Novel heterocyclic compound and organic light-emitting diode including same

Abstract

The present invention relates to a novel aromatic heterocyclic compound that can be used in an organic light-emitting diode and to an organic light-emitting diode including same.

Description

Novel heterocyclic compound and organic light-emitting device comprising the same

[0001] The present invention relates to a novel heterocyclic compound that can be used in an organic light-emitting device, and more specifically, to a novel heterocyclic compound that can be used as a host material of a light-emitting layer in an organic light-emitting device to implement device characteristics of low voltage, high efficiency, and long lifespan, and an organic light-emitting device comprising the same.

[0002]

[0003] Organic light emitting diodes (OLEDs) are displays that utilize the self-luminous phenomenon. They have advantages such as a large viewing angle, being thinner and simpler than liquid crystal displays, and having a fast response speed, and are expected to be applied to full-color displays or lighting.

[0004] In general, organic light emitting diodes (OLEDs) are devices that utilize the organic light emitting phenomenon, typically comprising an anode, a cathode, and an organic layer between them. These organic layers are often multilayered, made of different materials, to enhance the efficiency and stability of the device. For example, they may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this device, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. Excitons form when the injected holes and electrons meet, and light is emitted when these excitons fall back to their ground state. These devices are known to exhibit characteristics such as self-luminescence, high brightness, high efficiency, low operating voltage, wide viewing angle, high contrast, and high-speed response.

[0005] Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge-transporting materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions. The light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons depending on their luminescence mechanisms.

[0006] Meanwhile, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a longer wavelength due to intermolecular interaction, resulting in a decrease in color purity or a decrease in device efficiency due to a light-emitting attenuation effect. Therefore, a host-dopant system can be used as a light-emitting material to increase color purity and light-emitting efficiency through energy transfer.

[0007] The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, resulting in high-efficiency light emission. At this time, the wavelength of the host shifts to the wavelength of the dopant, so light of a desired wavelength can be obtained depending on the type of dopant used.

[0008] Among these light-emitting layers, heterocyclic compounds containing heteroatoms such as nitrogen and oxygen have been recently studied as host compounds for organic light-emitting devices utilizing phosphorescence. As related prior art, Patent Publication No. 10-2023-0028739 (2023.03.02) discloses an organic light-emitting device using an aromatic heterocyclic compound having a carbazole structure as a first host and a second host material, respectively, and Patent Publication No. 10-2020-0139834 (2020.12.14) describes an organic light-emitting device including an aromatic heterocyclic compound having a polycyclic structure as a phosphorescent host.

[0009] However, despite the fact that various types of compounds have been manufactured for use in the light-emitting layer of organic light-emitting devices, including the above-mentioned conventional technology, there is still a continuous need for the development of novel compounds that can be applied to organic light-emitting devices and have device characteristics such as low-voltage operation, high efficiency, and long lifespan, and organic light-emitting devices including the same.

[0010]

[0011] Therefore, the first technical task to be achieved by the present invention is to provide a novel organic compound that can be used as a phosphorescent host material in a light-emitting layer in an organic light-emitting device.

[0012] In addition, the second technical task to be achieved by the present invention is to provide an organic light emitting diode (OLED) having low voltage, high efficiency, and long lifespan, which includes the organic compound as a host material in the organic light emitting diode.

[0013]

[0014] To solve the above problem, the present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] The above X1 and X2 are the same or different from each other, and are each independently O or S,

[0019] The above connecting groups L1 to L4 are the same or different from each other, and each independently represents a single bond or a connecting 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, in which an aliphatic hydrocarbon ring is condensed.

[0020] The above substituents Y1 to Y4 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic group having 7 to 30 carbon atoms. A cycloalkyl group having a condensed hydrocarbon ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted Any one selected from among an 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0021] m1 is 4, and at this time, each L1-Y1 is the same or different from each other,

[0022] m2 is 4, and at this time, each L2-Y2 is the same or different from each other,

[0023] m3 is 2, and at this time, each L3-Y3 is the same or different from each other,

[0024] m4 is 1 or 2, and when m4 is 2, each L4 is equal to or different from each other,

[0025] Among the identical or different substituents L1-Y1, the adjacent substituents, among the identical or different substituents L2-Y2, the adjacent substituents, and among the identical or different substituents L3-Y3, the adjacent substituents, and the identical or different substituents L3-Y3 may be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0026] At least one of the four identical or different substituents L1-Y1, four identical or different substituents L2-Y2, two identical or different substituents L3-Y3, and (L4)m4-Y4 is a substituent represented by [Structural Formula 1],

[0027] [Structural formula 1]

[0028]

[0029] In the above structural formula 1,

[0030] The above Z is Si or Ge,

[0031] The above connecting groups L5 to L8 are the same or different from each other, and are each independently a single bond or a connecting 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, in which an aliphatic hydrocarbon ring is condensed.

[0032] The above substituents R5 to R7 are the same or different from each other, and each independently represents 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms. A condensed cycloalkyl group, a condensed cycloalkyl group with a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms, a condensed heterocycloalkyl group with a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a condensed aryl group with a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a condensed heteroaryl group with a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group with 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group with 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group with 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group with 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0033] The above m5 to m8 are 1 or 2, and when they are each 2, each L5, each L6, each L7 and each L8 are the same or different from each other,

[0034] In the above chemical formula 1 and structural formula 1, 'substitution' in 'substituted or unsubstituted' means deuterium, 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, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed 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 It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium.

[0035]

[0036] When the aromatic heterocyclic compound represented by the above chemical formula 1 according to the present invention is used as a phosphorescent host material of a light-emitting layer in an organic light-emitting device, it can provide an organic light-emitting device that can implement characteristics of lower voltage, higher efficiency, and longer lifespan compared to an organic light-emitting device according to the prior art.

[0037]

[0038] FIG. 1 is a drawing illustrating the structure of an organic light-emitting device according to one embodiment of the present invention.

[0039]

[0040] Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the sizes and dimensions of structures are illustrated enlarged or reduced from the actual size to ensure clarity of the present invention, and well-known components are omitted to highlight characteristic components, so the present invention is not limited to the drawings.

[0041] In addition, since the size and thickness of each component shown in the drawings are arbitrarily shown for the convenience of explanation, the present invention is not necessarily limited to what is shown, and in order to clearly express various layers and regions in the drawings, the thicknesses are shown in an enlarged manner. And in the drawings, for the convenience of explanation, the thicknesses of some layers and regions are shown exaggeratedly. When it is said that a part such as a layer, film, region, or plate is "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part in between.

[0042] Additionally, throughout the specification, when a part is said to "include" a component, this does not exclude other components, but rather implies the inclusion of other components, unless otherwise specifically stated. Furthermore, throughout the specification, "on" means located above or below the target part, and does not necessarily mean located above in the direction of gravity.

[0043]

[0044] The present invention provides a heterocyclic compound represented by the following [chemical formula 1].

[0045] [Chemical Formula 1]

[0046]

[0047] In the above chemical formula 1,

[0048] The above X1 and X2 are the same or different from each other, and are each independently O or S,

[0049] The above connecting groups L1 to L4 are the same or different from each other, and each independently represents a single bond or a connecting 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, in which an aliphatic hydrocarbon ring is condensed.

[0050] The above substituents Y1 to Y4 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic group having 7 to 30 carbon atoms. A cycloalkyl group having a condensed hydrocarbon ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted Any one selected from among an 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0051] m1 is 4, and at this time, each L1-Y1 is the same or different from each other,

[0052] m2 is 4, and at this time, each L2-Y2 is the same or different from each other,

[0053] m3 is 2, and at this time, each L3-Y3 is the same or different from each other,

[0054] m4 is 1 or 2, and when m4 is 2, each L4 is equal to or different from each other,

[0055] Among the identical or different substituents L1-Y1, the adjacent substituents, among the identical or different substituents L2-Y2, the adjacent substituents, and among the identical or different substituents L3-Y3, the adjacent substituents, and the identical or different substituents L3-Y3 may be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0056] At least one of the four identical or different substituents L1-Y1, four identical or different substituents L2-Y2, two identical or different substituents L3-Y3, and (L4)m4-Y4 is a substituent represented by [Structural Formula 1],

[0057] [Structural formula 1]

[0058]

[0059] In the above structural formula 1,

[0060] The above Z is Si or Ge,

[0061] The above connecting groups L5 to L8 are the same or different from each other, and are each independently a single bond or a connecting 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, in which an aliphatic hydrocarbon ring is condensed.

[0062] The above substituents R5 to R7 are the same or different from each other, and each independently represents 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms. A condensed cycloalkyl group, a condensed cycloalkyl group with a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms, a condensed heterocycloalkyl group with a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a condensed aryl group with a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a condensed heteroaryl group with a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group with 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group with 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group with 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group with 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0063] The above m5 to m8 are 1 or 2, and when they are each 2, each L5, each L6, each L7 and each L8 are the same or different from each other,

[0064] In the above chemical formula 1 and structural formula 1, 'substitution' in 'substituted or unsubstituted' means deuterium, 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, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed 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 It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium.

[0065]

[0066] Meanwhile, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms", etc. in the present invention, the range of carbon atoms of the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 50 carbon atoms respectively refers to the total number of carbon atoms constituting the alkyl moiety or aryl moiety when the substituent is viewed as unsubstituted without considering the substituted portion. For example, a phenyl group substituted with a butyl group at the para-position should be viewed as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0067] 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 the removal of one hydrogen, and when the aryl group has a substituent, it can be fused with an adjacent substituent to form an additional ring, and further, the aryl group can include an organic radical obtained by the removal of one hydrogen from an arene ring formed by the condensation of two arene rings.

[0068] Specific examples of the above 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, a triphenylenyl group, and the like, but are not limited thereto, and may also include an organic radical formed by the removal of one hydrogen from an arene ring formed by the condensation of two arene rings, such as an arene ring formed by the condensation of a fluorene ring and a phenylene ring, or an arene ring formed by the condensation of a fluorene ring and a phenanthrene ring.

[0069] In addition, at least one hydrogen atom of the aryl group is selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amine group, a germanium group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid 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 a alkyl group having 3 to 24 carbon atoms. It can be substituted with an alkylheteroaryl group.

[0070] In the present invention, the aromatic hydrocarbon ring means an aromatic ring composed of carbon and hydrogen, and further, the aliphatic hydrocarbon ring means a hydrocarbon ring composed of carbon and hydrogen but not belonging to an aromatic hydrocarbon ring, and at this time, the aliphatic hydrocarbon ring preferably has at least 30% or more of the carbon atoms forming the ring as sp 3 It may be a hydrocarbon ring that forms a bond through an orbital structure and contains 0 to 3 double bonds and / or triple bonds within the ring, and more preferably, at least 50% or more of the carbon atoms forming the ring are sp 3 It may be a hydrocarbon ring that is bonded by orbitals and contains 0 to 2 double bonds and / or triple bonds within the ring.

[0071] In addition, the aryl group in which the aliphatic hydrocarbon ring is condensed in the present invention means a cyclic substituent in which two adjacent carbon atoms in the aliphatic hydrocarbon ring and two adjacent carbon atoms excluding the carbon atom that becomes an organic radical by hydrogen removal from one of the carbon atoms forming the ring in the aryl group are condensed with each other to share one double bond and have overall non-aromaticity, and specific examples include, but are not limited to, a tetrahydronaphthyl group, a tetrahydrobenzocycloheptene, a tetrahydrophenanthrene group, a tetrahydroanthracenyl group, and an octahydrotriphenylene group.

[0072] The heteroaryl group, which is a substituent used in the compound of the present invention, refers to an aryl group of a ring aromatic system having 2 to 24 carbon atoms, which contains 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in an aromatic ring, and the remaining ring atoms are carbon, and the rings can be fused to form a ring. In addition, one or more hydrogen atoms in the heteroaryl group can be substituted with a substituent similar to that in the case of the aryl group.

[0073] Specific examples of the above 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 pyrimidinyl group, a triazinyl group, a triazolyl 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 phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, Examples thereof include, but are not limited to, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoselenophene group, a dibenzothiophenyl group, a dibenzofuranyl group, a dibenzoselenophene group, a phenanthrolinyl group, a thiazolinyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group, a phenothiazinyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzoselenophene group, and an indolocarbazole group.

[0074] In addition, in the present invention, the aromatic heterocycle means an aromatic hydrocarbon ring in which at least one aromatic carbon is substituted with a heteroatom, and the aromatic heterocycle may preferably be one in which 1 to 3 aromatic carbons in the aromatic hydrocarbon are substituted with at least one heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te.

[0075] In addition, the heteroaryl group having a condensed aliphatic hydrocarbon ring is a substituent having a structure in which a heteroaryl group is substituted instead of an aryl group in the condensed aliphatic hydrocarbon ring aryl group, and specific examples thereof include, but are not limited to, a tetrahydroindole group, a tetrahydrobenzofuranyl group, a tetrahydrobenzothiophene group, a tetrahydrocarbazole group, a tetrahydrodibenzofuranyl group, a tetrahydrobenzothiophene group, a tetrahydroquinoline group, and a tetrahydroquinoxaline group.

[0076] In addition, in the present invention, the aromatic heterocycle means an aromatic hydrocarbon ring in which at least one aromatic carbon is substituted with a heteroatom, and the aromatic heterocycle may preferably be one in which 1 to 3 aromatic carbons in the aromatic hydrocarbon are substituted with at least one heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te.

[0077] In the present invention, the 'condensed ring in which an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring are condensed' means a condensed ring in which two adjacent carbon atoms in an aromatic hydrocarbon ring and two adjacent carbon atoms in an aliphatic hydrocarbon ring are condensed so that they are shared with each other, and examples thereof include tetrahydronaphthalene and dihydroindene rings in which two adjacent carbon atoms in a benzene ring and a cyclohexane ring are condensed so that they are shared with each other.

[0078] In addition, the 'condensed ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are condensed' in the present invention means a condensed ring in which two adjacent carbon atoms in an aromatic heterocycle and two adjacent carbon atoms in an aliphatic hydrocarbon ring are condensed so that they are shared with each other, and as an example, a hexahydrodibenzofuran ring in which two adjacent carbon atoms in each ring of a benzofuran ring and a cyclohexane ring are condensed so that they are shared with each other can be mentioned.

[0079] The alkyl group, which is a substituent used in the present invention, is a substituent in which one hydrogen is removed from an alkane, and has a structure including a straight chain or a branched type, and 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-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohectylmethyl group, an octyl group, an n-octyl group, Examples thereof include, but are not limited to, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, and at least one hydrogen atom of the alkyl group may be replaced with a substituent similar to that of the aryl group.

[0080] The halogenated alkyl group used as a substituent in the present invention means a substituent in which at least one hydrogen atom in the alkyl group as a substituent is replaced with a halogen group, and preferably, the halogen group may be a fluorine atom.

[0081] In the compound of the present invention, the 'cyclo' in the cycloalkyl group, cycloalkoxy group, etc., which are substituents, means a substituent having a structure capable of forming a single ring or multiple rings of a saturated hydrocarbon in the alkyl group or the alkoxy group, and for example, specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc., but are not limited thereto, and one or more hydrogen atoms in the cycloalkyl group can be substituted with a substituent similar to the case of the aryl group, and this can also be applied to cycloalkoxy.

[0082] Also, in the present invention, the heterocycloalkyl group means that at least one of the carbon atoms in the ring of a substituent forming a cycloalkyl structure is substituted with a heteroatom, and preferably, 1 to 3 carbon atoms may be substituted with at least one heteroatom selected from N, O, P, S, Si, Ge, Se, and Te.

[0083] In addition, the cycloalkyl group in which the aromatic hydrocarbon ring or aromatic heterocycle is condensed means a cyclic substituent in which two adjacent carbon atoms within the aromatic hydrocarbon ring or aromatic heterocycle and two adjacent carbon atoms, excluding a carbon atom that becomes an organic radical by the removal of hydrogen from one of the carbon atoms forming the ring within the cycloalkyl group, are condensed with each other to share one double bond and exhibit overall non-aromaticity, and specific examples include, but are not limited to, tetrahydronaphthyl, tetrahydrophenanthrene, tetrahydroquinoline, tetrahydroquinoxaline, and cyclopentabenzofuran.

[0084] In addition, the heterocycloalkyl group in which the aromatic hydrocarbon ring is condensed means a cycloalkyl group in which at least one of the carbon atoms in the cycloalkyl ring is substituted with a heteroatom in the cycloalkyl group in which the aromatic hydrocarbon ring is condensed, and preferably, it is a substituent having a structure in which 1 to 3 carbons in the cycloalkyl ring are substituted with at least one heteroatom selected from N, O, P, S, Si, Ge, Se, and Te, and specific examples include, but are not limited to, a hexahydrodibenzofuranyl group, a hexahydrocarbazole group, a hexahydrodibenzothiophene group, and a dihydrobenzodioxine group, and overall, it exhibits non-aromaticity.

[0085] In addition, the aryl group or heteroaryl group to which an aliphatic heterocycle is condensed is a substituent having a structure in which an aliphatic heterocycle is condensed instead of an aliphatic hydrocarbon ring in the aryl group or heteroaryl group to which an aliphatic hydrocarbon ring is condensed, and specific examples thereof include, but are not limited to, a chroman group, a dihydropyranopyridine group, a thiochroman group, a dihydrobenzodioxine group, a dihydrothiopyranopyridine group, and a dihydropyranopyrimidine group, and the like, and overall, exhibits non-aromaticity.

[0086] In addition, the above aliphatic heterocycle means that at least one of the carbons in the aliphatic hydrocarbon ring is replaced with a heteroatom, and the above aliphatic heterocycle may preferably be such that 1 to 3 carbons in the aliphatic hydrocarbon ring are replaced with at least one heteroatom selected from N, O, S, etc.

[0087] 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 methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantaneoxy, dicyclopentaneoxy, bornyloxy, isobornyloxy, etc., but are not limited thereto, and one or more hydrogen atoms of the alkoxy group may be substituted with a substituent similar to the case of the aryl group.

[0088] 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 at least one hydrogen atom of the arylalkyl group may be substituted with a substituent similar to that of the aryl group.

[0089] 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, t-butylphenanthryl, etc., and at least one hydrogen atom of the alkylaryl group may be substituted with a substituent similar to that of the aryl group.

[0090] Additionally, in the present invention, an alkenyl group means an alkyl substituent including one carbon-carbon double bond formed by two carbon atoms, and an alkynyl group means an alkyl substituent including one carbon-carbon triple bond formed by two carbon atoms.

[0091] In addition, the alkylene group used in the present invention is an organic radical derived by the removal of two hydrogens in an alkane molecule, which is a saturated hydrocarbon in a straight or branched form. 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, a hexylene group, and the like. One or more hydrogen atoms in the alkylene group may be replaced with a substituent similar to the case of the aryl group.

[0092] In addition, in the present invention, the amine group may include -NH2, an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, etc., and the arylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an aryl group, the alkylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an alkyl group, the alkylarylamine group means an amine in which one hydrogen in -NH2 is substituted with an alkyl group and the other hydrogen in -NH2 is substituted with an aryl group, the arylheteroarylamine group means an amine in which one hydrogen in -NH2 is substituted with an aryl group and the other hydrogen in -NH2 is substituted with a heteroaryl group, and the heteroarylamine group means an amine in which one or two hydrogens in -NH2 are substituted with a heteroaryl group, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted There is a diarylamine group, and the same applies to the alkylamine group and heteroarylamine group.

[0093] Here, each aryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0094] The silyl group, which is a substituent used in the compound of the present invention, may include -SiH3, an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, a heteroarylsilyl group, etc., and the arylsilyl group means a silyl group in which one, two, or three hydrogens in -SiH are substituted with an aryl group, and the alkylsilyl group means a silyl in which one, two, or three hydrogens in -SiH3 are substituted with an alkyl group, and the alkylarylsilyl group means a silyl group in which at least one hydrogen in -SiH3 is substituted with an alkyl group and an aryl group, and includes one or two alkyl groups and two or one corresponding aryl groups, and the arylheteroarylsilyl group means a silyl group in which at least one hydrogen in -SiH3 is substituted with an aryl group and a heteroaryl group, and includes one or two aryl groups and two or one corresponding heteroaryl groups. It means a silyl group, and a heteroarylsilyl group means a silyl group in which one, two, or three hydrogens in -SiH3 are substituted with a heteroaryl group, and examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group, and the same applies to the alkylsilyl group and the heteroarylsilyl group.

[0095] Here, each aryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0096] In addition, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., and at least one hydrogen atom of the silyl group can be substituted with a substituent similar to that of the aryl group.

[0097] In addition, in the present invention, the germanium group (or germanium group, or germane group) may include -GeH3, an alkylgermanium group, an arylgermanium group, a heteroarylgermanium group, an alkylarylgermanium group, an alkylheteroarylgermanium group, an arylheteroarylgermanium group, etc., and the definitions of these are as described for the silyl group, but can be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) for a silicon atom (Si) in the silyl group.

[0098] In addition, specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, etc., and one or more hydrogen atoms of the germanium group can be substituted with a substituent similar to that of the aryl group.

[0099] In addition, in the present invention, the substituent (A) in the aromatic ring and the "mutually adjacent substituent (B)" mean the substituent (B) bonded to the aromatic ring carbon atom(s) adjacent to the aromatic ring carbon atom to which the substituent A in the aromatic ring is bonded, and further, the substituent (A) in the alicyclic ring and the "mutually adjacent substituent (B)" mean the substituent (B) bonded to the ring carbon atom(s) adjacent to the ring carbon atom to which the substituent A in the alicyclic ring is bonded, and further, the substituent (A) bonded to a specific carbon atom in the aliphatic chain structure and the "mutually adjacent substituent (B)" mean the substituent (B) bonded to the carbon atom(s) adjacent to the specific carbon atom to which the substituent A in the aliphatic chain structure is bonded.

[0100]

[0101] Meanwhile, as a more preferable example of 'substitution' in the 'substituted or unsubstituted' in the above chemical formula 1, it is a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 3 to 18 carbon atoms, an alkylheteroaryl group having 3 to 18 carbon atoms, an aromatic group having 9 to 20 carbon atoms. It may be substituted with one or more substituents selected from the group consisting of a cycloalkyl group having a condensed hydrocarbon ring, a cycloalkyl group having a condensed aromatic heterocycle having 7 to 20 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 9 to 20 carbon atoms, an aryl group having a condensed aliphatic hydrocarbon ring having 9 to 20 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 7 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an amine group having 1 to 18 carbon atoms, a silyl group having 1 to 18 carbon atoms, a germanium group having 1 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms, and at least one hydrogen in each of the above substituents may be substituted with deuterium.

[0102] In addition, in the present invention, a more preferable example of the cycloalkyl group having a condensed aromatic hydrocarbon ring having 7 to 30 carbon atoms, which is substituted or unsubstituted, may be a cycloalkyl group having a condensed aromatic hydrocarbon ring having 9 to 20 carbon atoms, which is substituted or unsubstituted.

[0103] In addition, in the present invention, a more preferable example of the cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms may be a cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 7 to 20 carbon atoms.

[0104] In addition, in the present invention, a more preferable example of the heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms is a heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 9 to 20 carbon atoms.

[0105] In addition, in the present invention, a more preferable example of the aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is an aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 9 to 20 carbon atoms.

[0106] In addition, in the present invention, a more preferable example of the heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms is a heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 7 to 20 carbon atoms.

[0107] In addition, in the present invention, a more preferable example of the aryl group having a substituted or unsubstituted carbon number of 6 to 30, aliphatic heterocycle condensed therein may be an aryl group having a substituted or unsubstituted carbon number of 7 to 20, aliphatic heterocycle condensed therein.

[0108] In addition, in the present invention, a more preferable example of the heteroaryl group having a substituted or unsubstituted carbon number of 5 to 30, aliphatic heterocycle condensed therein may be a heteroaryl group having a substituted or unsubstituted carbon number of 6 to 20, aliphatic heterocycle condensed therein.

[0109]

[0110] Meanwhile, in the present invention, in the case of 'each of the substituents L1-Y1, each of the substituents adjacent to each other, each of the substituents L2-Y2, and each of the substituents L3-Y3 can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,' this means that a ring can be additionally formed by removing one hydrogen radical from each of the adjacent substituents L1-Y1 and connecting them, and this can be similarly applied to each of the adjacent substituents L2-Y2, each of the substituents L3-Y3.

[0111]

[0112] In the present invention, the heterocyclic compound represented by the above-mentioned [chemical formula 1] is characterized in that a 6-membered ring including X1 and X2 is condensed between one benzene ring of a carbazole structure and a benzene ring including substituents L2-Y2, so that the heterocyclic compound has a core structure of '6-membered benzene ring - 6-membered ring including X1 and X2 - carbazole ring' as a whole, and a substituent represented by the above-mentioned structural formula 1 is bonded to at least one of the aromatic carbon atoms in each of the three benzene rings and the nitrogen atom of the carbazole.

[0113]

[0114] As one embodiment of the present invention, X1 and X2 in the chemical formula 1 may each be S.

[0115] As one embodiment of the present invention, only one or two of the four identical or different substituents L1-Y1, four identical or different substituents L2-Y2, two identical or different substituents L3-Y3, and (L4)m4-Y4 in the chemical formula 1 may be substituents represented by [Structural Formula 1], and more preferably, only one of them may be a substituent represented by Structural Formula 1.

[0116] In the present invention, the linking groups L1 to L8 are more preferably the same as or different from each other, and each independently represent a single bond, or any one linking group selected from a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, and an arylene group having a substituted or unsubstituted aliphatic hydrocarbon ring condensed therewith, and even more preferably, the same as or different from each other, and each independently represent a single bond, or any one linking group selected from a substituted or unsubstituted arylene group having 6 to 14 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 14 carbon atoms, and an arylene group having a substituted or unsubstituted aliphatic hydrocarbon ring condensed therewith.

[0117]

[0118] As an embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 in Chemical Formula 1 may be a compound represented by any one of Chemical Formulas 1-1 to 1-4 below.

[0119] [Chemical Formula 1-1]

[0120]

[0121] [Chemical Formula 1-2]

[0122]

[0123] [Chemical Formula 1-3]

[0124]

[0125] [Chemical Formula 1-4]

[0126]

[0127] In the above chemical formulas 1-1 to 1-4,

[0128] Substituents X1 and X2, Y1 to Y4, R5 to R7, linking groups L1 to L 8,m1 to m8 are the same as defined in chemical formula 1 and structural formula 1.

[0129] As an embodiment of the present invention, the substituents R5 to R7 in the structural formula 1 are the same as or different from each other, and may each independently be any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, and preferably any one selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, and an aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring condensed with 9 to 20 carbon atoms.

[0130] As one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may be substituted with at least one deuterium.

[0131] As one embodiment of the present invention, the connecting groups L5 to L8 in the structural formula 1 are the same as or different from each other, and each can independently be a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

[0132] As a more preferred embodiment of the present invention, the substituents Y1 to Y3 in the chemical formulas 1-1 to 1-4 are the same as or different from each other, are each independently hydrogen or deuterium, and L1 to L3 may each be a single bond.

[0133] As an embodiment of the present invention, L8 in the chemical formula 1-1 may be the same as or different from each other, and may be any one independently selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0134] As one embodiment of the present invention, the linking group L8 in the structural formula 1 may be a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

[0135] As a more specific example of the heterocyclic compound represented by the above chemical formula 1 according to the present invention, it may be any one compound selected from the group represented by Compound 1 to Compound 75 below.

[0136]

[0137] Compound 1 Compound 2 Compound 3

[0138]

[0139] Compound 4 Compound 5 Compound 6

[0140]

[0141] Compound 7 Compound 8 Compound 9

[0142]

[0143] Compound 10 Compound 11 Compound 12

[0144]

[0145] Compound 13 Compound 14 Compound 15

[0146]

[0147] Compound 16 Compound 17 Compound 18

[0148]

[0149] Compound 19 Compound 20 Compound 21

[0150]

[0151] Compound 22 Compound 23 Compound 24

[0152]

[0153] Compound 25 Compound 26 Compound 27

[0154]

[0155] Compound 28 Compound 29 Compound 30

[0156]

[0157] Compound 31 Compound 32 Compound 33

[0158]

[0159] Compound 34 Compound 35 Compound 36

[0160]

[0161] Compound 37 Compound 38 Compound 39

[0162]

[0163] Compound 40 Compound 41 Compound 42

[0164]

[0165] Compound 43 Compound 44 Compound 45

[0166]

[0167] Compound 46 Compound 47 Compound 48

[0168]

[0169] Compound 49 Compound 50 Compound 51

[0170]

[0171] Compound 52 Compound 53 Compound 54

[0172]

[0173] Compound 55 Compound 56 Compound 57

[0174]

[0175] Compound 58 Compound 59 Compound 60

[0176]

[0177] Compound 61 Compound 62 Compound 63

[0178]

[0179] Compound 64 Compound 65 Compound 66

[0180]

[0181] Compound 67 Compound 68 Compound 69

[0182]

[0183] Compound 70 Compound 71 Compound 72

[0184]

[0185] Compound 73 Compound 74 Compound 75

[0186]

[0187] In addition, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode facing the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one heterocyclic compound according to the present invention, and the organic light-emitting device according to the present invention can exhibit low-voltage operation, high efficiency, and long-life characteristics.

[0188] In addition, the light-emitting layer in the organic light-emitting device according to the present invention includes a host and a dopant, and the heterocyclic compound according to the present invention can be used as a phosphorescent host.

[0189] Meanwhile, in the present invention, “(the organic layer) includes at least one organic compound” can be interpreted as “(the organic layer) can include 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.”

[0190] In addition, the organic light-emitting device of the present invention may 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 transport layer, and an electron injection layer in addition to the light-emitting layer.

[0191] As one embodiment of the present invention, the host in the light-emitting layer may be a heterocyclic compound represented by the chemical formula 1, and at least one host compound different from the heterocyclic compound may be mixed and used, or may be used in a laminated manner.

[0192] That is, the host according to the present invention may further include at least one additional host compound different from the compound represented by the above chemical formula 1, so that two or more host compounds may be mixed or laminated and used. In the case of the lamination, a host compound different from the heterocyclic compound may be laminated on the upper or lower portion of the layer including the heterocyclic compound according to the present invention.

[0193] Here, in the case where at least one additional host compound is additionally included in addition to one compound represented by the above chemical formula 1, and two or more host compounds are mixed or laminated and used, more preferably, a compound having an electron acceptor moiety can be used as the additional host, and due to the HOMO / LUMO level of the high hole injection and electron injection barrier resulting from mixing or laminating with the chemical formula 1 having an amine group as an electron donor moiety, the recombination region is limited to the interface of the two hosts, thereby minimizing current loss, etc., it is possible to implement a high-efficiency, long-life organic light-emitting device.

[0194] At this time, the compound having the electron acceptor moiety is a compound having a moiety that has an environment that is easy to receive electrons from the outside, such as an azine compound which is a nitrogen-containing aromatic heterocycle such as pyridine, pyrimidine, triazine, etc. in the molecule, and a compound substituted with a cyano group (-CN), and preferably, may include a compound including a heteroaryl group including 1 to 3 N (nitrogen) in the molecule; or an aryl group including 1 to 3 cyano groups (-CN) in the molecule.

[0195] More specifically, the host in the light-emitting layer of the organic light-emitting device may be used by mixing one or more organic compounds represented by the following chemical formula B in addition to the heterocyclic compound represented by the above chemical formula 1, or the organic compound represented by the following chemical formula B may be used by layering it on the upper or lower part of a layer including the heterocyclic compound represented by the above chemical formula 1.

[0196] [Chemical Formula B]

[0197]

[0198] In the above [chemical formula B],

[0199] X 11 Inland X 13 are identical or different from each other, and each independently represents N or CR 24 However, the above X 11 Inland X 13 At least one of them is N, and the X 11 Inland X 13 CR for middle school 2nd grade and above 24 In each case, CR 24 are the same or different,

[0200] L 21 Inland L 23are the same or different from each other, 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, which is a condensed aliphatic hydrocarbon ring,

[0201] The above m 21 Inland m 23 are identical or different, and are each independently an integer from 1 to 2, provided that when they are 2, each L 21 Inland L 23 are each other Same or different,

[0202] R 21 Inland R 24are the same or different from each other, and each independently represents hydrogen, deuterium, 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms, A cycloalkyl group, a cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, 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 cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted Any one selected from among an arylthio group, 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0203] In the above chemical formula B, 'substitution' in 'substituted or unsubstituted' means a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 30 carbon atoms, a halogenated alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkylheteroaryl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a halogen group having 7 to A cycloalkyl group having a condensed aromatic hydrocarbon ring of 30, a cycloalkyl group having a condensed aromatic heterocycle of 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring of 6 to 30 carbon atoms, an aryl group having a condensed aliphatic hydrocarbon ring of 7 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring of 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic heterocycle of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic heterocycle of 5 to 30 carbon atoms, 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 a carbon number It means being substituted with one or more substituents selected from the group consisting of 6 to 30 arylthionyl groups, and one or more hydrogens in the substituents can be replaced with deuterium.

[0204] As a more preferred embodiment of the present invention, the X in the chemical formula B 11 Inland X 13 are N and R respectively 21 Inland R 23 At least one of them may be a substituted or unsubstituted carbazole group, preferably one or two may be substituted or unsubstituted carbazole groups.

[0205] Meanwhile, in the present invention, the light-emitting layer may use a dopant material in addition to a host. When the light-emitting layer includes a host and a dopant, the content of the dopant may typically be selected in 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.

[0206] In this case, an organometallic compound containing a transition metal may be used as the dopant in the light-emitting layer of the organic light-emitting device.

[0207] In the present invention, the dopant compound included in the light-emitting layer is not a fluorescent dopant material that only transfers to a singlet state using the Förster energy transfer method in the existing Host-Dopant system, but a phosphorescent dopant material of a metal complex including at least one metal selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, Pd, etc. that transfers without distinguishing between singlet and triplet states using the Dexter energy transfer method, and any known dopant material can be used without special limitation as long as it emits light from a triplet exciton.

[0208] Preferably, Ir, Pt and Pd can be selected as metal complexes, and 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, FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP,

[0209] Ir(chpy)3, P0-01(C31H23IrN2O2S2), Ir(ppz)3, Ir(dfppz)3, PtNON, Pt-10, Pt-11, etc., but are not limited thereto.

[0210] In addition, the light-emitting layer may additionally include various hosts and various dopant materials in addition to the dopant and host, and preferably, the dopant in the light-emitting layer of the organic light-emitting device may be used by mixing or laminating one or more types of dopant compounds containing boron, which are different from the organic metal compound containing the transition metal.

[0211] More specifically, the dopant in the light-emitting layer of the organic light-emitting device may be used by mixing one or more polycyclic ring compounds represented by the following chemical formula 2 in addition to the organometallic compound containing the transition metal, or the polycyclic ring compound represented by the above chemical formula 2 may be used by laminating the light-emitting layer on the upper or lower portion of the light-emitting layer containing the organometallic compound.

[0212] [Chemical Formula 2]

[0213]

[0214] In the above [chemical formula 2],

[0215] Above Y 11 and Y 12 are identical or different from each other, and are each independently O, S, NR 11 , CR 12 R 13 , SiR 14 R 15 and GeR 16 R 17 One of the following is selected:

[0216] The above A1 to A3 are the same or different from each other, 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, an aromatic hydrocarbon ring having 8 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring condensed therewith, 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,

[0217] The above substituent R 11 Inland R 17are the same or different from each other, and each independently represents hydrogen, deuterium, 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms, A cycloalkyl group, a cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, 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 cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted Any one selected from among an arylthio group, 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0218] The above substituent R 11 Inland R 17 can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0219] The above R 12 Wow R 13 , R 14 Wow R 15 and R 16 and R 17 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring,

[0220] In the above chemical formula 2, 'substitution' in 'substituted or unsubstituted' means a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 30 carbon atoms, a halogenated alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 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, an alkylheteroaryl group having 3 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, a halogen group having 7 to A cycloalkyl group having a condensed aromatic hydrocarbon ring of 30, a cycloalkyl group having a condensed aromatic heterocycle of 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring of 6 to 30 carbon atoms, an aryl group having a condensed aliphatic hydrocarbon ring of 7 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring of 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic heterocycle of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic heterocycle of 5 to 30 carbon atoms, 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 a carbon number It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 atoms, and one or more hydrogens in the substituents can be replaced with deuterium.

[0221] Here, the polycyclic ring compound represented by the above chemical formula 2 is a boron thermally activated delayed fluorescence emitter, which enables Förster energy transfer from the triplet of the phosphorescence sensitizer to the singlet of the boron thermally activated delayed fluorescence emitter, thereby reducing the number of long-lived triplet excitons involved in the deterioration of the device and improving the lifespan. In addition, since it has a high molar absorption coefficient, it has the advantage of improving efficiency and lifespan due to effects such as an increase in the speed of fluorescence resonance energy transfer from the phosphorescence sensitizer to the emitter and a narrowing of the emission spectrum due to the multi-resonance effect, thereby increasing color purity.

[0222] As a more preferred embodiment of the present invention, A1 to A3 in the above chemical formula 2 are the same as or different from each other, and may each independently be any one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring having 8 to 30 carbon atoms.

[0223]

[0224] Hereinafter, an organic light-emitting device according to the present invention will be described with reference to the drawings.

[0225] FIG. 1 is a drawing illustrating the structure of an organic light-emitting device according to one embodiment of the present invention.

[0226] As illustrated in FIG. 1, an organic light-emitting device according to an embodiment of the present invention is an organic light-emitting device that sequentially includes an anode (20), a hole transport layer (40), a light-emitting layer (50) including a host and a dopant, an electron transport layer (60), and a cathode (80), wherein the anode is a first electrode, the cathode is a second electrode, a hole transport layer is included between the anode and the light-emitting layer, and an electron transport layer is included between the light-emitting layer and the cathode.

[0227] In addition, the organic light-emitting device according to an 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).

[0228] Referring to the above drawing 1, the organic light-emitting device of the present invention and the manufacturing method thereof will be described as follows.

[0229] First, a material for an anode electrode is coated on the upper portion of a substrate (10) to form an anode (20). Here, a substrate used in a typical organic EL device is used as the substrate (10), and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofing is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used as the material for the anode electrode.

[0230] A hole injection layer (30) is formed by vacuum thermal deposition or spin coating of a hole injection layer material on top of the above anode (20) electrode. Next, a hole transport layer (40) is formed by vacuum thermal deposition or spin coating of a hole transport layer material on top of the hole injection layer (30).

[0231] The above hole injection layer material can be used without particular limitation as long as it is commonly used in the art, and 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], HATCN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile], etc. can be used, but is not limited thereto.

[0232] In addition, as a material of the hole transport layer, it is not particularly limited as long as it is commonly used in the art, and for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD), N-[[1,1'-biphenyl]-4-yl]-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine (BCFN) can be used, but is not limited thereto.

[0233] Meanwhile, the present invention can additionally form an electron blocking layer on the hole transport layer. The electron blocking layer is a layer for improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole transport layer through the light emitting layer, and can be formed at an appropriate portion between the light emitting layer and the hole injection layer, preferably, can be formed between the light emitting layer and the hole transport layer, and for example, 6,9-diphenyl-9H-3,9'-bicarbazole (PBCz), N-[[1,1'-biphenyl]-4-yl]-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine (BCFN), 1,3-bis(12-phenylindolo[3,2-a]carbazol-5(12H)-yl)benzene, Any one compound selected from among N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-4-amine, N,N-di([1,1'-biphenyl]-4-yl)-3,9,9-triphenyl-9H-fluoren-2-amine, etc. may be used, but is not limited thereto.

[0234] Next, a light-emitting layer (50) can be laminated on top of the hole transport layer (40) or electron blocking layer using a vacuum deposition method or a spin coating method.

[0235] Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.

[0236] In addition, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably 50 to 2,000 Å.

[0237] The present invention can optionally form a hole blocking layer (not shown) as a thin film on top of the organic light-emitting layer (50) using a vacuum deposition method or a spin coating method.

[0238] The above hole-blocking layer prevents the lifespan and efficiency of the device from decreasing when holes pass through the light-emitting layer and flow into the cathode by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level. At this time, the hole-blocking material used is not particularly limited, but must have an electron transport ability and a higher ionization potential than the light-emitting compound, and as a material used in the hole-blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq, and chemical formulas 1001 to 1007, and mSiTrz may be used, but is not limited thereto.

[0239] BAlq BCP Bphen

[0240]

[0241] TPBI NTAZ BeBq2

[0242]

[0243] OXD-7 Liq

[0244]

[0245] Chemical Formula 1001 Chemical Formula 1002 Chemical Formula 1003

[0246]

[0247] Chemical Formula 1004 Chemical Formula 1005 Chemical Formula 1006

[0248]

[0249] Chemical formula 1007 mSiTrz

[0250]

[0251]

[0252] Meanwhile, an electron transport layer (60) is deposited on the light-emitting layer or hole-blocking layer using a vacuum deposition method or a spin coating method.

[0253] As the above electron transport layer material, a known electron transport material can be used, which has the function of stably transporting electrons injected from an electron injection electrode (cathode). Examples of the known electron transport material include, but are not limited to, materials such as quinoline derivatives, tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives PBD, BMD, and BND.

[0254]

[0255] TAZ BAlq

[0256]

[0257] Compound 201 <Compound 202> BCP

[0258]

[0259]

[0260] In addition, in the organic light-emitting device of the present invention, after forming the electron transport layer, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from a cathode, may be laminated on top of the electron transport layer, and this does not particularly limit the material.

[0261] Any material known as an electron injection layer forming material, such as CsF, NaF, LiF, Li2O, BaO, Liq, etc., can be used as the electron injection layer forming material. The deposition conditions of the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions almost identical to those for forming the hole injection layer.

[0262] The thickness of the electron injection layer may be from about 1 Å to about 100 Å, or from about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0263] In addition, in the present invention, the cathode may use a material having a low work function to facilitate electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or an alloy thereof, aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used, or a transparent cathode using ITO or IZO may be used.

[0264] In addition, the organic light-emitting device of the present invention may additionally include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the light-emitting layer of the present invention is a plurality of light-emitting layers, and the blue light-emitting material, the green light-emitting material, or the red light-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.

[0265] In addition, in the present invention, one or more layers selected from each of the layers may be formed by a single molecule deposition process or a solution process.

[0266] Here, the deposition process means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process means a method of forming a thin film by mixing a material used as a material for forming each layer with a solvent and using a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, or spin coating.

[0267] In addition, the organic light-emitting element of the present invention can be used in any one device selected from a flat panel display device; a flexible display device; a flat panel lighting device of a single color or white color; and a flexible lighting device of a single color or white color; a vehicle display device; and a virtual or augmented reality display device.

[0268]

[0269] Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these embodiments are intended to illustrate the present invention more specifically, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

[0270]

[0271] (Example)

[0272] Synthesis Example 1. Synthesis of [Compound 1]

[0273] Synthesis Example 1-1. Synthesis of A-1

[0274]

[0275] <a-1a> <a-1b> <a-1>

[0276] In a round bottom flask <a-1a> 38.6 g, <a-1b>25 g, Pd[PPh3]42.9 g, K2CO329 g, THF 245 mL, and water 147 mL were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature and extracted using ethyl acetate and water. A small amount of water was removed with MgSO4, and after filtration under reduced pressure, the organic solvent was concentrated and purified using column chromatography. <a-1>(35 g, 83.8%) was obtained.

[0277]

[0278] Synthesis Example 1-2. Synthesis of A-2

[0279]

[0280] <a-1> <a-2>

[0281] In a round bottom flask <a-1>35 g, PPh31.4 g, o-DCB 280 mL were added and refluxed for 24 hours. After the reaction was completed, the organic layer was filtered through Celite and concentrated under reduced pressure and purified using column chromatography. <a-2>(26 g, 82.1%) was obtained.

[0282]

[0283] Synthesis Example 1-3. Synthesis of [Compound 1]

[0284]

[0285] <a-2> <a-3a>[Compound 1]

[0286] In a round bottom flask <a-2> 10 g, <a-3a>16.3 g of sodium tert-butoxide, 6.3 g of Pd2(dba), 30.6 g of P(t-bu)350% in toluene, 0.53 g of toluene, and 80 mL of toluene were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, filtered, washed with methanol, and recrystallized with toluene to obtain [Compound 1]. (15 g, 71.6%)

[0287] MS (MALDI-TOF): m / z 639.15 [M + ]

[0288]

[0289] Synthesis Example 2. Synthesis of [Compound 4]

[0290] Synthesis Example 2-1. Synthesis of B-1

[0291]

[0292] <b-1a> <b-1b> <b-1c> <b-1>

[0293] In a round bottom flask (1) under nitrogen atmosphere <b-1a>Add 45 g, 180 mL of diethyl ether and stir at -78°C. In a round bottom flask (2) under a nitrogen atmosphere. <b-1b>43 g, add 344 mL of diethyl ether and slowly dropwise add 122 mL of 1.6 M n-BuLi at -78 ℃. After stirring for 30 minutes, slowly dropwise add the reaction solution in the round-bottom flask (2) to the round-bottom flask (1). Stir for 2 hours while maintaining the temperature. In the round-bottom flask (3) <b-1c>50 g, add 408 mL of diethyl ether and slowly add 116 mL of 1.6 M n-BuLi at -78 ℃ dropwise. After stirring for 30 minutes, add the reaction solution of the round bottom flask (3) dropwise to the round bottom flask (1). Raise the temperature to room temperature and stir for 16 hours. When the reaction is complete, extract with ethyl acetate and water. Remove a small amount of water with MgSO4, filter under reduced pressure, concentrate under reduced pressure, and separate through column chromatography. <b-1>(35.7 g, 40%)

[0294]

[0295] Synthesis Example 2-2. Synthesis of [Compound 4]

[0296]

[0297] <a-2> <b-1>[Compound 4]

[0298] Used in the above synthesis example 1-3 <a-3a>instead <b-1>Compound 4 was obtained by the same method except that it was synthesized using . (Yield 58.6%)

[0299] MS (MALDI-TOF): m / z 728.26 [M + ]

[0300]

[0301] Synthesis Example 3. Synthesis of [Compound 10]

[0302] Synthesis Example 3-1. Synthesis of C-1

[0303]

[0304] [Compound 1] <c-1>

[0305] Add 15 g of [compound 1] and 270 mL of MC to a round-bottom flask and stir. Dissolve 4.6 g of N-bromosuccineimide in 45 mL of DMF and slowly add it to the round-bottom flask, and stir for 3 hours at room temperature. When the reaction is complete, extract with MC and water. Remove a small amount of water from the obtained organic layer with MgSO4, filter under reduced pressure, and concentrate the organic solvent and use column chromatography to purify. <c-1>was obtained. (16 g, 95%)

[0306]

[0307] Synthesis Example 3-2. Synthesis of [Compound 10]

[0308]

[0309] <c-1> <c-2a>[Compound 10]

[0310] In a round bottom flask <c-1> 16 g, <c-2a>6.8 g, Pd[PPh3]40.5 g, K2CO35.2 g, Toluene 112 mL, EtOH 28 mL, and water 19 mL were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and extracted with ethyl acetate and water. A small amount of water was removed with MgSO4, and after filtration under reduced pressure, the organic solvent was concentrated and column chromatography was used to obtain [Compound 10]. (10 g, 62.7%)

[0311] MS (MALDI-TOF): m / z 715.18 [M + ]

[0312]

[0313] Synthesis Example 4. Synthesis of [Compound 19]

[0314] Synthesis Example 4-1. Synthesis of D-1

[0315]

[0316] <a-2> <d-1a> <d-1>

[0317] Used in the above synthesis example 1-3 <a-3a>instead <d-1a>Synthesized in the same way except that <d-1>was obtained. (Yield 80.1%)

[0318]

[0319] Synthesis Example 4-2. Synthesis of D-2

[0320]

[0321] <d-1> <d-2>

[0322] Instead of [compound 1] used in the above synthesis example 3-1, <d-1>Synthesized in the same way except that <d-2>was obtained. (Yield 87%)

[0323]

[0324] Synthesis Example 4-3. Synthesis of [Compound 19]

[0325]

[0326] <d-3a> <d-2>[Compound 19]

[0327] In a round bottom flask under nitrogen atmosphere <d-2>Add 20 g, 160 mL of THF and stir at -78°C. Slowly add 32.6 mL of 1.6 M n-BuLi dropwise. After stirring for 30 minutes, <d-3a>Dissolve 6.2 g in THF and slowly add dropwise. After that, raise to room temperature and stir for 12 hours. When the reaction is complete, extract with ethyl acetate and water. A small amount of water is removed with MgSO4, and after filtration under reduced pressure, the residue is concentrated under reduced pressure and separated by column chromatography to obtain [Compound 19]. (9 g, 71.9%)

[0328] MS (MALDI-TOF): m / z 639.15 [M + ]

[0329]

[0330] Synthesis Example 5. Synthesis of [Compound 23]

[0331] Synthesis Example 5-1. Synthesis of E-1

[0332]

[0333] <e-1a> <c-2a> <e-1>

[0334] In a round bottom flask <e-1a> 25 g, <c-2a>36.4 g, Pd[PPh3]41.1 g, K2CO349.5 g, Sphos 3.9 g, Toluene 175 mL, EtOH 44 mL, and water 179 mL were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and extracted using ethyl acetate and water. A small amount of water was removed with MgSO4, and after filtration under reduced pressure, the organic solvent was concentrated and purified using column chromatography. <e-1>(27 g, 91.1%) was obtained.

[0335]

[0336] Synthesis Example 5-2. Synthesis of E-2

[0337]

[0338] <a-2> <e-1> <e-2>

[0339] In a round bottom flask <a-2> 24 g, <e-1>15 g, Cs2CO3 59 g, N,N-dimethyl acetamide 120 mL were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and slowly poured into a beaker containing water. The solid obtained by filtration under reduced pressure was washed with methanol. <e-2>(27 g, 83.7%) was obtained.

[0340]

[0341] Synthesis Example 5-3. Synthesis of E-3

[0342]

[0343] <e-2> <e-3>

[0344] Instead of [compound 1] used in the above synthesis example 3-1, <e-2>Synthesized in the same way except that <e-3>was obtained. (Yield 80.7%)

[0345]

[0346] Synthesis Example 5-4. Synthesis of [Compound 23]

[0347]

[0348] <d-3a> <e-3>[Compound 23]

[0349] Used in the above synthesis example 4-3 <d-2>instead <e-3>[Compound 23] was obtained by the same method except that [compound 23] was used. (Yield 79.1%)

[0350] MS (MALDI-TOF): m / z 791.21 [M + ]

[0351]

[0352] Synthesis Example 6. Synthesis of [Compound 42]

[0353] Synthesis Example 6-1. Synthesis of [Compound 42]

[0354]

[0355] <c-1> <f-1a>[Compound 42]

[0356] In a round bottom flask <c-1> 20 g, <f-1a>14.7 g, Pd[PPh3]40.6 g, K2CO36.5 g, Toluene 140 mL, EtOH 35 mL, and water 23 mL were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and extracted with ethyl acetate and water. A small amount of water was removed with MgSO4, and after filtration under reduced pressure, the organic solvent was concentrated and column chromatography was used to obtain [Compound 42]. (16 g, 71.3%)

[0357] MS (MALDI-TOF): m / z 805.19 [M + ]

[0358]

[0359] Synthesis Example 7. Synthesis of [Compound 48]

[0360] Synthesis Example 7-1. Synthesis of G-1

[0361]

[0362] <a-2> <g-1a> <g-1>

[0363] Used in the above synthesis example 1-3 <a-3a>instead <g-1a>Synthesized in the same way except that <g-1>was obtained. (Yield 75.2%)

[0364]

[0365] Synthesis Example 7-2. Synthesis of G-2

[0366]

[0367] <g-1> <g-2>

[0368] Instead of [compound 1] used in the above synthesis example 3-1, <g-1>Synthesized in the same way except that <g-2>was obtained. (Yield 77.4%)

[0369]

[0370] Synthesis Example 7-3. Synthesis of [Compound 48]

[0371]

[0372] <d-3a> <g-2>[Compound 48]

[0373] Used in the above synthesis example 4-3 <d-2>instead <g-2>Compound 48 was obtained by the same method except that it was synthesized using (yield 75%).

[0374] MS (MALDI-TOF): m / z 771.19 [M + ]

[0375]

[0376] Synthesis Example 8. Synthesis of [Compound 54]

[0377] Synthesis Example 8-1. Synthesis of H-1

[0378]

[0379] <a-1a> <h-1a> <h-1>

[0380] Used in the above synthesis example 1-1 <a-1b>instead <h-1a>Synthesized in the same way except that <h-1>was obtained. (Yield 86.4%)

[0381]

[0382] Synthesis Example 8-2. Synthesis of H-2

[0383]

[0384] <h-1> <h-2>

[0385] Used in the above synthesis example 1-2 <a-1>instead <h-1>Synthesized in the same way except that <h-2>was obtained. (Yield 83.3%)

[0386]

[0387] Synthesis Example 8-3. Synthesis of H-3

[0388]

[0389] <h-2> <h-3a> <h-3>

[0390] In a round bottom flask <h-2> 24.6 g, <h-3a>33.9 g, CuI 0.7 g, K3PO4 30 g, dioxane 197 mL, trans-1,2-diaminocyclohexane 16.1 g were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and after the reaction was completed, the organic layer was concentrated under reduced pressure after filtration through Celite and column chromatography was used. <h-3>(35.8 g, 81%) was obtained.

[0391]

[0392] Synthesis Example 8-4. Synthesis of [Compound 54]

[0393]

[0394] <d-3a> <h-3>[Compound 54]

[0395] Used in the above synthesis example 4-3 <d-2>instead <h-3>Compound 54 was obtained by the same method except that it was synthesized using . (Yield 77.2%)

[0396] MS (MALDI-TOF): m / z 804.21 [M + ]

[0397]

[0398] Examples 1 to 8: Manufacturing of organic light-emitting devices

[0399] After patterning the ITO glass to have a light-emitting area of ​​2 mm Х 2 mm, it was cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 Х 10 -6 After making it torr, HATCN (50 Å) is deposited as a hole injection layer on the ITO, BCFN (600 Å) is deposited as a hole transport layer, and PBCz (50 Å) is deposited as an electron blocking layer. As a light-emitting layer, the first host compound and the second host compound according to the present invention and the PBD below as a dopant compound are mixed at 12 wt% of the total amount of the light-emitting layer and deposited (350 Å), and then mSiTrz (50 Å) is deposited as a hole-blocking layer, and mSiTrz: Liq (300 Å) is deposited as an electron injection and transport layer at a ratio of 1:1, and then Liq (10 Å) is deposited sequentially as an electron injection layer, and Al (1000 Å) is deposited as a cathode to manufacture an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0400] [HATCN] [BCFN] [PBCz]

[0401]

[0402] [PBD] [mSiTrz] [Liq]

[0403]

[0404] [ET-1]

[0405]

[0406] Comparative Examples 1 to 6

[0407] Organic light-emitting devices for comparative examples were manufactured and tested in the same manner as in the above-described examples, except that [RH-1] to [RH-6] were used instead of the compounds according to the present invention used as hosts in the device structure of the above-described examples. The luminescence characteristics of the above-described organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 1 below. Here, the structures of [RH-1] to [RH-6] are as follows.

[0408] [RH-1] [RH-2] [RH-3]

[0409]

[0410] [RH-4] [RH-5] [RH-6]

[0411]

[0412] Classification Host (1:1) Driving voltage (V) External quantum efficiency (EQE) Lifespan (T95, hr) Emission color (color) Example 1 Compound 1 ET-14.4 15.7 148 Blue Example 2 Compound 4 ET-14.6 16.1 165 Blue Example 3 Compound 10 ET-14.6 15.8 156 Blue Example 4 Compound 19 ET-14.5 15.5 143 Blue Example 5 Compound 23 ET-14.5 15.9 131 Blue Example 6 Compound 42 ET-14.6 14.9 142 Blue Example 7 Compound 48 ET-14.6 15.0 129 Blue Example 8 Compound 54ET-14.615.1149Blue Comparison Example 1RH-1ET-15.212.399Blue Comparison Example 2RH-2ET-14.910.882Blue Comparison Example 3RH-3ET-15.19.869Blue Comparison Example 4RH-4ET-15.39.265Blue Comparison Example 5RH-5ET-15.49.563Blue Comparison Example 6RH-6ET-14.910.273Blue

[0413] As can be seen in the above [Table 1], it can be seen that a device employing a compound according to the present invention as a host compound of a light-emitting layer in an organic light-emitting device can realize a high-efficiency, long-life organic light-emitting device with excellent external quantum efficiency and lifespan characteristics at a low driving voltage compared to devices (Comparative Examples 1 to 6) employing a compound widely used in the past, which is in contrast to the characteristic structure of the compound according to the present invention.

[0414]

[0415] Examples 9 to 16: Manufacturing of organic light-emitting devices

[0416] The organic light-emitting devices used in Examples 1 to 8 above were manufactured and tested in the same manner, except that the TBD compound below was additionally mixed as a dopant compound according to the present invention at 0.5 wt% of the total amount of the light-emitting layer. 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. Here, the structure of [TBD] is as follows.

[0417] [TBD]

[0418]

[0419]

[0420] Comparative examples 7 to 12

[0421] An organic light-emitting device for comparative example was manufactured in the same manner as the above-described example, except that [RH-1] to [RH-6] were used instead of the compound according to the present invention as a host compound in the device structure of the above-described example, and the luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0422] Classification Host (1:1) Driving voltage (V) External quantum efficiency (EQE) Lifespan (T95, hr) Emission color (color) Example 9 Compound 1 ET-14.1 18.1 198 Blue Example 10 Compound 4 ET-14.3 18.3 203 Blue Example 11 Compound 10 ET-14.3 16.9 186 Blue Example 12 Compound 19 ET-14.2 16.5 165 Blue Example 13 Compound 23 ET-14.2 17.2 159 Blue Example 14 Compound 42 ET-14.3 15.9 168 Blue Example 15 Compound 48 ET-14.3 16.1 150 Blue Example 16 Compound 54ET-14.316.3171 Blue Comparison Example 7RH-1ET-14.813.2109 Blue Comparison Example 8RH-2ET-14.712.0101 Blue Comparison Example 9RH-3ET-15.010.081 Blue Comparison Example 10RH-4ET-15.210.572 Blue Comparison Example 11RH-5ET-15.210.375 Blue Comparison Example 12RH-6ET-14.813.280 Blue

[0423] As shown in Table 2 above, it can be seen that a device employing a compound according to the present invention as a host compound of a light-emitting layer in an organic light-emitting device can realize a high-efficiency, long-life organic light-emitting device with excellent external quantum efficiency and lifespan characteristics at a low driving voltage compared to devices (Comparative Examples 7 to 12) employing a compound widely used in the past that has a characteristic structure of the compound according to the present invention.

[0424]

[0425] Examples 17 to 24: Manufacturing of organic light-emitting devices

[0426] The organic light-emitting devices used in Examples 1 to 8 above were manufactured and tested in the same manner, except that the heterocyclic compound according to the present invention was used alone as a host in the light-emitting layer. The light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 3 below.

[0427]

[0428] Comparative Examples 13 to 18

[0429] Organic light-emitting devices for comparative examples were manufactured and tested in the same manner as in the above-described examples, except that [RH-1] to [RH-6] were used instead of the heterocyclic compound according to the present invention used as a host in the device structure of the above-described examples. The luminescence characteristics of the organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 3 below.

[0430] Classification Host driving voltage (V) External quantum efficiency (EQE) Lifespan (T95, hr) Emission color (color) Example 17 Compound 15.3 14.0 115 Blue Example 18 Compound 45.5 14.5 134 Blue Example 19 Compound 105.5 14.4 129 Blue Example 20 Compound 195.5 14.2 102 Blue Example 21 Compound 235.4 14.3 126 Blue Example 22 Compound 425.5 14.1 106 Blue Example 23 Compound 485.5 13.9 112 Blue Example 24 Compound 545.5 13.8 120 Blue Comparative example 13RH-15.99.268 Blue Comparison Example 14RH-25.98.972 Blue Comparison Example 15RH-36.08.259 Blue Comparison Example 16RH-45.88.162 Blue Comparison Example 17RH-55.98.565 Blue Comparison Example 18RH-65.69.176 Blue

[0431] As shown in Table 3 above, it can be seen that the device employing the host compound of the light-emitting layer in the organic light-emitting device of the present invention can realize a high-efficiency, long-life organic light-emitting device with excellent external quantum efficiency and lifespan characteristics at a low driving voltage compared to the device (Comparative Examples 13 to 18) employing a compound widely used in the past that has a characteristic structure of the compound according to the present invention.

[0432]

[0433] The novel heterocyclic compound according to the present invention, when used as a host material in an organic light-emitting device, has characteristics of lower power consumption, longer lifespan, and higher efficiency compared to existing materials, and thus exhibits improved characteristics when applied to an organic light-emitting device, and thus has high industrial applicability in organic light-emitting devices and related industrial fields. < / d-3a> < / h-2> < / h-3a> < / h-2> < / h-1> < / h-1a> < / a-1a> < / d-3a> < / g-1> < / g-1a> < / a-2> < / c-1> < / c-1> < / d-3a> < / e-2> < / a-2> < / e-1> < / a-2> < / e-1a> < / c-2a> < / e-1a> < / d-3a> < / d-1> < / d-1a> < / a-2> < / c-1> < / c-1> < / a-2> < / b-1c> < / b-1b> < / b-1a> < / a-2> < / a-2> < / a-1> < / a-1a> < / a-1b> < / a-1a>

Claims

1. A heterocyclic compound represented by the following chemical formula 1. [Chemical Formula 1] In the above chemical formula 1, Above X 1 and X 2 are identical or different from each other, and each is independently O or S, The above connector L 1 Inside L 4 are the same or different from each other, and each independently represents 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 an arylene group having a condensed aliphatic hydrocarbon ring having 8 to 24 carbon atoms, The above substituent Y 1 Inland Y 4 are the same as or different from each other, and each independently represents hydrogen, deuterium, 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms, A cycloalkyl group, a cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a condensed aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted Any one selected from among an arylthio group, 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, m 1 is 4, and at this time, each L 1 -Y 1 are identical or different from each other, m 2 is 4, and at this time, each L 2 -Y 2 are identical or different from each other, m 3 is 2, and at this time, each L 3 -Y 3 are identical or different from each other, m 4 is 1 or 2, and the above m 4 If the number is 2, each L 4 are identical or different from each other, Each of the above identical or different substituents L 1 -Y 1 Among the substituents adjacent to each other, each substituent L is identical or different. 2 -Y 2 Among the substituents adjacent to each other, and each substituent L which is identical or different 3 -Y 3 are each linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above four identical or different substituents L 1 -Y 1 , four identical or different substituents L 2 -Y 2 , two identical or different substituents L 3 -Y 3 , and (L 4 )m4-Y 4 At least one of them is a substituent represented by [Structural Formula 1], [Structural formula 1] In the above structural formula 1, The above Z is Si or Ge, The above connector L 5 Inland L 8 are the same or different from each other, and each independently represents 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 an arylene group having a condensed aliphatic hydrocarbon ring having 8 to 24 carbon atoms, The above substituent R 5 Inland R 7 are the same as or different from each other, and each independently represents 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, a substituted or An unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted Any one selected from an 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above m5 to m8 are 1 or 2, and when each of them is 2, each L 5 , each L 6 , each L 7 and each L 8 are identical or different from each other, In the chemical formula 1 and structural formula 1 above, 'substitution' in 'substituted or unsubstituted' means deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 30 carbon atoms, a halogenated alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 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, an alkylheteroaryl group having 3 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 aromatic hydrocarbon rings condensed, a cycloalkyl group having 5 to 30 aromatic heterocycles condensed, a heterocycloalkyl group having 6 to 30 aromatic hydrocarbon rings condensed, an aryl group having 7 to 30 aliphatic hydrocarbon rings condensed, a heteroaryl group having 5 to 30 aliphatic hydrocarbon rings condensed, a substituted or unsubstituted aryl group having 6 to 30 aliphatic heterocycles condensed, a substituted or unsubstituted heteroaryl group having 5 to 30 aliphatic heterocycles condensed, 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 It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium.

2. In paragraph 1, X in the above chemical formula 1 1 and X 2 A heterocyclic compound, each characterized by being S.

3. In paragraph 1, The above heterocyclic compound is a heterocyclic compound characterized in that it is a compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, Substituent X 1 and X 2 , Y 1 Inland Y 4 , R 5 Inland R 7 , connector L 1 Inside L 8, m1 to m8 are the same as defined in chemical formula 1 and structural formula 1 in the first paragraph above.

4. In paragraph 1, Substituent R in the above structural formula 1 5 Inland R 7 A heterocyclic compound characterized in that each of the above is the same as or different from the other, and is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and an aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms.

5. In paragraph 1, The above heterocyclic compound is a heterocyclic compound characterized in that at least one deuterium in the chemical formula 1 is substituted.

6. In paragraph 1, The above connector L 5 Inside L 8 A heterocyclic compound characterized in that each of the above groups is the same or different and each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

7. In paragraph 3, L in the above chemical formula 1-1 8 A heterocyclic compound characterized in that each of the above is the same or different and is independently selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

8. In paragraph 1, Connector L in the above structural formula 1 8 A heterocyclic compound characterized by a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

9. In paragraph 1, A heterocyclic compound characterized in that the compound represented by the above chemical formula 1 is one selected from the group represented by compounds 1 to 75 below. Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 Compound 19 Compound 20 Compound 21 Compound 22 Compound 23 Compound 24 Compound 25 Compound 26 Compound 27 Compound 28 Compound 29 Compound 30 Compound 31 Compound 32 Compound 33 Compound 34 Compound 35 Compound 36 Compound 37 Compound 38 Compound 39 Compound 40 Compound 41 Compound 42 Compound 43 Compound 44 Compound 45 Compound 46 Compound 47 Compound 48 Compound 49 Compound 50 Compound 51 Compound 52 Compound 53 Compound 54 Compound 55 Compound 56 Compound 57 Compound 58 Compound 59 Compound 60 Compound 61 Compound 62 Compound 63 Compound 64 Compound 65 Compound 66 Compound 67 Compound 68 Compound 69 Compound 70 Compound 71 Compound 72 Compound 73 Compound 74 Compound 75 10. First electrode; a second electrode opposite to the first electrode; and A light-emitting layer interposed between the first electrode and the second electrode; An organic light-emitting device, characterized in that the light-emitting layer comprises at least one heterocyclic compound described in any one of claims 1 to 9.

11. In paragraph 10, The above-mentioned light-emitting layer comprises a host and a dopant, An organic light-emitting device characterized in that the above heterocyclic compound is used as a host.

12. In paragraph 11, An organic light-emitting device, characterized in that the host in the light-emitting layer of the organic light-emitting device is used by mixing or layering at least one host compound different from the heterocyclic compound in addition to the heterocyclic compound.

13. In paragraph 10, An organic light-emitting device, characterized in that the dopant in the light-emitting layer of the organic light-emitting device uses an organometallic compound containing a transition metal.

14. In paragraph 13, An organic light-emitting device characterized in that the dopant in the light-emitting layer of the organic light-emitting device is used by mixing at least one polycyclic compound represented by the following chemical formula 2 in addition to the organometallic compound containing the transition metal, or by using the polycyclic compound represented by the above chemical formula 2 in a layered manner on or below a layer containing the organometallic compound: [Chemical formula 2] In the above [chemical formula 2], Above Y 11 and Y 12 are identical or different from each other, and are each independently O, S, NR 11 , CR 12 R 13 , SiR 14 R 15 and GeR 16 R 17 One of the following is selected: A above 1 Inland A 3 are the same as or different from each other, 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, an aromatic hydrocarbon ring formed by condensing substituted or unsubstituted aliphatic hydrocarbon rings having 8 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle formed by condensing aliphatic hydrocarbon rings having 5 to 50 carbon atoms, The above substituent R 11 Inland R 17 are the same as or different from each other, and each independently represents hydrogen, deuterium, 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 cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms, A cycloalkyl group, a cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a condensed aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted Any one selected from among an arylthio group, 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above substituent R 11 Inland R 17 Silver is above A 1 Inland A 3 It can be connected to a ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, Above R 12 Wow R 13 , R 14 Wow R 15 and R 16 And R 17 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring, In the above chemical formula 2, 'substitution' in 'substituted or unsubstituted' means a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 30 carbon atoms, a halogenated alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 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, an alkylheteroaryl group having 3 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 3 to 24 carbon atoms, an alkylheteroaryl group having 3 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkyl group having 7 to 24 carbon atoms. A cycloalkyl group having a condensed aromatic hydrocarbon ring of 30, a cycloalkyl group having a condensed aromatic heterocycle of 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring of 6 to 30 carbon atoms, an aryl group having a condensed aliphatic hydrocarbon ring of 7 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring of 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic heterocycle of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic heterocycle of 5 to 30 carbon atoms, 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 a carbon atom It means being substituted with one or more substituents selected from the group consisting of 6 to 24 arylthionyl groups, and one or more hydrogens in the substituents can be replaced with deuterium.

15. In paragraph 10, The organic light-emitting device is an organic light-emitting device used in any one of a flat panel display device; a flexible display device; a flat panel lighting device of a single color or white color; a flexible lighting device of a single color or white color; a vehicle display device; and a virtual or augmented reality display device.

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