Novel heterocyclic compounds and organic light-emitting devices containing the same

Abstract

The present invention relates to a pyrene heterocyclic compound that can be used in an organic light-emitting device and an organic light-emitting device including the same, and more particularly to a compound represented by [Chemical Formula A] or [Chemical Formula B] and an organic light-emitting device including the same, wherein [Chemical Formula A] and [Chemical Formula B] are the same as those described in the detailed description of the invention.

Description

Technical Field

[0001] The present invention relates to a novel heterocyclic compound that can be used in an organic light-emitting device. More specifically, the present invention relates to a novel heterocyclic compound that can be used as a host material for a light-emitting layer in an organic light-emitting device, thereby realizing high luminous efficiency and long device lifetime characteristics, and an organic light-emitting device containing the same.

Background Art

[0002] An organic light-emitting diode (OLED) is a display that utilizes the self-luminous phenomenon, has a large viewing angle, can be made thinner, lighter, and shorter than a liquid crystal display, and has advantages such as a fast response speed, and is expected to be applied to full-color displays or lighting.

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using an organic substance. An organic light-emitting device that utilizes the organic light-emitting phenomenon usually has a structure including an anode, a cathode, and an organic layer interposed therebetween. Here, the organic layer often has a multilayer structure composed of different substances in order to improve the efficiency and stability of the organic light-emitting device. For example, it may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in such a structure of the organic light-emitting device, holes are injected into the organic layer at the anode and electrons are injected into the organic layer at the cathode. When the injected holes and electrons combine, excitons are generated, and light is emitted when these excitons fall back to the ground state again. Such an organic light-emitting device is known to have characteristics such as self-luminance, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed responsiveness.

[0004] In an organic light-emitting device, the materials used as organic layers can be classified, according to their functions, into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. The light-emitting materials can be classified, according to their molecular weights, into high molecular weight types and low molecular weight types, and can be classified, according to their light-emitting mechanisms, into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons.

[0005] On the other hand, when only one substance is used as the light-emitting material, problems such as the maximum emission wavelength shifting to a longer wavelength due to intermolecular interaction, the color purity decreasing, or the efficiency of the device decreasing due to the emission attenuation effect occur. Therefore, in order to increase the color purity and the emission efficiency by energy transfer, a host-dopant system can be used as the light-emitting material.

[0006] The principle is that when a small amount of a dopant with an energy band gap smaller than that of the host forming the light-emitting layer is mixed into the light-emitting layer, the excitons generated from the light-emitting layer are transported to the dopant to emit highly efficient light. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

[0007] Recently, research has been conducted on heterocyclic compounds as host compounds in such light-emitting layers. As related prior art, Korean Patent Publication No. 10-2017-0116843 (October 20, 2017) discloses a compound having a structure in which a nitrogen-containing heterocycle is condensed with a benzofluorene ring, and an organic light-emitting device including the same. Also, Korean Patent Publication No. 10-2017-0055743 (May 22, 2017) discloses a compound in which an aryl substituent or a heteroaryl substituent is bonded to a condensed fluorene ring containing heteroatoms such as oxygen, nitrogen, and sulfur, and an organic light-emitting device including them.

[0008] However, despite the production of various forms of compounds for use in the light-emitting layer of organic light-emitting devices, including these prior arts, there is still a continuing need for the development of novel compounds that are applicable for use in organic light-emitting devices and have the properties of stability, high efficiency, and long lifespan, as well as organic light-emitting devices containing the same.

Summary of the Invention

Problems to be Solved by the Invention

[0009] Therefore, an object of the present invention is to provide a novel heterocyclic compound that can be used as a host material for the light-emitting layer in an organic light-emitting device.

[0010] Another object of the present invention is to provide an organic light-emitting diode (OLED) having high luminous efficiency and long lifespan characteristics by applying the heterocyclic compound to the host material in an organic light-emitting device.

Means for Solving the Problems

[0011] To achieve the above object, the present invention provides a heterocyclic compound represented by the following [Chemical Formula A] or [Chemical Formula B].

[0012] [Chemical Formula A] JPEG0007710025000001.jpg64152

[0013] [Chemical Formula B] JPEG0007710025000002.jpg84152

[0014] In the above [Chemical Formula A] and [Chemical Formula B], A1, A2, E, and F may each be the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms. Two adjacent carbon atoms in the aromatic ring of A1 and two adjacent carbon atoms in the aromatic ring of A2 each form a fused ring by forming a 5-membered ring with the carbon atom to which the substituents R1 and R2 are attached. The linking groups L1 to L4 may be the same as or different from each other, and each is independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. M is any one selected from N-R3, CR4R5, O, and S. M' is any one selected from N-R6, CR7R8, O, and S. The substituents R1 to R8, R 11 ~R 15 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. R1 and R2 may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring. s1 to s4 may be the same as or different from each other, and each is independently an integer of 1 to 3. When each of these is 2 or more, the linking groups L1 to L4 may be the same as or different from each other. x, y, z, and w may be the same as or different from each other, and each is independently an integer of 0 or 1. In Chemical Formula A, x + y + z = 1 or x + y + z = 2 is satisfied. In Chemical Formula B, x + y + z + w = 1 or x + y + z + w = 2 is satisfied. In the Chemical Formula A, two adjacent carbon atoms in the A2 ring are bonded to the * of the Structural Formula Q1 to form a fused ring. In the chemical formula B, two adjacent carbon atoms in the A1 ring are bonded to the * in the structural formula Q2 to form a condensed ring, and two adjacent carbon atoms in the A2 ring are bonded to the * in the structural formula Q1 to form a condensed ring. Ar1 to Ar4 may be the same as or different from each other, and are independently represented by the following [Structural Formula C]. [Structural Formula C] JPEG0007710025000003.jpg4970R in the structural formula C 21 ~R 30 may be the same as or different from each other, and are independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. The R 21 ~R 30 Any of them is a single bond connecting to the linking groups L1 to L4. In the above [Chemical Formula A], [Chemical Formula B] and [Structural Formula C], the "substitution" in the "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheteroarylamino group having 2 to 24 carbon atoms, aryl(heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms, and arylthionyl group having 6 to 24 carbon atoms.

Advantages of the Invention

[0015] When the novel heterocyclic compound according to the present invention is used as a host material in an organic light-emitting device, an organic light-emitting device can be provided which exhibits more improved efficiency and longer lifespan characteristics compared to the organic light-emitting devices according to the prior art.

Brief Description of the Drawings

[0016]

Figure 1

Embodiments for Carrying Out the Invention

[0017] Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimensions of the structure are shown enlarged or reduced compared to the actual ones for the sake of clarity of the present invention, and known configurations are omitted from the illustration so that the characteristic configurations appear, and thus it is not limited to the drawings.

[0018] In addition, the sizes and thicknesses of the components shown in the drawings are arbitrarily shown for convenience of explanation. Therefore, the present invention is not necessarily limited to the drawings, and the thicknesses are enlarged in the drawings to clearly represent a plurality of layers and regions. In the drawings, for convenience of explanation, the thicknesses of some layers and regions are exaggerated. When a part such as a layer, a film, a region, or a plate is "on" another part, this includes not only the case where it is directly "above" the other part but also the case where another part is interposed therebetween.

[0019] In addition, throughout the specification, when a certain part "includes" a certain component, this means that, unless otherwise stated to the contrary, it does not exclude other components but can further include other components. Also, throughout the specification, "on" means being located above or below the target part, and does not necessarily mean being located on the upper side with reference to the direction of gravity.

[0020] The present invention provides a heterocyclic compound represented by the following [Chemical Formula A] or [Chemical Formula B].

[0021] [Chemical Formula A] JPEG0007710025000004.jpg64143

[0022] [Chemical Formula B] JPEG0007710025000005.jpg86143

[0023] In the above [Chemical Formula A] and [Chemical Formula B], A1, A2, E, and F may be the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms. Two adjacent carbon atoms in the aromatic ring of A1 and two adjacent carbon atoms in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with the carbon atoms to which the substituents R1 and R2 are attached. The linking groups L1 to L4 may be the same as or different from each other, and each is independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, M is any one selected from N-R3, CR4R5, O, and S, M' is any one selected from N-R6, CR7R8, O, and S, The substituents R1 to R8, R 11 ~R 15 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group, R1 and R2 may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, s1 to s4 may be the same as or different from each other, and each is independently an integer of 1 to 3. When each of these is 2 or more, the linking groups L1 to L4 may be the same as or different from each other, x, y, z, and w may be the same as or different from each other, and each is independently an integer of 0 or 1, In Chemical Formula A, x + y + z = 1 or x + y + z = 2 is satisfied, In Chemical Formula B, x + y + z + w = 1 or x + y + z + w = 2 is satisfied, In the Chemical Formula A, two adjacent carbon atoms in the A2 ring are bonded to the * of the Structural Formula Q1 to form a condensed ring, In the Chemical Formula B, two adjacent carbon atoms in the A1 ring are bonded to the * of the Structural Formula Q2 to form a condensed ring, and two adjacent carbon atoms in the A2 ring are bonded to the * of the Structural Formula Q1 to form a condensed ring, Each of Ar1 to Ar4 may be the same as or different from one another, and are independently represented by the following [Structural Formula C]: [Structural Formula C] JPEG0007710025000006.jpg4973R in the Structural Formula C 21 ~R 30 may be the same as or different from one another, and are independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. Among R 21 ~R 30 any one of them is a single bond connecting to the linking groups L1 to L4. In the [Chemical Formula A], [Chemical Formula B] and [Structural Formula C], the "substituted" in the "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl(heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms.

[0024] On one hand, considering the ranges of the alkyl group 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, the carbon number ranges of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms respectively mean the total number of carbon atoms constituting the alkyl moiety or aryl moiety when regarded as unsubstituted without considering the portion substituted by the substituent. For example, a phenyl group substituted with a butyl group at the para position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0025] The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen atom. When the aryl group has a substitution base, it can further form a ring by fusing with adjacent substituents.

[0026] Specific examples of the aryl group include aromatic groups such as phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl, fluoranthenyl group, etc. One or more hydrogen atoms in the aryl group can be substituted with deuterium atom, halogen atom, hydroxy group, nitro group, cyano group, silyl group, amino group (-NH2, -NH(R), -N(R’)(R’’), R’ and R’’ are independently alkyl groups having 1 to 10 carbon atoms, and in this case, it is called “alkylamino group”), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, or heteroarylalkyl group having 2 to 24 carbon atoms.

[0027] The heteroaryl group, which is a substituent used in the compounds of the present invention, contains one, two or three heteroatoms selected from among N, O, P, Si, S, Ge, Se, and Te, and the remaining ring atoms are carbon, meaning a cyclic aromatic system having 2 to 24 carbon atoms. These rings can be fused to form a ring. And one or more hydrogen atoms in the heteroaryl group can be substituted with the same substituents as in the case of the aryl group.

[0028] Also, in the present invention, the aromatic heterocyclic ring means a ring in which one or more of the aromatic carbons in the aromatic hydrocarbon ring are substituted with heteroatoms. Preferably, one to three of the aromatic carbons in the aromatic hydrocarbon can be substituted with one or more heteroatoms selected from among N, O, P, Si, S, Ge, Se, and Te.

[0029] The alkyl group, which is a substituent used in the compounds of the present invention, is a substituent obtained by removing one hydrogen from an alkane, and has a structure including linear and branched forms. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc. One or more hydrogen atoms in the alkyl group can be substituted with the same substituents as in the case of the aryl group.

[0030] In the cycloalkyl group, which is a substituent used in the compounds of the present invention, "cyclo" means a substituent having a structure capable of forming a monocyclic or polycyclic saturated hydrocarbon within the alkyl group. For example, specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc. One or more hydrogen atoms in the cycloalkyl group can be substituted with the same substituents as in the case of the aryl group.

[0031] The alkoxy group, which is a substituent used in the compounds of the present invention, is a substituent in which an oxygen atom is bonded to the end of an alkyl group or a cycloalkyl group. Specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantyloxy, dicyclopentyloxy, bornyloxy, isobornyloxy, etc. One or more hydrogen atoms in the alkoxy group can be substituted with the same substituents as in the case of the aryl group.

[0032] Specific examples of the arylalkyl group, which is a substituent used in the compounds of the present invention, include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc. One or more hydrogen atoms in the arylalkyl group can be substituted with the same substituents as in the case of the aryl group.

[0033] Specific examples of the silyl group, which is a substituent used in the compounds of the present invention, include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc. One or more hydrogen atoms in the silyl group can be substituted with the same substituents as in the case of the aryl group.

[0034] Also, in the present invention, an alkenyl group means an alkyl substituent containing one carbon-carbon double bond composed of two carbon atoms, and an alkynyl group means an alkyl substituent containing one carbon-carbon triple bond composed of two carbon atoms.

[0035] In addition, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens from an alkane molecule which is a linear or branched saturated hydrocarbon. Specific examples of the alkylene group include a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group, an iso-amylene group, a hexylene group, etc. One or more hydrogen atoms of the alkylene group can be substituted with substituents similar to those in the case of the aryl group.

[0036] In addition, the diarylamino group in the present invention means an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom. Also, in the present invention, the diheteroarylamino group means an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom, and the aryl(heteroaryl)amino group means an amine group in which the aryl group and the heteroaryl group are each bonded to a nitrogen atom.

[0037] On the other hand, more preferable examples of the "substituted or unsubstituted" in the above [Chemical Formula A], [Chemical Formula B] and [Structural Formula C] for "substitution" are deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 12 to 18 carbon atoms, a diheteroarylamino group having 2 to 18 carbon atoms, an aryl(heteroaryl)amino group having 7 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms, and can be substituted with one or more substituents selected from the group consisting of them.

[0038] Also, in the present invention, in the case of "R1 and R2 can be linked to each other to form an alicyclic, monocyclic or polycyclic aromatic ring", this means that one hydrogen radical can be removed from each of the R1 and R2, and by linking these, a further ring can be formed.

[0039] In the present invention, the heterocyclic compound represented by the above [Chemical Formula A] or [Chemical Formula B] is characterized in that in [Chemical Formula A], a substituent containing a pyrene structure represented by the following [Structural Formula C] is bonded to one (x + y + z = 1) or two (x + y + z = 2) of the rings of A1, A2, and E which are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, and in [Chemical Formula B], a substituent containing a pyrene structure represented by the following [Structural Formula C] is bonded to one (x + y + z + w = 1) or two (x + y + z + w = 2) of the rings of A1, A2, E, and F which are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms.

[0040] [Structural Formula C] JPEG0007710025000007.jpg4973 A1, A2, E, and F in the above [Chemical Formula A] and [Chemical Formula B] according to the present invention may be the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, and more preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 carbon atoms.

[0041] As described above, when A1, A2, E, and F in Chemical Formula A or Chemical Formula B may be the same as or different from each other and each independently correspond to a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, the aromatic hydrocarbon rings may be the same as or different from each other and each independently may be any one selected from [Structural Formula 10] to [Structural Formula 21].

[0042] JPEG0007710025000008.jpg131165

[0043] In the above [Structural Formula 10] to [Structural Formula 21], “-*” means a bonding position for forming a 5-membered ring containing a carbon atom linked to the substituents R1 and R2, or forming a 5-membered ring containing M in the structural formulas Q1 and Q2. front When the aromatic hydrocarbon rings of the above [Structural Formula 10] to [Structural Formula 21] correspond to the A1 ring or the A2 ring and are bonded to the structural formula Q1 or the structural formula Q2, two adjacent carbon atoms among them are bonded to * of the structural formula Q1 or bonded to * of the structural formula Q2 to form a condensed ring. the aforesaid In [Structural Formula 10] to [Structural Formula 21], R is the R defined for the aforesaid Chemical Formula A or Chemical Formula B 1 and R 2 can be the same as, preferably R is any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. The above m is an integer from 1 to 8. When m is 2 or more or R is 2 or more, each R may be the same as or different from each other.

[0044] As one embodiment, the linking groups L1 to L4 in the chemical formula A or the chemical formula B of the present invention are each a single bond or any one selected from the following [Structural Formula 1] to [Structural Formula 5], and s1 to s4 can each be 1 or 2.

[0045] JPEG0007710025000009.jpg65165 Hydrogen or deuterium can be bonded to the carbon of the aromatic ring in the linking group.

[0046] Also, as one embodiment of the present invention, the compound represented by the above [Chemical Formula A] is a compound in which any one of A1, A2, and E is bonded to a pyrene substituent represented by the following [Structural Formula C], where x is 1, y and z are each 0, or said y is 1, x and z are each 0, or said z is 1, and x and y each correspond to 0. Two of A1, A2, and E in the compound represented by the above [Chemical Formula A] are compounds bonded to a pyrene substituent represented by the following [Structural Formula C], where x and y are each 1, z is 0, or said x and z are each 1, y is 0, or y and z are each 1, and x corresponds to 0. The compound represented by the above [Chemical Formula B] is a structure in which any one of A1, A2, E, and F is bonded to a pyrene substituent represented by the following [Structural Formula C], where x is 1, y, z, and w are each 0, or two of A1, A2, E, and F are structures bonded to a pyrene substituent represented by the following [Structural Formula C], where x and y are each 1, and z and w correspond to 0.

[0047] Also, as one embodiment of the present invention, the substituents R1 and R2 in the above Chemical Formula A or Chemical Formula B may be the same or different from each other, and independently of each other, are a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, may be linked to each other to form a ring, or may not be linked to each other and not form a ring.

[0048] Also, as one embodiment of the present invention, R in the pyrene structure of the above Structural Formula C 21 ~R 23 may be a single bond bonded to the linking groups L1 to L4.

[0049] Also, as one embodiment of the present invention, R in the above Structural Formula C 21 ~R 30are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, which may be the same as or different from each other, provided that R not linked to L1 to L4 in the structural formula C 21 ~R 30 at least one of which may be selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.

[0050] Also, as one embodiment according to the present invention, the R 11 ~R 15 may each independently be a substituent selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and a halogen group, which may be the same as or different from each other.

[0051] Also, the compound represented by the above [Chemical formula A] or [Chemical formula B] according to the present invention may be any one selected from [H1] to [H180].

[0052] JPEG0007710025000010.jpg217170JPEG0007710025000011.jpg228170JPEG0007710025000012.jpg226170JPEG0007710025000013.jpg252170JPEG0007710025000014.jpg252170JPEG0007710025000015.jpg247170JPEG0007710025000016.jpg240170JPEG0007710025000017.jpg237170JPEG0007710025000018.jpg245170JPEG0007710025000019.jpg243170JPEG0007710025000020.jpg245170JPEG0007710025000021.jpg246170

[0053] Further, the present invention provides an organic light-emitting device including a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains one or more compounds represented by the above [Chemical Formula A] or [Chemical Formula B] according to the present invention.

[0054] On the other hand, in the present invention, “(the organic layer) contains one or more organic compounds” can be interpreted as “(the organic layer) can contain one organic compound belonging to the scope of the present invention or two or more different compounds belonging to the scope of the organic compound”.

[0055] At this time, the organic layer in the organic light-emitting device of the present invention can include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0056] As a more preferred embodiment of the present invention, in the present invention, the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, the light-emitting layer is composed of a host and a dopant, and at least one of the compounds represented by the above [Chemical Formula A] or [Chemical Formula B] in the present invention can be included as a host compound in the light-emitting layer.

[0057] In the present invention, as the dopant compound used in the light-emitting layer, at least one compound represented by any one of the following [Chemical Formula D1] to [Chemical Formula D10] can be included.

[0058] [Chemical Formula D1] JPEG0007710025000022.jpg110170

[0059] [Chemical Formula D2] JPEG0007710025000023.jpg124170

[0060] In the above [Chemical Formula D1] and [Chemical Formula D2], A 31 , A 32 , E1 and F1 may be the same or different from each other, and independently of each other, are a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms. Two adjacent carbon atoms in the aromatic ring of the above A 31 and two adjacent carbon atoms in the aromatic ring of the above A 32 form a condensed ring by forming a 5-membered ring with the carbon atom to which the substituents R 51 and R 52 are attached. The linking groups L 21 ~L 32 may be the same or different from each other, and independently of each other, are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. The above W and W' may be the same or different from each other, and independently of each other, are N-R 53 , CR 54 R 55 , SiR56 R 57 、 GeR 58 R 59 、 is any one selected from O, S, Se, the substituent R 51 ~R 59 、 Ar 21 ~Ar 28 may be the same or different from each other, and independently of each other, are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group, the R 51 and R 52 may be linked to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring can be substituted with at least one heteroatom selected from N, O, P, Si, S, Ge, Se, Te, the p11~p14, r11~r14 and s11~s14 are each an integer from 1 to 3, but when each of these is 2 or more, each linking group L 21 ~L 32 may be the same or different from each other, x1 is 1, y1, z1, and z2 may be the same or different from each other, and are each independently an integer from 0 to 1, the said Ar 21 and Ar 22 Ar 23 and Ar 24 Ar 25 and Ar 26 and Ar 27 and Ar 28 can each be connected to each other to form a ring, In the chemical formula D1, A 32 Two adjacent carbon atoms in the ring are bonded to the * of the said structural formula Q 11 to form a condensed ring, In the chemical formula D2, the said A 31 Two adjacent carbon atoms in the ring are bonded to the * of the said structural formula Q 12 to form a condensed ring, and the said A 32 Two adjacent carbon atoms in the ring are bonded to the * of the said structural formula Q 11 to form a condensed ring.

[0061] [Chemical formula D3] JPEG0007710025000024.jpg50103

[0062] In the said [Chemical formula D3], the said X1 is any one selected from B, P, and P=O, the said T1 to T3 may be the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms, the said Y1 is any one selected from N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 and the said Y2 is any one selected from N-R , CR 66 R 66 , O, S, SiR 68 R 69 R 70is any one selected from among, said R 61 ~R 70 may be the same as or different from each other, and independently of each other, is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, or a halogen group, and said R 61 ~R 70 may each be bonded to at least one ring selected from among said T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0063] JPEG0007710025000025.jpg65136

[0064] In said [Chemical Formula D4] and [Chemical Formula D5], said X2 is any one selected from among B, P, and P=O, said T4 to T6 are the same as T1 to T3 in [Chemical Formula D3], said Y4 is N-R 61 CR 62 R 63 O, S, SiR 64 R 65 is any one selected from among, said Y5 is N-R 66 CR 66 R 68 O, S, SiR 69 R 70 is any one selected from among, Said Y6 is N-R 71 , CR 72 R 73 , O, S, SiR 74 R 75 and is any one selected from among them, said R 61 ~R 75 is the same as said R 61 ~R 70 in [Chemical Formula D3].

[0065] JPEG0007710025000026.jpg59136

[0066] Said X3 is any one selected from among B, P, and P=O, said T7~T9 are the same as T1~T3 in [Chemical Formula D3], said Y6 is N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 and is any one selected from among them, said substituents R 61 ~R 65 , R 71 ~R 72 are respectively the same as said R 61 ~R 70 in [Chemical Formula D3], said R 71 and R 72 are respectively connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, or can be combined with said T7 ring or T9 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0067] JPEG0007710025000027.jpg96130

[0068] In said [Chemical Formula D8]~[Chemical Formula D10], said X is any one selected from among B, P, and P=O, said Q1~Q3 are respectively the same as T1~T3 in [Chemical Formula D3], The linking group Y is any one selected from N-R3, CR4R5, O, S, and Se, and the substituents R3 to R5 are each the R in [Chemical Formula D3] 61 ~R 70 and are the same, and R3 to R5 can each be bonded to the Q2 ring or Q3 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring, and R4 and R5 can each be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, The ring formed by Cy1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding the nitrogen (N) atom, the aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and the aromatic carbon atom in the Q1 ring to which Cy1 is bonded, In Chemical Formula D9, "Cy2" can be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding the carbon atoms contained in Cy1, In Chemical Formula D10, the ring formed by Cy3 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding the aromatic carbon atom in the Q3 ring to which Cy3 is bonded, the aromatic carbon atom in Q3 bonded to the nitrogen (N) atom, the nitrogen (N) atom, and the carbon atoms in Cy1 to which the nitrogen (N) atom is bonded, Here, the "substitution" in the "substituted or unsubstituted" in the above [Chemical Formula D1] to [Chemical Formula D10] means substitution with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms.

[0069] In addition, in the case of the boron compound represented by any of the above [Chemical Formula D3] to [Chemical Formula D10] among the dopant compounds according to the present invention, as substituents that can be substituted on the aromatic hydrocarbon ring or aromatic heterocyclic ring of the above T1 to T9 or Q1 to Q3, deuterium, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, and an arylamino group having 6 to 24 carbon atoms can be substituted. Here, the alkyl group or aryl group in each of the alkylamino group having 1 to 24 carbon atoms and the arylamino group having 6 to 24 carbon atoms can be linked to each other. More preferable substituents are an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, and an arylamino group having 6 to 18 carbon atoms can be substituted, and the alkyl group or aryl group in each of the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms can be linked to each other.

[0070] On the other hand, among the dopant compounds used in the light-emitting layer in the organic light-emitting device according to the present invention, specific examples of the compounds represented by any of the above [Chemical Formula D1] to [Chemical Formula D2] are as follows <d1> ~ <d239>It may be a compound represented by any of them.

[0071] JPEG0007710025000028.jpg226170JPEG0007710025000029.jpg220170JPEG0007710025000030.jpg212170JPEG0007710025000031.jpg213170JPEG0007710025000032.jpg220170JPEG0007710025000033.jpg244170JPEG0007710025000034.jpg228170JPEG0007710025000035.jpg235170JPEG0007710025000036.jpg216170JPEG0007710025000037.jpg225170JPEG0007710025000038.jpg239170JPEG0007710025000039.jpg226170JPEG0007710025000040.jpg251170JPEG0007710025000041.jpg227170JPEG0007710025000042.jpg239170JPEG0007710025000043.jpg89170

[0072] Also, in the present invention, among the dopant compounds in the light-emitting layer, the compound represented by [Chemical Formula D3] is as follows <d101> ~ <d130>It can be a compound represented by any one selected from among them.

[0073] JPEG0007710025000044.jpg245170JPEG0007710025000045.jpg202170

[0074] In the present invention, among the dopant compounds in the light-emitting layer, the compound represented by any one of the above [Chemical Formula D4] and [Chemical Formula D5] can be a compound represented by any one selected from the following [D201] to [D280].

[0075] JPEG0007710025000046.jpg250170JPEG0007710025000047.jpg239170JPEG0007710025000048.jpg223170

[0076] In the present invention, among the dopant compounds in the light-emitting layer, the compound represented by any one of [Chemical Formula D6] and [Chemical Formula D7] is as follows <d301> ~ <d387>It can be a compound represented by any one selected from among them.

[0077] JPEG0007710025000049.jpg253170JPEG0007710025000050.jpg237170JPEG0007710025000051.jpg255169JPEG0007710025000052.jpg235170JPEG0007710025000053.jpg239170JPEG0007710025000054.jpg53170

[0078] Also, in the present invention, among the dopant compounds in the light-emitting layer, the compound represented by any one of [Chemical Formula D8] to [Chemical Formula D10] is as follows <d401> ~ <d532>It can be a compound represented by any one selected from among them.

[0079] JPEG0007710025000055.jpg224170JPEG0007710025000056.jpg221170JPEG0007710025000057.jpg231170JPEG0007710025000058.jpg236170JPEG0007710025000059.jpg231170JPEG0007710025000060.jpg229170JPEG0007710025000061.jpg242170JPEG0007710025000062.jpg248170JPEG0007710025000063.jpg190170

[0080] Further, as one embodiment of the organic light-emitting device according to the present invention, the present invention includes a first electrode and a second electrode facing the first electrode; between the first electrode and the second electrode, a first light-emitting layer including a first host and a first dopant; and a second light-emitting layer including a second host and a second dopant; are sequentially included, and at least one of the first host and the second host includes one or more of any one compound selected from the compounds represented by the [chemical formula A] or [chemical formula B], and an organic light-emitting device is provided, whereby the organic light-emitting device can have characteristics of high efficiency and long life.

[0081] In this case, the organic light-emitting device is provided with at least one of a hole transport layer and a hole injection layer between the first electrode and the first light-emitting layer, and at least one of an electron transport layer and an electron injection layer between the second light-emitting layer and the second electrode. Preferably, a hole transport layer and a hole injection layer are respectively provided between the first electrode and the first light-emitting layer, and an electron transport layer and an electron injection layer can be respectively provided between the second light-emitting layer and the second electrode.

[0082] Further, as a preferred embodiment of the organic light-emitting device according to the present invention, the first light-emitting layer can include one or more of any compound selected from the compounds represented by the [chemical formula A] or [chemical formula B].

[0083] Here, when the first light-emitting layer in the organic light-emitting device according to the present invention contains any compound selected from the compounds represented by [Chemical Formula A] or [Chemical Formula B], an anthracene derivative represented by the following Chemical Formula E can be used as a host in the second light-emitting layer.

[0084] [Chemical Formula E] JPEG0007710025000064.jpg59106

[0085] In the above [Chemical Formula E], the substituents R 41 ~R 48 may be the same or different, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. the substituents Ar5 and Ar6 may be the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms. the linking group L1 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms. n is an integer of 1 to 2, and when n is 2 or more, the respective linking groups L1 may be the same as or different from each other.

[0086] In the above [Chemical Formula E], the "substitution" in the "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 6 to 24 carbon atoms, heteroarylamino group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms.

[0087] As a preferred embodiment of the organic light-emitting device according to the present invention, when the second light-emitting layer contains an anthracene derivative represented by the above [Chemical Formula E] as a host, a more preferred structure of the anthracene derivative represented by the [Chemical Formula E] is an anthracene derivative represented by the following [Chemical Formula E-1] or [Chemical Formula E-2].

[0088] [Chemical Formula E-1] JPEG0007710025000065.jpg95106

[0089] [Chemical Formula E-2] JPEG0007710025000066.jpg92106

[0090] In the above [Chemical Formula E-1] and [Chemical Formula E-2], the substituent R 41 ~R 48 、R 49 ~R 55 may be the same or different from each other, and independently of each other, are each selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group, the substituent Ar5 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, the linking group L 11 is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, k is an integer of 1 to 2. When k is 2 or more, each linking group L 11 may be the same or different from each other, in the said "[Formula E-1]" and "[Formula E-2]", the "substituted" in the "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms.

[0091] Here, as shown in the following Scheme 1, in the compound represented by the above [Chemical Formula E-1] or [Chemical Formula E-2], the 1-position or 2-position of one phenyl ring of dibenzofuran or the 1'-position or 2'-position of the other phenyl ring of dibenzofuran is bonded to the 9-position of an anthracenyl group or a linking group L 11 characterized in that it is bonded thereto.

[0092] JPEG0007710025000067.jpg3773[Scheme 1]

[0093] On the other hand, in the present invention, the substituent Ar5 in the anthracene derivative represented by any one of the above [Chemical Formula E], [Chemical Formula E-1] and [Chemical Formula E-2] may be a substituent represented by the following [Structural Formula C-1].

[0094] [Structural Formula C-1] JPEG0007710025000068.jpg4166

[0095] At this time, R 61 ~R 65 may be the same or different from each other, and are independently of each other hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, or a halogen group, and "-*" in the above [Structural Formula C-1] is a bonding position bonded to the 10-position of the anthracenyl group in [Chemical Formula E], [Chemical Formula E-1] or [Chemical Formula E-2].

[0096] In one embodiment, as a preferred example of the organic light-emitting device according to the present invention, the linking group L in the above [Chemical Formula E-1] or [Chemical Formula E-2] 11 It may be a single bond or an arylene group having 6 to 14 carbon atoms which may be substituted or unsubstituted. At this time, k is an integer of 1 to 2. When k is 2 or more, each L 13 may be the same as or different from each other.

[0097] The anthracene derivative represented by the [Chemical formula E] in the organic light-emitting element according to the present invention may be any one selected from the following <Compound 101> to <Compound 187>.

[0098] JPEG0007710025000069.jpg244170JPEG0007710025000070.jpg231170JPEG0007710025000071.jpg226170JPEG0007710025000072.jpg216170JPEG0007710025000073.jpg232170JPEG0007710025000074.jpg186170

[0099] As another embodiment, specific examples of the anthracene derivative represented by any one of the [Chemical formula E-1] and [Chemical formula E-2] in the organic light-emitting element according to the present invention may be any one selected from the following <Compound 201> to <Compound 260>.

[0100] JPEG0007710025000075.jpg227170JPEG0007710025000076.jpg254170JPEG0007710025000077.jpg235170JPEG0007710025000078.jpg235168JPEG0007710025000079.jpg230170

[0101] As a more preferred embodiment of the present invention, the present invention includes a first electrode and a second electrode facing the first electrode; between the first electrode and the second electrode, a first light-emitting layer including a first host and a first dopant; and a second light-emitting layer including a second host and a second dopant are sequentially included. The first light-emitting layer includes one or more compounds represented by the [chemical formula A] or [chemical formula B]. When the second light-emitting layer includes an anthracene derivative represented by the chemical formula E as a host, the first light-emitting layer and the second light-emitting layer may be the same or different, and one or more dopant compounds selected from the chemical formulas D1 to D10 can be independently used for each of them.

[0102] [Chemical formula D1] JPEG0007710025000080.jpg106167

[0103] [Chemical formula D2] JPEG0007710025000081.jpg119167

[0104] [Chemical formula D3] JPEG0007710025000082.jpg4465

[0105] JPEG0007710025000083.jpg192146

[0106] At this time, the content of the dopant in the light-emitting layer can usually be selected in the range of about 0.01 to about 20 parts by weight with respect to about 100 parts by weight of the host, but is not limited thereto.

[0107] In addition to the dopant and the host, the light-emitting layer can further include various hosts and various dopant substances.

[0108] Hereinafter, an organic light-emitting device according to an embodiment of the present invention will be described with reference to the drawings.

[0109] FIG. 1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.

[0110] As shown in FIG. 1, an organic light-emitting device according to an embodiment of the present invention is an organic light-emitting device including 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 in this order. Using the anode as the first electrode and the cathode as the second electrode, it corresponds to an organic light-emitting device including a hole transport layer between the anode and the light-emitting layer and an electron transport layer between the light-emitting layer and the cathode.

[0111] Further, in the organic light-emitting device according to an embodiment of the present invention, a hole injection layer 30 may be included between the anode 20 and the hole transport layer 40, and an electron injection layer 70 may be included between the electron transport layer 60 and the cathode 80.

[0112] Hereinafter, with reference to FIG. 1, an organic light-emitting device of the present invention and a method for manufacturing the same will be described.

[0113] First, an anode (anode) electrode material is coated on the upper part of the substrate 10 to form the anode 20. Here, as the substrate 10, a substrate usually used in an ordinary organic EL device is used, but an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handleability, and waterproofness is preferable. As the anode electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

[0114] A hole injection layer material is vacuum thermally evaporated or spin-coated on the upper part of the anode 20 electrode to form a hole injection layer 30. Next, a hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the hole injection layer 30 to form a hole transport layer 40.

[0115] The material of the hole injection layer can be used without particular limitation as long as it is commonly used in the art. For example, 2-TNATA [4,4’,4’’-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N’-di(1-naphthyl)-N,N’-diphenylbenzidine)], TPD [N,N’-diphenyl-N,N’-bis(3-methylphenyl)-1,1’-biphenyl-4,4’-diamine], DNTPD [N,N’-diphenyl-N,N’-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4’-diamine], etc. can be used. However, the present invention is not necessarily limited thereto.

[0116] Also, the material of the hole transport layer is not particularly limited as long as it is 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(naphthalen-1-yl)-N,N’-diphenylbenzidine (a-NPD), etc. can be used. However, the present invention is not necessarily limited thereto.

[0117] On the other hand, the present invention can further form an electron blocking layer on the upper part of the hole transport layer. The electron blocking layer is a layer for improving the lifetime and efficiency of the device by preventing the electrons injected from the electron injection layer from entering the hole transport layer through the light-emitting layer, and can be formed at an appropriate part between the light-emitting layer and the hole injection layer, preferably, can be formed between the light-emitting layer and the hole transport layer.

[0118] Next, the light-emitting layer 50 can be laminated on the upper part of the hole transport layer 40 or the electron blocking layer by a vacuum evaporation method or a spin coating method.

[0119] Here, the light-emitting layer may be composed of a host and a dopant. The materials constituting these are the same as those described above.

[0120] Also, the light-emitting layer is a first light-emitting layer (not shown) and a second light-emitting layer (not shown), and the first light-emitting layer and the second light-emitting layer can be formed using the same or different host and dopant materials respectively through separate vapor deposition processes or coating processes.

[0121] More preferably, the first light-emitting layer contains one or more compounds represented by the chemical formula A or chemical formula B as a fluorescent host, and the second light-emitting layer contains one or more anthracene derivatives represented by the chemical formula E. As the respective fluorescent dopants in the first light-emitting layer and the second light-emitting layer, materials that are the same or different independently of each other and are selected from any of the chemical formulas D1 to D10 can be used.

[0122] In addition, as the host materials that can be used in the first light-emitting layer and the second light-emitting layer in the present invention, the host material (BH1) used in the first light-emitting layer has a lower lowest unoccupied molecular orbital function (LUMO) and a higher highest occupied molecular orbital function (HOMO) than the host material (BH2) used in the second light-emitting layer. By using such a material, it is preferable to have a structure that facilitates the injection of holes and / or electrons compared to the host (BH2) used in the second light-emitting layer.

[0123] According to a specific example of the present invention, the thickness of the light-emitting layer is preferably 50 to 2,000 Å.

[0124] On the other hand, an electron transport layer 60 is deposited on the light-emitting layer by a vacuum vapor deposition method or a spin coating method.

[0125] On the one hand, in the present invention, as the material of the electron transport layer, it should have the function of stably transporting the electrons injected from the electron injection electrode (cathode), and known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq3), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 201, Compound 202, BCP, and materials such as PBD, BMD, and BND which are oxadiazole derivatives. However, it is not limited thereto.

[0126] JPEG0007710025000084.jpg161170

[0127] In addition, in the organic light-emitting device of the present invention, after forming the electron transport layer, an electron injection layer (EIL), which is a substance having the function of facilitating the injection of electrons from the cathode, can be laminated on the upper part of the electron transport layer. There is no particular limitation on the material.

[0128] As the electron injection layer forming material, any substance known as an electron injection layer forming material such as CsF, NaF, LiF, Li2O, BaO can be used. The evaporation conditions of the electron injection layer vary depending on the compound used, but generally, they can be selected from within substantially the same condition range as that for forming the hole injection layer.

[0129] The thickness of the electron injection layer can be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0130] In the present invention, for the cathode, a material with a small work function can be used for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys such as aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used, or a transmissive cathode using ITO or IZO can be used.

[0131] In addition, the organic light-emitting device in the present invention can further include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in the wavelength range of 380 nm to 800 nm. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the further formed light-emitting layer can be a fluorescent material or a phosphorescent material.

[0132] In the present invention, one or more layers selected from each of the above layers can be formed by a single-molecule vapor deposition process or a solution process.

[0133] Here, the vapor deposition process means a method of evaporating a substance used as a material for forming each of the above layers by heating in a vacuum or low-pressure state to form a thin film, and the solution process means mixing a substance used as a material for forming each of the above layers with a solvent and forming a thin film by methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc.

[0134] In addition, the organic light-emitting device in the present invention can be used in any device selected from a flat panel display device, a flexible display device, a single-color or white flat panel lighting device, and a single-color or white flexible lighting device.

[0135] Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these embodiments are for more specifically explaining the present invention. It is self-evident to those having ordinary knowledge in the art that the scope of the present invention is not limited by these embodiments.

[0136] (Example) Synthesis Example 1. Synthesis of [H1] Synthesis Example 1-(1): Synthesis of <1-a>

[0137] JPEG0007710025000085.jpg40165

[0138] A 500 mL round-bottom flask reactor was charged with methyl 2-bromobenzoate (30.0 g, 0.140 mol), 4-dibenzofuranboronic acid (32.5 g, 0.153 mol), tetrakis(triphenylphosphine)palladium (3.2 g, 3 mmol), and potassium carbonate (38.6 g, 0.279 mol), and 210 mL of toluene, 90 mL of methanol, and 60 mL of water were added. The reactor was refluxed and stirred overnight. After the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. After concentrating the organic layer under reduced pressure, <1-a> was obtained by column chromatography. (25.0 g, 59.1%)

[0139] Synthesis Example 1-(2): Synthesis of <1-b>

[0140] JPEG0007710025000086.jpg37165

[0141] A 500 ml round-bottom flask reactor was charged with bromobenzene (28.6 g, 182 mmol) and 220 ml of tetrahydrofuran, and cooled to -78 °C in a nitrogen atmosphere. n-Butyllithium (104.6 ml, 167 mmol) was added dropwise to the cooled reaction solution at the same temperature. The reaction solution was stirred for 2 hours, then <1-a> (22.0 g, 73 mmol) was added little by little, and stirred at room temperature. Then, 50 ml of H2O was added to terminate the reaction, and extracted with ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure to obtain <1-b>. (28.0 g, 90%)

[0142] Synthesis Example 1-(3): Synthesis of <1-c>

[0143] JPEG0007710025000087.jpg37165

[0144] 1-b (28.0 g, 66 mmol), 310 ml of acetic acid and 2 ml of hydrochloric acid were charged into a 500 ml round-bottom flask reactor and refluxed with stirring for 1 hour. When a solid was formed, after confirming the end of the reaction by thin layer chromatography, it was cooled to room temperature. The resulting solid was filtered, washed with H2O and methanol, and then dried to obtain <1-c>. (22.3 g, 83.2%)

[0145] Synthesis Example 1-(4): Synthesis of <1-d>

[0146] JPEG0007710025000088.jpg37165

[0147] <1-c> (22.3 g, 55 mmol) and 500 ml of methylene chloride were charged into a 2 L round-bottom flask reactor and dissolved. Bromine (8.72 g, 55 mmol) was mixed with 250 ml of methylene chloride and slowly added dropwise to the reactor, and then stirred at room temperature for 3 hours. After the reaction was completed, the reaction solution was washed with an aqueous sodium bicarbonate solution. After filtering the solid, <1-d> was obtained by recrystallization with toluene and acetone. (25.0 g, 94%)

[0148] Synthesis Example 1-(5): Synthesis of [H1]

[0149] JPEG0007710025000089.jpg48156

[0150] 10 g (0.021 mol) of <1-d> was added to a reaction vessel, along with 6.1 g (0.025 mol) of Pyrene-1-boronic acid, 5.7 g (0.041 mol) of K2CO3, 0.5 g of Pd(PPh3)4, 40 mL of toluene, 30 mL of ethanol, and 30 mL of distilled water. After refluxing and stirring for 6 hours, the reaction solution was cooled, slurried with methanol, and then filtered. After hot filtering with toluene, recrystallization with acetone was carried out to synthesize [H1] (4 g, 32%). MS (MALDI-TOF): m / z 608.21 [M+]

[0151] Synthesis Example 2. Synthesis of [H25] Synthesis Example 2-(1): Synthesis of <2-a>

[0152] JPEG0007710025000090.jpg41156

[0153] Methyl 2-iodobenzoate (19.1 g, 73 mmol), 4-dibenzofuranboronic acid (18.7 g, 88 mmol), tetrakis(triphenylphosphine)palladium (1.7 g, 0.15 mmol), and potassium carbonate (20.2 g, 146.7 mmol) were charged into a 500 mL round-bottom flask reactor. 125 mL of toluene, 125 mL of tetrahydrofuran, and 50 mL of water were added. The temperature of the reactor was raised to 80 °C and stirred for 10 hours. After the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. After concentrating the organic layer under reduced pressure, it was separated by column chromatography to obtain <2-a>. (9.5 g, 43%)

[0154] Synthesis Example 2-(2): Synthesis of <2-b>

[0155] JPEG0007710025000091.jpg45156

[0156] A 2L round-bottom flask reactor was charged with bromobenzene (13.2 g, 83.97 mmol) and 250 ml of tetrahydrofuran, and stirred in a low-temperature nitrogen environment. Approximately 58 ml of n-butyllithium was slowly added dropwise over 2 hours at -78 °C, and then <2-a> (9.4 g, 31.1 mmol) was added. After the reaction was completed, 100 ml of water was added and stirred for 30 minutes, followed by extraction to obtain <2-b>. (3.2 g, 24%)

[0157] Synthesis Example 2-(3): Synthesis of <2-c>

[0158] JPEG0007710025000092.jpg52140

[0159] <2-b> (55.0 g, 129 mmol), 500 ml of acetic acid and 10 ml of sulfuric acid were charged into a 2L round-bottom flask reactor, and refluxed with stirring for 5 hours. After the reaction was completed, it was cooled to room temperature, and the resulting solid was filtered. After washing with methanol, <2-c> was obtained. (50 g, 95%)

[0160] Synthesis Example 2-(4): Synthesis of <2-d>

[0161] JPEG0007710025000093.jpg49140

[0162] <2-c> (50 g, 122 mmol) and 600 ml of dichloromethane were charged into a 2L round-bottom flask reactor and stirred at room temperature. Bromine (13.7 ml, 85 mmol) was diluted in 50 ml of dichloromethane and added dropwise, followed by stirring for about 3 hours. Recrystallization with methanol gave <2-d>. (45.6 g, 66%)

[0163] Synthesis Example 2-(5): Synthesis of [H25]

[0164] JPEG0007710025000094.jpg52170

[0165] 12.0 g (0.021 mol) of <2-d>, 11.5 g (0.047 mol) of Pyrene-1-boronic acid, 11.71 g (0.085 mol) of K2CO3, 0.98 g of Pd(PPh3)4, 72 mL of toluene, 36 mL of ethanol, and 36 mL of distilled water were added to a reaction vessel and refluxed with stirring overnight. After the reaction solution was cooled, it was extracted with EA / distilled water and then hot filtered using toluene. Recrystallization was carried out with methanol, and after column purification, recrystallization was carried out with toluene / acetone to synthesize [H25] (7.8 g, 45%). MS (MALDI-TOF): m / z 810.29 [M+]

[0166] Synthesis Example 3. Synthesis of [H39] Synthesis Example 3-(1): Synthesis of <3-a>

[0167] JPEG0007710025000095.jpg46141

[0168] 35 g (118 mmol) of dibenzofuran-1-boronic acid pinacol ester, 40.5 g (118 mmol) of methyl 5-bromo-2-iodobenzoate, 2.7 g (2.3 mmol) of tetrakis triphenylphosphine palladium, 33 g (237 mmol) of potassium carbonate, 200 ml of toluene, 200 ml of 1,4-dioxane, and 100 ml of water were charged under a nitrogen atmosphere and refluxed for 12 hours. After the reaction was completed, the reaction product was separated into layers, the organic layer was concentrated under reduced pressure, and then separated by column chromatography and dried, and as a result, 33.5 g of <3-a> was obtained. (Yield 74%)

[0169] Synthesis Example 3-(2): Synthesis of <3-b>

[0170] JPEG0007710025000096.jpg46141

[0171] Charge <3-a> 33.5 g (110 mmol) into a round-bottom flask containing 150 ml of tetrahydrofuran, cool it to -10 °C, and then slowly add dropwise 85 ml (254 mmol) of 3M methylmagnesium bromide. Then, heat it at 40 °C and stir for 4 hours. After that, cool the temperature to -10 °C, slowly add dropwise 70 ml of 2N HCl, add 70 ml of ammonium chloride aqueous solution, and then raise the temperature to room temperature. After the reaction is completed, wash the reaction product with water, extract it with ethyl acetate, separate the layers, concentrate the organic layer under reduced pressure, and then separate and dry it by column chromatography. As a result, <3-b> 27 g was obtained. (Yield: 80%)

[0172] Synthesis Example 3-(3): Synthesis of <3-c>

[0173] JPEG0007710025000097.jpg42141

[0174] Charge <3-b> 27 g (89.2 mmol) and 70 ml of phosphoric acid into a round-bottom flask under a nitrogen atmosphere, stir at room temperature for 12 hours. After the reaction is completed, extract with ethyl acetate and water, concentrate the organic layer, separate and dry it by column chromatography. As a result, <3-c> 17.6 g was obtained. (Yield: 70%)

[0175] Synthesis Example 3-(4): Synthesis of <3-d>

[0176] JPEG0007710025000098.jpg39133

[0177] Charge <3-c> 17.6 g (48.4 mmol) into a round-bottom flask, add 200 ml of tetrahydrofuran under a nitrogen atmosphere, lower the temperature to -78 °C, and then slowly add dropwise 36.3 ml (58.1 mmol) of 1.6M n-butyllithium. After 1 hour, slowly add 7.0 ml (62.9 mmol) of trimethyl borate while keeping the temperature low, raise the temperature to room temperature and stir. After the reaction is completed, separate the layers of the reaction product, concentrate the organic layer under reduced pressure, and then recrystallize with hexane and dry. As a result, <3-d> 33 g (yield: 71%) was obtained.

[0178] Synthesis Example 3-(5): Synthesis of <3-e>

[0179] JPEG0007710025000099.jpg39151

[0180] The round-bottom flask was purged with nitrogen, and 100 g (0.278 mol) of 1,6-dibromopyrene, 33.9 g (0.278 mol) of phenylboronic acid, 6.4 g (0.006 mol) of tetrakis(triphenylphosphine)palladium (Pd[PPh3]4), 88.3 g (0.833 mol) of sodium carbonate, 1400 ml of toluene and 420 ml of water were added, and the mixture was refluxed for 9 hours. After the reaction was completed, it was cooled to room temperature, and the resulting solid was filtered off and discarded. The filtrate was extracted with ethyl acetate and water, and then the organic layer was dried. After drying, it was concentrated under reduced pressure, and then separated by column chromatography to obtain 45.4 g of <3-e> (yield 45.7%).

[0181] Synthesis Example 3-(6): Synthesis of [H39]

[0182] JPEG0007710025000100.jpg50157

[0183] 10 g (27.9 mmol) of intermediate <3-e>, 9.2 g (27.9 mmol) of intermediate <3-d>, 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium, 7.7 g (55.9 mmol) of potassium carbonate, 35 ml of toluene, 35 ml of 1,4-dioxane and 30 ml of water were charged into a round-bottom flask under a nitrogen atmosphere and refluxed for 12 hours. After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure and separated by column chromatography and dried, and as a result, 9.8 g of [H39] was obtained. (Yield 63%) MS (MALDI-TOF): m / z 560.21 [M+]

[0184] Synthesis Example 4. Synthesis of [H44] Synthesis Example 4-(1): Synthesis of <4-a>

[0185] JPEG0007710025000101.jpg48101

[0186] Compound <4-a> was obtained in the same manner as in Synthesis Examples 3-1 to 3-3, except that methyl 2-iodobenzoate was used instead of methyl 5-bromo-2-iodobenzoate used in Synthesis Example 3-1. (Yield: 60%)

[0187] Synthesis Example 4-(2): Synthesis of <4-b>

[0188] JPEG0007710025000102.jpg40118

[0189] 37.8 g (133 mmol) of <4-a>, 23.8 g (133 mmol) of N-bromosuccinimide, and 600 mL of dimethylformamide were charged into a round-bottomed flask under a nitrogen atmosphere and stirred at 50 °C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 33.8 g of <4-b>. (Yield: 70%)

[0190] Synthesis Example 4-(3): Synthesis of <4-c>

[0191] JPEG0007710025000103.jpg47118

[0192] Compound <4-c> was obtained in the same manner as above, except that <4-b> was used instead of <3-c> used in Synthesis Example 3-4. (Yield: 70%) Synthesis Example 4-(4): Synthesis of [H44]

[0193] JPEG0007710025000104.jpg48167

[0194] Compound [H44] was obtained in the same manner as above, except that <4-c> was used instead of <3-d> used in Synthesis Example 3-6. (Yield: 70%) MS (MALDI-TOF): m / z 560.21 [M]+

[0195] Synthesis Example 5. Synthesis of [H58] Synthesis Example 5-(1): Synthesis of <5-a>

[0196] JPEG0007710025000105.jpg40151

[0197] <5-a> was obtained by synthesis in the same manner except that 9-phenylcarbazole-2-boronic acid was used instead of dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1 and methyl 4-bromo-2-iodobenzoate was used instead of methyl 5-bromo-2-iodobenzoate. (Yield 68%)

[0198] Synthesis Example 5-(2): Synthesis of <5-b>

[0199] JPEG0007710025000106.jpg33144

[0200] <5-b> was obtained by synthesis in the same manner except that <5-a> was used instead of <3-a> used in Synthesis Example 3-2. (Yield 80%)

[0201] Synthesis Example 5-(3): Synthesis of <5-c>

[0202] JPEG0007710025000107.jpg33144

[0203] The intermediate <5-c> was obtained by synthesis in the same manner except that <5-b> was used instead of <3-b> used in Synthesis Example 3-3. (Yield 70%)

[0204] Synthesis Example 5-(4): Synthesis of <5-d>

[0205] JPEG0007710025000108.jpg37144

[0206] The intermediate <5-d> was obtained by synthesis in the same manner except that <5-c> was used instead of <3-c> used in Synthesis Example 3-4. (Yield 72%)

[0207] Synthesis Example 5-(5): Synthesis of [H58]

[0208] JPEG0007710025000109.jpg57163

[0209] [H58] was obtained by synthesizing in the same manner except that <5-d> was used instead of <3-d> used in Synthesis Examples 3-6 above. (Yield: 70%) MS (MALDI-TOF): m / z 635.26 [M]+

[0210] Synthesis Example 6. Synthesis of [H85] Synthesis Example 6-(1): Synthesis of <6-a>

[0211] JPEG0007710025000110.jpg34148

[0212] 50 g (183 mmol) of 2-bromo-9,9-dimethylfluorene, 59.3 g (1098 mmol) of sodium methoxide solution, 10.4 g (54.9 mmol) of copper(I) iodide, and 200 ml of methanol were charged into a round-bottom flask under a nitrogen atmosphere and refluxed for 12 hours. After completion of the reaction, the reaction mixture was subjected to liquid separation, and the organic layer was concentrated under reduced pressure and separated by column chromatography and dried, whereby 33.2 g of <6-a> was obtained. (Yield: 81%)

[0213] Synthesis Example 6-(2): Synthesis of <6-b>

[0214] JPEG0007710025000111.jpg34148

[0215] 30 g (133 mmol) of <6-a>, 23.8 g (133 mmol) of N-bromosuccinimide, and 600 ml of dimethylformamide were charged into a round-bottom flask under a nitrogen atmosphere and stirred at 50 °C for 12 hours. After completion of the reaction, the reaction mixture was subjected to liquid separation, and the organic layer was concentrated under reduced pressure and separated by column chromatography and dried, whereby 28 g of <6-b> was obtained. (Yield: 70%)

[0216] Synthesis Example 6-(3): Synthesis of <6-c>

[0217] JPEG0007710025000112.jpg32148

[0218] Compound <6-c> was obtained in the same manner except that <6-b> was used instead of <3-c> used in Synthesis Example 3-4. (Yield: 72%)

[0219] Synthesis Example 6-(4): Synthesis of <6-d>

[0220] JPEG0007710025000113.jpg43157

[0221] Compound <6-d> was obtained in the same manner except that <6-c> was used instead of dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1 and 1-bromo-2-iodo-3-fluorobenzene was used instead of methyl 5-bromo-2-iodobenzoate. (Yield: 70%)

[0222] Synthesis Example 6-(5): Synthesis of <6-e>

[0223] JPEG0007710025000114.jpg48133

[0224] 30 g (85 mmol) of <6-d> and 300 ml of dichloromethane were charged into a round-bottomed flask under a nitrogen atmosphere. After cooling the temperature to 0 °C, 63.9 g (255 mmol) of boron tribromide was diluted with 150 ml of dichloromethane and slowly added dropwise. Then, after raising the temperature to room temperature, the mixture was stirred for 6 hours. After completion of the reaction, the reaction product was subjected to liquid separation, the organic layer was concentrated under reduced pressure, separated by column chromatography and dried, and as a result, 21.3 g of <6-e> was obtained. (Yield: 74%)

[0225] Synthesis Example 6-(6): Synthesis of <6-f>

[0226] JPEG0007710025000115.jpg40133

[0227] A round-bottom flask was charged with <6-e> 20 g (59 mmol), potassium carbonate 13 g (94.5 mmol), and 1-methyl-2-pyrrolidinone 200 ml under a nitrogen atmosphere, and stirred at 150 °C for 12 hours. After completion of the reaction, the reaction mixture was subjected to liquid separation, and the organic layer was concentrated under reduced pressure, separated by column chromatography, and dried. As a result, 13.5 g of <6-f> was obtained. (Yield 72%)

[0228] Synthesis Example 6-(7): Synthesis of <6-g>

[0229] JPEG0007710025000116.jpg42133

[0230] A round-bottom flask was charged with <6-f> 13 g (40.8 mmol), bis(pinacolato)diboron 12.4 g (48.9 mmol), tris(dibenzylideneacetone)palladium 2 g (2.4 mmol), potassium acetate 11.6 g (122 mmol), tricyclohexylphosphine 2.7 g (9.8 mmol), and N,N-dimethylformamide 150 ml under a nitrogen atmosphere, and refluxed. After completion of the reaction, the reaction mixture was subjected to liquid separation, and the organic layer was concentrated under reduced pressure, separated by column chromatography, and dried. As a result, 10.8 g of <6-g> was obtained. (Yield 65%)

[0231] Synthesis Example 6-(8): Synthesis of [H85]

[0232] JPEG0007710025000117.jpg54152

[0233] Except that <6-g> was used instead of <3-d> used in Synthesis Example 3-6, [H85] was synthesized in the same manner. (Yield 65%) MS (MALDI-TOF): m / z 560.21 [M]+

[0234] Synthesis Example 7. Synthesis of [H102] Synthesis Example 7-(1): Synthesis of <7-a>

[0235] JPEG0007710025000118.jpg38104

[0236] <7-a> was obtained in the same manner as in Synthesis Examples 3-1 to 3-3 and Synthesis Examples 4-2 to 4-3, except that dibenzofuran-3-boronic acid was used instead of dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, and methyl 1-iodobenzoate was used instead of methyl 5-bromo-2-iodobenzoate. (Yield: 70%)

[0237] Synthesis Example 7-(2): Synthesis of [H102]

[0238] JPEG0007710025000119.jpg51104

[0239] [H102] was obtained in the same manner as in Synthesis Examples 3-5 to 3-6, except that 1-naphthaleneboronic acid was used instead of phenylboronic acid used in Synthesis Example 3-5, and <7-a> was used instead of <3-d> used in Synthesis Example 3-6. (Yield: 68%) MS (MALDI-TOF): m / z 610.23 [M]+

[0240] Synthesis Example 8. Synthesis of [H54] Synthesis Example 8-(1): Synthesis of <8-a>

[0241] JPEG0007710025000120.jpg39162

[0242] 30 g (0.117 mol) of 1-fluoro-9,9'-dimethylfluorene-2-boronic acid, 30.5 g (0.141 mol) of 2-bromo-1,4-dimethoxybenzene, 2.7 g (0.002 mol) of tetrakistriphenylphosphine palladium, 27.5 g (0.199 mol) of potassium carbonate, 210 ml of toluene, 51 ml of ethanol, and 100 ml of water were charged into a round-bottomed flask and refluxed for 12 hours. After completion of the reaction, the reaction product was separated into layers, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 28 g of <8-a>. (Yield: 72.2%)

[0243] Synthesis Example 8-(2): Synthesis of <8-b>

[0244] JPEG0007710025000121.jpg33162

[0245] Compound <8-b> was obtained in the same manner except that compound <8-a> was used instead of <6-d> used in Synthesis Example 6-5. (Yield 93.2%)

[0246] Synthesis Example 8-(3): Synthesis of <8-c>

[0247] JPEG0007710025000122.jpg31162

[0248] Compound <8-c> was obtained in the same manner except that compound <8-b> was used instead of <6-e> used in Synthesis Example 6-6. (Yield 84.4%)

[0249] Synthesis Example 8-(4): Synthesis of <8-d>

[0250] JPEG0007710025000123.jpg33162

[0251] 19 g (0.063 mol) of <8-c>, 6.5 g (0.082 mol) of pyridine and 190 ml of dichloromethane were charged into a round-bottomed flask and cooled to 0 °C or below in a nitrogen atmosphere. Then, 19.6 g (0.070 mol) of trifluoromethanesulfonic anhydride was slowly added dropwise. After the addition, the reaction solution was warmed to room temperature and stirred for 5 hours. When the reaction was completed, water was added to the reaction solution and stirred, followed by liquid separation. The organic layer was dried and then concentrated under reduced pressure. After concentration, separation by column chromatography gave 23 g of <8-d>. (Yield 84.1%)

[0252] Synthesis Example 8-(5): Synthesis of <8-e>

[0253] JPEG0007710025000124.jpg39159

[0254] 23 g (0.053 mol) of <8-d>, 16.2 g (0.064 mol) of bis(pinacolato)diboron, 0.9 g (0.001 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 13.1 g (0.133 mol) of calcium acetate, and 230 ml of 1,4-dioxane were charged into a round-bottomed flask and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and then filtered through celite. After concentrating the filtrate, it was separated by column chromatography to obtain 17 g of <8-e>. (Yield 77.9%)

[0255] Synthesis Example 8-(6): Synthesis of [H54]

[0256] JPEG0007710025000125.jpg44170

[0257] Except for using <8-e> instead of <3-d> used in Synthesis Example 3-6, it was synthesized in the same manner to obtain 16 g of [H54]. (Yield 78.4%) MS (MALDI-TOF): m / z 560.21 [M]+

[0258] Synthesis Example 9. Synthesis of [H7] Synthesis Example 9-(1): Synthesis of <9-a>

[0259] JPEG0007710025000126.jpg41170

[0260] Except for using dibenzofuran-4-boronic acid instead of dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, it was synthesized in the same manner to obtain 48 g of <9-a> (yield 74%)

[0261] Synthesis Example 9-(2): Synthesis of <9-b>

[0262] JPEG0007710025000127.jpg44133

[0263] Except for using <9-a> instead of <3-a> used in Synthesis Example 3-2, it was synthesized in the same manner to obtain 47 g of <9-b>. (Yield 97.9%)

[0264] Synthesis Example 9-(3): Synthesis of <9-c>

[0265] JPEG0007710025000128.jpg44133

[0266] Except for using <9-b> instead of <3-b> used in Synthesis Example 3-3, it was synthesized in the same manner to obtain 30 g of <9-c>. (Yield 67.1%)

[0267] Synthesis Example 9-(4): Synthesis of <9-d>

[0268] JPEG0007710025000129.jpg50133

[0269] Except for using <9-c> instead of <8-d> used in Synthesis Example 8-5, it was synthesized in the same manner to obtain 27 g of <9-d>. (Yield 79.8%)

[0270] Synthesis Example 9-(5): Synthesis of [H7]

[0271] JPEG0007710025000130.jpg43170

[0272] Except for using <9-d> instead of <3-d> used in Synthesis Example 3-6, it was synthesized in the same manner to obtain 14 g of [H7]. (Yield 62.4%) MS (MALDI-TOF): m / z 560.21 [M]+

[0273] Synthesis Example 10. Synthesis of [H14] Synthesis Example 10-(1): Synthesis of <10-a>

[0274] JPEG0007710025000131.jpg31162

[0275] Except for using 6-bromo-1-methoxydibenzofuran instead of <3-c> used in Synthesis Example 3-4, it was synthesized in the same manner to obtain 43 g of <10-a>. (Yield 95.1%)

[0276] Synthesis Example 10-(2): Synthesis of <10-b>

[0277] JPEG0007710025000132.jpg37164

[0278] Instead of using dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, <10-a> was used, and 2-bromobenzoic acid methyl was used instead of methyl 5-bromo-2-iodobenzoate. Synthesis was carried out in the same manner to obtain 52 g of <10-b>. (Yield 96.1%)

[0279] Synthesis Example 10-(3): Synthesis of <10-c>

[0280] JPEG0007710025000133.jpg40132

[0281] Instead of using <3-a> used in Synthesis Example 3-2, <10-b> was used. Synthesis was carried out in the same manner to obtain 48 g of <10-c>. (Yield 92.3%)

[0282] Synthesis Example 10-(4): Synthesis of <10-d>

[0283] JPEG0007710025000134.jpg40132

[0284] Instead of using <3-b> used in Synthesis Example 3-3, <10-c> was used. Synthesis was carried out in the same manner to obtain 38 g of <10-d>. (Yield 83.8%)

[0285] Synthesis Example 10-(5): Synthesis of <10-e>

[0286] JPEG0007710025000135.jpg40132

[0287] Instead of using <6-d> used in Synthesis Example 6-5, <10-d> was used. Synthesis was carried out in the same manner to obtain 28 g of <10-e>. (Yield 77.1%)

[0288] Synthesis Example 10-(6): Synthesis of <10-f>

[0289] JPEG0007710025000136.jpg44132

[0290] Except for using <10 - e> instead of <8 - c> used in the said Synthesis Example 8 - 4, it was synthesized in the same manner to obtain 35 g of <10 - f>. (Yield 87.5%)

[0291] Synthesis Example 10-(7): Synthesis of <10-g>

[0292] JPEG0007710025000137.jpg54136

[0293] Except for using <10 - f> instead of <8 - d> used in the said Synthesis Example 8 - 5, it was synthesized in the same manner to obtain 26 g of <10 - g>. (Yield 78.3%)

[0294] Synthesis Example 10-(8): Synthesis of [H14]

[0295] JPEG0007710025000138.jpg46170

[0296] Except for using <10 - g> instead of <3 - d> used in the said Synthesis Example 3 - 6, it was synthesized in the same manner to obtain 12 g of [H14]. (Yield 52.4%) MS (MALDI - TOF): m / z 560.21 [M]+

[0297] Synthesis Example 11. Synthesis of [H17] Synthesis Example 11-(1): Synthesis of <11-a>

[0298] JPEG0007710025000139.jpg4671

[0299] Except for using 2 - bromo - 3 - methoxydibenzofuran instead of 6 - bromo - 1 - methoxydibenzofuran in the said Synthesis Example 10 - 1, it was synthesized in the same manner as in Synthesis Examples 10 - 1 to 10 - 7 to obtain 23 g of <11 - a>. (Yield 54.3%)

[0300] Synthesis Example 11-(2): Synthesis of [H17]

[0301] JPEG0007710025000140.jpg50170

[0302] Except for using <11-a> instead of <3-d> used in Synthesis Examples 3-6, it was synthesized in the same manner to obtain 16.7 g of [H17]. (Yield 57.5%) MS (MALDI-TOF): m / z 560.21 [M]+

[0303] Synthesis Example 12. Synthesis of [H90] Synthesis Example 12-(1): Synthesis of <12-a>

[0304] JPEG0007710025000141.jpg49170

[0305] Except for using phenylboronic acid (D5) instead of phenylboronic acid used in Synthesis Examples 3-5, it was synthesized in the same manner to obtain 46 g of <12-a>. (Yield 45.7%)

[0306] Synthesis Example 12-(2): Synthesis of [H90]

[0307] JPEG0007710025000142.jpg52170

[0308] Except for using <12-a> instead of <3-e> used in Synthesis Examples 6-8, it was synthesized in the same manner to obtain 8.7 g of [H90]. (Yield 68.7%) MS (MALDI-TOF): m / z 565.25 [M]+

[0309] Synthesis Example 13. Synthesis of [H51] Synthesis Example 13-(1): Synthesis of [H51]

[0310] JPEG0007710025000143.jpg62170

[0311] Except for using <12-a> instead of <3-e> used in Synthesis Example 4-4, it was synthesized in the same manner to obtain 12.4 g of [H51]. (Yield 75%) MS (MALDI-TOF): m / z 565.25 [M]+

[0312] Examples 1 to 14: Fabrication of Organic Light-Emitting Devices After patterning the ITO glass so that the light-emitting area was 2 mm × 2 mm in size, it was washed. After attaching the ITO glass to a vacuum chamber, the base pressure was set to 1×10 -7 torr, and then, DNTPD (700 Å) and α-NPD (300 Å) were sequentially deposited on the ITO. As the light-emitting layer, after mixing the host compound according to the present invention and the following dopant (BD) compound (1 wt%) and depositing a film (200 Å), [E-1] and [ET5] were deposited in a ratio of 1:1 at 300 Å as the electron transport layer, [E-1] was deposited at 10 Å as the electron injection layer, and Al was deposited at 1000 Å in sequence to manufacture an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA and shown in Tables 1 and 2 below.

[0313] JPEG0007710025000144.jpg58170

[0314] JPEG0007710025000145.jpg48170

[0315] Comparative Examples 1 and 2 For the organic light-emitting device for comparative example, except for using the following Compound 312 (Compound 312 in Korean Patent Publication No. 10-2018-0077887) or [BH1] instead of the compound according to the present invention used as the host in the device structure of the above example, it was fabricated and experimented in the same manner. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA and shown in Tables 1 and 2 below.

[0316] (Compound 312 in Korean Patent Publication No. 2018-0077887) JPEG0007710025000146.jpg4171 JPEG0007710025000147.jpg4864

[0317]

Table 1

[0318] As shown in Table 1 above, the organic light-emitting device according to the present invention exhibits characteristics superior in luminous efficiency to the organic light-emitting device using the compound of Comparative Example 1 according to the prior art, indicating that it has high application potential as an organic light-emitting device.

[0319]

Table 2

[0320] As shown in Table 2 above, the organic light-emitting device according to the present invention exhibits characteristics of high efficiency and long life compared to the organic light-emitting device using the compound of Comparative Example 2 according to the prior art, indicating that it has high application potential as an organic light-emitting device.

[0321] Examples 15 to 19: Fabrication of Organic Light-Emitting Devices Containing a First Light-Emitting Layer and a Second Light-Emitting Layer After patterning the ITO glass so that the light-emitting area becomes 2 mm × 2 mm in size, it was washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1×10 -7 torr, and then, DNTPD (700 Å) and α-NPD (300 Å) were sequentially deposited on the ITO. The light-emitting layer according to the present invention is formed by sequentially forming a first light-emitting layer and a second light-emitting layer. The first light-emitting layer is formed by mixing the host compound according to the present invention and the BD dopant compound (1 wt%) and depositing the film (50 Å). The second light-emitting layer is formed by mixing the following Compound 313 (Compound 313 in Korean Patent Publication No. 2018-0077887) and the BD dopant compound (1 wt%) and depositing the film (150 Å). Then, [E-1] and [ET5] were sequentially deposited at a ratio of 1:1 for 300 Å as the electron transport layer, [E-1] was deposited for 10 Å as the electron injection layer, and Al was deposited for 1000 Å to manufacture an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA and are shown in the following [Table 3].

[0322] Comparative Example 3 For the organic light-emitting device of the comparative example, except that Compound 313 below (Compound 313 in Korean Patent Publication No. 10-2018-0077887) was used instead of the compound according to the present invention used as a host in the device structures of Examples 1 to 14, it was fabricated and experimented in the same manner. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA and shown in Table 3 below.

[0323] (Compound 313 in Korean Patent Publication No. 2018-0077887) JPEG0007710025000150.jpg4668 JPEG0007710025000151.jpg4868

[0324]

Table 3

[0325] As shown in Table 3 above, the organic light-emitting device containing the host compound according to the present invention and the host compound used in the prior art in the first light-emitting layer and the second light-emitting layer respectively shows characteristics superior in light-emitting efficiency to the organic light-emitting device using only Compound 313 according to the prior art as a host material. Thus, it can be confirmed that it has high application potential as an organic light-emitting device. Also, in the case of the organic light-emitting device using two light-emitting layers (double light-emitting layers) containing the host represented by Chemical Formula A or Chemical Formula B according to the present invention in Table 3, it can be seen that the voltage decreases and high efficiency is obtained compared to the organic light-emitting device using a single light-emitting layer containing the host represented by Chemical Formula A or Chemical Formula B according to the present invention in Table 1 or Table 2.

Industrial Applicability

[0326] The organic light-emitting device manufactured using the compound according to the present invention exhibits improved characteristics when applied to an organic light-emitting device because its efficiency and long-life characteristics are improved compared to conventional compounds, and thus has high industrial applicability in the field of organic light-emitting devices and related industries. < / d401> < / d301> < / d101> < / d1>

Claims

1. A compound represented by the following [Chemical Formula A]. [Chemical Formula A] (In the above [Chemical Formula A], A 1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, A 2 and E may each be the same as or different from one another, and each independently is a substituted or unsubstituted aromatic hydrocarbon ring having 6 carbon atoms. Said A 1 Two adjacent carbon atoms in the aromatic ring of said A 2 Two adjacent carbon atoms in the aromatic ring of said A are each condensed with the carbon atom linked to said substituents R 1 and R 2 to form a 5-membered ring, thereby forming a condensed ring respectively. The linking group L 1 ~L 3 may be the same as or different from each other, and each independently is a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, Wherein M is O, The substituent R 1 to R 2 , R 11 to R 12 may be the same as or different from each other, and independently of each other, are each selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. S1 to S3 may be the same or different from each other, and are each an integer of 1 to 3 and independent of each other. When each of these is 2 or more, each linking group L 1 ~L 3 may be the same as or different from each other, x, y, and z may be the same or different and are each independently an integer of 0 or 1, satisfying x + y + z = 1 or x + y + z = 2, In the chemical formula A, A 2 Two adjacent carbon atoms within the ring are bonded to the * of the structural formula Q 1 to form a condensed ring, Said Ar 1 to Ar 3 may be the same as or different from each other, and are each independently represented by the following [Structural Formula C]: [Structural Formula C] R in the structural formula C 21 ~R 30 may be the same or different from each other, and independently of each other, each is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms. Said R 21 ~R 30 Any one of them is a single bond that binds to the linking group L 1 ~L 3 and is In the above [Chemical Formula A], the "substitution" in the "substituted or unsubstituted" means substitution with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms. In the above [Structural Formula C], the "substitution" in the "substituted or unsubstituted" means substitution with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, and an alkylaryl group having 7 to 24 carbon atoms.

2. A in the chemical formula A 1 The compound according to claim 1, wherein A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms.

3. The substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms may be the same or different and is independently selected from any of [Structural Formula 10] to [Structural Formula 21]. The compound according to Claim 2, characterized in that. (In the above [Structural Formula 10] to [Structural Formula 21], "-*" represents a 5-membered ring containing a carbon atom linked to the substituents R 1 and R 2 to form a 5-membered ring, or represents a bonding position for forming a 5-membered ring containing M in the above Structural Formula Q 1 and Q 2 . The aromatic hydrocarbon rings of the above [Structural Formula 10] to [Structural Formula 21] are A 1 ring or A 2 ring, and when they are bonded to Structural Formula Q 1 or Structural Formula Q 2 in the case of bonding, two adjacent carbon atoms among them are bonded to the * of the above Structural Formula Q 1 or bonded to the * of Structural Formula Q 2 to form a condensed ring, In the above [Structural formula 10] to [Structural formula 21], the R is the same as the R defined in claim 1 1 and R 2 are the same, m is an integer from 1 to 8, and when m is 2 or more or R is 2 or more, the respective Rs may be the same as or different from each other.

4. The linking group L in the chemical formula A 1 ~L 3 is each a single bond or any one selected from the following [Structural formula 1] to [Structural formula 5], s1 to s4 are each 1 or 2. The compound according to Claim 1, characterized in that. Hydrogen or deuterium can be bonded to the carbon of the aromatic ring in the linking group.

5. x in the above chemical formula A is 1, and y and z are each 0, or alternatively, y is 1, and x and z are each 0, or alternatively, z is 1, and x and y are each 0. The compound according to Claim 1, characterized in that.

6. The substituent R in the chemical formula A 1 and R 2 may be the same or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. The compound according to claim 1 is characterized by this.

7. R in the structural formula C 21 ~R 23 Any one of them is a single bond connecting to the linking group L 1 ~L 3 and is a single bond Said R 11 to R 12 may be the same or different from each other, and independently of each other, are substituents selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and a halogen group. The compound according to claim 1, characterized in that.

8. R in the structural formula C 21 ~R 30 may be the same as or different from each other, and each independently is any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, L in the structural formula C 1 ~L 3 R not linked to 21 ~R 30 At least one of is selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and the compound according to claim 1 is characterized in that

9. The compound according to claim 1, wherein the compound is any one selected from the group represented by the following H1 to H4, H7, H10 to H21, H25, H32, H33, H38, H39, H44, H48, H51, H53, H54, H60, H61, H65, H68, H71, H72, H76, H79, H81, H83, H85, H89, H90, H93, H95, H96, H102, H103, H106, H107, H110, H114 to H116, H119, H122, H123, H126, H134, H137, H140 to H144, H149, H153, H154, H157 to H159, H164, H169, H171, H172, H174, H177 to H180.

10. The first electrode; A second electrode facing the first electrode; and An organic layer interposed between the first electrode and the second electrode; The organic light-emitting device includes the organic layer containing one or more of the compounds according to any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10, wherein the organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light-emitting layer, an electron transport layer, and an electron injection layer.

12. The organic light-emitting device according to claim 11, wherein the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, the light-emitting layer is composed of a host and a dopant, and the compound is used as the host.

13. The organic light-emitting device according to claim 12, wherein at least one selected from the following [Chemical Formula D1] to [Chemical Formula D10] is used as the dopant. (In the above [Chemical Formula D1] and [Chemical Formula D2], A 31 , A 32 , E 1 and F 1 may be the same or different from each other, and independently of one another, are a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms, Said A 31 Two adjacent carbon atoms within the aromatic ring of said A 32 Two adjacent carbon atoms within the aromatic ring of said A are each linked to the carbon atom to which the substituents R 51 and R 52 are attached to form a 5-membered ring, thereby forming a fused ring respectively The linking group L 21 to L 32 may be the same or different from each other, and independently of each other, is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, and is selected from among Said W and W' are any one selected from N-R 53 , CR 54 R 55 , SiR 56 R 57 , GeR 58 R 59 , O, S, Se, and is any one selected therefrom The substituent R 51 to R 59 , Ar 21 to Ar 28 may be the same or different from each other, and independently of one another, are each hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group, and are each selected from among them, Said R 51 and R 52 can be connected to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring can be substituted with at least one heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te. The p11 to p14, r11 to r14, and s11 to s14 are each an integer from 1 to 3, and when each of these is 2 or more, the respective linking groups L 21 ~L 32 may be the same as or different from each other, The x1 is 1, and y1, z1, and z2 may be the same or different and are each independently an integer of 0 to 1. said Ar 21 and Ar 22 、Ar 23 and Ar 24 、Ar 25 and Ar 26 、and Ar 27 and Ar 28 can be connected to each other to form a ring, In the chemical formula D1, A 32 Two adjacent carbon atoms within the ring are bonded to the * of the structural formula Q 11 to form a condensed ring, In the chemical formula D2, the A 31 Two adjacent carbon atoms within the ring are bonded to the * of the structural formula Q 12 to form a condensed ring, and the A 32 Two adjacent carbon atoms within the ring can be bonded to the * of the structural formula Q 11 to form a condensed ring. (In the [Chemical Formula D3], Said X 1 is any one selected from B, P, and P=O, Said T 1 to T 3 may be the same as or different from each other, and each independently is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms, Said Y 1 is any one selected from N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 and is any one selected therefrom, Said Y 2 is any one selected from N-R 66 , CR 66 R 68 , O, S, SiR 69 R 70 and is any one selected therefrom, Said R 61 to R 70 may be the same as or different from each other, and independently of each other, are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, or a halogen group, and said R 61 to R 70 can each be bonded to at least one ring selected from said T 1 to T 3 to further form an alicyclic or aromatic monocyclic or polycyclic ring. ) (In the [Chemical Formula D4] and [Chemical Formula D5], Said X 2 is any one selected from B, P, and P=O, Said T 4 to T 6 is the same as T in [Chemical Formula D3] 1 to T 3 and Said Y 4 is any one selected from N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 and is any one selected therefrom, Said Y 5 is either N-R 66 , CR 66 R 68 , O, S, SiR 69 R 70 selected from any of them, Said Y 6 is any one selected from N-R 71 , CR 72 R 73 , O, S, SiR 74 R 75 and is any one selected therefrom, Said R 61 to R 75 is the same as said R 61 to R 70 in [Chemical Formula D3].) (wherein X 3 is any one selected from B, P, and P=O, The said T 7 to T 9 is the same as T in [Chemical Formula D3] 1 to T 3 and Said Y 6 is any one selected from N-R 61 CR 62 R 63 O, S, SiR 64 R 65 and is any one selected therefrom the substituent R 61 ~R 65 、R 71 ~R 72 are each the R 61 ~R 70 in [Chemical Formula D3], and are the same as Said R 71 and R 72 are each connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, or are combined with the T 7 ring or the T 9 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring.) (In the [Chemical Formula D8] to [Chemical Formula D10], The X is any one selected from B, P, and P=O. Said Q 1 ~Q 3 are respectively the same as T 1 ~T 3 in [Chemical Formula D3], and The linking group Y is N—R 3 , CR 4 R 5 , O, S, Se, and is selected from any of them The substituent R 3 to R 5 is respectively the same as the R 61 to R 70 in [Chemical Formula D3] Said R 3 ~R 5 each combines with said Q 2 ring or Q 3 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring, Said R 4 and R 5 can each be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, The ring formed by Cy1 is a nitrogen (N) atom, Q to which the nitrogen (N) atom is bonded 1 aromatic carbon atoms in the ring, and Q bonded to Cy1 1 except for the aromatic carbon atoms in the ring, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms In the chemical formula D9, The "Cy2" can be added to the Cy1 to form a saturated hydrocarbon ring, and the ring formed by the Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms excluding the carbon atoms contained in the Cy1. In the chemical formula D10, The ring formed by the Cy3 binds to the Q that binds to the Cy3 3 Q binds to an aromatic carbon atom or a nitrogen (N) atom within the ring 3 is an alkylene group having 1 to 10 carbon atoms, which may be substituted or unsubstituted, excluding the aromatic carbon atom, nitrogen (N) atom within the ring, and the carbon atom within the Cy1 to which the nitrogen (N) atom binds Here, the "substitution" in the "substituted or unsubstituted" in the above [Chemical Formula D1] to [Chemical Formula D10] means substitution with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 6 to 24 carbon atoms, heteroarylamino group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms.

14. A first electrode, A second electrode facing the first electrode, and Between the first electrode and the second electrode, a first light-emitting layer including a first host and a first dopant, and a second light-emitting layer including a second host and a second dopant are sequentially included, An organic light-emitting device, wherein at least one of the first host and the second host contains one or more compounds according to any one of Claims 1 to 9.

15. The organic light-emitting device according to Claim 14, wherein at least one of a hole transport layer and a hole injection layer is provided between the first electrode and the first light-emitting layer, and at least one of an electron transport layer and an electron injection layer is provided between the second light-emitting layer and the second electrode.

16. The organic light-emitting device according to Claim 14, wherein the first light-emitting layer contains one or more compounds according to any one of Claims 1 to 9.

17. The organic light-emitting device according to Claim 16, wherein an anthracene derivative represented by the following Chemical Formula E is used as a host in the second light-emitting layer. [Chemical Formula E] (In the above [Chemical Formula E], The substituent R 41 to R 48 may be the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. the substituent Ar 5 and Ar 6 may be the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, The linking group L 1 is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, wherein n is an integer of 1 to 2, and when n is 2 or more, each linking group L 1 may be the same as or different from each other The "substitution" in the "substituted or unsubstituted" in the above [Chemical Formula E] means substitution with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 6 to 24 carbon atoms, heteroarylamino group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, and aryloxy group having 6 to 24 carbon atoms.)

18. The anthracene derivative represented by the above [Chemical Formula E] is an anthracene compound represented by the following Chemical Formula E-1 or Chemical Formula E-2, and the organic light-emitting device according to claim 17 is characterized in that. (In the above [Chemical Formula E-1] and [Chemical Formula E-2], The substituent R 41 to R 48 , R 49 to R 55 may be the same or different from each other, and independently of one another, are each selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group. The substituent Ar 5 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, The linking group L 11 is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, wherein k is an integer of 1 to 2, and when k is 2 or more, each linking group L 11 may be the same as or different from each other, The "substitution" in the "substituted or unsubstituted" in the above [Chemical Formula E-1] and [Chemical Formula E-2] means substitution with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 6 to 24 carbon atoms, heteroarylamino group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, and aryloxy group having 6 to 24 carbon atoms.)

19. In the first light-emitting layer or the second light-emitting layer, at least one selected from the following Chemical Formulas D1 to D10 may be the same or different and may be used independently of each other, and the organic light-emitting device according to claim 17 is characterized in that. (The above [Chemical Formula D1] to [Chemical Formula D10] are the same as those described in claim 13, respectively.)

20. The organic light-emitting device according to claim 11, wherein one or more layers selected from the respective layers are formed by a vapor deposition process or a solution process.

21. The organic light-emitting device according to claim 10, wherein the organic light-emitting device is used in any device selected from a flat panel display device, a flexible display device, a single-color or white flat panel lighting device, and a single-color or white flexible lighting device.

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