Low-voltage, highly efficient and long-life organic light-emitting element

Abstract

To provide an organic light-emitting element that has low voltage, high efficiency, and long life characteristics by including compounds with specific structures in the light-emitting layer and the light-emitting auxiliary layer of the organic light-emitting device.SOLUTION: The present invention relates to an organic light-emitting element with high efficiency characteristics, and more specifically, to an organic light-emitting element that exhibits low voltage, high efficiency, and long life by containing an amine compound represented by Chemical Formula 1 as a material for the light-emitting layer and an amine compound represented by Chemical Formula 2 or Chemical Formula 3 as a material for the light-emitting auxiliary layer, and Chemical Formulas 1 to 3 are as described in the detailed description of the invention.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to an organic light-emitting device having a low voltage, high efficiency, and long life, and more particularly to an organic light-emitting device that can exhibit a low voltage, high efficiency, and long life by using amine compounds having specific structures as a light-emitting layer material and a light-emitting auxiliary 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] Furthermore, in recent years, in order to solve the light emission problem in the hole transport layer of an organic light emitting element, it has become necessary to have a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and there is a demand for the development of different light emitting auxiliary layers corresponding to each light emitting layer (R, G, B).

[0008] 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.

[0009] However, since materials used in the hole transport layer must have a low HOMO value, most of them have a low T1 value. This can cause excitons generated in the light emitting layer to migrate to the hole transport layer, resulting in a charge imbalance within the light emitting layer, which can cause light emission at the interface of the hole transport layer. If light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic light emitting device can be reduced, and its lifespan can be shortened.

[0010] To solve this problem, there is an urgent need to develop a light-emitting auxiliary layer having a high T1 value and a HOMO energy level between the HOMO energy levels of the hole transport layer and the light-emitting layer.

[0011] As prior art related to organic light-emitting devices including the light-emitting auxiliary layer, Korean Patent Registration No. 10-1455156 (publication date: October 27, 2014) discloses a technology related to an organic light-emitting device in which a light-emitting auxiliary layer having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer is formed between the hole transport layer and the light-emitting layer, and Korean Patent Publication No. 10-2022-0123954 (publication date: September 13, 2022) discloses an organic light-emitting device that uses an amine compound having both a carbazole structure and a fluorene structure as a light-emitting auxiliary layer material.

[0012] 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 the light-emitting auxiliary layer and simultaneously have improved luminous efficiency and long life characteristics. [Prior art documents] [Patent documents]

[0013] [Patent Document 1] Korean Patent Registration No. 10-1455156 (Publication Date: October 27, 2014) [Patent Document 2] Korean Patent Publication No. 10-2022-0123954 (Publication Date: September 13, 2022) Summary of the Invention [Problem to be solved by the invention]

[0014] Therefore, the 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 compounds with specific structures in the light emitting layer and the light emitting auxiliary layer of the organic light emitting device. [Means for solving the problem]

[0015] In order to solve the above problems, the present invention provides a liquid crystal display device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, the organic layer including a light-emitting layer and a light-emitting auxiliary layer, The organic light-emitting device is characterized in that the light-emitting layer contains one or more amine compounds represented by the above Chemical Formula 1, and the light-emitting auxiliary layer contains one or more amine compounds represented by the following Chemical Formula 2 or Chemical Formula 3:

[0016] [Chemical formula 1] JPEG2025185715000002.jpg56170

[0017] In the above Chemical Formula 1, the substituents R1 to R4 may be the same or different and are each independently selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; The above substituents R5~R 12may 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 ... is any one selected from an alkylthio group having 1 to 30 prime numbers, 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, a halogen group, and structural formula Q; The above substituents R5~R 12 one or two of the substituents are a single bond connected to the linking group L1 or the nitrogen atom (N) in the structural formula Q; The substituents R1 to R 12two adjacent substituents among the above may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic fused ring; The substituent R 13 and R 14 may be the same or different, and each independently represent one selected from a substituted or unsubstituted 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R 13 and R 14 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, the linking groups L1 to L3 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 m1 to m3 may be the same or different from one another and each independently represents 1 or 2. In this case, when the m1 is 2, the respective L1s may be the same or different from one another; when the m2 is 2, the respective L2s may be the same or different from one another; and when the m3 is 2, the respective L3s may be the same or different from one another; The substituents Ar1 and Ar2 may be the same or different and are each independently selected from 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 heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having a condensed aliphatic hydrocarbon ring.

[0018] [Chemical formula 2] JPEG2025185715000003.jpg35170[Chemical formula 3] JPEG2025185715000004.jpg54170

[0019] In the above Chemical Formula 2, The substituent R 15 and R 16 may be the same or different, and each independently represent one selected from a substituted or unsubstituted 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R 15 and R 16 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, R 17 is any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having a condensed aliphatic hydrocarbon ring; The n1 is 7, and at this time, each R 17 may be the same or different from each other, Two adjacent substituents R 17 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, the linking groups L4 to L6 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 m4 to m6 may be the same or different from each other and each independently represents 1 or 2, but when the m4 is 2, the respective L4s may be the same or different from each other, when the m5 is 2, the respective L5s may be the same or different from each other, and when the m6 is 2, the respective L6s may be the same or different from each other, the substituents Ar3 and Ar4 may be the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; In the above Chemical Formula 3, The substituent R 18 is any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having a condensed aliphatic hydrocarbon ring; The n2 is 5, and at this time, each R 18 may be the same or different from each other, The Five Rs 18 at least one of the groups is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Two adjacent substituents R 18 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The linking groups L7 to L9 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 m7 to m9 may be the same or different from one another and each independently represents 1 or 2. In this case, when the m7 is 2, the respective L7s may be the same or different from one another; when the m8 is 2, the respective L8s may be the same or different from one another; and when the m9 is 2, the respective L9s may be the same or different from one another; the substituents Ar5 and Ar6 may be the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; The term "substituted" in "substituted or unsubstituted" in Chemical Formulas 1 to 3 above refers to deuterium, tritium, cyano, halogen, hydroxy, nitro, alkyl groups having 1 to 30 carbon atoms, halogenated alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 24 carbon atoms, alkynyl groups having 2 to 24 carbon atoms, cycloalkyl groups having 3 to 24 carbon atoms, heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, arylalkyl groups having 7 to 24 carbon atoms, alkylaryl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, heteroarylalkyl groups having 3 to 24 carbon atoms, alkylheteroaryl groups having 3 to 24 carbon atoms, alkoxy groups having 1 to 24 carbon atoms, cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, carbon and aryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, heterocycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, aryl groups having 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, aryl groups having 6 to 30 carbon atoms fused with an aliphatic heterocycle, heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic heterocycle, amine groups having 1 to 30 carbon atoms, silyl groups having 1 to 30 carbon atoms, germanium groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 24 carbon atoms, and arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium. [Effects of the Invention]

[0020] 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.

[0021] In particular, when the compound represented by Chemical Formula 1 used in the light-emitting layer of the organic light-emitting device according to the present invention and the compound represented by Chemical Formula 2 or Chemical Formula 3 used in the light-emitting auxiliary layer are used together, the device can exhibit low-voltage driving, high luminous efficiency, and long life. [Brief explanation of the drawings]

[0022] [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

[0023] 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.

[0024] 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.

[0025] 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.

[0026] The present invention provides a liquid crystal display device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, the organic layer including a light-emitting layer and a light-emitting auxiliary layer, The organic light-emitting device is characterized in that the light-emitting layer contains one or more amine compounds represented by the above Chemical Formula 1, and the light-emitting auxiliary layer contains one or more amine compounds represented by the following Chemical Formula 2 or Chemical Formula 3:

[0027] [Chemical formula 1] JPEG2025185715000005.jpg56170

[0028] In the above Chemical Formula 1, the substituents R1 to R4 may be the same or different and are each independently selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; The above substituents R5~R 12may 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 ... is any one selected from an alkylthio group having 1 to 30 prime numbers, 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, a halogen group, and structural formula Q; The above substituents R5~R 12 one or two of the substituents are a single bond connected to the linking group L1 or the nitrogen atom (N) in the structural formula Q; The substituents R1 to R 12two adjacent substituents among the above may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic fused ring; The substituent R 13 and R 14 may be the same or different, and each independently represent one selected from a substituted or unsubstituted 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R 13 and R 14 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, the linking groups L1 to L3 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 m1 to m3 may be the same or different from one another and each independently represents 1 or 2. In this case, when the m1 is 2, the respective L1s may be the same or different from one another; when the m2 is 2, the respective L2s may be the same or different from one another; and when the m3 is 2, the respective L3s may be the same or different from one another; The substituents Ar1 and Ar2 may be the same or different and are each independently selected from 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 heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having a condensed aliphatic hydrocarbon ring.

[0029] [Chemical formula 2] JPEG2025185715000006.jpg35170[Chemical formula 3] JPEG2025185715000007.jpg54170

[0030] In the above Chemical Formula 2, The substituent R 15 and R 16 may be the same or different, and each independently represent one selected from a substituted or unsubstituted 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R 15 and R 16 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, R 17 is any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having a condensed aliphatic hydrocarbon ring; The n1 is 7, and at this time, each R 17 may be the same or different from each other, Two adjacent substituents R 17 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, the linking groups L4 to L6 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 m4 to m6 may be the same or different from each other and each independently represents 1 or 2, but when the m4 is 2, the respective L4s may be the same or different from each other, when the m5 is 2, the respective L5s may be the same or different from each other, and when the m6 is 2, the respective L6s may be the same or different from each other, the substituents Ar3 and Ar4 may be the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; In the above Chemical Formula 3, The substituent R 18 is any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having a condensed aliphatic hydrocarbon ring; The n2 is 5, and at this time, each R 18 may be the same or different from each other, The Five Rs 18 at least one of the groups is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Two adjacent substituents R 18 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The linking groups L7 to L9 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 m7 to m9 may be the same or different from one another and each independently represents 1 or 2. In this case, when the m7 is 2, the respective L7s may be the same or different from one another; when the m8 is 2, the respective L8s may be the same or different from one another; and when the m9 is 2, the respective L9s may be the same or different from one another; the substituents Ar5 and Ar6 may be the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; The term "substituted" in "substituted or unsubstituted" in Chemical Formulas 1 to 3 above refers to deuterium, tritium, cyano, halogen, hydroxy, nitro, alkyl groups having 1 to 30 carbon atoms, halogenated alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 24 carbon atoms, alkynyl groups having 2 to 24 carbon atoms, cycloalkyl groups having 3 to 24 carbon atoms, heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, arylalkyl groups having 7 to 24 carbon atoms, alkylaryl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, heteroarylalkyl groups having 3 to 24 carbon atoms, alkylheteroaryl groups having 3 to 24 carbon atoms, alkoxy groups having 1 to 24 carbon atoms, cycloalkyl groups having 7 to 30 carbon atoms fused with an aromatic hydrocarbon ring, carbon and aryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, heterocycloalkyl groups having 6 to 30 carbon atoms fused with an aromatic hydrocarbon ring, aryl groups having 7 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, aryl groups having 6 to 30 carbon atoms fused with an aliphatic heterocycle, heteroaryl groups having 5 to 30 carbon atoms fused with an aliphatic heterocycle, amine groups having 1 to 30 carbon atoms, silyl groups having 1 to 30 carbon atoms, germanium groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 24 carbon atoms, and arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.

[0031] 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.

[0032] 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.

[0033] 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.

[0034] Furthermore, one or more hydrogen atoms in the aryl group can be substituted with a deuterium atom, a tritium 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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, Examples of such alkyl groups include, but are not limited to, an isoquinolinyl group, 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, a thiadiazolyl group, a phenoxazinyl group, a phenothiazinyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzoselenophene group, and an indolocarbazole group.

[0039] 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.

[0040] 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 tetrahydroquinoline group, and a tetrahydroquinoxaline group.

[0041] 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 is preferably an aromatic carbon in an aromatic hydrocarbon. In the present invention, 1 to 3 of the aromatic heterocycle may be substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

[0042] 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.

[0043] 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.

[0044] 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 has 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- Examples of alkyl groups include, but are not limited to, dimethylbutyl, 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, 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] Specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl.

[0064] 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.

[0065] Specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, and dimethylfurylgermane.

[0066] 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.

[0067] On the other hand, more preferred examples of the "substituted" in the "substituted or unsubstituted" in the above Chemical Formulas 1 to 3 include deuterium, tritium, 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 heteroaryl group having 9 to 20 carbon atoms, an alkyl ... and one or more substituents selected from the group consisting of an aliphatic hydrocarbon ring-fused cycloalkyl group, a C7-20 aromatic heterocyclic ring-fused cycloalkyl group, a C9-20 aromatic heterocyclic ring-fused heterocycloalkyl group, a C9-20 carbon atom-fused aryl group, a C7-20 carbon atom-fused heteroaryl group, an aliphatic hydrocarbon ring-fused aryl group, a C7-20 carbon atom-fused heteroaryl group, an aliphatic hydrocarbon ring-fused alkoxy group, a C1-12 carbon atom-fused amine group, a C1-18 carbon atom-fused silyl group, a C1-18 carbon atom-fused germanium group, a C6-18 carbon atom-fused aryloxy group, and a C6-18 carbon atom-fused arylthionyl group, and one or more hydrogen atoms in each of the substituents can be substituted with deuterium or tritium.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] The present invention is technically characterized in that the amine compound represented by Chemical Formula 1 is used as a light-emitting layer material in an organic light-emitting device, and the amine compound represented by Chemical Formula 2 or Chemical Formula 3 is used as a light-emitting auxiliary layer material, and in this case, the amine compound represented by Chemical Formula 1 is a compound having a structure in which the substituents R5 to R6 on the phenanthrene ring side of the indenophenanthrene ring structure are each independently selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 39, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 69, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 110, 120, 130, 140, 150, 160, 170, 181, 190, 1 12and one or two of the substituents are linked to an amine group represented by the structural formula Q. In the structure in which an amine group is bonded to the indenophenanthrene ring, the nitrogen atom in the amine group represented by Q causes uneven distribution of electrons in the molecule. By adding a substituent such as an aryl or heteroaryl to the amine group, the electron distribution as a whole is made unevenly distributed, and it is presumed that this can stabilize the organic light-emitting element and produce a long-life effect. As a result, an organic light-emitting element can be realized that exhibits higher efficiency and longer life than conventional organic light-emitting elements.

[0076] Meanwhile, as previously explained, in order to solve the light emission problem in the hole transport layer in recent organic light emitting devices, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and it may be necessary to develop different light emitting auxiliary layers for each light emitting layer (R, G, B).

[0077] Therefore, in the present invention, the amine compound represented by Chemical Formula 1 is used as the light-emitting layer material, and the light-emitting auxiliary layer is formed using the amine compound represented by Chemical Formula 2 or 3. This optimizes the energy level and T1 value between each organic material layer, the inherent properties of the material (mobility, interface properties, etc.), and the like, thereby improving the lifespan and efficiency of the organic light-emitting device.

[0078] In order to achieve the above object, the present invention provides a light-emitting auxiliary layer material for an organic light-emitting device, the amine compound represented by Chemical Formula 2 being a compound having a carbon atom in one of the benzene rings at both ends of a fluorene ring and an amine group. JPEG2025185715000008.jpg33170 or a nitrogen atom (N), and the amine compound represented by the chemical formula 3 is a light-emitting auxiliary layer material in an organic light-emitting device, and the amine compound represented by the chemical formula 3 has a structure that bonds to the linking group L4 or a nitrogen atom (N) in the 18 One carbon atom in the benzene ring containing an amine group It is characterized by a structure that bonds to the linking group L8 or nitrogen atom (N) in JPEG2025185715000009.jpg27170.

[0079] In addition, in the light-emitting layer material in the organic light-emitting device according to the present invention, the amine compound represented by Chemical Formula 1 may preferably be one of the amine compounds represented by Chemical Formulas 1-1 to 1-4 below.

[0080] JPEG2025185715000010.jpg120170

[0081] In the above Chemical Formulas 1-1 to 1-4, The substituents R1 to R 12 may be the same or different and are each independently hydrogen or deuterium; The substituent R 13 and R 14 may be the same or different, and each independently represent one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; the linking groups L1 to L3 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 substituents Ar1 and Ar2 may be the same or different and are each independently selected from 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 heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, and at least one of Ar1 and Ar2 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, The m1 to m3 are each 1 or 2, and in this case, when the m1 is 2, each L1 may be the same as or different from one another, when the m2 is 2, each L2 may be the same as or different from one another, and when the m3 is 2, each L3 may be the same as or different from one another, The substituents R1 to R 12 two adjacent substituents among the above may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R 13 and R 14 can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The "substituted" in the "substituted or unsubstituted" in Chemical Formulas 1-1 to 1-4 is the same as defined above.

[0082] In one embodiment, at least one of Ar1 and Ar2 in Chemical Formula 1 may be a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms and containing an oxygen atom (O) or a sulfur atom (S), and is preferably a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms and containing one or two oxygen atoms (O) only, or a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms and containing one or two sulfur atoms (S) only.

[0083] In one embodiment, R in Formula 1 and Formula 2 13 ~R 16 may be the same or different, and each may independently be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0084] In one embodiment, at least one of Ar3 and Ar4 in Chemical Formula 2 may be a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms. In this case, Ar3 and Ar4 in Chemical Formula 2 may be the same or different and may each independently be a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms.

[0085] In one embodiment, when at least one of Ar3 and Ar4 in Chemical Formula 2 is a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, the ring structure in the substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms may be any one selected from the following Structural Formulas 1 to 6.

[0086] [Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4] [Structural Formula 5] [Structural Formula 6] JPEG2025185715000011.jpg15170

[0087] Here, in the structural formulas 1 to 6, one hydrogen atom in the ring structure is removed, and the carbon atom in the ring structure bonded to the removed hydrogen atom is bonded to the linking group L5 or L6 or the nitrogen atom (N) in chemical formula 2.

[0088] In one embodiment, Ar5 and Ar6 in Chemical Formula 3 may be the same or different, and each may independently be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0089] In one embodiment, R in Formula 2 17 may be the same or different and may each independently be hydrogen or deuterium.

[0090] In one embodiment, the specific amine compound represented by Chemical Formula 1 may be any one selected from the group represented by Compounds 1-1 to 1-120 below.

[0091] JPEG2025185715000012.jpg253170JPEG2025185715000013.jpg245170JPEG20251857150 00014.jpg223170JPEG2025185715000015.jpg226170JPEG2025185715000016.jpg226170 JPEG2025185715000017.jpg229170JPEG2025185715000018.jpg243170JPEG20251857150 00019.jpg237170JPEG2025185715000020.jpg214170JPEG2025185715000021.jpg113170

[0092] In one embodiment, the specific amine compound represented by Chemical Formula 2 may be any one selected from the group represented by Compounds 2-1 to 2-48 below.

[0093] JPEG2025185715000022.jpg242170JPEG2025185715000023.jpg223170JPEG2025185715000024.jpg233170

[0094] In one embodiment, the specific amine compound represented by Chemical Formula 3 may be any one selected from the group represented by Compounds 3-1 to 3-39 below.

[0095] JPEG2025185715000025.jpg234170JPEG2025185715000026.jpg242170JPEG2025185715000027.jpg214170

[0096] On the other hand, in the present invention, "(the organic layer or the light-emitting layer or the light-emitting auxiliary 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."

[0097] The light-emitting layer of the organic light-emitting device according to the present invention includes a host and a dopant, and the amine compound represented by Chemical Formula 1 can be used as the host in the light-emitting layer. That is, the organic light-emitting device according to the present invention can include one or more of the compounds for organic light-emitting devices represented by Chemical Formula 1 as host materials in the light-emitting layer.

[0098] More specifically, the organic light emitting device according to the present invention comprises a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, the organic layer including an emitting layer and an emitting auxiliary layer, the emitting layer including one or more amine compounds represented by Chemical Formula 1, and the emitting auxiliary layer including one or more amine compounds represented by Chemical Formula 2 or Chemical Formula 3. In this case, the emitting layer includes a host and a dopant, and the amine compound represented by Chemical Formula 1 can be used as a host in the emitting layer. Due to these structural features, the organic light emitting device according to the present invention can have high efficiency, low voltage characteristics, and long life characteristics.

[0099] In one embodiment, the organic layer in 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.

[0100] In one embodiment, the organic light emitting device according to the present invention may include at least one of a hole transport layer and a hole injection layer between the first electrode and the light emitting auxiliary layer, and at least one of an electron transport layer and an electron injection layer between the light emitting layer and the second electrode.

[0101] In one embodiment, the light-emitting layer of the organic light-emitting device according to the present invention may further include, as a host, one or more host compounds different from the amine compound represented by Chemical Formula 1. That is, the host according to the present invention may include two or more host compounds by further including one or more additional host compounds different from the compound represented by Chemical Formula 1. In this case, the host compounds may be mixed or stacked for use, and in the case of stacking, a different host compound may be stacked on top of or below a layer containing the amine compound according to the present invention.

[0102] Here, when one or more additional host compounds are further included in addition to one compound represented by Chemical Formula 1, and two or more host compounds are mixed or stacked, more preferably, a compound having an electron donor moiety can be used as the additional host. By mixing or stacking the compound represented by Chemical Formula 1 having an amine group, which is an electron acceptor moiety, a high hole injection and electron injection barrier HOMO / LUMO level can be achieved, thereby limiting the recombination region to the interface between the two hosts, thereby minimizing current loss, and thus realizing an organic light emitting device with high efficiency and long life.

[0103] In this case, the compound having an electron donor moiety is a compound having a moiety that is easily capable of accepting electrons from the outside, such as an azine compound, which is a nitrogen-containing aromatic heterocycle such as pyridine, pyrimidine, or triazine, and a compound substituted with a cyano group (-CN), and preferably includes a compound having a heteroaryl group containing 1 to 3 N (nitrogen) atoms in the molecule; or an aryl group containing 1 to 3 cyano groups (-CN) in the molecule.

[0104] When two or more host compounds are used, the content ratio of the compound represented by Chemical Formula 1 to the remaining additional host compounds may be in the range of 1:9 to 9:1, preferably 2:8 to 8:2, and more preferably 4:6 to 6:4.

[0105] More specifically, the host in the light-emitting layer of the organic light-emitting device may be a mixture of the amine compound represented by Chemical Formula 1 and one or more organic compounds represented by the following Chemical Formula B, or the organic compound represented by Chemical Formula B may be laminated on or under a layer containing the amine compound represented by Chemical Formula 1.

[0106] [Chemical formula B] JPEG2025185715000028.jpg50170

[0107] In the above chemical formula B, X1 to X3 may be the same or different, and each independently represents N or CR 24 However, at least one of X1 to X3 is N, and two or more of X1 to X3 are CR. 24 If so, then each CR 24 may be the same or different, L 21 ~L 23 may be the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 20 carbon atoms and fused with an aliphatic hydrocarbon ring, m 21 ~m 23 may be the same or different and each independently represents an integer of 1 to 2. When each of these is 2, 21 ~L 23 may be the same or different from each other, R 21 ~R 24may 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 aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alicyclic 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 "substituted" in "substituted or unsubstituted" in the above chemical formula B 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 30 carbon atoms, alkynyl group having 2 to 30 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, alkylheteroaryl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 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, alkoxy group having 1 to 30 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 ... It means that the group is substituted with one or more substituents selected from the group consisting of a cycloalkyl group having a fused ring, a heterocycloalkyl group having 6 to 30 carbon atoms and having an aromatic hydrocarbon ring fused, an aryl group having 7 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused, a heteroaryl group having 5 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and having an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and having an aliphatic heterocycle fused, 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 30 carbon atoms, and an arylthionyl group having 6 to 30 carbon atoms, and one or more hydrogen atoms in the substituents can be substituted with deuterium or tritium.

[0108] In a more preferred embodiment of the present invention, X1 to X3 in the chemical formula B are each N, and R 21 ~R 23 At least one of the groups may be a substituted or unsubstituted carbazole group.

[0109] In one embodiment, the light-emitting layer of the organic light-emitting device according to the present invention includes a host and a dopant. When the amine compound represented by Chemical Formula 1 is used as the host, the dopant in the light-emitting layer may include one or more organometallic compounds containing a transition metal.

[0110] Hereinafter, when the amine compound represented by Chemical Formula 1 of the present invention is used as a host in the light-emitting layer, the dopant compound used in the light-emitting layer will be described in more detail.

[0111] In a more preferred embodiment of the present invention, the organic light emitting device according to the present invention includes, as a dopant in the light emitting layer, one or more phosphorescent dopant materials that are organometallic compounds containing one or more metals selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, Pd, etc., that use Dexter energy transfer, which transitions between singlet and triplet states without distinguishing between them, rather than fluorescent dopant materials that transition only to a singlet state using Förster energy transfer in a conventional host-dopant system. Any known dopant material may be used without any particular limitation, as long as it emits light from triplet excitons.

[0112] Preferably, an organometallic compound containing a transition metal can be used as the phosphorescent dopant. In this case, Ir, Pt, Pd, or the like can be selected as the transition metal complex to be more preferably used. Specific examples include Ir(ppy)3, Ir(ppy)2acac, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(mppy)3, Ir(piq)3, Ir(piq)2acac, Ir(pq)2acac, Ir(mpp)2acac, F2Irpic, (F2ppy)2Ir(tmd), Ir(ppy)2tmd, Ir(pmi)3, Ir(pmb)3, FCN1r, FCN1rpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy)3, P0-01(C 31 H 23 IrN2O2S2), Ir(ppz)3, Ir(dfppz) 3、 PtNON, Pt-10, Pt-11, etc. can be used, but are not limited to these.

[0113] When the light-emitting layer contains a host and a dopant, the content of the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0114] In addition, the light-emitting layer may further contain various hosts and various dopant materials in addition to the dopant and host. Preferably, the dopant in the light-emitting layer of the organic light-emitting device may include, in addition to the organometallic compound, one or more boron-containing dopant compounds different from the organometallic compound, and these may be mixed or stacked.

[0115] More specifically, the dopant in the light-emitting layer of the organic light-emitting device may be a mixture of one or more polycyclic compounds represented by the following Chemical Formula 4 in addition to the organometallic compound containing the transition metal, or the polycyclic compound represented by the Chemical Formula 4 may be stacked on or under a layer containing the organometallic compound.

[0116] [Chemical formula 4] JPEG2025185715000029.jpg47170

[0117] In the above Chemical Formula 4, 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 of the following: A1 to A3 may be the same or different and are each independently 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; R31 ~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 10 carbon atoms, 30 cycloalkenyl group, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 7 to 30 aromatic hydrocarbon rings fused thereto, substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms fused thereto an aromatic heterocycle, substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms fused thereto an aromatic hydrocarbon ring, substituted or unsubstituted aryl group having 8 to 30 carbon atoms fused thereto an aliphatic hydrocarbon ring, substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms fused thereto an aliphatic hydrocarbon ring, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, 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 further form an alicyclic or aromatic monocyclic or polycyclic ring by linking with the A1 to A3 rings, 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 4 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 heteroaryl group having 5 to 30 carbon atoms, a cycloalkyl group having a fused ring, a heterocycloalkyl group having 6 to 30 carbon atoms having a fused aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms having a fused aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms having a fused aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms having a fused aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms having a fused 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.

[0118] Here, the polycyclic compound represented by Chemical Formula 4 is a boron thermally activated delayed fluorescent emitter, and enables Forster energy transfer from the triplet state of a phosphorescence sensitizer to the singlet state of a boron thermally activated delayed fluorescent emitter, thereby reducing the number of long-lived triplet excitons that are involved in device degradation and improving device lifetime. In addition, since the polycyclic compound has a high molar absorption coefficient, it has the advantages of improving efficiency and lifetime by increasing the rate of fluorescence resonance energy transfer from the phosphorescence sensitizer to the emitter and narrowing the emission spectrum due to the multiple resonance effect, thereby increasing color purity.

[0119] 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.

[0120] In one embodiment, the light-emitting auxiliary layer of the organic light-emitting device may be a mixture or laminate of two or more different compounds.

[0121] More specifically, the light-emitting auxiliary layer of the organic light-emitting device according to the present invention may further include, in addition to the amine compound represented by Chemical Formula 2 or Chemical Formula 3, one or more light-emitting auxiliary layer compounds different from the amine compound represented by Chemical Formula 2 or Chemical Formula 3, and these may be mixed and deposited, co-deposited, or stacked.

[0122] Here, the light-emitting auxiliary layer compound in the organic light-emitting device, which is different from the amine compound represented by Chemical Formula 2 or Chemical Formula 3, may be a mixture of two or more different light-emitting auxiliary layer compounds, which may be vapor-deposited, co-deposited, or stacked, as described above for the compound used as an additional host in the light-emitting layer. In the case of stacking, a host compound different from the amine compound represented by Chemical Formula 2 or Chemical Formula 3 may be stacked on or under a layer containing the amine compound according to the present invention.

[0123] Meanwhile, the "amine compound represented by Chemical Formula 2 or 3, and a compound for an emitting auxiliary layer other than the amine compound represented by Chemical Formula 2 or 3" means, when one of the amine compounds represented by Chemical Formula 2 or 3 is used, a compound other than the one compound used and usable for the emitting auxiliary layer, and is not limited in type.

[0124] For example, when one compound represented by Chemical Formula 2 is used in the light-emitting auxiliary layer, a further compound may be a compound represented by Chemical Formula 3, which is different from Chemical Formula 2, or a compound different from both the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3.

[0125] More preferably, the light-emitting auxiliary layer according to the present invention may contain two or more different amine compounds represented by Chemical Formula 2 or 3, which may be mixed and deposited, co-deposited, or laminated. That is, the light-emitting auxiliary layer according to the present invention may contain two or more amine compounds represented by Chemical Formula 2 or 3, which may be mixed and deposited, co-deposited, or laminated.

[0126] That is, when the first host is composed of two or more compounds, these compounds may be mixed in one deposition source and deposited by sublimation or vaporization, or may be sublimated or vaporized in multiple deposition sources and co-deposited in the light-emitting layer, or these compounds may be stacked to form the first light-emitting layer.

[0127] That is, the method for forming the light-emitting layer may be to form a thin film by depositing (co-depositing) a plurality of first host materials from a plurality of different deposition sources, or to mix the plurality of first hosts in advance and deposit the mixed host, or to form the light-emitting layer by a lamination method when depositing the hosts.

[0128] In a more preferred embodiment of the present invention, the organic light emitting device according to the present invention includes a first electrode as an anode, a second electrode as a cathode, an emitting layer and an emitting auxiliary layer between the anode and the cathode, a hole injection layer and a hole transport layer, which may be sequentially included between the anode and the emitting auxiliary layer, and an electron transport layer and an electron injection layer, which may be sequentially included between the emitting layer and the cathode.

[0129] Hereinafter, an organic light emitting device according to an embodiment of the present invention will be described with reference to the drawings.

[0130] FIG. 1 is a diagram showing the structure of an organic light-emitting device according to one embodiment of the present invention.

[0131] 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 light emitting auxiliary layer 50′, a light emitting layer 50 containing a host and a dopant, 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 auxiliary layer, and an electron transport layer between the light emitting layer and the cathode.

[0132] 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.

[0133] Next, the organic light-emitting device of the present invention and the method for producing the same will be described with reference to FIG.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] 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).

[0138] 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.

[0139] Then, the light-emitting auxiliary layer 50' and the light-emitting layer 50 can be deposited on the hole transport layer 40 by vacuum deposition or spin coating, respectively.

[0140] Here, the amine compound represented by Chemical Formula 2 or Chemical Formula 3 can be used as a material for the light-emitting auxiliary layer in the organic light-emitting device, and the light-emitting layer 50 can be composed of a host and a dopant, and the materials constituting these are as described above.

[0141] The light-emitting auxiliary layer 50' and the light-emitting layer 50 may be formed by mixing or laminating two or more different components.

[0142] According to an embodiment of the present invention, the thickness of the light-emitting auxiliary layer 50' may be in the range of 300 to 1500 Å, preferably 400 to 1200 Å, and the thickness of the light-emitting layer 50 may be in the range of 100 to 500 Å, preferably 200 to 400 Å.

[0143] Meanwhile, an electron transport layer 60 is deposited on the light emitting layer by vacuum deposition or spin coating.

[0144] 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.

[0145] JPEG2025185715000030.jpg45170TAZ BAlq JPEG2025185715000031.jpg51170<Compound 201> <Compound 202> BCP JPEG2025185715000032.jpg38170JPEG2025185715000033.jpg39170

[0146] After forming the electron transport layer, an electron injection layer (EIL) that is a material having a function of facilitating injection of electrons from the cathode can be laminated on the electron transport layer, and the material is not particularly limited.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] (Example) Synthesis Example 1. Synthesis of [Chemical 1-1]

[0156] Synthesis Example 1-1. Synthesis of A-1 JPEG2025185715000034.jpg35170 <a-1a> <a-1b> <a-1>

[0157] In the reactor <a-1a> 44.7g、 <a-1b>50g of tetrakistriphenylphosphine palladium, 4.3g of tetrakistriphenylphosphine palladium, 52g of potassium carbonate, 600mL of toluene, and 150mL of water were charged under nitrogen atmosphere and refluxed for 12 hours. After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure and then separated by column chromatography. <a-1>(43g, 75%)

[0158] Synthesis Example 1-2. Synthesis of A-2 JPEG2025185715000035.jpg35170 <a-1> <a-2>

[0159] 65 mL of 1 M potassium t-butoxide was placed in a reactor containing 200 mL of tetrahydrofuran, and the temperature was lowered to 0°C under nitrogen. 33.5 g of (methoxymethyl)triphenylphosphonium chloride was dissolved in 200 mL of tetrahydrofuran and slowly added dropwise. After 30 minutes, <a-1>Dissolve 20g of this in 200mL of tetrahydrofuran and slowly add it to the flask, then stir at room temperature for 2 hours. After the reaction is complete, wash with water, concentrate the organic layer under reduced pressure, and separate it by column chromatography. <a-2>(20.7g, 95%)

[0160] Synthesis Example 1-3. Synthesis of A-3 JPEG2025185715000036.jpg33170 <a-2> <a-3>

[0161] In a nitrogen atmosphere, <a-2>20g of bismuth(III) trifluoromethanesulfonate, 1.9g of bismuth(III) trifluoromethanesulfonate, and 300mL of 1,2-dichloroethane were added and stirred at room temperature for 3 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then separated by column chromatography. <a-3>(10.2 g, 52%)

[0162] Synthesis Example 1-4. Synthesis of A-4 JPEG2025185715000037.jpg45170 <a-3> <a-4>

[0163] In the reactor <a-3>10g of toluene, 500mL of D6-benzene, and 20mL of triflic acid were added and refluxed for 48 hours. After the reaction was completed, water was added, and the layers were separated. The organic layer was concentrated under reduced pressure, and then separated by column chromatography. <a-4>(8.7g, 83%)

[0164] Synthesis Example 1-5. Synthesis of [Compound 1-1] JPEG2025185715000038.jpg61170 <a-4> <a-5a>[Compound 1-1]

[0165] In the reactor <a-4> 10g、 <a-5a>A mixture of 10.7 g of methyl methylcellulose, 0.3 g of bis(tri-t-butylphosphine)palladium, 5.57 g of sodium t-butoxide, and 100 mL of toluene was added under nitrogen and refluxed for 2 hours. After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure, then separated by column chromatography to obtain compound 1-1 (12.5 g, 67%). MS (MALDI-TOF): m / z 644.36 [M + ]

[0166] Synthesis Example 2. Synthesis of [Compound 1-2]

[0167] Synthesis Example 2-1. Synthesis of B-1 JPEG2025185715000039.jpg41170 <a-1a> <b-1a> <b-1>

[0168] <a-1b>instead of <b-1a>The compound was synthesized in the same manner as in Synthesis Example 1-1, except that <b-1>(Yield 78%)

[0169] Synthesis Example 2-2. Synthesis of B-2 JPEG2025185715000040.jpg41170 <b-1> <b-2>

[0170] <a-1>instead of <b-1>The compound was synthesized in the same manner as in Synthesis Example 1-2, except that <b-2>(yield 94%)

[0171] Synthesis Example 2-3. Synthesis of B-3 JPEG2025185715000041.jpg38170 <b-2> <b-3>

[0172] <a-2>instead of <b-2>The compound was synthesized in the same manner as in Synthesis Example 1-3, except that <b-3>(yield 56%)

[0173] Synthesis Example 2-4. Synthesis of B-4 JPEG2025185715000042.jpg40170 <b-3> <b-4>

[0174] <a-3>instead of <b-3>The compound was synthesized in the same manner as in Synthesis Example 1-4, except that <b-4>(yield 89%)

[0175] Synthesis Example 2-5. Synthesis of [Compound 1-2] JPEG2025185715000043.jpg59170 <b-4> <b-5a>[Compounds 1-2]

[0176] <a-4>instead of <b-4>Using <a-5a>instead of <b-5a>Compound 1-2 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 52%) MS (MALDI-TOF): m / z 644.36 [M + ]

[0177] Synthesis Example 3. Synthesis of [Compound 1-3]

[0178] Synthesis Example 3-1. Synthesis of [Compound 1-3] JPEG2025185715000044.jpg61170 <b-4> <c-1a>[Compounds 1-3]

[0179] <a-4>instead of <b-4>Using <a-5a>instead of <c-1a>Compound 1-3 was obtained in the same manner as in Synthesis Example 1-5, except that the following was used: (Yield: 55%) MS (MALDI-TOF): m / z 644.36 [M + ]

[0180] Synthesis Example 4. Synthesis of [Compound 1-7]

[0181] Synthesis Example 4-1. Synthesis of [Compound 1-7] JPEG2025185715000045.jpg44170 <a-4> <d-1a>[Compounds 1-7]

[0182] <a-5a>instead of <d-1a>Compound 1-7 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 59%) MS (MALDI-TOF): m / z 644.36 [M + ]

[0183] Synthesis Example 5. Synthesis of [Compound 1-10]

[0184] Synthesis Example 5-1. Synthesis of [Compound 1-10] JPEG2025185715000046.jpg56170 <b-4> <e-1a>[Compounds 1-10]

[0185] <a-4>instead of <b-4>Using <a-5a>instead of <e-1a>Compound 1-10 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 48%) MS (MALDI-TOF): m / z 644.36 [M + ]

[0186] Synthesis Example 6. Synthesis of [Compound 1-15]

[0187] Synthesis Example 6-1. Synthesis of F-1 JPEG2025185715000047.jpg2195 <f-1a> <f-1b> <f-1>

[0188] <a-1b>instead of <f-1a>Using <a-1a>instead of <f-1b>The compound was synthesized in the same manner as in Synthesis Example 1-1, except that <f-1>(Yield 78%)

[0189] Synthesis Example 6-2. Synthesis of F-2 JPEG2025185715000048.jpg25123 <f-1> <f-2a> <f-2>

[0190] In the reactor <f-1> 15g、 <f-2a>10.9g of toluene, 1.04g of tris(dibenzylideneacetone)dipalladium, 11.1g of sodium t-butoxide, 0.93g of Sphos, and 150mL of toluene were added under nitrogen atmosphere and refluxed for 2 hours. After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure and then separated by column chromatography. <f-2>(17.3g, 74%)

[0191] Synthesis Example 6-3. Synthesis of [Compound 1-15] JPEG2025185715000049.jpg54170 <b-4> <f-2>[Compounds 1-15]

[0192] <a-4>instead of <b-4>Using <a-5a>instead of <f-2>Compound 1-15 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 52%) MS (MALDI-TOF): m / z 720.39 [M + ]

[0193] Synthesis Example 7. Synthesis of [Compound 1-17]

[0194] Synthesis Example 7-1. Synthesis of G-1 JPEG2025185715000050.jpg22112 <f-1> <g-1a> <g-1>

[0195] <f-2a>instead of <g-1a>The compound was synthesized in the same manner as in Synthesis Example 6-2, except that <g-1>(Yield 77%)

[0196] Synthesis Example 7-2. Synthesis of [Compound 1-17] JPEG2025185715000051.jpg51170 <b-4> <g-1>[Compounds 1-17]

[0197] <a-4>instead of <b-4>Using <a-5a>instead of <g-1>Compound 1-17 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 52%) MS (MALDI-TOF): m / z 720.39 [M + ]

[0198] Synthesis Example 8. Synthesis of [Compound 1-32]

[0199] Synthesis Example 8-1. Synthesis of H-1 JPEG2025185715000052.jpg41170 <h-1a> <b-1a> <h-1>

[0200] <a-1a>instead of <h-1a>Using <a-1b>instead of <b-1a>The compound was synthesized in the same manner as in Synthesis Example 1-1, except that <h-1>(Yield 79%)

[0201] Synthesis Example 8-2. Synthesis of H-2 JPEG2025185715000053.jpg41170 <h-1> <h-2>

[0202] <a-1>instead of <h-1>The compound was synthesized in the same manner as in Synthesis Example 1-2, except that <h-2>(yield 97%) Synthesis Example 8-3. Synthesis of H-3 JPEG2025185715000054.jpg38170 <h-2> <h-3>

[0203] <a-2>instead of <h-2>The compound was synthesized in the same manner as in Synthesis Example 1-3, except that <h-3>(yield 55%)

[0204] Synthesis Example 8-4. Synthesis of H-4 JPEG2025185715000055.jpg40170 <h-3> <h-4>

[0205] <a-3>instead of <h-3>The compound was synthesized in the same manner as in Synthesis Example 1-4, except that <h-4>was obtained (yield 84%).

[0206] Synthesis Example 8-5. Synthesis of H-5 JPEG2025185715000056.jpg40170 <h-4> <h-5a> <h-5>

[0207] In the reactor <h-4>20g of ethanol, 30mL of dimethyl sulfoxide, and 0.51g of benzyltriethylammonium chloride were added under nitrogen atmosphere, and the mixture was stirred for 30 minutes. After 30 minutes, 13mL of 50wt% sodium hydroxide was added. <h-5a>After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure and then separated by column chromatography. <h-5>(21.5g, 84%)

[0208] Synthesis Example 8-6. Synthesis of [Compound 1-32] JPEG2025185715000057.jpg54170 <h-5> <b-5a>[Compounds 1-32]

[0209] <a-4>instead of <h-5>Using <a-5a>instead of <b-5a>Compound 1-32 was obtained in the same manner as in Synthesis Example 1-5, except that the following was used: (12.5 g, 57%) MS (MALDI-TOF): m / z 678.36 [M + ]

[0210] Synthesis Example 9. Synthesis of [Compound 1-38]

[0211] Synthesis Example 9-1. Synthesis of I-1 JPEG2025185715000058.jpg33170 <a-1a> <i-1a> <i-1>

[0212] <a-1b>instead of <i-1a>The compound was synthesized in the same manner as in Synthesis Example 1-1, except that <i-1>(Yield 74%)

[0213] Synthesis Example 9-2. Synthesis of I-2 JPEG2025185715000059.jpg35170 <i-1> <i-2>

[0214] <a-1>instead of <i-1>The compound was synthesized in the same manner as in Synthesis Example 1-2, except that <i-2>(yield 93%)

[0215] Synthesis Example 9-3. Synthesis of I-3 JPEG2025185715000060.jpg33170 <i-2> <i-3>

[0216] <a-2>instead of <i-2>The compound was synthesized in the same manner as in Synthesis Example 1-3, except that <i-3>(yield 54%).

[0217] Synthesis Example 9-4. Synthesis of I-4 JPEG2025185715000061.jpg36170 <d-1a> <i-4a> <i-4>

[0218] <a-4>instead of <i-4a>Using <a-5a>instead of <d-1a>The compound was synthesized in the same manner as in Synthesis Example 1-5, except that <i-4>(yield 61%)

[0219] Synthesis Example 9-5. Synthesis of I-5 JPEG2025185715000062.jpg41170 <i-4> <i-5>

[0220] In the reactor <i-4>After adding 15g of bis-pinacolatodiboron, 13.9g of tris(dibenzylideneacetone)palladium, 1.67g of Sphos, 1.5g of Sphos, and 150mL of 1,4-dioxane, the mixture was stirred for 4 hours. After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure and then separated by column chromatography. <i-5>(20g, 82%)

[0221] Synthesis Example 9-6. Synthesis of I-6 JPEG2025185715000063.jpg41170 <i-3> <i-5> <i-6>

[0222] In the reactor <i-3> 18g、 <i-5>29.42 g, tetrakis(triphenylphosphine)palladium 3.16 g, potassium carbonate 18.91 g, toluene 72 mL, ethanol 54 mL, and water 54 mL were charged under nitrogen atmosphere and refluxed for 2 hours. After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure and then separated by column chromatography. <i-6>(16.5g, 52%)

[0223] Synthesis Example 9-7. Synthesis of [Compound 1-38] JPEG2025185715000064.jpg46170 <i-6>[Compounds 1-38]

[0224] <a-3>instead of <i-6>Compound 1-38 was obtained in the same manner as in Synthesis Example 1-4, except that the following compound was used: (Yield 77%) MS (MALDI-TOF): m / z 740.52 [M + ]

[0225] Synthesis Example 10. Synthesis of [Compound 1-107]

[0226] Synthesis Example 10-1. Synthesis of J-1 JPEG2025185715000065.jpg15170 <j-1a> <f-2a> <j-1>

[0227] In the reactor <j-1a> 30g、 <f-2a>21.6g of benzophenone, 2.06g of tris(dibenzylideneacetone)dipalladium, 22g of sodium t-butoxide, 1.84g of BINAP, and 300mL of toluene were charged under nitrogen and refluxed for 2 hours. After the reaction was completed, the layers were separated and the organic layer was concentrated under reduced pressure and then separated by column chromatography. <j-1>(37.3 g, 90%)

[0228] Synthesis Example 10-2. Synthesis of [Compound 1-107] JPEG2025185715000066.jpg49170 <b-4> <j-1>[Compounds 1-107]

[0229] <a-4>instead of <b-4>Using <a-5a>instead of <j-1>Compound 1-107 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 54%) MS (MALDI-TOF): m / z 678.44 [M + ]

[0230] Synthesis Example 11. Synthesis of [Compound 1-108]

[0231] Synthesis Example 11-1. Synthesis of K-1 JPEG2025185715000067.jpg33170 <b-3> <k-1>

[0232] In the reactor <b-3>20g, 3.35g of silver carbonate, 8.16g of cyclohexyldiphenylphosphine, 8.40g of potassium carbonate, and 24.4g of deuterium oxide were added and refluxed. After 12 hours, the mixture was cooled to room temperature and then saturated aqueous ammonium chloride solution was added. The layers were separated and the organic layer was concentrated under reduced pressure, followed by separation by column chromatography. <k-1>(18.2 g, 90%)

[0233] Synthesis Example 11-2. Synthesis of K-2 JPEG2025185715000068.jpg25123 <f-1> <k-2a> <k-2>

[0234] <f-2a>instead of <k-2a>The compound was synthesized in the same manner as in Synthesis Example 6-2, except that <k-2>(Yield 71%)

[0235] Synthesis Example 11-3. Synthesis of [Compound 1-108] JPEG2025185715000069.jpg54170 <k-1> <k-2>[Compounds 1-108]

[0236] <a-4>instead of <k-1>Using <a-5a>instead of <k-2>Compound 1-108 was obtained in the same manner as in Synthesis Example 1-5, except that the following was used: (60% yield) MS (MALDI-TOF): m / z 722.28 [M + ]

[0237] Synthesis Example 12. Synthesis of [Compound 2-12]

[0238] Synthesis Example 12-1. Synthesis of [Compound 2-12] JPEG2025185715000070.jpg41170 <l-1a> <l-1b>[Compound 2-12]

[0239] <a-4>instead of <l-1a>Using <a-5a>instead of <l-1b>Compound 2-12 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 53%) MS (MALDI-TOF): m / z 525.34 [M + ]

[0240] Synthesis Example 13. Synthesis of [Compound 2-30]

[0241] Synthesis Example 13-1. Synthesis of M-1 JPEG2025185715000071.jpg48125 <l-1a> <m-1a> <m-1>

[0242] <j-1a>instead of <l-1a>Using <f-2a>instead of <m-1a>The compound was synthesized in the same manner as in Synthesis Example 10-1, except that <m-1>(yield 89%)

[0243] Synthesis Example 13-2. Synthesis of [Compound 2-30] JPEG2025185715000072.jpg44170 <m-1> <m-2a>[Compounds 2-30]

[0244] <a-4>instead of <m-2a>Using <a-5a>instead of <m-1>Compound 2-30 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 59%) MS (MALDI-TOF): m / z 577.37 [M + ]

[0245] Synthesis Example 14. Synthesis of [Compound 2-33]

[0246] Synthesis Example 14-1. Synthesis of [Compound 2-33] JPEG2025185715000073.jpg39170 <n-1a> <n-1b>[Compounds 2-33]

[0247] <a-4>instead of <n-1b>Using <a-5a>instead of <n-1a>Compound 2-33 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 56%) MS (MALDI-TOF): m / z 531.29 [M + ]

[0248] Synthesis Example 15. Synthesis of [Compound 3-11]

[0249] Synthesis Example 15-1. Synthesis of O-1 JPEG2025185715000074.jpg38170 <o-1a> <o-1b> <o-1>

[0250] <a-1a>instead of <o-1b>Using <a-1b>instead of <o-1a>The compound was synthesized in the same manner as in Synthesis Example 1-1, except that <o-1>(yield 81%)

[0251] Synthesis Example 15-2. Synthesis of [Compound 3-11] JPEG2025185715000075.jpg54170 <o-1> <o-2a>[Compound 3-11]

[0252] <a-4>instead of <o-1>Using <a-5a>instead of <o-2a>Compound 3-11 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 58%) MS (MALDI-TOF): m / z 725.31 [M + ]

[0253] Synthesis Example 16. Synthesis of [Compound 3-13]

[0254] Synthesis Example 16-1. Synthesis of P-1 JPEG2025185715000076.jpg30170 <p-1a> <p-1b> <p-1>

[0255] <a-1a>instead of <p-1b>Using <a-1b>instead of <p-1a>The compound was synthesized in the same manner as in Synthesis Example 1-1, except that <p-1>(yield 81%)

[0256] Synthesis Example 16-2. Synthesis of [Compound 3-13] JPEG2025185715000077.jpg46170 <p-1> <p-2a>[Compound 3-13]

[0257] <a-4>instead of <p-1>Using <a-5a>instead of <p-2a>Compound 3-13 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 53%) MS (MALDI-TOF): m / z 638.27 [M + ]

[0258] Synthesis Example 17. Synthesis of [Compound 3-25]

[0259] Synthesis Example 17-1. Synthesis of [Compound 3-25] JPEG2025185715000078.jpg51170 <q-1a> <q-1b>[Compound 3-25]

[0260] <a-4>Instead, it was synthesized in the same manner as in the literature "Angewandte Chemie, International Edition (2016) 55 (27) 7728" <q-1a>Using <a-5a>instead of <q-1b>Compound 3-25 was obtained in the same manner as in Synthesis Example 1-5, except that the following compound was used: (Yield: 51%) MS (MALDI-TOF): m / z 665.31 [M + ]

[0261] Synthesis Example 18. Synthesis of [Compound 3-34]

[0262] Synthesis Example 18-1. Synthesis of [Compound 3-34] JPEG2025185715000079.jpg51170[Compound 3-25] <r-1a>[Compound 3-34]

[0263] 17 g of [Compound 3-25], 10.2 g of aluminum chloride, and 170 mL of methylene chloride were placed in a reactor under nitrogen and cooled to 0°C. <r-1a>After 1 hour, saturated aqueous sodium bicarbonate solution was added. The layers were separated, and the organic layer was concentrated under reduced pressure. Compound 3-34 was obtained by column chromatography (yield 45%). MS (MALDI-TOF): m / z 775.42 [M + ]

[0264] Synthesis Example 19. Synthesis of [RPH-1]

[0265] Synthesis Example 19-1. Synthesis of S-1 JPEG2025185715000080.jpg49170 <b-3> <s-1>

[0266] <i-4>instead of <b-3>The compound was synthesized in the same manner as in Synthesis Example 9-5, except that <s-1>(yield 83%)

[0267] Synthesis Example 19-2. Synthesis of [RPH-1] JPEG2025185715000081.jpg56170 <s-2a> <s-1>[RPH-1]

[0268] <i-3>instead of <s-2a>Using <i-5>instead of <s-1>[RPH-1] was obtained in the same manner as in Synthesis Example 9-6, except that the following compound was used (yield: 54%). MS (MALDI-TOF): m / z 665.25 [M + ]

[0269] Synthesis Example 20. Synthesis of [RPH-2]

[0270] Synthesis Example 20-1. Synthesis of T-1 JPEG2025185715000082.jpg49170 <t-1a> <t-1>

[0271] <i-4>instead of <t-1a>The compound was synthesized in the same manner as in Synthesis Example 9-5, except that <t-1>(Yield 77%)

[0272] Synthesis Example 20-2. Synthesis of [RPH-2] JPEG2025185715000083.jpg56170 <s-2a> <t-1>[RPH-2]

[0273] <i-3>instead of <s-2a>Using <i-5>instead of <t-1>[RPH-2] was obtained in the same manner as in Synthesis Example 9-6, except that the following compound was used (yield: 59%). MS (MALDI-TOF): m / z 575.20 [M + ]

[0274] Examples 1 to 55: Fabrication of organic light-emitting devices The ITO glass was patterned so that the light-emitting area was 2 mm × 2 mm, and then washed. The ITO glass was placed in a vacuum chamber, and the base pressure was adjusted to 1 × 10 ―6 The pressure was adjusted to torr, and then HAT-CN (50 Å) and NPD (1500 Å) were deposited in this order on the ITO as hole injection and hole transport layers. A light-emitting auxiliary layer compound (750 Å) according to the present invention was then deposited. A light-emitting layer was then formed (400 Å) by mixing a host compound according to the present invention with one of the following [RPH-1] to [RPH-3] in a 1:1 ratio and adding 5 wt% of a dopant compound [RD]. Subsequently, ET:Liq=1:1 (300 Å) was deposited sequentially as electron transport and electron injection layers, and Al (1000 Å) was deposited as a cathode to fabricate an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0275] JPEG2025185715000084.jpg147170

[0276] Comparative Examples 1 to 31 The organic light-emitting device for the comparative example was fabricated and tested in the same manner as in the example, except that the compounds according to the present invention used as hosts were replaced with the compounds [RH-1] and [RH-2] below, and the compounds according to the present invention were replaced with the compounds [RP-1] and [RP-2] below as light-emitting auxiliary layer compounds. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA, and the measurement results are shown in Table 1 below.

[0277] Here, the structures of [RH-1] to [RH-2] and [RP-1] to [RP-2] are as follows:

[0278] JPEG2025185715000085.jpg61150

[0279] JPEG2025185715000086.jpg61150

[0280] [Table 1] JPEG2025185715000088.jpg219170

[0281] 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 light-emitting layer in the organic light-emitting device according to the present invention and in the light-emitting auxiliary layer interposed between the light-emitting layer and the hole transport layer, exhibits high efficiency and long life organic light-emitting devices with excellent light-emitting efficiency and life characteristics at a low driving voltage, compared to the organic light-emitting devices (Comparative Examples 1 to 31) which use the comparative compounds according to the prior art.

[0282] Examples 56 to 101: Production of organic light-emitting devices The organic light-emitting devices used in Examples 1 to 55 were fabricated in the same manner as above, except that two different compounds were used as the light-emitting auxiliary layer compounds according to the present invention, instead of a single compound, and the two compounds were used as the first and second light-emitting auxiliary layer materials, respectively, as shown in Table 2 below. The light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 2 below.

[0283] Comparative Examples 32 to 51: Production of organic light-emitting devices The organic light emitting devices for the comparative examples were fabricated in the same manner as in the examples, except that RH-1 or RH-2 was used as the host compound in the light emitting layer instead of the compound according to the present invention, or RP-1 or RP-2 was used as the light emitting auxiliary layer compound instead of the compound according to the present invention. The light emitting characteristics of the organic light emitting devices were measured at 0.4 mA.

[0284] [Table 2] JPEG2025185715000090.jpg110170

[0285] As shown in Table 2 above, it can be seen that elements employing the light-emitting layer host compound and the first and second light-emitting auxiliary layer compounds in the organic light-emitting element of the present invention can realize highly efficient, long-life organic light-emitting elements with excellent light-emitting efficiency and life characteristics at a lower driving voltage than elements employing conventional compounds (Comparative Examples 32 to 51) that are contrasted with the characteristic structure of the compounds of the present invention. < / s-2a> < / t-1> < / t-1a> < / s-2a> < / s-1> < / b-3> < / q-1a> < / p-1> < / p-1> < / p-1b> < / p-1a> < / o-1> < / o-1> < / o-1b> < / o-1a> < / n-1a> < / m-1> < / m-1> < / m-1a> < / l-1a> < / l-1a> < / k-1> < / k-2> < / k-2a> < / f-1> < / b-3> < / b-4> < / j-1a> < / f-2a> < / j-1a> < / i-3> < / i-5> < / i-3> < / i-4> < / i-4> < / i-4a> < / d-1a> < / i-3> < / i-2> < / i-2> < / i-1> < / i-1> < / i-1a> < / a-1a> < / h-5> < / h-5a> < / h-4> < / h-4> < / h-3> < / h-3> < / h-2> < / h-2> < / h-1> < / h-1> < / b-1a> < / h-1a> < / b-4> < / g-1> < / g-1a> < / f-1> < / b-4> < / f-1> < / f-2a> < / f-1> < / f-1> < / f-1b> < / f-1a> < / b-4> < / a-4> < / b-4> < / b-4> < / b-4> < / b-3> < / b-3> < / b-2> < / b-2> < / b-1> < / b-1> < / b-1a> < / a-1a> < / a-4> < / a-4> < / a-3> < / a-2> < / a-1> < / a-1a> < / a-1b> < / a-1a>

Claims

1. A first electrode; a second electrode facing the first electrode; an organic layer interposed between the first electrode and the second electrode, the organic layer including a light-emitting layer and a light-emitting auxiliary layer; the light-emitting layer contains one or more amine compounds represented by Chemical Formula 1, The organic light emitting device, wherein the light emitting auxiliary layer comprises one or more amine compounds represented by the following Chemical Formula 2 or 3: [Chemical formula 1] (In the above chemical formula 1, The substituent R １ ~R ４ 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R ５ ~R １２ 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 substituted or unsubstituted cycloalkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl 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 aryl group having 8 to 30 carbon atoms fused with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms 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 ... is any one selected from an alkylthio group having 1 to 30 prime numbers, 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, a halogen group, and structural formula Q; The substituent R ５ ~R １２ One or two of the substituents are the linking group L in the structural formula Q. １ or a single bond connecting to a nitrogen atom (N), The substituent R １ ~R １２ two adjacent substituents among the above may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic fused ring; The substituent R １３ and R １４ may be the same or different, and each independently represent any one selected from a substituted or unsubstituted 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R １３ and R １４ can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The linking group L １ ~L ３ 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, Said m １ ~m ３ may be the same or different and each independently represents 1 or 2. １ If is 2, then each L １ may be the same or different, and ２ If is 2, then each L ２ may be the same or different, and the m ３ If is 2, then each L ３ may be the same or different from each other, The substituent Ar １ and Ar ２ may be the same or different, and are each independently selected from 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 heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto. [Chemical formula 2] [Chemical formula 3] (In the above chemical formula 2, The substituent R １５ and R １６ may be the same or different, and each independently represent any one selected from a substituted or unsubstituted 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The substituent R １５ and R １６ can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The R １７ is any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The n １ is 7, and then each R １７ may be the same or different from each other, Two adjacent substituents R １７ can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The linking group L ４ ~L ６ 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, Said m ４ ~m ６ may be the same or different and each independently represents 1 or 2. ４ If is 2, then each L ４ may be the same or different, and ５ If is 2, then each L ５ may be the same or different, and the m ６ If is 2, then each L ６ may be the same or different from each other, The substituent Ar ３ and Ar ４ may be the same or different, and each independently represent one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; In the above Chemical Formula 3, The substituent R １８ is any one selected from hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The n ２ is 5, and then each R １８ may be the same or different from each other, The five Rs １８ at least one of the groups is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Two adjacent substituents R １８ can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The linking group L ７ ~L ９ 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, Said m ７ ~m ９ may be the same or different and each independently represents 1 or 2. ７ If is 2, then each L ７ may be the same or different, and the m ８ If is 2, then each L ８ may be the same or different, and the m ９ If is 2, then each L ９ may be the same or different from each other, The substituent Ar ５ and Ar ６ 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 cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring condensed thereto; The "substituted" in "substituted or unsubstituted" in Chemical Formulas 1 to 3 above 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, carbon and one or more substituents selected from the group consisting of a cycloalkyl group having 5 to 30 carbon atoms 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, an aryl group having 6 to 30 carbon atoms fused with an aliphatic heterocycle, a 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.

2. 10. The organic light emitting device according to claim 1, wherein the amine compound represented by Chemical Formula 1 is any one of amine compounds represented by the following Chemical Formulas 1-1 to 1-4. (In the above Chemical Formula 1-1 to Chemical Formula 1-4, The substituent R １ ~R １２ may be the same or different and are each independently hydrogen or deuterium; The substituent R １３ and R １４ may be the same or different, and each independently represent one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and having an aliphatic hydrocarbon ring fused thereto; The linking group L １ ~L ３ 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 substituent Ar １ and Ar ２ may be the same or different and are each independently selected from 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 heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and fused with an aliphatic hydrocarbon ring. １ and Ar ２ at least one of is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, Said m １ ~m ３ are each 1 or 2, and in this case, １ If is 2, then each L １ may be the same or different, and the m ２ If is 2, then each L ２ may be the same or different, and the m ３ If is 2, then each L ３ may be the same or different from each other, The substituent R １ ~R １２ two adjacent substituents among The R １３ and R １４ can be further linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, The "substituted" in "substituted or unsubstituted" in Chemical Formula 1-1 to Chemical Formula 1-4 is the same as defined in Claim 1.

3. Ar in Formula 1 １ and Ar ２ 2. The organic light-emitting element according to claim 1, wherein at least one of the groups is a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms and containing an oxygen atom (O) or a sulfur atom (S).

4. R in Formula 1 and Formula 2 １３ ~R １６ may be the same or different, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

5. Ar in the above Chemical Formula 2 ３ and Ar ４ 2. The organic light-emitting device according to claim 1, wherein at least one of the groups is a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms.

6. Ar in the above Chemical Formula 2 ３ and Ar ４ and may be the same or different and each independently represent a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms.

7. 6. The organic light-emitting element according to claim 5, wherein the ring structure in the substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms is any one selected from the following structural formulas 1 to 6: [Structural formula 1] [Structural formula 2] [Structural formula 3] [Structural formula 4] [Structural formula 5] [Structural formula 6] (Here, in the structural formulas 1 to 6, one hydrogen atom in the ring structure is removed, and the carbon atom in the ring structure bonded to the removed hydrogen atom is a linking group L in chemical formula 2. ５ or L ６ Or bonded to a nitrogen atom (N).

8. Ar in the above Chemical Formula 3 ５ and Ar ６ may be the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

9. R in the above Chemical Formula 2 １７ may be the same or different and each independently represents hydrogen or deuterium.

10. 2. The organic light emitting device according to claim 1, wherein the amine compound represented by Chemical Formula 1 is any one selected from the group consisting of Compounds 1-1 to 1-120:

11. The organic light-emitting device according to claim 1, wherein the amine compound represented by Chemical Formula 2 is any one selected from the group consisting of Compounds 2-1 to 2-48 below.

12. 2. The organic light-emitting device according to claim 1, wherein the amine compound represented by Chemical Formula 3 is any one selected from the group consisting of Compounds 3-1 to 3-39 below.

13. 10. The organic light emitting device according to claim 1, wherein the light emitting layer of the organic light emitting device further comprises, as a host, one or more host compounds different from the amine compound represented by Chemical Formula 1.

14. 10. The organic light-emitting device according to claim 1, wherein the light-emitting auxiliary layer of the organic light-emitting device further comprises, in addition to the amine compound represented by Chemical Formula 2 or Chemical Formula 3, one or more light-emitting auxiliary layer compounds different from the amine compound represented by Chemical Formula 2 or Chemical Formula 3.

15. 10. The organic light-emitting device according to claim 1, wherein the organic light-emitting device is used in any one device selected from the group consisting of 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 vehicle or aircraft display device, and a virtual or augmented reality display device.

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