Novel heterocyclic compound and organic light-emitting element including same

Abstract

The present invention relates to a novel aromatic heterocyclic compound capable of being used in an organic light-emitting element, and an organic light-emitting element comprising the same.

Description

Technical Field

[0001] The present invention relates to a novel compound that can be used in an organic light-emitting element, and more specifically, to a novel heterocyclic compound that can be used as a main material of a light-emitting layer in an organic light-emitting element and can achieve element characteristics of low voltage, high efficiency and long life through the compound, and an organic light-emitting element including the heterocyclic compound. Background Art

[0002] Organic light emitting diodes (OLEDs) are displays that utilize the phenomenon of self-luminescence. They not only have a wide viewing angle but are also thinner, lighter, and smaller than liquid crystal displays and have a fast response speed. Therefore, they are expected to be used in full-color displays or lighting.

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. The organic light-emitting element using the organic light-emitting phenomenon generally has a structure including an anode, a cathode and an organic layer therebetween. Here, in most cases, in order to improve the efficiency and stability of the organic light-emitting element, the organic layer is constituted as a multilayer structure composed of different substances from each other, for example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of such an organic light-emitting element, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons re-transition to the ground state. It is known that such an organic light-emitting element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed responsiveness.

[0004] The materials used as the organic layer in the organic light-emitting element can be classified into light-emitting materials and charge transport materials (e.g., hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.) according to their functions. The light-emitting materials can be classified into high-molecular and low-molecular types according to their molecular weights, and can be classified into fluorescent materials from the singlet excited state of electrons and phosphorescent materials from the triplet excited state of electrons according to their light-emitting mechanisms.

[0005] In addition, when only one substance is used as a light-emitting material, the maximum emission wavelength shifts to a longer wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the element decreases due to the luminescence attenuation effect. Therefore, in order to increase the color purity and increase the luminescence efficiency through energy transfer, a host-dopant system can be used as a light-emitting material.

[0006] The principle is that if a small amount of dopant with a smaller energy band gap than the main body forming the light-emitting layer is mixed in the light-emitting layer, the excitons generated from the light-emitting layer are transferred to the dopant and emit light with high efficiency. At this time, the wavelength of the main body moves to the wavelength band of the dopant, so the desired wavelength of light can be obtained according to the type of dopant used.

[0007] Recently, research is being conducted on heterocyclic compounds containing heteroatoms such as nitrogen and oxygen as the main compounds for organic light-emitting elements that utilize phosphorescence in such a light-emitting layer. As a related prior art, the Korean Patent Gazette No. 10-2020-0139834 (2020.12.14) records an organic light-emitting element that includes an aromatic heterocyclic compound with a polycyclic structure as the phosphorescent main body.

[0008] However, despite the manufacture of various forms of compounds for the light-emitting layer of organic light-emitting elements including the above-mentioned prior art, there is still a continuous demand for the development of new compounds that can be applied to organic light-emitting elements and have element characteristics of low voltage driving, high efficiency and long life, as well as organic light-emitting elements including the compounds. Summary of the invention

[0009] Technical issues

[0010] Therefore, the first technical problem to be solved by the present invention is to provide a novel organic compound that can be used as a phosphorescent host material of a light-emitting layer in an organic light-emitting element.

[0011] Furthermore, the second technical problem to be solved by the present invention is to provide an organic light emitting diode (OLED) with low voltage, high efficiency and long life, which comprises the organic compound as a host material in the organic light emitting diode.

[0012] Technical Solution

[0013] In order to achieve the above technical problem, the present invention provides an aromatic heterocyclic compound represented by the following chemical formula A.

[0014] [Chemical formula A][Structural formula Q]

[0015]

[0016] In the chemical formula A and the structural formula Q,

[0017] Ar1 to Ar3 are identical to or different from each other, and are independently selected from any one of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, and at least one of Ar1 to Ar3 is represented by the structural formula Q;

[0018] In the case where Ar1 or Ar3 is represented by the structural formula Q, two adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N) and Ar2 in the chemical formula A,

[0019] In the case where Ar2 is represented by the structural formula Q, three adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N), Ar1 and Ar3 in the chemical formula A,

[0020] The R1 to R 10The same or different from each other, are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms condensed with an aromatic heterocyclic ring, substituted or unsubstituted heterocycloalkyl having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0021] R1 to R 10 At least one of the substituents is selected from any one of the following structural formulas H and I,

[0022]

[0023] In the structural formula H and the structural formula I,

[0024] L1 and L2 are the same as or different from each other, and are independently selected from any one of a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring,

[0025] The m is an integer from 0 to 4. When m is 2 or more, the linking groups L1 are the same or different from each other.

[0026] The n is an integer from 0 to 4. When n is 2 or more, each linking group L2 is the same or different from each other.

[0027] X1 to X6 in the structural formula I are the same or different from each other and are independently N or CR 13 , and at least one of X1 to X6 is N,

[0028] In the X1 to X6, multiple CR 13 In the case of 13 Same or different,

[0029] The R 11 To R 13 The same or different from each other, are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms condensed with an aromatic heterocyclic ring, substituted or unsubstituted heterocycloalkyl having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0030] In the structural formula I, the X1 to X6 include a plurality of CR 13 In the case of multiple adjacent R 13 can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0031] In the structural formula Q, R1 to R 10 can be connected to adjacent groups to form an additional alicyclic or aromatic monocyclic or polycyclic ring,

[0032] The term "substituted" in "substituted or unsubstituted" in the chemical formula A, the structural formula Q, the structural formula H and the structural formula I means that the alkyl group is substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxyl, nitro, alkyl having 1 to 30 carbon atoms, haloalkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, alkylaryl having 7 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroaralkyl having 3 to 30 carbon atoms, alkylheteroaryl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, The present invention further comprises a cycloalkyl group having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, a cycloalkyl group having 5 to 30 carbon atoms condensed with an aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms condensed with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms condensed with an aliphatic heterocycle, an amino group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and an arylsulfinyl group having 6 to 30 carbon atoms, and one or more hydrogen atoms in the substituent group may be substituted by deuterium.

[0033] Technical Effects

[0034] When the heterocyclic compound represented by the chemical formula A according to the present invention is used as a phosphorescent host material of a light-emitting layer in an organic light-emitting element, an organic light-emitting element can be provided that can achieve lower voltage, higher efficiency and longer life than organic light-emitting elements according to the prior art. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 is a schematic diagram of an organic light emitting element according to a specific example of the present invention. DETAILED DESCRIPTION

[0036] In the drawings of the present invention, the size or dimensions of the structures are enlarged or reduced compared to the actual size for the clarity of the present invention, and the well-known structures are omitted for highlighting the characteristic structures, so the present invention is not limited to the drawings.

[0037] Furthermore, the size and thickness of each structure shown in the drawings are arbitrarily shown for the convenience of explanation, and the present invention is not limited to the contents shown in the drawings, and the thickness is enlarged in order to clearly indicate multiple layers and regions in the drawings. Furthermore, in the drawings, the thickness of some layers and regions is exaggerated for the convenience of explanation. When it is mentioned that a layer, film, region, plate, etc. is located "on" other parts, it includes not only the case of being located "immediately above" other parts, but also the case of having another part in the middle.

[0038] Furthermore, in the entire specification, when it is mentioned that a certain part "includes" a certain constituent element, in the absence of a special contrary description, other constituent elements are not excluded, but other constituent elements may also be included. Furthermore, in the entire specification, "located on..." means located above or below the object part, and does not necessarily mean located on the upper side based on the direction of gravity.

[0039] The present invention provides a heterocyclic compound represented by the following chemical formula A.

[0040]

[0041] In the chemical formula A and the structural formula Q,

[0042] Ar1 to Ar3 are identical to or different from each other, and are independently selected from any one of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, and at least one of Ar1 to Ar3 is represented by the structural formula Q;

[0043] In the case where Ar1 or Ar3 is represented by the structural formula Q, two adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N) and Ar2 in the chemical formula A,

[0044] In the case where Ar2 is represented by the structural formula Q, three adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N), Ar1 and Ar3 in the chemical formula A,

[0045] The R1 to R 10 The same or different from each other, are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms condensed with an aromatic heterocyclic ring, substituted or unsubstituted heterocycloalkyl having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0046] R1 to R 10 At least one of the substituents is selected from any one of the following structural formulas H and I,

[0047]

[0048] In the structural formula H and the structural formula I,

[0049] L1 and L2 are the same as or different from each other, and are independently selected from any one of a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring,

[0050] The m is an integer from 0 to 4. When m is 2 or more, the linking groups L1 are the same or different from each other.

[0051] The n is an integer from 0 to 4. When n is 2 or more, each linking group L2 is the same or different from each other.

[0052] X1 to X6 in the structural formula I are the same or different from each other and are independently N or CR 13 , and at least one of X1 to X6 is N,

[0053] In the X1 to X6, multiple CR 13 In the case of 13 Same or different,

[0054] The R 11 To R 13The same or different from each other, are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms condensed with an aromatic heterocyclic ring, substituted or unsubstituted heterocycloalkyl having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0055] In the structural formula I, the X1 to X6 include a plurality of CR 13 In the case of multiple adjacent R 13 can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0056] In the structural formula Q, R1 to R 10 can be connected to adjacent groups to form an additional alicyclic or aromatic monocyclic or polycyclic ring,

[0057] The term "substituted" in "substituted or unsubstituted" in the chemical formula A, the structural formula Q, the structural formula H and the structural formula I means that the alkyl group is substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxyl, nitro, alkyl having 1 to 30 carbon atoms, haloalkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, alkylaryl having 7 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroaralkyl having 3 to 30 carbon atoms, alkylheteroaryl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, The present invention further comprises a cycloalkyl group having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, a cycloalkyl group having 5 to 30 carbon atoms condensed with an aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms condensed with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms condensed with an aliphatic heterocycle, an amino group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and an arylsulfinyl group having 6 to 30 carbon atoms, and one or more hydrogen atoms in the substituent group may be substituted by deuterium.

[0058] In addition, if the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention is considered, the range of carbon atoms of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms respectively represents the total number of carbon atoms constituting the alkyl part or aryl part when the part substituted by the substituent is considered to be unsubstituted. For example, a phenyl group substituted with a butyl group at the para position should be regarded as an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0059] The aryl group as a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and when a substituent is present in the aryl group, it can be fused with adjacent substituents to additionally form a ring, and the aryl group may include an organic radical obtained by removing one hydrogen from an aromatic hydrocarbon ring formed by condensing two aromatic hydrocarbon rings with each other.

[0060] Specific examples of the aryl group include phenyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, peryl, The invention also includes aromatic free radical groups such as benzo[9,10]phenanthryl, tetraphenyl, fluoranthene, benzo[9,10]phenanthryl, etc., but is not limited thereto, and may also include organic free radicals obtained by removing one hydrogen from an aromatic hydrocarbon ring formed by condensing two aromatic hydrocarbon rings, such as an aromatic hydrocarbon ring condensed with a fluorene ring and a phenylene ring, or an aromatic hydrocarbon ring condensed with a fluorene ring and a phenanthrene ring.

[0061] Furthermore, one or more hydrogen atoms in the aryl group may be substituted by a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH(R), -N(R')(R"), R' and R" are independently an alkyl group having 1 to 10 carbon atoms, in which case it is referred to as "alkylamino"), an amidine group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphate group, an alkyl group having 1 to 24 carbon atoms, a haloalkyl 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 aralkyl 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 heteroaralkyl group having 3 to 24 carbon atoms, or an alkylheteroaryl group having 3 to 24 carbon atoms.

[0062] In the present invention, the aromatic hydrocarbon ring may represent an aromatic ring composed of carbon and hydrogen, and the aliphatic hydrocarbon ring may represent a hydrocarbon ring composed of carbon and hydrogen and not belonging to an aromatic hydrocarbon ring. In this case, preferably, the aliphatic hydrocarbon ring may be a ring in which at least 30% of the carbon atoms forming the ring are sp 3 The hydrocarbon ring is a hydrocarbon ring formed by bonding with an orbital structure and including 0 to 3 double bonds and / or triple bonds in the ring. More preferably, the aliphatic hydrocarbon ring may be a hydrocarbon ring in which at least 50% of the carbon atoms forming the ring are bonded by sp 3 A hydrocarbon ring that is bonded to the ring by the orbitals and includes 0 to 2 double and / or triple bonds within the ring.

[0063] Furthermore, the aromatic group condensed with the aliphatic hydrocarbon ring in the present invention may represent a cyclic substituent having non-aromaticity as a whole, which is formed by condensing two adjacent carbon atoms in the aliphatic hydrocarbon ring and two connected carbon atoms other than a carbon atom that becomes an organic radical by removing one hydrogen from the carbon atom forming the ring in the aromatic group, and sharing a double bond. Specific examples include, but are not limited to, tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthryl, tetrahydroanthracenyl, octahydrobenzo[9,10]phenanthryl, and the like.

[0064] The heteroaryl group used as a substituent in the compound of the present invention may represent an aromatic group of a ring aromatic system having 2 to 24 carbon atoms, including one, two or three heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aromatic ring, and the remaining ring atoms are carbon, and the ring may be fused to form a ring. In addition, one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituents as in the case of the aryl group.

[0065] Specific examples of the heteroaryl group include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, carbolyl, acenaphthoquinoxalinyl, indenoquinazolinyl, indenoisoquinolinyl, indenoquinolinyl, pyridoindolyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, Quinolyl, indolyl, carbazolyl, benzoxazole group, benzimidazole group, benzothiazolyl, benzocarbazolyl, benzofuranyl, benzothiophenyl, benzoselenophene, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophene, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenoxazinyl, phenothiazinyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzoselenophene, indolecarbazolyl and the like, but are not limited thereto.

[0066] Furthermore, in the present invention, the aromatic heterocycle may represent that one or more aromatic carbons in the aromatic hydrocarbon ring are replaced by heteroatoms. Preferably, 1 to 3 aromatic carbons in the aromatic hydrocarbon in the aromatic heterocycle may be replaced by one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

[0067] Furthermore, as a substituent in a structure in which a heteroaryl group is substituted instead of an aryl group in an aryl group condensed with an aliphatic hydrocarbon ring, specific examples include, but are not limited to, tetrahydroindolyl, tetrahydrobenzofuranyl, tetrahydrobenzothienyl, tetrahydrocarbazolyl, tetrahydrodibenzofuranyl, tetrahydrobenzothienyl, tetrahydroquinolyl, and tetrahydroquinoxalinyl.

[0068] Furthermore, in the present invention, the aromatic heterocycle may represent that one or more aromatic carbons in the aromatic hydrocarbon ring are replaced by heteroatoms. Preferably, 1 to 3 aromatic carbons in the aromatic hydrocarbon in the aromatic heterocycle may be replaced by one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

[0069] In the present invention, the "condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring" may refer to a condensed ring in which two adjacent carbon atoms in the aromatic hydrocarbon ring and two adjacent carbon atoms in the aliphatic hydrocarbon ring are condensed in a manner that they share each other. Examples thereof include a tetralin ring and a dihydroindene ring that are condensed by sharing two adjacent carbon atoms in a benzene ring and a cyclohexane ring.

[0070] Furthermore, in the present invention, the "condensed ring of an aromatic heterocycle and an aliphatic hydrocarbon ring" may refer to a condensed ring in which two adjacent carbon atoms in the aromatic heterocycle and two adjacent carbon atoms in the aliphatic hydrocarbon ring are condensed in a manner that they share each other, and an example thereof may be a hexahydrodibenzofuran ring in which a benzofuran ring and a cyclohexane ring are condensed in such a manner that they share each other's two adjacent carbon atoms.

[0071] The alkyl group used as a substituent in the present invention is a substituent in which one hydrogen is removed from an alkane, and includes a straight chain type and a branched chain type structure. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., and one or more hydrogen atoms in the alkyl group may be substituted by the same substituent as in the case of the aryl group.

[0072] The "ring" in the cycloalkyl, cycloalkoxy and the like used as substituents in the compounds of the present invention may represent a substituent that can form a monocyclic or polycyclic structure of a saturated hydrocarbon in the alkyl or alkoxy group. For example, specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl and the like, but are not limited thereto. One or more hydrogen atoms in the cycloalkyl group may be substituted by the same substituents as in the case of the aryl group, and the same may also be applied to the cycloalkoxy group.

[0073] Furthermore, in the present invention, the heterocycloalkyl group may represent that one or more carbon atoms in the ring of the substituent constituting the cycloalkane structure are substituted by heteroatoms, and preferably, 1 to 3 carbon atoms may be substituted by one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te.

[0074] Furthermore, the cycloalkyl group condensed with the aromatic hydrocarbon ring or aromatic heterocycle may represent a cyclic substituent group which is non-aromatic as a whole and is formed by condensing two adjacent carbon atoms in the aromatic hydrocarbon ring or aromatic heterocycle and two adjacent carbon atoms other than a carbon atom which becomes an organic radical by removing one hydrogen from the carbon atoms constituting the ring in the cycloalkyl group and sharing a double bond. Specific examples include, but are not limited to, tetrahydronaphthyl, tetrahydrophenanthrenyl, tetrahydroquinolyl, tetrahydroquinoxalinyl, cyclopentabenzofuranyl and the like.

[0075] Furthermore, the heterocycloalkyl group condensed with the aromatic hydrocarbon ring may represent a cycloalkyl group condensed with the aromatic hydrocarbon ring in which one or more carbon atoms in the cycloalkyl ring are replaced by heteroatoms. Preferably, it may be a substituent group having a structure in which 1 to 3 carbon atoms in the cycloalkyl ring are replaced by one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te. Specific examples include hexahydrodibenzofuranyl, hexahydrocarbazolyl, hexahydrodibenzothienyl, dihydrobenzodioxinyl, etc., but are not limited thereto, and the group exhibits non-aromaticity as a whole.

[0076] Furthermore, the aryl or heteroaryl group condensed with an aliphatic heterocyclic ring is used as a substituent in a structure in which an aliphatic heterocyclic ring replaces an aliphatic hydrocarbon ring in the aryl or heteroaryl group condensed with the aliphatic hydrocarbon ring. Specific examples include chromanyl, dihydropyrazinopyridinyl, dihydrobenzothiopyranyl, dihydrobenzodioxinyl, dihydrothiopyridopyrimidinyl, dihydropyrazinopyrimidinyl and the like, but are not limited thereto, and the whole exhibits non-aromaticity.

[0077] Furthermore, the aliphatic heterocycle may represent that one or more carbon atoms in the aliphatic hydrocarbon ring are replaced by heteroatoms. Preferably, 1 to 3 carbon atoms in the aliphatic hydrocarbon in the aliphatic heterocycle may be replaced by one or more heteroatoms selected from N, O and S.

[0078] The alkoxy group as a substituent used in the compound of the present invention is a substituent having an oxygen atom bonded to the terminal of an alkyl group or a cycloalkyl group. Specific examples thereof include methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantyloxy, dicyclopentyloxy, bornyloxy, isobornyloxy and the like, but are not limited thereto. One or more hydrogen atoms in the alkoxy group may be substituted by the same substituents as in the case of the aryl group.

[0079] Specific examples of the aralkyl group as a substituent used in the compound of the present invention include benzyl, phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc., but are not limited thereto. One or more hydrogen atoms in the aralkyl group may be substituted with the same substituent as in the case of the aryl group.

[0080] Specific examples of the alkylaryl group used as a substituent in the compound of the present invention include tolyl, xylyl, dimethylnaphthyl, tert-butylphenyl, tert-butylnaphthyl, tert-butylphenanthrenyl, etc., but are not limited to these. One or more hydrogen atoms in the alkylaryl group may be substituted by the same substituent as in the case of the aryl group.

[0081] Specific examples of the silyl group used as a substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, dibenzhydrylsilyl, distyrylsilyl, naphthyldiphenylsilyl, dibenzothienyldiphenylsilyl, dibenzofuranyldiphenylsilyl, bisdibenzothienylphenylsilyl, bisdibenzofuranylphenylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, fluorenyldiphenylsilyl and the like, but are not limited thereto. One or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

[0082] Furthermore, in the present invention, alkenyl refers to an alkyl substituent including one carbon-carbon double bond consisting of two carbon atoms, and alkynyl refers to an alkyl substituent including one carbon-carbon triple bond consisting of two carbon atoms.

[0083] Furthermore, the alkylene group used in the present invention is an organic free radical derived by removing two hydrogen atoms from an alkane molecule of a saturated hydrocarbon in a straight or branched form. Specific examples of the alkylene group include methylene, ethylene, propylene, isopropylene, isobutylene, sec-butylene, tert-butylene, pentylene, isopentylene, hexylene, etc., but are not limited to these. One or more hydrogen atoms in the alkylene group may be substituted by the same substituents as in the case of the aryl group.

[0084] Furthermore, the diarylamino group in the present invention represents an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom, and the diheteroarylamino group in the present invention represents an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom, and the aryl (heteroaryl)amino group represents an amine group in which the aryl group and the heteroaryl group are respectively bonded to a nitrogen atom.

[0085] In addition, as a more preferred example, the "substituted" in the "substituted or unsubstituted" in the chemical formula A may refer to being substituted by one or more substituents selected from the group consisting of: deuterium, cyano, halogen, hydroxyl, nitro, alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkynyl having 2 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, heteroalkyl having 1 to 12 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 20 carbon atoms, alkylaryl having 7 to 20 carbon atoms, heteroaryl having 2 to 18 carbon atoms, heteroaralkyl having 3 to 18 carbon atoms, The substituent may be an alkyl heteroaryl group having 3 to 18 carbon atoms, a cycloalkyl group having 9 to 20 carbon atoms condensed with an aromatic hydrocarbon ring, a cycloalkyl group having 7 to 20 carbon atoms condensed with an aromatic heterocyclic ring, a heterocycloalkyl group having 9 to 20 carbon atoms condensed with an aromatic hydrocarbon ring, an aryl group having 9 to 20 carbon atoms condensed with an aliphatic hydrocarbon ring, a heteroaryl group having 7 to 20 carbon atoms condensed with an aliphatic hydrocarbon ring, an alkoxy group having 1 to 12 carbon atoms, an amine group having 1 to 18 carbon atoms, a silyl group having 1 to 18 carbon atoms, a germanium group having 1 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylsulfinyl group having 6 to 18 carbon atoms, and one or more hydrogen in each of the substituents may be substituted by deuterium.

[0086] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms and condensed with an aromatic hydrocarbon ring may be a substituted or unsubstituted cycloalkyl group having 9 to 20 carbon atoms and condensed with an aromatic hydrocarbon ring.

[0087] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms and condensed with an aromatic heterocycle may be a substituted or unsubstituted cycloalkyl group having 7 to 20 carbon atoms and condensed with an aromatic heterocycle.

[0088] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms and condensed with an aromatic hydrocarbon ring may be a substituted or unsubstituted heterocycloalkyl group having 9 to 20 carbon atoms and condensed with an aromatic hydrocarbon ring.

[0089] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring may be a substituted or unsubstituted aryl group having 9 to 20 carbon atoms and condensed with an aliphatic hydrocarbon ring.

[0090] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring may be a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms and condensed with an aliphatic hydrocarbon ring.

[0091] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms and condensed with an aliphatic heterocycle may be a substituted or unsubstituted aryl group having 7 to 20 carbon atoms and condensed with an aliphatic heterocycle.

[0092] Furthermore, in the present invention, as a more preferred example, the substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic heterocycle may be a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms and condensed with an aliphatic heterocycle.

[0093] In addition, in the present invention, the "R1 to R 10 In the case of "being able to connect with adjacent groups to form an additional alicyclic or aromatic monocyclic or polycyclic ring", this means being able to be selected from the group consisting of R1 to R 10 Two substituents in the ring are additionally formed by removing a hydrogen radical and connecting them.

[0094] In the present invention, the technical feature of the heterocyclic compound represented by the chemical formula A is that, with the nitrogen atom as the center, the Ar1 ring to the Ar3 ring are bonded to the nitrogen atom, the Ar2 ring is connected to the Ar1 ring and the Ar3 ring, and at least one of the Ar1 to Ar3 is a phenanthrene ring represented by the structural formula Q, and R1 to R 10 At least one of the substituents is selected from any one of the structural formulas H and I.

[0095]

[0096] As an embodiment of the present invention, the remaining rings in Ar1 to Ar3 of the chemical formula A that are not of the structural formula Q may be substituted or unsubstituted aromatic hydrocarbon rings having 6 to 12 carbon atoms.

[0097] As an embodiment of the present invention, the compound represented by the chemical formula A may include at least one deuterium.

[0098] As an embodiment of the present invention, the Ar 1 or Ar 3 It can be represented by the structural formula Q.

[0099] As an embodiment of the present invention, the Ar 2 It can be represented by the structural formula Q.

[0100] As an embodiment of the present invention, R1 to R 10 Only one of R5 to R8 may be a substituent represented by the structural formula H. Preferably, only one of R5 to R8 may be a substituent represented by the structural formula H.

[0101] As an embodiment of the present invention, R1 to R 10 Only one of R5 to R8 may be a substituent represented by the structural formula (I), preferably, only one of R5 to R8 may be a substituent represented by the structural formula (I).

[0102] As an embodiment of the present invention, the ring including X1 to X6 in the structural formula I can be any one ring selected from a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring and a substituted or unsubstituted triazine ring.

[0103] As an embodiment of the present invention, in the structural formula H and the structural formula I, the linking groups L1 and L2 may be the same as or different from each other, and may be independently a single bond or an arylene group having 6 to 14 carbon atoms.

[0104] Furthermore, as specific examples of the heterocyclic compound represented by the chemical formula A of the present invention, it may be any one compound selected from the following 1 to 486, but is not limited thereto.

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] Furthermore, the present invention can provide a heterocyclic compound represented by the following [Chemical Formula A'].

[0138]

[0139] In the [Chemical Formula A'] and the Structural Formula Q,

[0140] Ar1 to Ar3 are identical to or different from each other, and are independently selected from any one of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, and at least one of Ar1 to Ar3 is represented by the structural formula Q;

[0141] In the case where Ar1 or Ar3 is represented by the structural formula Q, two adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N) and Ar2 in the chemical formula A,

[0142] In the case where Ar2 is represented by the structural formula Q, three adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N), Ar1 and Ar3 in the chemical formula A,

[0143] The R1 to R 10The same or different from each other, are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms condensed with an aromatic heterocyclic ring, substituted or unsubstituted heterocycloalkyl having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted at least one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 60 carbon atoms, a substituted or unsubstituted silyl group having 0 to 60 carbon atoms, a germanium group having 0 to 60 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0144] R1 to R 10 At least one of is not hydrogen or deuterium,

[0145] In the structural formula Q, R1 to R 10 may be connected to adjacent groups to form an alicyclic or aromatic monocyclic or polycyclic ring,

[0146] The term "substituted" in "substituted or unsubstituted" in the above [Chemical Formula A'] and the above Structural Formula Q means that the alkyl group is substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxyl, nitro, alkyl having 1 to 30 carbon atoms, haloalkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, alkaryl having 7 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroaralkyl having 3 to 30 carbon atoms, alkylheteroaryl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, The present invention further comprises a cycloalkyl group having a carbon number of 5 to 30 and condensed with an aromatic hydrocarbon ring, a cycloalkyl group having a carbon number of 5 to 30 and condensed with an aromatic heterocycle, a heterocycloalkyl group having a carbon number of 6 to 30 and condensed with an aromatic hydrocarbon ring, an aryl group having a carbon number of 7 to 30 and condensed with an aliphatic hydrocarbon ring, a heteroaryl group having a carbon number of 5 to 30 and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having a carbon number of 6 to 30 and condensed with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having a carbon number of 5 to 30 and condensed with an aliphatic heterocycle, an amine group having a carbon number of 1 to 40, a silyl group having a carbon number of 1 to 40, a germanium group having a carbon number of 1 to 40, an aryloxy group having a carbon number of 6 to 30, and an arylsulfinyl group having a carbon number of 6 to 30, and one or more hydrogen in the substituent group may be substituted by deuterium.

[0147] In the present invention, the technical feature of the heterocyclic compound represented by the [chemical formula A'] is that, with the nitrogen atom as the center, the Ar1 ring to the Ar3 ring are bonded to the nitrogen atom, the Ar2 ring is connected to the Ar1 ring and the Ar3 ring, and at least one of Ar1 to Ar3 is a phenanthrene ring represented by the structural formula Q, and R1 to R 10 At least one of the substituents is not hydrogen or deuterium.

[0148] Furthermore, the present invention provides an organic light-emitting element, characterized in that it may include: a first electrode; a second electrode, opposite to the first electrode; and an organic layer, sandwiched between the first electrode and the second electrode, wherein the organic layer includes at least one heterocyclic compound represented by the chemical formula A according to the present invention. The organic light-emitting element according to the present invention can exhibit the characteristics of low voltage driving, high efficiency and long life.

[0149] In addition, in the present invention, "(the organic layer) contains more than one organic compound" can be interpreted as "(the organic layer) can contain one organic compound belonging to the category of the present invention or two or more different compounds belonging to the category of the organic compound."

[0150] At this time, the organic layer in the organic light-emitting element of the present invention may additionally include, in addition to the light-emitting layer, at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, an electron transport layer, an electron injection layer, a functional layer having both an electron injection function and an electron transport function, and a hole blocking layer, and at least one of the organic layers may include one or more heterocyclic compounds represented by the chemical formula A.

[0151] As a more preferred embodiment of the present invention, the present invention can provide an organic light-emitting element, which includes: a first electrode; a second electrode, opposite to the first electrode; and an organic layer, sandwiched between the first electrode and the second electrode, wherein the organic layer includes: a light-emitting layer, including a host and a dopant; and at least one of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport functions, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer, the host includes more than one of the heterocyclic compounds according to the present invention. In this case, the heterocyclic compound represented by the chemical formula A according to the present invention can be used as a red phosphorescent host.

[0152] In addition, in the present invention, not only the host but also the dopant material can be used in the light-emitting layer. In the case where the light-emitting layer includes the host and the dopant, the content of the dopant can be selected within 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.

[0153] In the present invention, as a dopant compound included in the light-emitting layer, the dopant may include a phosphorescent dopant substance comprising a metal complex of one or more metals selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, and Pd that utilizes a Dexter Energy transfer method that does not distinguish between singlet and triplet states for transfer, rather than a fluorescent dopant substance that is included in an existing host-dopant system and transfers only to a singlet state using a Forster energy transfer method. As long as light is emitted from triplet excitons, known dopant substances can be used without particular limitation.

[0154] Preferably, as the phosphorescent dopant, an organic metal compound containing a transition metal can be used. In this case, Ir, Pt, Pd, etc. can be selected as the transition metal complex. Specific examples include Ir(ppy)3, Ir(ppy)2acac, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(mppy)3, Ir(piq3, 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, Ir(chpy)3, P0-01(C 31 H 23 IrN2O2S2), Ir(ppz)3, Ir(dfppz)3, PtNON, Pt-10, Pt-

[0155] 11, etc., but not limited to these. More preferably, PtOEP, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(piq)3, Ir(piq)2acac, Ir(pq)2acac, etc., which are used as red phosphorescent dopants, can be used, but not limited to these.

[0156] As a more preferred embodiment of the present invention, in the present invention, the organic layer sandwiched between the first electrode and the second electrode may include a light-emitting layer, in which the host may be mixed or stacked with one or more host compounds different from the compound represented by the chemical formula A. That is, the host according to the present invention may include one or more additional host compounds different from the compound represented by the chemical formula A in addition to the compound represented by the chemical formula A, so that two or more host compounds may be mixed or stacked for use.

[0157] Here, in addition to a compound represented by the chemical formula A, one or more additional host compounds are additionally included. Therefore, when two or more host compounds are mixed or stacked for use, it is more preferred that a compound having an electron acceptor portion be used as the additional host. By means of the HOMO / LUMO level of high hole injection and electron injection barriers generated by mixing or stacking with the chemical formula A having an amine group as an electron donor portion, the recombination region is limited to the interface of the two hosts, thereby realizing a high-efficiency, long-life organic light-emitting element due to the advantage of minimizing current loss, etc.

[0158] At this time, the compound having the electron acceptor part can be a compound having a part in the molecule that has an environment that is easy to receive electrons from the outside, such as an azine compound such as pyridine, pyrimidine, triazine, etc., and a compound substituted with a cyano group (-CN). Preferably, it can include a heteroaryl compound containing 1 to 3 N (nitrogen) in the molecule or an aromatic compound containing 1 to 3 cyano groups (-CN) in the molecule.

[0159] Furthermore, in addition to the dopant and the host, the light-emitting layer may additionally include a plurality of hosts and a plurality of dopant substances. Preferably, the dopant in the light-emitting layer of the organic light-emitting element may be mixed or stacked with one or more boron-containing dopant compounds different from each other other than the organic metal compound containing the transition metal.

[0160] Hereinafter, an organic light emitting element according to the present invention will be described with reference to the accompanying drawings.

[0161] Figure 1 FIG. 1 is a diagram showing the structure of an organic light emitting element according to an embodiment of the present invention.

[0162] As mentioned above Figure 1 As shown, the organic light-emitting element according to an embodiment of the present invention is an organic light-emitting element 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, which is equivalent to an organic light-emitting element that uses the anode as the first electrode, the cathode as the second electrode, includes a hole transport layer between the anode and the light-emitting layer, and includes an electron transport layer between the light-emitting layer and the cathode.

[0163] Furthermore, the organic light emitting element according to the embodiment of the present invention may include a hole injection layer 30 between the anode 20 and the hole transport layer 40 , and may include an electron injection layer 70 between the electron transport layer 60 and the cathode 80 .

[0164] Refer to the above Figure 1 , the organic light emitting element and the method for manufacturing the same of the present invention are described as follows.

[0165] First, an anode (positive electrode) electrode material is coated on the upper part of the substrate 10 to form the anode 20. The substrate 10 is generally a substrate used in an organic electroluminescent (EL) element, preferably an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, easy handling and waterproofness. In addition, as the anode electrode material, transparent and excellently conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. are used.

[0166] The hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the anode 20. Then, the hole transport layer 40 is formed by vacuum thermal deposition or spin coating of a hole transport layer material on the hole injection layer 30.

[0167] The hole injection layer material can be used without particular limitation as long as it is a material commonly used in the art, for example, 4,4',4"-tris(2-naphthylphenyl-phenylamino)triphenylamine (2-TNATA: 4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD: N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), N,N'-diphenyl-N,N'-bis(3- N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD: N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD: N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), etc. However, the present invention is not limited thereto.

[0168] Furthermore, the material of the hole transport layer can be used without particular limitation as long as it is a material commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (a-NPD) can be used. However, the present invention is not necessarily limited thereto.

[0169] In addition, the present invention may additionally form an electron blocking layer on the upper portion of the hole transport layer. The electron blocking layer is a layer that improves the life and efficiency of the element by preventing electrons injected from the electron injection layer from passing through the light-emitting layer into the hole transport layer, and may be formed in a suitable portion between the light-emitting layer and the hole injection layer, preferably, between the light-emitting layer and the hole transport layer.

[0170] Next, the light emitting layer 50 may be stacked on the upper portion of the hole transport layer 40 or the electron blocking layer by a vacuum deposition method or a spin coating method.

[0171] Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting these are as described above.

[0172] Furthermore, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably to

[0173] In the present invention, a hole blocking layer (not shown) may be selectively formed as a thin film on the upper portion of the organic light emitting layer 50 by a vacuum deposition method or a spin coating method.

[0174] When holes flow into the cathode through the light-emitting layer, the life and efficiency of the element are reduced in the hole blocking layer. Therefore, by using a substance with a very low highest occupied molecular orbital (HOMO: Highest Occupied Molecular Orbital) level, this problem can be prevented. At this time, the hole blocking substance used is not particularly displayed, but it is necessary to have an electron transport ability and an ionization potential higher than that of the light-emitting compound. As a substance used in the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq and any one of Chemical Formulas 1001 to 1007 can be used, but it is not limited thereto.

[0175]

[0176]

[0177] In addition, the electron transport layer 60 is deposited on the light emitting layer or the hole blocking layer by a vacuum deposition method or a spin coating method.

[0178] In addition, in the present invention, as the material of the electron transport layer, a known electron transport material that plays a role in stably transporting electrons injected from an electron injection electrode (Cathode) can be used. As an example of a known electron transport material, a quinoline derivative can be used, and in particular, materials such as tris(8-hydroxyquinoline)aluminum (Alq3), Liq, TAZ, BAlq, bis(10-hydroxybenzo[h]quinoline)beryllium (beryllium bis(benzoquinolin-10-olate: Bebq2), compound 201, compound 202, BCP, PBD, BMD, BND, etc., which are oxadiazole derivatives, can be used, but it is not limited thereto.

[0179]

[0180] Furthermore, after forming the electron transport layer, the organic light emitting element of the present invention may stack an electron injection layer EIL on the electron transport layer as a material having the function of facilitating electron injection from the cathode, and the material thereof is not particularly limited.

[0181] The electron injection layer can be formed using any material known as a material for forming an electron injection layer, such as CsF, NaF, LiF, Li2O, BaO, etc. Although the deposition conditions of the electron injection layer vary depending on the compound used, they can generally be selected from a range of conditions that are almost the same as those for forming a hole injection layer.

[0182] The thickness of the electron injection layer may be about to about about to about When the thickness of the electron injection layer satisfies the above-mentioned range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

[0183] Furthermore, in the present invention, the cathode can use a material with a small work function to easily inject electrons. Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys such as aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, or a transmissive cathode using ITO or IZO can be used.

[0184] Furthermore, in the present invention, one or more layers selected from the various layers may be formed by a single molecule deposition process or a solution process.

[0185] Here, the deposition process refers to a method of forming a thin film by evaporating a substance used as a material for forming the various layers by heating or the like under a vacuum or low pressure state, and the solution process refers to a method of forming a thin film by mixing a substance used as a material for forming the various layers with a solvent and subjecting it to a method such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, spin coating, or the like.

[0186] Furthermore, the organic light-emitting element in the present invention can be used in any device selected from a flat panel display device; a flexible display device; a monochrome or white flat panel lighting device; a monochrome or white flexible lighting device; a vehicle display device, and a virtual or augmented reality display device.

[0187] Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these embodiments are only used to describe the present invention in more detail, and the scope of the present invention is not limited thereto, which is obvious to those with basic knowledge in the art.

[0188] (Example)

[0189] Synthesis Example 1. Synthesis of [Compound 161]

[0190] Synthesis Example 1-1. Synthesis of A-1

[0191]

[0192] In the reactor, 200 g <a-1a> 、110.5g <a-1b>, 12.6 g of tetrakis(triphenylphosphine)palladium(0), 150.6 g of potassium carbonate, 800 mL of toluene, 800 mL of ethanol, and 600 mL of water, and heated to 80°C. After 16 hours, the mixture was cooled to room temperature, and the solid generated during the reaction was filtered. Monochlorobenzene was added and heated, and the dissolved solution was filtered through silica gel, and then concentrated under reduced pressure and recrystallized to obtain <a-1>(129g, 62.3%).

[0193] Synthesis Example 1-2. Synthesis of A-2

[0194]

[0195] In a reactor purged with nitrogen, 57.2 g of potassium tert-butoxide and 645 mL of tetrahydrofuran were added and stirred. The mixture was cooled to -20°C and 174.6 g of (methoxymethyl)triphenylphosphonium chloride was added. After 30 minutes, 129 g of <a-1>and 645 mL of tetrahydrofuran. After 2 hours, the temperature was raised to room temperature, and then water and ethyl acetate were added and the layers were separated. The organic layer was concentrated under reduced pressure and separated by silica gel column chromatography to obtain <a-2>(138g, 99.6%).

[0196] Synthesis Example 1-3. Synthesis of A-3

[0197]

[0198] In the reactor, add 142g <a-2>and 1700 mL of dichloromethane, and 14.2 mL of Eaton's Reagent was added dropwise. After 2 hours, the reaction solution was concentrated under reduced pressure and recrystallized to obtain <a-3>(100g, 76.4%).

[0199] Synthesis Example 1-4. Synthesis of [Compound 161]

[0200]

[0201] In a nitrogen-purged reactor, 5.5 g <a-3> 、4.66g <a-4a>, 0.15 g of di(tri-tert-butylphosphine)palladium(0), 2.81 g of sodium tert-butoxide, and 55 mL of toluene were added and heated to 110°C. After 4 hours, the mixture was cooled to room temperature, and then water and ethyl acetate were added and the layers were separated. The organic layer was concentrated under reduced pressure and separated by silica gel column chromatography to obtain [Compound 161] (2.5 g, 25.3%).

[0202] MS (MALDI-TOF): m / z 674.24 [M + ]

[0203] Synthesis Example 2. Synthesis of [Compound 80]

[0204] Synthesis Example 2-1. Synthesis of B-1

[0205]

[0206] In addition to using <b-1a>Instead of the one used in the above-mentioned Synthesis Example 1-1 <a-1a>In addition, the same method was used to synthesize <b-1>(Yield 62.3%).

[0207] Synthesis Example 2-2. Synthesis of B-2

[0208]

[0209] In addition to using <b-1>Instead of the one used in the above Synthesis Example 1-2 <a-1>In addition, the same method was used to synthesize <b-2>(Yield 99.6%).

[0210] Synthesis Example 2-3. Synthesis of B-3

[0211]

[0212] In addition to using <b-2>Instead of the one used in the above-mentioned Synthesis Example 1-3 <a-2>In addition, the same method was used to synthesize <b-3>(Yield 76.4%).

[0213] Synthesis Example 2-4. Synthesis of [Compound 80]

[0214]

[0215] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 80] (yield 46.6%).

[0216] MS (MALDI-TOF): m / z 674.24 [M + ]

[0217] Synthesis Example 3. Synthesis of [Compound 106]

[0218] Synthesis Example 3-1. Synthesis of [Compound 106]

[0219]

[0220] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <c-1a>replace <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 106] (yield 36.2%).

[0221] MS (MALDI-TOF): m / z 674.24 [M + ]

[0222] Synthesis Example 4. Synthesis of [Compound 32]

[0223] Synthesis Example 4-1. Synthesis of [Compound 32]

[0224]

[0225] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <d-1a>replace <a-4a>The same method was used to synthesize the compound 32 except for the above (yield: 37.2%).

[0226] MS (MALDI-TOF): m / z 674.24 [M + ]

[0227] Synthesis Example 5. Synthesis of [Compound 7]

[0228] Synthesis Example 5-1. Synthesis of E-1

[0229]

[0230] In addition to using <b-1a>Instead of the one used in the above-mentioned Synthesis Example 1-1 <a-1a>,use <e-1a>replace <a-1b>In addition, the same method was used to synthesize <e-1>(Yield 92.1%).

[0231] Synthesis Example 5-2. Synthesis of E-2

[0232]

[0233] In addition to using <e-1>Instead of the one used in the above Synthesis Example 1-2 <a-1>In addition, the same method was used to synthesize <e-2>(Yield 82.8%).

[0234] Synthesis Example 5-3. Synthesis of E-3

[0235]

[0236] In addition to using <e-2>Instead of the one used in the above-mentioned Synthesis Example 1-3 <a-2>In addition, the same method was used to synthesize <e-3>(Yield 90%).

[0237] Synthesis Example 5-4. Synthesis of [Compound 7]

[0238]

[0239] In addition to using <e-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <e-4a>replace <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 7] (yield 56.9%).

[0240] MS (MALDI-TOF): m / z 508.19 [M + ]

[0241] Synthesis Example 6. Synthesis of [Compound 113]

[0242] Synthesis Example 6-1. Synthesis of [Compound 113]

[0243]

[0244] In addition to using <d-1a>Instead of the one used in the above synthesis examples 1-4 <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 113] (yield 60.8%).

[0245] MS (MALDI-TOF): m / z 674.24 [M + ]

[0246] Synthesis Example 7. Synthesis of [Compound 141]

[0247] Synthesis Example 7-1. Synthesis of [Compound 141]

[0248]

[0249] In addition to using <g-1a>Instead of the one used in the above synthesis examples 1-4 <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 141] (yield 52.2%).

[0250] MS (MALDI-TOF): m / z 674.24 [M + ]

[0251] Synthesis Example 8. Synthesis of [Compound 477]

[0252] Synthesis Example 8-1. Synthesis of H-1

[0253]

[0254] In a nitrogen-purged reactor, 50 g <b-1a>, 62.5g aluminum chloride, 1000mL dichloromethane, cooled to 0°C, and then 85.8g <h-1a>After 5 minutes, the temperature was raised to room temperature, and then a saturated aqueous solution of sodium bicarbonate was added and the layers were separated. The organic layer was concentrated under reduced pressure, toluene was added and heated, and the dissolved solution was filtered through silica gel, and then concentrated under reduced pressure and recrystallized to obtain <h-1>(28.9 g, 34.2%).

[0255] Synthesis Example 8-2. Synthesis of H-2

[0256]

[0257] In addition to using <h-1>Instead of the one used in the above-mentioned Synthesis Example 1-1 <a-1a>In addition, the same method was used to synthesize <h-2>(Yield 61%).

[0258] Synthesis Example 8-3. Synthesis of H-3

[0259]

[0260] In addition to using <h-2>Instead of the one used in the above Synthesis Example 1-2 <a-1>In addition, the same method was used to synthesize <h-3>(Yield 97.7%).

[0261] Synthesis Example 8-4. Synthesis of H-4

[0262]

[0263] In addition to using <h-3>Instead of the one used in the above-mentioned Synthesis Example 1-3 <a-2>In addition, the same method was used to synthesize <h-4>(Yield 80.9%).

[0264] Synthesis Example 8-5. Synthesis of [Compound 477]

[0265]

[0266] In addition to using <h-4>Instead of the one used in the above synthesis examples 1-4 <a-3>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 477] (yield 35.8%).

[0267] MS (MALDI-TOF): m / z 895.45 [M + ]

[0268] Synthesis Example 9. Synthesis of [Compound 49]

[0269] Synthesis Example 9-1. Synthesis of [Compound 49]

[0270]

[0271] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <i-1a>replace <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 49] (yield 60.3%).

[0272] MS (MALDI-TOF): m / z 714.27 [M + ]

[0273] Synthesis Example 10. Synthesis of [Compound 111]

[0274] Synthesis Example 10-1. Synthesis of [Compound 111]

[0275]

[0276] In addition to using <j-1a>Instead of the one used in the above synthesis examples 1-4 <a-4a>The same method was used to synthesize other compounds to obtain [Compound 111] (yield 56.7%).

[0277] MS (MALDI-TOF): m / z 674.24 [M + ]

[0278] Synthesis Example 11. Synthesis of [Compound 81]

[0279] Synthesis Example 11-1. Synthesis of [Compound 81]

[0280]

[0281] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <k-1a>replace <a-4a>The same method was used to synthesize other compounds to obtain [Compound 81] (yield 56.3%).

[0282] MS (MALDI-TOF): m / z 700.29 [M + ]

[0283] Synthesis Example 12. Synthesis of [Compound 47]

[0284] Synthesis Example 12-1. Synthesis of [Compound 47]

[0285]

[0286] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <l-1a>replace <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 47] (yield 55.8%).

[0287] MS (MALDI-TOF): m / z 714.27 [M + ]

[0288] Synthesis Example 13. Synthesis of [Compound 243]

[0289] Synthesis Example 13-1. Synthesis of [Compound 243]

[0290]

[0291] In addition to using <m-1a>Instead of the one used in the above synthesis examples 1-4 <a-4a>The synthesis was carried out in the same manner except for the above, thereby obtaining [Compound 243] (yield 54.5%).

[0292] MS (MALDI-TOF): m / z 740.32 [M + ]

[0293] Synthesis Example 14. Synthesis of [Compound 21]

[0294] Synthesis Example 14-1. Synthesis of [Compound 21]

[0295]

[0296] In addition to using <b-3>Instead of the one used in the above synthesis examples 1-4 <a-3>,use <n-1a>replace <a-4a>The same method was used to synthesize the compound 21 except for the above (yield: 60%).

[0297] MS (MALDI-TOF): m / z 674.24 [M + ]

[0298] Synthesis Example 15. Synthesis of [Compound 420]

[0299] Synthesis Example 15-1. Synthesis of O-1

[0300]

[0301] In a nitrogen-purged reactor, 7 g <e-3> 、6.62g <o-1a>, 0.21g of palladium (II) acetate, 9.88g of potassium phosphate, 0.99g of SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl), 70mL of 1,4-dioxane, and heated to 100°C. After 4 hours, it was cooled to room temperature, and then toluene was added to the solid obtained after filtration and heated. The dissolved solution was filtered through silica gel, and then concentrated under reduced pressure and recrystallized to obtain <o-1>(6g, 68.9%).

[0302] Synthesis Example 15-2. Synthesis of [Compound 420]

[0303]

[0304] In a nitrogen-purged reactor, 6.14 g <o-1> 、4.84g <o-2a>, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 3.63 g of potassium carbonate, 25 mL of toluene, 18 mL of ethanol, and 18 mL of water, and the temperature was raised to 80° C. After 4 hours, the mixture was cooled to room temperature, and then dichlorobenzene was added to the solid obtained after filtration and heated. The dissolved solution was filtered through silica gel, and then concentrated under reduced pressure and recrystallized to obtain [Compound 420] (3 g, 34.5%).

[0305] MS (MALDI-TOF): m / z 662.21 [M + ]

[0306] Synthesis Example 16. Synthesis of [Compound 416]

[0307] Synthesis Example 16-1. Synthesis of P-1

[0308]

[0309] In addition to using <b-3>Instead of the one used in the above Synthesis Example 15-1 <e-3>In addition, the same method was used to synthesize <p-1>(Yield 65.1%).

[0310] Synthesis Example 16-2. Synthesis of [Compound 416]

[0311]

[0312] In addition to using <p-1>Instead of the one used in Synthesis Example 15-2 <o-1>,use <p-2a>replace <o-2a>The same method was used to synthesize the compound 416 except for the above (yield: 64.7%).

[0313] MS (MALDI-TOF): m / z 572.20 [M + ]

[0314] Examples 1 to 23: Manufacturing of organic light-emitting elements

[0315] The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm and then cleaned. The ITO glass was installed in a vacuum chamber and the base pressure was set to 1 × 10 -7 Then, [HATCN] of the following structure is formed on the ITO. The hole injection layer is formed into a film, and [NPD] is used as The main compound prepared by the present invention and one of [ET-RH] or [HT-RH] were mixed to a weight ratio of 5:5 and then formed into a film together with a dopant [RD] (5 wt%). As the light-emitting layer, the following sequence is used: [ET]: Liq = 1:1 The film is formed as an electron transport layer by the method of Liq A film is formed as an electron injection layer, and Al The film was formed as a cathode to produce an organic light emitting element. The light emission characteristics of the organic light emitting element were measured at 0.4 mA, and the measurement results are shown in the following [Table 1].

[0316]

[0317] Comparative Examples 1 to 5

[0318] The organic light-emitting elements used in the comparative examples were manufactured and tested in the same manner except that the following [RH-1] to [RH-3] were used instead of the compound according to the present invention used as the host in the element structure of the above example, and the light-emitting characteristics of the organic light-emitting elements were measured at 0.4 mA. The measurement results are shown in the following [Table 1]. Here, the structures of [RH-1] to [RH-3] are as follows:

[0319]

[0320] [Table 1]

[0321]

[0322]

[0323] As shown in [Table 1], the heterocyclic compound according to the present invention exhibits uniformly good properties of low voltage drive, high efficiency and long life compared with Comparative Examples 1 to 5 according to the prior art, and therefore has high application potential as an organic light-emitting element. < / o-1> < / e-3> < / a-3> < / a-1a>

Claims

1. A heterocyclic compound, characterized in that It is represented by the following chemical formula A: In the chemical formula A and the structural formula Q, Ar1 to Ar3 are the same as or different from each other and are independently selected from any one of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle having 5 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, and at least one of Ar1 to Ar3 is represented by the structural formula Q; In the case where Ar1 or Ar3 is represented by the structural formula Q, two adjacent substituents among R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N) and Ar2 in the chemical formula A. In the case where Ar2 is represented by the structural formula Q, the three adjacent substituents in R1 to R4 of the structural formula Q are single bonds respectively bonded to the nitrogen atom (N), Ar1 and Ar3 in the chemical formula A. The R1 to R 10 The same or different radicals are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms condensed with an aromatic heterocycle, substituted or unsubstituted heterocycloalkyl groups having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms ... a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amino 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, R1 to R 10 At least one of the substituents is selected from any one of the following structural formulas H and I, In the structural formula H and the structural formula I, L1 and L2 are the same as or different from each other and are independently selected from any one of a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 50 carbon atoms condensed with an aliphatic hydrocarbon ring, The m is an integer from 0 to 4. When m is 2 or greater, the linking groups L1 are the same as or different from each other. The n is an integer from 0 to 4. When n is 2 or more, the linking groups L2 are the same or different from each other. X1 to X6 in the structural formula I are the same or different from each other and are independently N or CR 13 , and at least one of X1 to X6 is N, The X1 to X6 include multiple CR 13 In the case of each CR 13 Same or different, The R 11 to R 13 The same or different radicals are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms condensed with an aromatic heterocycle, substituted or unsubstituted heterocycloalkyl groups having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms ... a substituted or unsubstituted aryl group having 8 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted any one of a substituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amino group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, In the structural formula I, the X1 to X6 include multiple CR 13 In the case of multiple adjacent R 13 can be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, In the structural formula Q, R1 to R 10 can be connected to adjacent groups to form an additional alicyclic or aromatic monocyclic or polycyclic ring, The term "substituted" in "substituted or unsubstituted" in Formula A, Formula Q, Formula H and Formula I means that the group is substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 30 carbon atoms, haloalkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, alkaryl having 7 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroaralkyl having 3 to 30 carbon atoms, alkylheteroaryl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, a cycloalkyl group having 7 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, a cycloalkyl group having 5 to 30 carbon atoms condensed with an aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms condensed with an aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms condensed with an aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms condensed with an aliphatic heterocycle, an amino group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and an arylsulfinyl group having 6 to 30 carbon atoms, wherein one or more hydrogen atoms in the substituents may be substituted by deuterium.

2. The heterocyclic compound according to claim 1, characterized in that The remaining rings among Ar1 to Ar3 in the chemical formula A that are not of the structural formula Q are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 12 carbon atoms.

3. The heterocyclic compound according to claim 1, characterized in that The compound represented by the chemical formula A includes at least one deuterium.

4. The heterocyclic compound according to claim 1, characterized in that The Ar 1 or Ar 3 Represented by the structural formula Q.

5. The heterocyclic compound according to claim 1, characterized in that The Ar 2 Represented by the structural formula Q.

6. The heterocyclic compound according to claim 1, characterized in that Only one of R5 to R8 in the structural formula Q is a substituent represented by the structural formula H.

7. The heterocyclic compound according to claim 1, characterized in that Only one of R5 to R8 in the structural formula Q is a substituent represented by the structural formula I.

8. The heterocyclic compound according to claim 1, characterized in that The ring including X1 to X6 in the structural formula I is any one ring selected from a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring and a substituted or unsubstituted triazine ring.

9. The heterocyclic compound according to claim 1, characterized in that The compound represented by the chemical formula A is any one compound selected from the group represented by 1 to 486 below:

10. An organic light-emitting element, characterized in that: include: a first electrode; a second electrode, facing the first electrode; as well as an organic layer, sandwiched between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer comprising a host and a dopant, The host includes at least one heterocyclic compound according to any one of claims 1 to 9.

11. The organic light emitting element according to claim 10, wherein In addition to the light-emitting layer, the organic layer further includes at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport functions, an electron blocking layer, an electron transport layer, an electron injection layer, a functional layer having both electron injection and electron transport functions, and a hole blocking layer.

12. The organic light emitting element according to claim 10, wherein: The host in the light-emitting layer of the organic light-emitting element is used by mixing or stacking one or more host compounds other than the heterocyclic compound.

13. The organic light emitting element according to claim 10, wherein: As a dopant in the light-emitting layer of the organic light-emitting element, an organometallic compound containing a transition metal is used.

14. The organic light emitting element according to claim 13, wherein: The dopant in the light-emitting layer of the organic light-emitting element is a mixture or stacking of one or more boron-containing dopant compounds other than the organometallic compound containing the transition metal and different from the organometallic compound.

15. The organic light emitting element according to claim 10, wherein The heterocyclic compound used for the host is used as a red phosphorescent host.

16. The organic light emitting element according to claim 10, wherein: The organic light-emitting element is used in any one device selected from a flat panel display device; a flexible display device; a monochrome or white flat panel lighting device; a monochrome or white flexible lighting device; a vehicle display device and a virtual or augmented reality display device.

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