[0081] In one embodiment, R4 and R5 in Chemical Formula 1-1 and Chemical Formula 1-2 may be the same or different, and may each independently be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
[0082] In one embodiment, at least one of R4 and R5 in Chemical Formula 1-1 and Chemical Formula 1-2 may be a substituted or unsubstituted aryl group having 16 to 30 carbon atoms.
[0083] In one embodiment, more preferably, the compound represented by Chemical Formula 1-1 may be a compound represented by Chemical Formula 1-1-A below.
[0084] [Chemical formula 1-1-A] TIFF2026042720000008.tif54170
[0085] In the above chemical formula 1-1-A, the substituents R and R' may be the same or different and are each independently any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring; Z1 is Si or Ge, the linking group L4 is a single bond or a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, the substituent R5 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, the substituent R6 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, m1 is 9, and each R may be the same or different. m3 is 9, and each R' may be the same or different. The term "substituted" in "substituted or unsubstituted" in Chemical Formula 1-1-A has the same definition as that of "substituted" explained in Chemical Formula 1 above.
[0086] In one embodiment, in the compound represented by Chemical Formula 1, R1 and R2 may be the same or different and are each independently any one selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R3 may be a substituted or unsubstituted aryl group having 10 to 30 carbon atoms or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
[0087] In one embodiment, in the compound represented by Chemical Formula 1, R1 and R2 may be the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and R3 may be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
[0088] In one embodiment, a specific compound of the compound represented by Chemical Formula 1 may be any one selected from the group represented by Compounds 1-1 to 1-267 below.
[0089] JPEG2026042720000009.jpg237170JPEG2026042720000010.jpg225170JPEG2026042 720000011.jpg222170JPEG2026042720000012.jpg216170JPEG2026042720000013.j pg225170JPEG2026042720000014.jpg210170JPEG2026042720000015.jpg225170JPE G2026042720000016.jpg229170JPEG2026042720000017.jpg233170JPEG20260427200 00018.jpg200170JPEG2026042720000019.jpg234170JPEG2026042720000020.jpg23 3170JPEG2026042720000021.jpg241170JPEG2026042720000022.jpg229170JPEG202 6042720000023.jpg226170JPEG2026042720000024.jpg232170JPEG20260427200000 25.jpg240170JPEG2026042720000026.jpg220170JPEG2026042720000027.jpg102170
[0090] On the other hand, in the present invention, "(the organic layer or the light-emitting layer) contains one or more organic compounds" can be interpreted as "(the organic layer) can contain one organic compound belonging to the category of the present invention or two or more different compounds belonging to the category of the organic compound."
[0091] The compound represented by Chemical Formula 1 according to the present invention can be used as a host in the first or second light-emitting layer. That is, the organic light-emitting device according to the present invention can include one or more compounds for an organic light-emitting device represented by Chemical Formula 1 as a host material in the light-emitting layer.
[0092] In one embodiment, one of the first host and the second host in the organic light emitting device according to the present invention may include a compound represented by Chemical Formula 1, and the other may include an anthracene compound represented by Chemical Formula 2. For example, the first host in the organic light emitting device according to the present invention may include a compound represented by Chemical Formula 1, and the second host may include an anthracene compound represented by Chemical Formula 2, or vice versa.
[0093] [Chemical formula 2] TIFF2026042720000028.tif52170
[0094] In the above Chemical Formula 2, The substituent R 11 ~R 18may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 3 0 cycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms which is fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The linking group L 11 and L 12may be the same or different and each independently represent a single bond or a linking group selected from a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 24 carbon atoms and fused with an aliphatic hydrocarbon ring, The Ar 11 and Ar 12 may be the same or different, and each independently represent one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 24 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; In the formula 2, 0 to 60 hydrogen atoms may be substituted with deuterium or tritium atoms at the hydrogen sites bonded to the carbon atoms; The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 2 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
[0095] In one embodiment, R in Formula 2 11 ~R 18 may be the same or different, and each independently may be any one selected from hydrogen and deuterium.
[0096] In one embodiment, the compound represented by Formula 2 may contain at least one deuterium atom.
[0097] When the first host or the second host in the organic light-emitting device of the present invention contains one or more anthracene compounds represented by Chemical Formula 2, the Ar 12can be a substituent represented by the following structural formula 12:
[0098] [Structural formula 12] TIFF2026042720000029.tif36170
[0099] In the structural formula 12, X is O or S; R 21 ~R 24 One of the L in Chemical Formula 2 12 and preferably R 21 or R 22 The above L 12 is a single bond connecting Said L 12 R excluding the single bond connected to 21 ~R 28 may be the same or different, and each independently represents R defined in Chemical Formula 2 11 ~R 18 is the same as
[0100] In one embodiment, R in formula 12 21 ~R 28 is any one selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 24 carbon atoms and having a condensed aliphatic hydrocarbon ring; The "substituted" in "substituted or unsubstituted" in the structural formula 12 includes deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
[0101] In one embodiment, X in the formula 12 can be O.
[0102] In one embodiment, one of the first host and the second host in the organic light emitting device according to the present invention may include a compound represented by Chemical Formula 1, and the other may include two or more anthracene compounds represented by Chemical Formula 2, in which case the anthracene compounds represented by Chemical Formula 2 may be different from each other. For example, in the organic light emitting device according to the present invention, the first host may include a compound represented by Chemical Formula 1, and the second host may include two or more anthracene compounds represented by Chemical Formula 2, in which case the compounds represented by Chemical Formula 2 may be different from each other, or vice versa.
[0103] In one embodiment, when either the first host or the second host in the organic light-emitting device according to the present invention contains two or more anthracene compounds represented by Chemical Formula 2, one or more of the anthracene compounds represented by Chemical Formula 2 is 12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and one or more of the anthracene compounds represented by Chemical Formula 2 contained therein are 12 can be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
[0104] In one embodiment, more preferably, when either the first host or the second host in the organic light-emitting device according to the present invention contains two or more anthracene compounds represented by Chemical Formula 2, one or more of the anthracene compounds represented by Chemical Formula 2 is selected from the group consisting of Ar 12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and one or more of the anthracene compounds represented by Chemical Formula 2 contained therein are 12 can be a substituent represented by structural formula 12 above.
[0105] In one embodiment, the first emitting layer in the organic light emitting device according to the present invention may include one or more compounds represented by Chemical Formula 1 as a first host, and the second emitting layer may include one or more compounds represented by Chemical Formula 2 as a second host.
[0106] In one embodiment, when one of the first host and the second host in the organic light-emitting device according to the present invention includes a compound represented by Chemical Formula 1 and the other includes an anthracene compound represented by Chemical Formula 2, the first light-emitting layer may include, as the first host, the compound represented by Chemical Formula 1 and a host compound different from the compound represented by Chemical Formula 1 in a ratio of 1:9 to 9:1, more preferably 3:7 to 7:3.
[0107] In this case, when the first host is composed of two or more compounds, they may be mixed and deposited or co-deposited, or laminated for use. That is, the first host according to the present invention may further include one or more additional compounds different from the compound represented by Chemical Formula 1, and two or more first host compounds may be mixed and deposited or co-deposited, or laminated for use. In the case of the laminated structure, a compound different from the compound represented by Chemical Formula 1 may be laminated on or under a layer containing the compound represented by Chemical Formula 1 according to the present invention.
[0108] Here, when a compound represented by Chemical Formula 1 is mixed with a different host compound and deposited, the compound is mixed in one deposition source and deposited by sublimation or vaporization. In addition, in the case of co-deposition, the compound is mixed in multiple deposition sources and deposited by sublimation or vaporization, respectively, to deposit two or more hosts.
[0109] That is, the light-emitting layer can be formed by depositing (co-depositing) a plurality of host materials from different deposition sources to form a thin film, or by mixing the plurality of hosts in advance and depositing the mixed host, or by laminating the hosts to form the light-emitting layer.
[0110] Here, the host compound different from the compound represented by Chemical Formula 1 may be a compound having a structural formula different from that of Chemical Formula 1, or may be a compound that is included in the structure of Chemical Formula 1 but is different from the compound that has already been used (the compound that has already been used corresponding to the compound represented by Chemical Formula 1).
[0111] Meanwhile, examples of compounds having a structural formula different from that of Chemical Formula 1 in the first light-emitting layer include conventionally known anthracene-based compounds, benzanthracene-based compounds, phenanthrene-based compounds, pyrene-based compounds, fluorene-based compounds, spirofluorene-based compounds, chrysene-based compounds, carbazole-based compounds, and biphenyl-based compounds. Here, the anthracene-based compounds refer to compounds containing at least one, preferably 1 to 3, anthracene groups in the molecule. Similarly, the remaining benzanthracene-based compounds, phenanthrene-based compounds, pyrene-based compounds, fluorene-based compounds, spirofluorene-based compounds, chrysene-based compounds, carbazole-based compounds, and biphenyl-based compounds refer to compounds containing at least one, preferably 1 to 3, anthracene groups in the molecule.
[0112] In one embodiment, when one of the first host and the second host in the organic light emitting device according to the present invention includes a compound represented by Chemical Formula 1 and the other includes an anthracene compound represented by Chemical Formula 2, the other of the first host and the second host may include two or more different anthracene compounds represented by Chemical Formula 2. Preferably, the second light emitting layer in the organic light emitting device may include, as the second host, two different anthracene compounds represented by Chemical Formula 2 in a ratio of 1:9 to 9:1, preferably 3:7 to 7:3.
[0113] In one embodiment, the first emitting layer in the organic light emitting device according to the present invention may contain one or more compounds represented by Chemical Formula 1 as a first host, and the second emitting layer may contain one or more compounds represented by Chemical Formula 2 as a second host. In this case, the second emitting layer may further contain, as the second host, a host compound different from the compound represented by Chemical Formula 2 in addition to the compound represented by Chemical Formula 2. In this case, the second host used in the second emitting layer may contain two different anthracene compounds represented by Chemical Formula 2 in a ratio of 1:9 to 9:1, more preferably 3:7 to 7:3.
[0114] In this case, when the second host is composed of two or more compounds, they may be mixed in one deposition source and deposited by sublimation or vaporization, or may be sublimated or vaporized in multiple deposition sources and then co-deposited on the second light-emitting layer.
[0115] Here, the host compound different from the compound represented by Chemical Formula 2 may be a compound having a structural formula different from that of Chemical Formula 2, or a compound that is included in the structure of Chemical Formula 2 but is different from the compound already used (already used as the compound represented by Chemical Formula 2) may be used.
[0116] In addition, as the compound having a structural formula different from that of Chemical Formula 2 in the second light-emitting layer, conventionally known anthracene-based compounds, benzanthracene-based compounds, phenanthrene-based compounds, pyrene-based compounds, fluorene-based compounds, spirofluorene-based compounds, chrysene-based compounds, carbazole-based compounds, biphenyl-based compounds, etc. may be used, and the description thereof is the same as that described above.
[0117] In one embodiment, the first host in the first emission layer of the organic light emitting device according to the present invention may be a compound represented by Chemical Formula 1 used alone, and the second host in the second emission layer may include a compound represented by Chemical Formula 2 and a different compound in a ratio of 1:9 to 9:1, preferably 3:7 to 7:3.
[0118] In one embodiment, the first host in the first emission layer of the organic light emitting device according to the present invention may contain the compound represented by Chemical Formula 1 and a different compound in a ratio of 1:9 to 9:1, preferably 3:7 to 7:3, and the second host in the second emission layer may be the compound represented by Chemical Formula 2 alone.
[0119] In one embodiment, the first host in the first light-emitting layer of the organic light-emitting device according to the present invention contains the compound represented by Chemical Formula 1 and a compound other than the compound represented by Chemical Formula 1 in a ratio of 1:9 to 9:1, preferably 3:7 to 7:3, and the second host in the second light-emitting layer contains the compound represented by Chemical Formula 2 and a compound other than the compound represented by Chemical Formula 2 in a ratio of 1:9 to 9:1, preferably 3:7 to 7:3.
[0120] In one embodiment, specific examples of the compound represented by Chemical Formula 2 include, but are not limited to, the following compounds:
[0121] JPEG2026042720000030.jpg224170JPEG2026042720000031.jpg235170JPEG20260427200000 32.jpg206170JPEG2026042720000033.jpg229170JPEG2026042720000034.jpg230170JPEG202 6042720000035.jpg235170JPEG2026042720000036.jpg233170JPEG2026042720000037.jpg24 5170JPEG2026042720000038.jpg254170JPEG2026042720000039.jpg243170JPEG20260427200 00040.jpg248170JPEG2026042720000041.jpg233170JPEG2026042720000042.jpg250170JPE G2026042720000043.jpg235170JPEG2026042720000044.jpg217170JPEG2026042720000045.j pg243170JPEG2026042720000046.jpg230170JPEG2026042720000047.jpg237170JPEG2026042 720000048.jpg243170JPEG2026042720000049.jpg255168JPEG2026042720000050.jpg168170
[0122] In one embodiment, the organic light emitting device of the present invention may further include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the first electrode and the second electrode.
[0123] In one embodiment, the organic light emitting device according to the present invention includes at least one of a hole transport layer and a hole injection layer between the first electrode and the light emitting layer, and at least one of an electron transport layer and an electron injection layer between the light emitting layer and the second electrode.
[0124] In one embodiment, the first emitting layer of the organic light emitting device according to the present invention may include a first host and a first dopant, and the second emitting layer may include a second host and a second dopant. In this case, at least one of the first dopant in the first emitting layer and the second dopant in the second emitting layer of the organic light emitting device may include one or more polycyclic compounds represented by Chemical Formula 3 below. Preferably, both the first dopant in the first emitting layer and the second dopant in the second emitting layer may be the same or different and may include one or more polycyclic compounds represented by Chemical Formula 3.
[0125] [Chemical formula 3] TIFF2026042720000051.tif42170
[0126] In the above Chemical Formula 3, Y1 and Y2 may be the same or different and each independently represent O, S, NR 31 , C.R. 32 R 33 , SiR 34 R 35 and GeR 36 R 37 is one selected from A1 to A3 may be the same or different and each independently represent any one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle having 5 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring; R 31 ~R 37may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 3 0 cycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms which is fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one selected from a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; R 31 ~R 37 may be linked to the A1 to A3 rings to form an alicyclic or aromatic monocyclic or polycyclic ring.
[0127] R 32 and R 33 , R34 and R 35 , and R 36 and R 37 can be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 3 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, aromatic heterocyclic group having 5 to 30 carbon atoms, a cycloalkyl group fused with an aromatic hydrocarbon ring, a heterocycloalkyl group having 6 to 30 carbon atoms and fused with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and fused with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
[0128] In a more preferred embodiment of the present invention, A1 to A3 may be the same or different and may each independently be any one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms fused with an aliphatic hydrocarbon ring.
[0129] In one embodiment, the first dopant in the first light-emitting layer and the second dopant in the second light-emitting layer may both be the same compound, and may include one or more polycyclic compounds represented by Chemical Formula 3.
[0130] Furthermore, when the first dopant or the second dopant in the organic light-emitting device according to the present invention contains one or more polycyclic compounds represented by Chemical Formula 3, the polycyclic compounds represented by Chemical Formula 3 may be polycyclic compounds represented by Chemical Formula 3-1 or Chemical Formula 3-2 below, and preferably, both the first dopant in the first light-emitting layer and the second dopant in the second light-emitting layer may be polycyclic compounds represented by Chemical Formula 3-1 or Chemical Formula 3-2.
[0131] [Chemical formula 3-1] [Chemical formula 3-2] TIFF2026042720000052.tif47170
[0132] In Chemical Formula 3-1 and Chemical Formula 3-2, X1 is O or S; Y1 and Y2 may be the same or different and each independently represent O, S, NR 31 , C.R. 32 R 33 , SiR 34 R 35 and GeR 36 R 37 is one selected from A2 and A3 may be the same or different, and each independently represent one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle having 5 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring; R 31 ~R 38may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, a cycloalkenyl group having from 2 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having from 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having from 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 7 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having from 5 to 30 carbon atoms which is fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having from 6 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having from 8 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having from 5 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having from 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having from 2 to 30 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; R 31 ~R 37 may further be linked with the A2 and A3 rings to form an alicyclic or aromatic monocyclic or polycyclic ring; R 32 and R 33 , R 34 and R35 , and R 36 and R 37 can be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, O is 4, and the substituent R 38 may be the same or different from each other, The adjacent substituents R 38 can be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, The "substituted" in "substituted or unsubstituted" in Chemical Formula 3-1 and Chemical Formula 3-2 includes deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, and one or more substituents selected from the group consisting of a cycloalkyl group fused with an aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms fused with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
[0133] In one embodiment, specific examples of the compound represented by Chemical Formula 3 include, but are not limited to, the following compounds:
[0134] JPEG2026042720000053.jpg240170JPEG2026042720000054.jpg226170JPEG2026042720000055.jpg231170JPEG2026042720000056.jpg205170
[0135] Hereinafter, an organic light emitting device according to an embodiment of the present invention will be described with reference to the drawings.
[0136] FIG. 1 is a diagram showing the structure of an organic light-emitting device according to one embodiment of the present invention.
[0137] As shown in FIG. 1, the organic light emitting device according to the present invention is an organic light emitting device sequentially including an anode 20, a hole transport layer 40, a first light emitting layer 50′, a second light emitting layer 50, an electron transport layer 60, and a cathode 80, in which the anode is a first electrode and the cathode is a second electrode, and the organic light emitting device includes a hole transport layer between the anode and the light emitting layer, and an electron transport layer between the light emitting layer and the cathode.
[0138] In addition, the organic light emitting device according to the embodiment of the present invention may include a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron injection layer 70 between the electron transport layer 60 and the cathode 80.
[0139] Next, the organic light-emitting device of the present invention and the method for producing the same will be described with reference to FIG.
[0140] First, an anode material is coated on the top of the substrate 10 to form the anode 20. The substrate 10 can be a substrate commonly used in organic EL devices, but an organic substrate or transparent plastic substrate is preferred because of its transparency, surface smoothness, ease of handling, and water resistance. The anode material is typically indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or other materials that are transparent and highly conductive.
[0141] A hole injection layer material is vacuum thermally deposited or spin coated on the anode 20 to form a hole injection layer 30. Then, a hole transport layer material is vacuum thermally deposited or spin coated on the hole injection layer 30 to form a hole transport layer 40.
[0142] The material of the hole injection layer 30 is not particularly limited as long as it is a material commonly used in the art. For example, 2-TNATA [4,4',4''-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], HAT-CN [1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile], etc. may be used, but the present invention is not necessarily limited thereto.
[0143] Furthermore, the material for the hole transport layer 40 is not particularly limited as long as it is a material commonly used in the relevant field, and examples that can be used include, but are not limited to, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD), and N-[[1,1'-biphenyl]-4-yl]-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine (BCFN).
[0144] Meanwhile, in the present invention, an electron blocking layer may be further formed on the hole transport layer. The electron blocking layer is a layer for preventing electrons injected from the electron injection layer from entering the hole transport layer via the light emitting layer, thereby improving the life and efficiency of the device. The electron blocking layer may be formed at an appropriate location between the light emitting layer and the hole injection layer, preferably between the light emitting layer and the hole transport layer.
[0145] Then, the first light-emitting layer 50' and the second light-emitting layer 50 may be deposited or co-deposited or formed on the hole transport layer 40 by vacuum deposition or spin coating, respectively.
[0146] Here, the compound represented by Chemical Formula 1 or Chemical Formula 2 can be used as a host material in the first light-emitting layer or the second light-emitting layer of the organic light-emitting device, and the compound represented by Chemical Formula 3 can be used as a dopant material in the first light-emitting layer or the second light-emitting layer, and the materials constituting these are as described above.
[0147] The light-emitting layer can be formed by depositing (co-depositing) a plurality of or one first host materials and a dopant material from different deposition sources to form a thin film, or by mixing the plurality of hosts (e.g., a first host material and a second host material) in advance and co-depositing the mixed host and the dopant from a deposition source different from that of the dopant.
[0148] Here, when the respective hosts are separately co-deposited using a plurality of different deposition sources, there is a drawback in that the manufacturing process becomes complicated. However, when these materials are premixed using a single deposition source, a thin film is formed without the materials being in contact with each other in advance, and therefore, deterioration of device characteristics due to interactions between different compounds can be prevented. On the other hand, when these materials are premixed, there is an advantage in that the manufacturing equipment or manufacturing process can be simplified.
[0149] According to an embodiment of the present invention, the thickness of the first light-emitting layer 50' and the second light-emitting layer 50 may be in the range of 30 to 200 Å, preferably 50 to 150 Å.
[0150] Meanwhile, an electron transport layer 60 is deposited on the light emitting layer by vacuum deposition or spin coating.
[0151] Meanwhile, in the present invention, the material of the electron transport layer 60 functions to stably transport electrons injected from the electron injection electrode (cathode), and may be a known electron transport material. Examples of known electron transport materials include, but are not limited to, quinoline derivatives, particularly tris(8-quinolinolato)aluminum (Alq3), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND.
[0152] TIFF2026042720000057.tif40170TAZ BAlq TIFF2026042720000058.tif51170<Compound 201> <Compound 202> BCP TIFF2026042720000059.tif37170TIFF2026042720000060.tif40170
[0153] After forming the electron transport layer, an electron injection layer (EIL) having a function of facilitating injection of electrons from the cathode can be formed on the electron transport layer, and the material for the EIL is not particularly limited.
[0154] The electron injection layer 70 may be formed from any known material for forming electron injection layers, such as CsF, NaF, LiF, LiO, BaO, etc. The deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from the same range of conditions as those for forming the hole injection layer.
[0155] The thickness of the electron injection layer 70 may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
[0156] In addition, in the present invention, the cathode 80 can be made of a material with a low work function for easy electron injection, such as lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof such as aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or a transmission cathode using ITO or IZO.
[0157] The organic light-emitting device of the present invention may further include an emitting layer made of a blue, green, or red emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the emitting layer of the present invention may be a plurality of emitting layers, and the blue, green, or red emitting material in the further emitting layer may be a fluorescent material or a phosphorescent material.
[0158] In addition, in the present invention, one or more layers selected from the above-mentioned layers may be formed by a monomolecular deposition process or a solution process.
[0159] Here, the deposition process refers to a method of forming a thin film by evaporating a material used to form each layer by heating under vacuum or low pressure, and the solution process refers to a method of mixing a material used to form each layer with a solvent and forming a thin film by inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc.
[0160] In addition, the organic light emitting device of the present invention can be used in any one device selected from a flat panel display device, a flexible display device, a stretchable display device, a monochrome or white flat panel lighting device, a monochrome or white flexible lighting device, a display device for a vehicle or aircraft, and a virtual or augmented reality display device.
[0161] The present invention will be described in more detail below with reference to preferred examples. However, these examples are intended to more specifically explain the present invention. It will be obvious to those skilled in the art that the scope of the present invention is not limited by these examples.
[0162] (Example) Synthesis Example 1. Synthesis of [Compound 1-6] Synthesis Example 1-1. Synthesis of A-1 TIFF2026042720000061.tif26170 <a-1a> <a-1b> <a-1> In a round-bottom flask <a-1b>30g of the solution and 300mL of THF were added under nitrogen atmosphere, and after cooling to -78℃, 100.1mL of 1.6M n-butyllithium was slowly added dropwise. After stirring for 1 hour, <a-1a>14g was slowly added and stirred at -78°C for 1 hour, and then stirred at room temperature for 12 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, diluted with heptane, filtered to remove lithium chloride, and concentrated under reduced pressure. <a-1>(22.22g, 85%)
[0163] Synthesis Example 1-2. Synthesis of [Compound 1-6] TIFF2026042720000062.tif36170 <a-1> <a-2a>[Compound 1-6] In a round-bottom flask <a-2a>19g of ethanol and 225mL of THF were charged under nitrogen atmosphere, and after cooling to -78℃, 46.4mL of 1.6M n-butyllithium was slowly added dropwise. After stirring for 1 hour, <a-1>22.2 g was diluted in 66.6 mL of THF and slowly added, stirred at -78 ° C for 1 hour, and then stirred at room temperature for 12 hours. After the reaction was completed, the mixture was extracted with water, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain [Compound 1-6] (23.35 g, 74%). MS (MALDI-TOF): m / z 560.20 [M + ]
[0164] Synthesis Example 2. Synthesis of [Compound 1-14] Synthesis Example 2-1. Synthesis of B-1 TIFF2026042720000063.tif19170 <b-1a> <b-1b> <b-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1a>Using <a-1b>instead of <b-1b>By synthesizing in the same way except for using <b-1>(yield 55%)
[0165] Synthesis Example 2-2. Synthesis of B-2 TIFF2026042720000064.tif19170 <b-1> <b-2a> <b-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1>Using <a-1b>instead of <b-2a>By synthesizing in the same way except for using <b-2>(yield 64%)
[0166] Synthesis Example 2-3. Synthesis of [Compound 1-14] TIFF2026042720000065.tif44170 <b-2> <b-3a>[Compound 1-14] The compound used in Synthesis Example 1-2 <a-1>instead of <b-2>Using <a-2a>instead of <b-3a>Compound 1-14 was obtained in a similar manner except that the compound was used. (Yield: 52%) MS (MALDI-TOF): m / z 507.24 [M + ]
[0167] Synthesis Example 3. Synthesis of [Compound 1-22] Synthesis Example 3-1. Synthesis of C-1 TIFF2026042720000066.tif24170 <b-1a> <b-2a> <c-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1a>Using <a-1b>instead of <b-2a>By synthesizing in the same way except for using <c-1>(yield 63%)
[0168] Synthesis Example 3-2. Synthesis of [Compound 1-22] TIFF2026042720000067.tif34170 <c-1> <a-2a>[Compound 1-22] The compound used in Synthesis Example 1-2 <a-1>instead of <c-1>Compound 1-22 was obtained in a similar manner except that the compound was used instead of the above. (Yield: 54%) MS (MALDI-TOF): m / z 598.21 [M + ]
[0169] Synthesis Example 4. Synthesis of [Compound 1-28] Synthesis Example 4-1. Synthesis of D-1 TIFF2026042720000068.tif32170 <b-1> <d-1a> <d-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1>Using <a-1b>instead of <d-1a>By synthesizing in the same way except for using <d-1>(yield 58%)
[0170] Synthesis Example 4-2. Synthesis of [Compound 1-28] TIFF2026042720000069.tif32170 <d-1> <a-2a>[Compound 1-28] The compound used in Synthesis Example 1-2 <a-1>instead of <d-1>Compound 1-28 was obtained in a similar manner except that the compound was used instead of the above. (Yield: 54%) MS (MALDI-TOF): m / z 548.20 [M + ]
[0171] Synthesis Example 5. Synthesis of [Compound 1-31] Synthesis Example 5-1. Synthesis of E-1 TIFF2026042720000070.tif19170 <e-1a> <e-1> In a round-bottom flask <e-1a>50g of HCl and 500mL of THF were charged under nitrogen and cooled to -78℃, then 158mL of 1.6M n-butyllithium was slowly added dropwise. After stirring for 1 hour, 30.5mL of trimethyl borate was slowly added dropwise and stirred at room temperature for 12 hours. 1N HCl (aq) was added and stirred for 10 minutes. After layer separation, the mixture was extracted several times with water, treated with MgSO4, and recrystallized with heptane to obtain the product. <e-1>(34g, 80%)
[0172] Synthesis Example 5-2. Synthesis of E-2 TIFF2026042720000071.tif24170 <e-1> <e-2a> <e-2> In a round-bottom flask <e-1> 31.42g、 <e-2a>40g, 44.91g of Pd(PPh3), 48.85g of K2CO3, 400mL of 1,4-dioxane, and 146.56mL of water were charged under nitrogen atmosphere, stirred, and refluxed for 12 hours. After the reaction was completed, the mixture was extracted with water, treated with MgSO4, and separated by column chromatography. <e-2>(31.9 g, 72%)
[0173] Synthesis Example 5-3. Synthesis of E-3 TIFF2026042720000072.tif27170 <e-2> <e-3> The compound used in Synthesis Example 5-1 <e-1a>instead of <e-2>By synthesizing in the same way except for using <e-3>(yield 82%)
[0174] Synthesis Example 5-4. Synthesis of E-4 TIFF2026042720000073.tif27170 <e-3> <e-4a> <e-4> The compound used in Synthesis Example 5-2 <e-1>instead of <e-3>Using <e-2a>instead of <e-4a>By synthesizing in the same way except for using <e-4>(Yield 76%)
[0175] Synthesis Example 5-5. Synthesis of E-5 TIFF2026042720000074.tif27170 <e-4> <e-5> In a round-bottom flask <e-4>30g of toluene and 300mL of dichloromethane were added under nitrogen and cooled to 0℃, then 10.97mL of boron tribromide was slowly added dropwise and stirred at room temperature for 12 hours. After the reaction was completed, the mixture was extracted several times with water, treated with MgSO4, and separated by column chromatography. <e-5>(26g, 90%)
[0176] Synthesis Example 5-6. Synthesis of E-6 TIFF2026042720000075.tif24170 <e-5> <e-6> In a round-bottom flask <e-5>26g of HCl, 8.2g of pyridine, and 260mL of dichloromethane were charged under nitrogen and cooled to -10℃. Trifluoromethansulfonic anhydride was slowly added dropwise and stirred at room temperature for 12 hours. After the reaction was completed, the mixture was extracted with water, treated with MgSO4, and separated by column chromatography. <e-6>(24.6g, 70%)
[0177] Synthesis Example 5-7. Synthesis of E-7 TIFF2026042720000076.tif24170 <e-6> <e-7> In a round-bottom flask <e-6>24.6g, 20.54g of Pd(OAc), 1g of Sphos, 14.3g of KOAc, and 246mL of dimethylacetamide were charged under nitrogen and stirred at 100°C for 12 hours. After the reaction was completed, the mixture was extracted with water, treated with MgSO4, and separated by column chromatography. <e-7>(17g, 98%)
[0178] Synthesis Example 5-8. Synthesis of E-8 TIFF2026042720000077.tif27170 <b-1> <e-7> <e-8> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1>Using <a-1b>instead of <e-7>By synthesizing in the same way except for using <e-8>(yield 63%)
[0179] Synthesis Example 5-9. Synthesis of [Compound 1-31] TIFF2026042720000078.tif34170 <e-8> <a-2a>[Compound 1-31] The compound used in Synthesis Example 1-2 <a-1>instead of <e-8>Compound 1-31 was obtained in the same manner except for using the compound 1-31 (yield 66%). MS (MALDI-TOF): m / z 598.21 [M + ]
[0180] Synthesis Example 6. Synthesis of [Compound 1-39] Synthesis Example 6-1. Synthesis of F-1 TIFF2026042720000079.tif24170 <b-1a> <f-1a> <f-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1a>Using <a-1b>instead of <f-1a>By synthesizing in the same way except for using <f-1>(yield 67%)
[0181] Synthesis Example 6-2. Synthesis of [Compound 1-39] TIFF2026042720000080.tif42170 <f-1> <a-2a>[Compound 1-39] The compound used in Synthesis Example 1-2 <a-1>instead of <f-1>Compound 1-39 was obtained in the same manner except for using the compound 1-39. (Yield: 67%) MS (MALDI-TOF): m / z 572.20 [M + ]
[0182] Synthesis Example 7. Synthesis of [Compound 1-38] Synthesis Example 7-1. Synthesis of [Compound 1-38] TIFF2026042720000081.tif40170 <b-1> <b-3a>[Compound 1-38] The compound used in Synthesis Example 6-2 <f-1>instead of <b-1>Using <a-2a>instead of <b-3a>Compound 1-38 was obtained in a similar manner except that the compound was used instead. (Yield: 69%) MS (MALDI-TOF): m / z 540.29 [M + ]
[0183] Synthesis Example 8. Synthesis of [Compound 1-41] Synthesis Example 8-1. Synthesis of G-1 JPEG2026042720000082.jpg35133 Used in Synthesis Example 1-1 <a-1b>instead of <g-1a>By synthesizing in the same way except for using <g-1>(Yield 71%)
[0184] Synthesis Example 8-2. Synthesis of [Compound 1-41] TIFF2026042720000083.tif38170 <g-1> <a-2a>[Compound 1-41] The compound used in Synthesis Example 1-2 <a-1>instead of <g-1>Compound 1-41 was obtained in the same manner except for using the compound 1-41 (yield 69%). MS (MALDI-TOF): m / z 660.23 [M + ]
[0185] Synthesis Example 9. Synthesis of [Compound 1-56] Synthesis Example 9-1. Synthesis of [Compound 1-56] TIFF2026042720000084.tif50170 <a-1a> <a-2a>[Compound 1-56] The compound used in Synthesis Example 1-2 <a-1>instead of <a-1a>Compound 1-56 was obtained by synthesizing in the same manner except that the following compound was used: MS (MALDI-TOF): m / z 708.23 [M + ]
[0186] Synthesis Example 10. Synthesis of [Compound 1-61] Synthesis Example 10-1. Synthesis of H-1 TIFF2026042720000085.tif29170 <b-1a> <d-1a> <h-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1a>Using <a-1b>instead of <d-1a>By synthesizing in the same way except for using <h-1>(yield 54%)
[0187] Synthesis Example 10-2. Synthesis of [Compound 1-61] TIFF2026042720000086.tif39170 <h-1> <a-2a>[Compound 1-61] The compound used in Synthesis Example 1-2 <a-1>instead of <h-1>Compound 1-61 was obtained in the same manner except for using the compound 1-61 (yield 66%). MS (MALDI-TOF): m / z 672.23 [M + ]
[0188] Synthesis Example 11. Synthesis of [Compound 1-62] Synthesis Example 11-1. Synthesis of I-1 TIFF2026042720000087.tif29170 <e-3> <i-1a> <i-1> The compound used in Synthesis Example 5-2 <e-1>instead of <e-3>Using <e-2a>instead of <i-1a>By synthesizing in the same way except for using <i-1>(Yield 74%)
[0189] Synthesis Example 11-2. Synthesis of I-2 TIFF2026042720000088.tif26170 <i-1> <i-2> Used in Synthesis Example 5-5 <e-4>instead of <i-1>By synthesizing in the same way except using <i-2>(yield 92%)
[0190] Synthesis Example 11-3. Synthesis of I-3 TIFF2026042720000089.tif26170 <i-2> <i-3> Used in Synthesis Example 5-6 <e-5>instead of <i-2>By synthesizing in the same way except using <i-3>(yield 97%)
[0191] Synthesis Example 11-4. Synthesis of I-4 TIFF2026042720000090.tif24170 <i-3> <i-4> The compound used in Synthesis Examples 5-7 <e-6>instead of <i-3>By synthesizing in the same way except for using <i-4>(yield 96%)
[0192] Synthesis Example 11-5. Synthesis of I-5 TIFF2026042720000091.tif27170 <a-1a> <i-4> <i-5> The compound used in Synthesis Example 1-1 <a-1b>instead of <i-4>By synthesizing in the same way except using <i-5>(yield 59%)
[0193] Synthesis Example 11-6. Synthesis of [Compound 1-62] TIFF2026042720000092.tif42170 <i-5> <a-2a>[Compound 1-62] The compound used in Synthesis Example 1-2 <a-1>instead of <i-5>Compound 1-62 was obtained in the same manner except for using the compound 1-62 (yield 66%). MS (MALDI-TOF): m / z 784.26 [M + ]
[0194] Synthesis Example 12. Synthesis of [Compound 1-73] Synthesis Example 12-1. Synthesis of J-1 TIFF2026042720000093.tif29170 <j-1a> <j-1b> <j-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <j-1a>Using <a-1b>instead <j-1b>By synthesizing in the same way except for using <j-1>(yield 62%)
[0195] Synthesis Example 12-2. Synthesis of J-2 TIFF2026042720000094.tif42170 <j-1> <j-2a> <j-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <j-1>Using <a-1b>instead of <j-2a>By synthesizing in the same way except using <j-2>(yield 63%)
[0196] Synthesis Example 12-3. Synthesis of [Compound 1-73] TIFF2026042720000095.tif52170 <j-2> <a-2a>[Compound 1-73] The compound used in Synthesis Example 1-2 <a-1>instead of <j-2>Compound 1-73 was obtained in a similar manner except that the compound was used instead. (Yield: 64%) MS (MALDI-TOF): m / z 684.39 [M + ]
[0197] Synthesis Example 13. Synthesis of [Compound 1-78] Synthesis Example 13-1. Synthesis of K-1 TIFF2026042720000096.tif19170 <j-1a> <b-1b> <k-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <j-1a>Using <a-1b>instead of <b-1b>By synthesizing in the same way except for using <k-1>(yield 54%)
[0198] Synthesis Example 13-2. Synthesis of K-2 TIFF2026042720000097.tif29170 <k-1> <k-2a> <k-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <k-1>Using <a-1b>instead of <k-2a>By synthesizing in the same way except for using <k-2>(yield 67%)
[0199] Synthesis Example 13-3. Synthesis of [Compound 1-78] TIFF2026042720000098.tif29170 <k-2> <a-2a>[Compound 1-78] The compound used in Synthesis Example 1-2 <a-1>instead of <k-2>Compound 1-78 was obtained in a similar manner except that the compound was used instead of the above. (Yield: 53%) MS (MALDI-TOF): m / z 550.18 [M + ]
[0200] Synthesis Example 14. Synthesis of [Compound 1-90] Synthesis Example 14-1. Synthesis of L-1 TIFF2026042720000099.tif32170 <a-1a> <l-1a> <l-1> The compound used in Synthesis Example 1-1 <a-1b>instead of <l-1a>By synthesizing in the same way except for using <l-1>(yield 61%)
[0201] Synthesis Example 14-2. Synthesis of L-2 TIFF2026042720000100.tif39170 <l-1> <a-1b> <l-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <l-1>By synthesizing in the same way except for using <l-2>(yield 55%)
[0202] Synthesis Example 14-3. Synthesis of [Compound 1-90] JPEG2026042720000101.jpg56144 Used in Synthesis Example 1-2 <a-1>instead of <l-2>Compound 1-90 was obtained in the same manner except for using the compound 1-90 (yield 60%). MS (MALDI-TOF): m / z 675.24 [M + ]
[0203] Synthesis Example 15. Synthesis of [Compound 1-91] Synthesis Example 15-1. Synthesis of M-1 TIFF2026042720000102.tif29170 <a-1a> <k-2a> <m-1> The compound used in Synthesis Example 1-1 <a-1b>instead of <k-2a>By synthesizing in the same way except for using <m-1>(yield 57%)
[0204] Synthesis Example 15-2. Synthesis of [Compound 1-91] TIFF2026042720000103.tif39170 <m-1> <a-2a>[Compound 1-91] The compound used in Synthesis Example 1-2 <a-1>instead of <m-1>Compound 1-91 was obtained in the same manner except for using the compound 1-91 (yield 44%). MS (MALDI-TOF): m / z 640.19 [M + ]
[0205] Synthesis Example 16. Synthesis of [Compound 1-105] Synthesis Example 16-1. Synthesis of N-1 TIFF2026042720000104.tif32170 <b-1a> <n-1a> <n-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <b-1a>Using <a-1b>instead of <n-1a>By synthesizing in the same way except for using <n-1>(yield 57%)
[0206] Synthesis Example 16-2. Synthesis of [Compound 1-105] TIFF2026042720000105.tif42170 <n-1> <a-2a>[Compound 1-105] The compound used in Synthesis Example 1-2 <a-1>instead of <n-1>Compound 1-105 was obtained in the same manner except for using the compound 1-105 (yield 65%). MS (MALDI-TOF): m / z 685.22 [M + ]
[0207] Synthesis Example 17. Synthesis of [Compound 1-123] Synthesis Example 17-1. Synthesis of O-1 TIFF2026042720000106.tif27170 <k-1> <a-1b> <o-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <k-1>By synthesizing in the same way except for using <o-1>(Yield 75%)
[0208] Synthesis Example 17-2. Synthesis of [Compound 1-123] TIFF2026042720000107.tif29170 <o-1> <o-2a>[Compound 1-123] The compound used in Synthesis Example 1-2 <a-1>instead of <o-1>Using <a-2a>instead of <o-2a>Compound 1-123 was obtained in a similar manner except that the compound was used. (Yield: 49%) MS (MALDI-TOF): m / z 818.28 [M + ]
[0209] Synthesis Example 18. Synthesis of [Compound 1-134] Synthesis Example 18-1. Synthesis of [Compound 1-134] TIFF2026042720000108.tif44170 <p-1a> <o-2a>[Compound 1-134] The compound used in Synthesis Example 1-2 <a-1>instead of <p-1a>Using <a-2a>instead of <o-2a>Compound 1-134 was obtained in a similar manner except that the compound was used. (Yield: 50%) MS (MALDI-TOF): m / z 842.28 [M + ]
[0210] Synthesis Example 19. Synthesis of [Compound 1-151] Synthesis Example 19-1. Synthesis of Q-1 TIFF2026042720000109.tif24170 <q-1a> <g-1a> <q-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <q-1a>Using <a-1b>instead of <g-1a>By synthesizing in the same way except using <q-1>(Yield 71%)
[0211] Synthesis Example 19-2. Synthesis of Q-2 JPEG2026042720000110.jpg46160 Used in Synthesis Example 1-1 <a-1a>instead of <q-1>Using <a-1b>instead of <j-2a>By synthesizing in the same way except for using <q-2>(Yield 71%)
[0212] Synthesis Example 19-3. Synthesis of [Compound 1-151] TIFF2026042720000111.tif34170 <q-2> <a-2a>[Compound 1-151] The compound used in Synthesis Example 1-2 <a-1>instead of <q-2>Compound 1-151 was obtained in the same manner except for using the compound 1-151 (yield 69%). MS (MALDI-TOF): m / z 630.23 [M + ]
[0213] Synthesis Example 20. Synthesis of [Compound 1-154] Synthesis Example 20-1. Synthesis of R-1 TIFF2026042720000112.tif24170 <r-1a> <r-1b> <r-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <r-1a>Using <a-1b>instead of <r-1b>Similarly, except that <r-1>(yield 50%)
[0214] Synthesis Example 20-2. Synthesis of R-2 TIFF2026042720000113.tif44170 <r-1> <r-2a> <r-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <r-1>Using <a-1b>instead of <r-2a>Similarly, except that <r-2>(yield 50%)
[0215] Synthesis Example 20-3. Synthesis of [Compound 1-154] TIFF2026042720000114.tif44170 <r-2> <a-2a>[Compound 1-154] The compound used in Synthesis Example 1-2 <a-1>instead of <r-2>Compound 1-154 was obtained in the same manner except that the above compound was used. (Yield 61%) MS (MALDI-TOF): m / z 660.19 [M + ]
[0216] Synthesis Example 21. Synthesis of [Compound 1-155] Synthesis Example 21-1. Synthesis of S-1 TIFF2026042720000115.tif34170 <q-1a> <s-1a> <s-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <q-1a>Using <a-1b>instead of <s-1a>Similarly, except that <s-1>(yield 50%)
[0217] Synthesis Example 21-2. Synthesis of [Compound 1-155] TIFF2026042720000116.tif39170 <s-1> <a-2a>[Compound 1-155] The compound used in Synthesis Example 1-2 <a-1>instead of <s-1>Compound 1-155 was obtained in the same manner except that the above compound was used. (Yield 61%) MS (MALDI-TOF): m / z 656.07 [M + ]
[0218] Synthesis Example 22. Synthesis of [Compound 1-156] Synthesis Example 22-1. Synthesis of T-1 TIFF2026042720000117.tif27170 <q-1a> <j-2a> <t-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <q-1a>Using <a-1b>instead of <j-2a>Similarly, except that <t-1>(yield 50%)
[0219] Synthesis Example 22-2. Synthesis of [Compound 1-156] TIFF2026042720000118.tif34170 <t-1> <a-2a>[Compound 1-156] The compound used in Synthesis Example 1-2 <a-1>instead of <t-1>Compound 1-156 was obtained in the same manner except that the following was used (yield 61%). MS (MALDI-TOF): m / z 664.31 [M + ]
[0220] Synthesis Example 23. Synthesis of [Compound 1-169] Synthesis Example 23-1. Synthesis of U-1 TIFF2026042720000119.tif39170 <U-1a <u-1b> <u-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <u-1a>Using <a-1b>instead of <u-1b>By synthesizing in the same way except using <u-1>(Yield 75%)
[0221] Synthesis Example 23-2. Synthesis of [Compound 1-169] TIFF2026042720000120.tif42170 <u-1> <o-2a>[Compound 1-169] The compound used in Synthesis Example 1-2 <a-1>instead of <u-1>Using <a-2a>instead of <o-2a>Compound 1-169 was obtained in the same manner except for using the compound 1-169 (yield 49%). MS (MALDI-TOF): m / z 1004.25 [M + ]
[0222] Synthesis Example 24. Synthesis of [Compound 1-170] Synthesis Example 24-1. Synthesis of V-1 TIFF2026042720000121.tif47170 <v-1a> <v-1b> <v-1> The compound used in Synthesis Example 1-1 <a-1a>instead of <v-1a>Using <a-1b>instead of <v-1b>By synthesizing in the same way except for using <v-1>(Yield 75%)
[0223] Synthesis Example 24-2. Synthesis of V-2 TIFF2026042720000122.tif47170 <v-1> <v-2a> <v-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <v-1>Using <a-1b>instead of <v-2a>By synthesizing in the same way except for using <v-2>(Yield 75%)
[0224] Synthesis Example 24-3. Synthesis of [Compound 1-170] TIFF2026042720000123.tif65170 <v-2> <o-2a>[Compound 1-170] The compound used in Synthesis Example 1-2 <a-1>instead of <v-2>Using <a-2a>instead of <o-2a>Compound 1-170 was obtained in the same manner except for using the compound 1-170 (yield 49%). MS (MALDI-TOF): m / z 1160.55 [M + ]
[0225] Synthesis Example 25. Synthesis of [Compound 1-192] Synthesis Example 25-1. Synthesis of W-1 TIFF2026042720000124.tif37170 <p-1a> <o-2a> <w-1> The compound used in Synthesis Example 1-2 <a-1>instead of <p-1a>Using <a-2a>instead of <o-2a>By synthesizing in the same way except for using <w-1>(yield 50%)
[0226] Synthesis Example 25-2. Synthesis of [Compound 1-192] TIFF2026042720000125.tif52170 <w-1> <w-2a>[Compound 1-192] The compound used in Synthesis Example 1-2 <a-1>instead of <w-2a>Using <a-2a>instead of <w-1>Compound 1-192 was obtained in the same manner except for using the compound 1-192 (yield 65%). MS (MALDI-TOF): m / z 780.27 [M + ]
[0227] Synthesis Example 26. Synthesis of [Compound 1-206] Synthesis Example 26-1. Synthesis of [Compound 1-206] TIFF2026042720000126.tif60170 <b-1> <x-1a>[Compound 1-206] The compound used in Synthesis Example 1-2 <a-1>instead of <b-1>Using <a-2a>instead of <x-1a>Compound 1-206 was obtained in the same manner except for using the compound 1-206 (yield 63%). MS (MALDI-TOF): m / z 674.24 [M + ]
[0228] Synthesis Example 27. Synthesis of [Compound 1-208] Synthesis Example 27-1. Synthesis of [Compound 1-208] TIFF2026042720000127.tif50170 <b-1> <y-1a>[Compound 1-208] The compound used in Synthesis Example 1-2 <a-1>instead of <b-1>Using <a-2a>instead of <y-1a>Compound 1-208 was obtained in the same manner except for using the compound 1-208 (yield 63%). MS (MALDI-TOF): m / z 674.24 [M + ]
[0229] Synthesis Example 28. Synthesis of [Compound 1-243] Synthesis Example 28-1. Synthesis of [Compound 1-243] JPEG2026042720000128.jpg60122 <b-1> <z-1a>[Compound 1-243] The compound used in Synthesis Example 1-2 <a-1>instead of <b-1>Using <a-2a>instead of <z-1a>Compound 1-243 was obtained in a similar manner except that the compound was used. (Yield 77%) MS (MALDI-TOF): m / z 674.24 [M + ]
[0230] Examples 1 to 52: Fabrication of organic light-emitting devices including a first light-emitting layer and a second light-emitting layer The ITO glass was patterned so that the light-emitting area was 2 mm × 2 mm, and then washed. The ITO glass was attached to a vacuum chamber, and the base pressure was 1 × 10 -7 After the pressure is adjusted to torr, HAT-CN (700 Å) and α-NPD (300 Å) are deposited in this order on the ITO as a hole injection layer and a hole transport layer. Next, a first light-emitting layer and a second light-emitting layer are sequentially formed as light-emitting layers. The first light-emitting layer is deposited (50 Å) by mixing a pyrene compound represented by Chemical Formula 1 according to the present invention with a polycyclic compound (1 wt%) selected from [BD-1] to [BD-3] below. The second light-emitting layer is deposited (150 Å) by mixing an anthracene compound represented by [BH-1] or [BH-2] with a polycyclic compound (1 wt%) selected from [BD-1] to [BD-3] below. Then, [E-1] and [E-2] were deposited in a 1:1 ratio (300 Å) as an electron transport layer, and [E-2] (10 Å) and Al (1000 Å) were deposited as an electron injection layer in this order to fabricate an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.
[0231] JPEG2026042720000129.jpg156170
[0232] Comparative Examples 1 to 16 An organic light-emitting device for comparison was fabricated in the same manner as in the example, except that a polycyclic compound selected from [RH-1] to [RH-4] below was used instead of the compound according to the present invention used as the host in the first and second light-emitting layers. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA in the same manner, and the measurement results are shown in Table 1. The structures of [RH-1] to [RH-4] are as follows:
[0233] JPEG2026042720000130.jpg103156
[0234] [Table 1] JPEG2026042720000132.jpg131170
[0235] As shown in Table 1, it can be seen that the organic light-emitting device according to the present invention, which uses the compound according to the present invention in the first and second light-emitting layers, exhibits high efficiency and long life organic light-emitting devices with excellent luminous efficiency and life characteristics at a low driving voltage, compared to the organic light-emitting devices (Comparative Examples 1 to 13) which use the compounds of the comparative examples according to the prior art.
[0236] Furthermore, when the compounds of the Examples according to the present invention are compared with organic light-emitting devices (Comparative Examples 14 to 19) that use a single light-emitting layer with the same thickness as the sum of the thicknesses of the first and second light-emitting layers in the organic light-emitting material according to the present invention, rather than two light-emitting layers, it can be seen that the compounds of the Examples according to the present invention have significantly superior luminous efficiency and lifetime characteristics in all numerical aspects. This is presumably because, in the case of devices using multiple light-emitting layers according to the present invention, excitons are formed in the first light-emitting layer, and after the excitons are transferred to the second light-emitting layer, efficient energy transfer is possible through the process of triplet-triplet fusion occurring, which allows for high efficiency and long lifetime characteristics.
[0237] In contrast, in the case of a device using a single emitting layer as in the comparative example, all organic light emission must be performed in one layer, which reduces the probability of triplet-triplet fusion occurring, presumably resulting in device degradation and reduced efficiency and lifetime. For this reason, it can be confirmed that devices using first and second emitting layers are easier to fabricate into high-efficiency, long-life organic light-emitting devices than devices using a single emitting layer.
[0238] Examples 53 to 80: Fabrication of organic light-emitting devices including a first light-emitting layer and a second light-emitting layer Organic light-emitting devices including the first and second emitting layers of Examples 1 to 52 were manufactured in the same manner, except that two of the compounds [BH-3] to [BH-7] below were used as hosts in at least one of the first and second emitting layers, or in both of the two emitting layers, and the dopant in each emitting layer was [BD-4] below. Here, the structures of [BH-3] to [BH-7] and [BD-4] are as follows, and the luminescence characteristics of the organic light-emitting devices were measured at 0.4 mA.
[0239] JPEG2026042720000133.jpg129170
[0240] [Table 2]
[0241] As shown in Table 2, it can be seen that the organic light emitting device according to the present invention, which uses two or more different compounds as hosts in at least one of the first and second emitting layers, exhibits low driving voltage and excellent luminous efficiency and lifespan characteristics. < / b-1> < / b-1> < / b-1> < / w-1> < / o-2a> < / p-1a> < / v-2> < / v-2a> < / v-1> < / v-1b> < / v-1a> < / u-1> < / u-1b> < / t-1> < / j-2a> < / q-1a> < / s-1> < / s-1a> < / q-1a> < / r-2> < / r-2a> < / r-1> < / r-1b> < / r-1a> < / q-2> < / g-1a> < / q-1a> < / p-1a> < / o-1> < / a-1b> < / k-1> < / n-1> < / n-1a> < / b-1a> < / m-1> < / k-2a> < / a-1a> < / a-1b> < / l-1> < / l-1a> < / a-1a> < / k-2> < / k-2a> < / k-1> < / b-1b> < / j-1a> < / j-2> < / j-2a> < / j-1> < / j-1b> < / j-1a> < / i-5> < / i-4> < / a-1a> < / i-3> < / i-2> < / i-1> < / i-1a> < / e-3> < / h-1> < / d-1a> < / b-1a> < / a-1a> < / g-1> < / b-1> < / f-1> < / f-1a> < / b-1a> < / e-8> < / e-7> < / b-1> < / e-6> < / e-5> < / e-4> < / e-4a> < / e-3> < / e-2> < / e-1> < / e-2a> < / e-1> < / e-1a> < / d-1> < / d-1a> < / b-1> < / c-1> < / b-2a> < / b-1a> < / b-2> < / b-2a> < / b-1> < / b-1b> < / b-1a> < / a-1> < / a-1b> < / a-1a>
Claims
1. A first electrode; a second electrode facing the first electrode; a first light-emitting layer interposed between the first electrode and the second electrode and including a first host and a first dopant; a second light-emitting layer comprising a second host and a second dopant; An organic light emitting device, wherein at least one of the first host and the second host includes a compound represented by Chemical Formula 1: [Chemical formula 1] (In the above chemical formula 1, The substituents R may be the same or different and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon a cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused with an aromatic heterocycle, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms a fused heterocycloalkyl group, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The m is an integer of 1 to 9, and when the m is 2 or more, each R may be the same or different. When m is 8 or less, each may be the same or different from each other, Z is Si or Ge; The substituent R 1 and R 2 may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, cycloalkenyl groups having 0 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted heterocycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted aryl groups having 8 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy groups having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy groups having 2 to 30 carbon atoms, substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The substituent R 3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted is any one selected from an unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; However, R 1 ~R 3 are all substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, The linking group L 1 and L 2 may be the same or different, and each independently represent a linking group selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 24 carbon atoms and fused with an aliphatic hydrocarbon ring, The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 1 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, (meaning that the group is substituted with one or more substituents selected from the group consisting of a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.)
2. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 is a compound represented by the following Chemical Formula 1-1 or 1-2: [Chemical formula 1-1] [Chemical formula 1-2] (In the above Chemical Formula 1-1 and Chemical Formula 1-2, The substituent R is the same as R defined in claim 1, Z 1 and Z 2 may be the same or different and each independently represents Si or Ge; The substituent R 4 , R 5 , R 7 and R 8 may be the same or different, and each independently represents R defined in claim 1 1 and R 2 is the same as The substituent R 6 and R 9 may be the same or different, and each independently represents R defined in claim 1 3 is the same as However, R 4 ~R 6 are all substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, The linking group L 3 ~L 6 may be the same or different, and each independently represents a linking group L defined in claim 1 1 and L 2 is the same as Said m 1 is 9, and each R may be the same or different from each other, Said m 2 is 8, and each R may be the same or different from each other, The "substituted" in "substituted or unsubstituted" in Chemical Formula 1-1 and Chemical Formula 1-2 is the same as the "substituted" in "substituted or unsubstituted" in Chemical Formula 1 described in Claim 1.
3. 3. The organic light-emitting device according to claim 2, wherein R in Chemical Formula 1-1 and Chemical Formula 1-2 is any one selected from hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
4. 4. The organic light emitting device according to claim 3, wherein R in Formula 1-1 and Formula 1-2 is hydrogen or deuterium.
5. R in Chemical Formula 1-1 and Chemical Formula 1-2 6 3. The organic light-emitting device according to claim 2, wherein is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
6. R in Chemical Formula 1-1 and Chemical Formula 1-2 4 and R 5 and may be the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
7. The organic light-emitting device according to claim 2, wherein the compound represented by Chemical Formula 1-1 is a compound represented by the following Chemical Formula 1-1-A: [Chemical formula 1-1-A] (In the above chemical formula 1-1-A, the substituents R and R' may be the same or different and each independently represent any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; Z 1 is Si or Ge, The linking group L 4 represents a single bond or a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, The substituent R 5 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, The substituent R 6 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, Said m 1 is 9, and each R may be the same or different from each other, Said m 3 is 9, and each R' may be the same or different from each other; The "substituted" in "substituted or unsubstituted" in Chemical Formula 1-1-A is defined the same as the "substituted" explained in Chemical Formula 1 of Claim 1.
8. R in the compound represented by Chemical Formula 1 1 and R 2 may be the same or different, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and 3 2. The organic light-emitting device according to claim 1, wherein is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
9. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 is one selected from the group consisting of Compounds 1-1 to 1-267:
10. 10. The organic light emitting device according to claim 1, wherein one of the first host and the second host in the organic light emitting device includes a compound represented by Chemical Formula 1, and the other includes an anthracene compound represented by Chemical Formula 2: [Chemical formula 2] (In the above chemical formula 2, The substituent R 11 ~R 18 may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, 0 cycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms which is fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; Linking group L 11 and L 12 may be the same or different and each independently represent a single bond or a linking group selected from a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 24 carbon atoms and fused with an aliphatic hydrocarbon ring, The Ar 11 and Ar 12 may be the same or different, and each independently represent one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 24 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; In the formula 2, 0 to 60 hydrogen atoms may be substituted with deuterium or tritium atoms at the hydrogen sites bonded to the carbon atoms; The "substituted" in "substituted or unsubstituted" in the above chemical formula 2 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, (meaning that the group is substituted with one or more substituents selected from the group consisting of a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.)
11. The Ar in the anthracene compound represented by Chemical Formula 2 12 The organic light-emitting device according to claim 10, wherein is a substituent represented by the following structural formula 12: [Structural formula 12] (In the structural formula 12, X is O or S; The R 21 ~R 24 One of the groups is L in Chemical Formula 2. 12 is a single bond connecting Said L 12 R excluding the single bond connected to 21 ~R 28 may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, cycloalkenyl groups having 0 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted heterocycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted aryl groups having 8 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy groups having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy groups having 2 to 30 carbon atoms, substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The "substituted" in "substituted or unsubstituted" in the structural formula 12 includes deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, (meaning that the group is substituted with one or more substituents selected from the group consisting of a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.)
12. The organic light emitting device according to claim 10, wherein the compound represented by Formula 2 contains at least one deuterium atom.
13. The organic light emitting device according to claim 10, wherein one of the first host and the second host in the organic light emitting device includes two or more different anthracene compounds represented by Formula 2.
14. At least one of the anthracene compounds represented by the formula 2 is 12 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, In addition, one or more of the anthracene compounds represented by Chemical Formula 2 may be the Ar 12 The organic light-emitting device according to claim 13, wherein is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
15. The Ar in the anthracene compound represented by Chemical Formula 2 12 The organic light-emitting device according to claim 14 , wherein: is a substituent represented by the following structural formula 12: Here, the structural formula 12 is the same as defined in claim 11.
16. 11. The organic light-emitting device of claim 10, wherein the first light-emitting layer in the organic light-emitting device comprises a compound represented by Chemical Formula 1 as a first host and a host compound different from the compound represented by Chemical Formula 1 in a ratio of 1:9 to 9:
1.
17. 14. The organic light emitting device according to claim 13, wherein the second light emitting layer in the organic light emitting device comprises two different anthracene compounds represented by Chemical Formula 2 as second hosts in a ratio of 1:9 to 9:
1.
18. 10. The organic light emitting device according to claim 1, wherein at least one of the first dopant in the first emission layer and the second dopant in the second emission layer of the organic light emitting device comprises one or more polycyclic compounds represented by the following Chemical Formula 3: [Chemical formula 3] (In the above chemical formula 3, Y 1 and Y 2 may be the same or different, and each independently represents O, S, NR 31 , C.R. 32 R 33 , SiR 34 R 35 and GeR 36 R 37 is one selected from A 1 ~A 3 may be the same or different, and each independently represent any one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle having 5 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring, R 31 ~R 37 may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, 0 cycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms which is fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one selected from a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The R 31 ~R 37 is the above-mentioned A 1 ~A 3 The rings may be linked to form further alicyclic or aromatic monocyclic or polycyclic rings; The R 32 and R 33 , R 34 and R 35 , and R 36 and R 37 can be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 3 includes deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, aromatic heterocyclic group having 5 to 30 carbon atoms, and one or more substituents selected from the group consisting of a cycloalkyl group fused with an aromatic hydrocarbon ring, a heterocycloalkyl group having 6 to 30 carbon atoms and fused with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and fused with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.
19. The organic light-emitting device according to claim 18, wherein the polycyclic compound represented by Chemical Formula 3 is a polycyclic compound represented by Chemical Formula 3-1 or 3-2: [Chemical formula 3-1] [Chemical formula 3-2] (In the above Chemical Formula 3-1 and Chemical Formula 3-2, X 1 is O or S, Y 1 and Y 2 may be the same or different, and each independently represents O, S, NR 31 , C.R. 32 R 33 , SiR 34 R 35 and GeR 36 R 37 is one selected from A 2 and A 3 may be the same or different, and each independently represent one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle having 5 to 50 carbon atoms and fused with an aliphatic hydrocarbon ring, R 31 ~R 38 may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, a cycloalkenyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having from 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having from 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having from 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 7 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having from 5 to 30 carbon atoms which is fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having from 6 to 30 carbon atoms which is fused with an aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having from 8 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having from 5 to 30 carbon atoms which is fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having from 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having from 2 to 30 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The R 31 ~R 37 is the above-mentioned A 2 and A 3 The rings may be linked to form further alicyclic or aromatic monocyclic or polycyclic rings; The R 32 and R 33 , R 34 and R 35 , and R 36 and R 37 can be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, O is 4, and the substituent R 38 may be the same or different from each other, The mutually adjacent substituents R 38 can be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, The "substituted" in "substituted or unsubstituted" in Chemical Formula 3-1 and Chemical Formula 3-2 includes deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, aromatic heteroaryl group having 5 to 30 carbon atoms, aryl ... (This means that the group is substituted with one or more substituents selected from the group consisting of a cycloalkyl group fused with an aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms fused with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.)
20. A pyrene-based compound represented by the following chemical formula 1: [Chemical formula 1] (In the above chemical formula 1, The substituents R may be the same or different and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon a cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused with an aromatic heterocycle, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms a fused heterocycloalkyl group, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The m is an integer of 1 to 9, and when the m is 2 or more, each R may be the same or different. When m is 8 or less, each may be the same or different from each other, Z is Si or Ge; The substituent R 1 and R 2 may be the same or different, and each independently represent hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms, cycloalkenyl groups having 0 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms fused with an aromatic heterocycle, substituted or unsubstituted heterocycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, substituted or unsubstituted aryl groups having 8 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy groups having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy groups having 2 to 30 carbon atoms, substituted or unsubstituted is any one selected from an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; The substituent R 3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused with an aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, a substituted or unsubstituted is any one selected from an unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group; However, R 1 ~R 3 are all substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, The linking group L 1 and L 2 may be the same or different, and each independently represent a linking group selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 24 carbon atoms and fused with an aliphatic hydrocarbon ring, The "substituted" in "substituted or unsubstituted" in the above Chemical Formula 1 means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, (meaning that the group is substituted with one or more substituents selected from the group consisting of a cycloalkyl group having from 1 to 30 carbon atoms fused with an aromatic heterocycle, a heterocycloalkyl group having from 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, an aryl group having from 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, an aryl group having from 6 to 30 carbon atoms fused with an aliphatic heterocycle, a heteroaryl group having from 5 to 30 carbon atoms fused with an aliphatic heterocycle, an amine group having from 1 to 30 carbon atoms, a silyl group having from 1 to 30 carbon atoms, a germanium group having from 1 to 30 carbon atoms, an aryloxy group having from 6 to 24 carbon atoms, and an arylthionyl group having from 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.)
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Organic electroluminescent devices and electronic devices
KR1020210077686A