Novel Organic Compounds and Organic Light-Emitting Devices Containing the Same

Abstract

The present invention relates to a novel heterocyclic compound that can be used in an organic light-emitting device and an organic light-emitting device containing 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 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, low-voltage driving, and long-life device characteristics, and an organic light-emitting device including the same.

Background Art

[0002] An organic light-emitting diode (OLED) is a display that utilizes the self-luminous phenomenon. It 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. It 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 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 into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. The light-emitting materials can be classified into high molecular weight types and low molecular weight types according to their molecular weights, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to their light-emitting mechanisms.

[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 interactions, the color purity decreasing, and 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, heterocyclic compounds have been studied as host compounds in such light-emitting layers. As related prior art, Korean Patent Publication No. 10-2016-0089693 (July 28, 2016) describes a compound having a structure in which a dibenzofuran ring is bonded to an anthracene ring and an organic light-emitting device containing 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 containing the same.

[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 device characteristics of high efficiency, low-voltage driving, 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 organic 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) with high efficiency, low-voltage driving, and long lifespan by applying the organic 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 an organic compound represented by the following [Chemical Formula A] or [Chemical Formula B].

[0012] JPEG0007684399000001.jpg65170

[0013] In the above [Chemical Formula A] and [Chemical Formula B], the R 1 ~R 14may 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 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 alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 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, a cyano group, a nitro group, and a halogen group, the linking group L 1 and L 2 may be the same as or different from each other, and each independently 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, n1 and n2 may be the same as or different from each other, and each independently is an integer from 0 to 2. However, when each of them is 2, the respective linking groups L 1 and L 2 may be the same as or different from each other, R and R’ 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 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 alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 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, a cyano group, a nitro group, and a halogen group, n3 and n4 may be the same or different from each other, and are each independently an integer from 1 to 9. However, when each of these is 2 or more, each of R and R’ may be the same as or different from each other. In the “substituted or unsubstituted” in the above [Chemical Formula A] and [Chemical Formula B], “substituted” 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 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.

Advantages of the Invention

[0014] When the novel organic compound represented by the above Chemical Formula A or Chemical Formula B 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 that exhibits higher efficiency, lower voltage driving, and longer lifespan compared to the organic light-emitting device according to the prior art.

Brief Description of the Drawings

[0015]

Figure 1

Embodiments for Carrying Out the Invention

[0016] The present invention will be described in more detail below. In each of the drawings 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 shown omitting those that do not show the characteristic configurations, so it is not limited to the drawings.

[0017] Also, the sizes and thicknesses of the respective configurations shown are arbitrarily shown for convenience of explanation, so the present invention is not necessarily limited to the illustrations, and the thicknesses are shown enlarged to clearly represent a plurality of layers and regions in the drawings. And, in the drawings, for convenience of explanation, the thicknesses of some layers and regions are exaggeratedly shown. When a part such as a layer, film, region, plate, etc. 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 between them.

[0018] Also, 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.

[0019] The present invention provides an organic compound represented by the following [Chemical Formula A] or [Chemical Formula B].

[0020] JPEG0007684399000002.jpg65170

[0021] In the above [Chemical Formula A] and [Chemical Formula B], Said R 1 ~R 14may 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 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 alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 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, a cyano group, a nitro group, and a halogen group, the linking group L 1 and L 2 may be the same as or different from each other, and each independently 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, n1 and n2 may be the same as or different from each other, and each independently is an integer of 0 to 2, but when each of them is 2, the respective linking groups L 1 and L 2 may be the same as or different from each other, R and R’ 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 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 alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 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, a cyano group, a nitro group, and a halogen group, The n3 and n4 may be the same or different from each other, and are each independently an integer from 1 to 9. However, when each of these is 2 or more, each of the R and R’ may be the same as or different from each other. In the “substituted or unsubstituted” in the [Chemical Formula A] and [Chemical Formula B], “substituted” 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 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.

[0022] On the other hand, considering the ranges of the alkyl group or aryl group in the “substituted or unsubstituted alkyl group having 1 to 30 carbon atoms”, “substituted or unsubstituted aryl group having 5 to 50 carbon atoms”, etc. in the present invention, the ranges of the number of carbon atoms of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms each mean the total number of carbon atoms constituting the alkyl moiety or aryl moiety when regarded as unsubstituted without considering the portion substituted with 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.

[0023] The aryl group, which is a substituent used in the compounds of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen atom. When the aryl group has a substituent, it can be fused with an adjacent substituent to further form a ring.

[0024] 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 deuterium atom, halogen atom, hydroxy group, nitro group, cyano group, silyl group, amino group (-NH 2 , -NH(R), -N(R’)(R’’), where R’ and R’’ are independently alkyl groups having 1 to 10 carbon atoms, and in this case, it is called an “alkylamino group”). The aryl group can be substituted with an 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.

[0025] The heteroaryl group, which is a substituent used in the compounds of the present invention, means a cyclic aromatic system having 2 to 24 carbon atoms containing one, two or three heteroatoms selected from N, O, P, Si, S, Ge, Se, Te, and the remaining ring atoms being carbon. 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.

[0026] 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. The aromatic heterocyclic ring is preferably such that 1 to 3 of the aromatic carbons in the aromatic hydrocarbon can be substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, and Se.

[0027] The alkyl group, which is a substituent used in 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.

[0028] In the cycloalkyl group, which is a substituent used in the compound 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.

[0029] 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 terminal 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.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] 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 in the alkylene group can be substituted with substituents similar to those in the case of the aryl group.

[0034] 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, and the diheteroarylamino group in the present invention means an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom. Moreover, the aryl(heteroaryl)amino group means an amine group in which an aryl group and a heteroaryl group are each bonded to a nitrogen atom.

[0035] On the other hand, more preferable examples of the "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B] for "substitution" include deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 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.

[0036] In the present invention, the organic compound represented by the [Chemical Formula A] is characterized in that a linking group L1 is bonded to a specific position in a substituted or unsubstituted pyrene ring (see the following Structural Formula C), and the 1-position of a substituted or unsubstituted dibenzofuran group is bonded to the linking group L1. Further, the organic compound represented by the [Chemical Formula B] is characterized in that a linking group L2 is bonded to a specific position in a substituted or unsubstituted pyrene ring (see the following Structural Formula C), and the 2-position of a substituted or unsubstituted dibenzofuran group is bonded to the linking group L2.

[0037] [Structural Formula C] JPEG0007684399000003.jpg29134

[0038] In the [Chemical Formula A] and [Chemical Formula B] according to the present invention, the compound represented by the Chemical Formula A can contain at least one deuterium, and the compound represented by the Chemical Formula B can contain at least one deuterium.

[0039] More specifically, at least one of R 1 ~R 7 in the [Chemical Formula A] is a substituent containing deuterium, and at least one of R 8 ~R 14 in the [Chemical Formula B] can be a substituent containing deuterium.

[0040] Also, in the present invention, when the compound represented by the Chemical Formula A can contain at least one deuterium and the compound represented by the Chemical Formula B can contain at least one deuterium, at least one R in the [Chemical Formula A] is a substituent containing deuterium, and at least one R' in the [Chemical Formula B] can be a substituent containing deuterium.

[0041] Also, as an example of an embodiment according to the present invention, R 1 ~R 14, R, and R’ may be the same or different from each other and, independently of each other, may 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 heteroaryl group having 2 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.

[0042] Also, as an example of an embodiment of the present invention, R in the above [Chemical Formula A] 1 ~R 7 At least one of them may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and at least one of R in the above [Chemical Formula B] 8 ~R 14 May be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

[0043] As an example of an embodiment of the present invention, the linking groups L in the above Chemical Formula A and Chemical Formula B 1 And L 2 May each be a single bond or may be any selected from the following [Structural Formula 1] to [Structural Formula 5].

[0044] JPEG0007684399000004.jpg57136

[0045] Hydrogen or deuterium can be bonded to the carbon of the aromatic ring in the above [Structural Formula 1] to [Structural Formula 5].

[0046] Also, as an example of an embodiment of the present invention, the linking groups L 1 And L 2 May each be a single bond.

[0047] Also, as an example of an embodiment of the present invention, n3 and n4 in the above Chemical Formula A and Chemical Formula B may each be 1. Also, as an example of an embodiment according to the present invention, at least one R in the [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and at least one R' in the [Chemical Formula B] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. In this case, preferably, n3 and n4 in the Chemical Formula A and Chemical Formula B are each 1, R in the [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and R' in the [Chemical Formula B] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

[0048] Also, as an example of an embodiment according to the present invention, the organic compound represented by the [Chemical Formula A] or [Chemical Formula B] may be a compound represented by any of the following [Chemical Formula A-1] or [Chemical Formula B-1].

[0049] JPEG0007684399000005.jpg59170

[0050] At this time, in the [Chemical Formula A-1] and [Chemical Formula B-1], the substituents R 1 ~R 14 the linking group L 1 and L 2 n1 and n2 are the same as those defined in the [Chemical Formula A] or [Chemical Formula B] above, and the substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

[0051] Also, as an example of an embodiment according to the present invention, n3 and n4 in the Chemical Formula A and Chemical Formula B are each 1, and at least one of R 1 ~R 7 among R is a deuterium-substituted aryl group having 6 to 18 carbon atoms, and at least one of R 8 ~R 14 among R' and R' may be a deuterium-substituted aryl group having 6 to 18 carbon atoms.

[0052] Further, as an example of an embodiment according to the present invention, n3 and n4 in the chemical formula A and the chemical formula B are each 1, R in the [chemical formula A] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, and R' in the [chemical formula B] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

[0053] Further, the compound represented by the [chemical formula A] or [chemical formula B] according to the present invention may be any compound selected from chemical formulas 1 to 240.

[0054] JPEG0007684399000006.jpg222170JPEG0007684399000007.jpg225170JPEG0007684399000008.jpg229170JPEG0007684399000009.jpg209170JPEG0007684399000010.jpg217170JPEG0007684399000011.jpg210170JPEG0007684399000012.jpg231170JPEG0007684399000013.jpg223170JPEG0007684399000014.jpg234170JPEG0007684399000015.jpg216170JPEG0007684399000016.jpg222170JPEG0007684399000017.jpg223170JPEG0007684399000018.jpg229170JPEG0007684399000019.jpg233170JPEG0007684399000020.jpg227170JPEG0007684399000021.jpg238170

[0055] 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 [chemical formula A] or [chemical formula B] according to the present invention.

[0056] On the one 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".

[0057] At this time, the organic layer in the organic light-emitting device of the present invention can contain 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.

[0058] As a more preferred embodiment of the present invention, in the present invention, the organic layer intervening between the first electrode and the second electrode contains 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 material in the light-emitting layer.

[0059] In addition, in the present invention, as the dopant compound used in the light-emitting layer, at least one compound represented by any of the following [Chemical Formula D1] to [Chemical Formula D10] can be included.

[0060] JPEG0007684399000022.jpg237165

[0061] 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 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. The two adjacent carbon atoms in the aromatic ring of the above A 31 and the 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 atoms linked to the substituents R 51 and R 52 respectively. The linking group L21 ~L 32 may be the same or different from each other, and are independently 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, wherein W and W’ may be the same or different from each other, and are independently N-R 53 , CR 54 R 55 , SiR 56 R 57 , GeR 58 R 59 and are each independently selected from O, S, Se, wherein the substituents R 51 ~R 59 , Ar 21 ~Ar 28may 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, provided that said 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 may be substituted with at least one heteroatom selected from N, O, P, Si, S, Ge, Se, Te, said p11 to p14, r11 to r14 and s11 to s14 are each an integer of 1 to 3, and when each of these is 2 or more, each linking group L 21 ~L 32 may be the same as or different from each other, said x1 is 1, and y1, z1 and z2 may be the same as or different from each other and are each an integer of 0 to 1 independently of each other, said Ar 21 and Ar 22 、Ar 23 and Ar 24 、Ar 25 and Ar26 and Ar 27 and Ar 28 can be connected to each other to form a ring, A in the chemical formula D1 32 Two adjacent carbon atoms in the ring are bonded to the * of the structural formula Q 11 to form a condensed ring, A in the chemical formula D2 31 Two adjacent carbon atoms in 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 in the ring are bonded to the * of the structural formula Q 11 to form a condensed ring.)

[0062] JPEG0007684399000023.jpg48129

[0063] In the [chemical formula D3], the X 1 is any one selected from B, P, and P=O, the T1 to T3 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, the Y 1 is N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 any one selected from among, the Y 2 is N- R66 , CR 67 R 68 , O, S, SiR 69 R 70 any one selected from among, the R 61 ~R 70may 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 the said R 61 ~R 70 can each be bonded to one or more rings selected from among the said T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0064] JPEG0007684399000024.jpg58129

[0065] In the said [Chemical formula D4] and [Chemical formula D5], the said X 2 is any one selected from B, P, and P=O, the said T4 to T6 are the same as T1 to T3 in [Chemical formula D3], the said Y 4 is N-R 61 、CR 62 R 63 、O、S、SiR 64 R 6 5, and is any one selected from among them, the said Y 5 is N-R 66 、CR 67 R 68 、O、S、SiR 69 R 70 and is any one selected from among them, the said Y 6 is N-R71 、CR 72 R 73 、O, S, SiR 74 R 75 is any one selected from the following, said R 61 ~R 75 is the same as said R 61 ~R 70 in [Chemical formula D3].

[0066] JPEG0007684399000025.jpg53129

[0067] said X 3 is any one selected from B, P, P=O, said T7~T9 are the same as T1~T3 in [Chemical formula D3], said Y 6 is N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 is any one selected from the following, said substituent R 61 ~R 65 、R 71 ~R 72 are respectively the same as said R 61 ~R 70 in [Chemical formula D3], but said R 71 and R 72 can be 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.

[0068] JPEG0007684399000026.jpg92129

[0069] In said [Chemical formula D8]~[Chemical formula D10], said X is any one selected from B, P, P=O, said Q 1 ~Q 3is the same as T1 to T3 in [Chemical Formula D3], respectively, the linking group Y is N-R 3 , CR 4 R 5 and is any one selected from O, S, and Se, the substituents R 3 ~R 5 are the same as the R 61 ~R 70 in [Chemical Formula D3], respectively, but the R 3 ~R 5 are each bonded to the Q 2 ring or Q 3 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring, the R 4 and R 5 can be further connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, the ring formed by Cy1 is an alkylene group having 1 to 10 carbon atoms, which is unsubstituted or substituted, excluding a nitrogen (N) atom, an aromatic carbon atom in the Q 1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q 1 ring to which Cy1 is bonded, in the chemical formula D9, Cy2 can be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is an alkylene group having 1 to 10 carbon atoms, which is unsubstituted or substituted, excluding the carbon atoms contained in Cy1, in the chemical formula D10, the ring formed by Cy3 is an alkylene group having 1 to 10 carbon atoms, which is unsubstituted or substituted, excluding an aromatic carbon atom in the Q 3 ring to which Cy3 is bonded, an aromatic carbon atom in the Q 3 ring to which the nitrogen (N) atom is bonded, the nitrogen (N) atom, and a carbon atom in Cy1 to which the nitrogen (N) atom is bonded.

[0070] Here, in the “substituted or unsubstituted” in the above [Chemical Formula D1] to [Chemical Formula D10], “substituted” 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, 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. More preferable examples include 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 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, heteroalkyl group having 1 to 12 carbon atoms, aryl group having 6 to 18 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, alkylaryl group having 7 to 20 carbon atoms, heteroaryl group having 2 to 18 carbon atoms, heteroarylalkyl group having 2 to 18 carbon atoms, alkoxy group having 1 to 12 carbon atoms, alkylamino group having 1 to 12 carbon atoms, diarylamino group having 12 to 18 carbon atoms, diheteroarylamino group having 2 to 18 carbon atoms, aryl(heteroaryl)amino group having 7 to 18 carbon atoms, alkylsilyl group having 1 to 12 carbon atoms, arylsilyl group having 6 to 18 carbon atoms, aryloxy group having 6 to 18 carbon atoms, and arylthionyl group having 6 to 18 carbon atoms.

[0071] Further, in the case of the boron compound represented by any one of the above [Chemical Formula D3] to [Chemical Formula D10] among the dopant compounds according to the present invention, the above T1 to T9 or Q1 ~Q 3 Examples of substituents that can be substituted on the aromatic hydrocarbon ring or aromatic heterocyclic ring of ~Q include 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. Here, the alkyl group or aryl group in 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 include 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. The alkyl group or aryl group in 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.

[0072] 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 compound represented by any one of the above [Chemical Formula D1] to [Chemical Formula D2] are as follows <d1> ~ <d239>Compounds represented by any of the following are included.

[0073] JPEG0007684399000027.jpg215170JPEG0007684399000028.jpg214170JPEG0007684399000029.jpg207170JPEG0007684399000030.jpg206170JPEG0007684399000031.jpg211170JPEG0007684399000032.jpg207170JPEG0007684399000033.jpg221170JPEG0007684399000034.jpg225170JPEG0007684399000035.jpg208170JPEG0007684399000036.jpg211170JPEG0007684399000037.jpg238170JPEG0007684399000038.jpg240170JPEG0007684399000039.jpg209170JPEG0007684399000040.jpg225170JPEG0007684399000041.jpg227170JPEG0007684399000042.jpg125170

[0074] 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.

[0075] JPEG0007684399000043.jpg246170JPEG0007684399000044.jpg212170

[0076] 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], [Chemical Formula D5], [Chemical Formula D8] to [Chemical Formula D10] can be a compound represented by any one selected from the following [D201] to [D476].

[0077] JPEG0007684399000045.jpg223170JPEG0007684399000046.jpg223170JPEG0007684399000047.jpg238170JPEG0007684399000048.jpg240170JPEG0007684399000049.jpg243170JPEG0007684399000050.jpg232170JPEG0007684399000051.jpg236170JPEG0007684399000052.jpg238170JPEG0007684399000053.jpg227170JPEG0007684399000054.jpg213170JPEG0007684399000055.jpg220170JPEG0007684399000056.jpg239170JPEG0007684399000057.jpg255168JPEG0007684399000058.jpg226170

[0078] In the present invention, among the dopant compounds in the light-emitting layer, the compound represented by either [Chemical Formula D6] or [Chemical Formula D7] is the following <d501> ~ <d587>It can be a compound represented by any one selected from among them.

[0079] JPEG0007684399000059.jpg248170JPEG0007684399000060.jpg229170JPEG0007684399000061.jpg218170JPEG0007684399000062.jpg237170JPEG0007684399000063.jpg212170JPEG0007684399000064.jpg145170

[0080] At this time, the content of the dopant in the light-emitting layer can usually be selected from 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.

[0081] In addition to the dopant and the host, the light-emitting layer can further contain various hosts and various dopant substances.

[0082] Hereinafter, an organic light-emitting device according to an embodiment of the present invention will be described with reference to the drawings.

[0083] FIG. 1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.

[0084] As shown in FIG. 1, an organic light-emitting device according to an embodiment of the present invention is an organic light-emitting device sequentially 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. Using the anode as the first electrode and the cathode as the second electrode, a hole transport layer is included between the anode and the light-emitting layer, and an electron transport layer is included between the light-emitting layer and the cathode, which corresponds to an organic light-emitting device.

[0085] In addition, an organic light-emitting device according to an embodiment of the present invention can include a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron injection layer 70 can be included between the electron transport layer 60 and the cathode 80.

[0086] Next, with reference to FIG. 1, the organic light-emitting device of the present invention and its manufacturing method will be described.

[0087] 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 used in a normal organic EL device is used, but it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the anode electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 )), zinc oxide (ZnO), etc. are used.

[0088] 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. Then, 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.

[0089] The material of the hole injection layer is not particularly limited as long as it is commonly used in the art and can be used. 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.

[0090] In addition, 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) can be used. However, the present invention is not necessarily limited thereto.

[0091] On the other hand, in the present invention, an electron blocking layer can be further formed on the hole transport layer. The electron blocking layer is a layer for preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole transport layer, thereby improving the lifetime and efficiency of the device. It can be formed at an appropriate position between the light emitting layer and the hole injection layer, and preferably, it can be formed between the light emitting layer and the hole transport layer.

[0092] Next, the light emitting layer 50 can be laminated on the hole transport layer 40 or the electron blocking layer by a vacuum evaporation method or a spin coating method. Here, the light emitting layer can be composed of a host and a dopant, and the materials constituting these are as described above.

[0093] In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 Å.

[0094] On the other hand, an electron transport layer 60 is deposited on the light emitting layer by a vacuum evaporation method or a spin coating method.

[0095] In the present invention, as the material of the electron transport layer, it has a function of stably transporting electrons injected from the electron injection electrode (cathode), and known electron transport substances can be used. Examples of known electron transport substances include quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq 3 )、Liq、TAZ、BAlq、beryllium bis(benzoquinolin-10-olate:Bebq 2 ) Materials such as compound 201, compound 202, BCP, PBD which is an oxadiazole derivative, BMD, and BND can also be used, but are not limited thereto.

[0096] JPEG0007684399000065.jpg184170

[0097] 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 a function of facilitating the injection of electrons from the cathode, can be laminated on the electron transport layer. There is no particular limitation on the material.

[0098] As the material for forming the electron injection layer, any substance known as a material for forming an electron injection layer such as CsF, NaF, LiF, Li 2 O, BaO can be used. The deposition 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.

[0099] The thickness of the electron injection layer can be about 1 Å to about 100 Å, 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.

[0100] In addition, in the present invention, for the cathode, a substance with a small work function can be used for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof such as aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) can be used, or a transmissive cathode using ITO or IZO can be used.

[0101] 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.

[0102] In addition, in the present invention, one or more layers selected from among the respective layers can be formed by a single-molecule vapor deposition process or a solution process.

[0103] Here, the vapor deposition process means a method of forming a thin film by evaporating a substance used as a material for forming each of the layers by heating or the like in a vacuum or low-pressure state, and the solution process means mixing a substance used as a material for forming each of the layers with a solvent and forming a thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating.

[0104] In addition, the organic light-emitting device in the present invention can be used in any one device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device.

[0105] Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are for more specifically explaining the present invention. It is obvious to those having ordinary knowledge in the art that the scope of the present invention is not limited by these examples.

[0106] (Example) Synthesis Example 1. Synthesis of Chemical Formula 19 Synthesis Example 1-1. Synthesis of <1-a>

[0107] [Reaction formula 1] JPEG0007684399000066.jpg40144

[0108] A 3000 ml 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, tetrakis(triphenylphosphine)palladium (Pd[PPh 3 4 ) 6.4 g (0.006 mol), 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 dehydrated. Then, after concentration under reduced pressure, it was separated by column chromatography to obtain <1-a> 45.4 g (yield 45.7%).

[0109] Synthesis Example 1-2. Synthesis of <1-b>

[0110] [Reaction Formula 2] JPEG0007684399000067.jpg43144

[0111] A 500 ml round-bottom flask was purged with nitrogen, and 20 g (0.076 mol) of 6-bromo-1-dibenzofuranol, 11.6 g (0.091 mol) of phenylboronic acid (D5), tetrakis(triphenylphosphine)palladium (Pd[PPh 3 4 ) 1.8 g (0.002 mol), 17.9 g (0.129 mol) of potassium carbonate, 140 ml of toluene, 35 ml of ethanol and 65 ml of water were added, and the mixture was refluxed for 5 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate and water, and the organic layer was dehydrated. After concentrating the organic layer under reduced pressure, it was recrystallized from ethyl acetate and heptane to obtain <1-b> 15.2 g (yield 75.4%).

[0112] Synthesis Example 1-3. Synthesis of <1-c>

[0113] [Reaction Formula 3] JPEG0007684399000068.jpg39144​​

[0114] A 500 ml round-bottom flask was purged with nitrogen, charged with <1-b>15.2 g (0.058 mol), 6 g (0.076 mol) of pyridine and 150 ml of dichloromethane, and cooled to a temperature of 0 °C or lower. After cooling, 18.1 g (0.064 mol) of trifluoromethanesulfonic anhydride was slowly added dropwise. After the addition, the reaction solution was warmed to room temperature and stirred until the reaction was complete. When the reaction was complete, it was extracted with dichloromethane and water, the organic layer was dried, and then distilled under reduced pressure and separated by column chromatography to obtain <1-c>20 g (yield 87.3%).

[0115] Synthesis Example 1-4. Synthesis of <1-d>_

[0116] [Reaction formula 4] JPEG0007684399000069.jpg46144

[0117] A 300 ml round-bottom flask was purged with nitrogen, charged with <1-c>20 g (0.050 mol), 16.6 g (0.065 mol) of bis(pinacolato)diboron, 0.8 g (0.001 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 9.9 g (0.101 mol) of calcium acetate and 200 ml of 1,4-dioxane, and refluxed for 12 hours. When the reaction was complete, the reaction solution was cooled to room temperature, filtered through celite, the filtrate was concentrated, and then separated by column chromatography to obtain <1-d>14.8 g (yield 78.4%).

[0118] Synthesis Example 1-5. Synthesis of [Chemical Formula 19]

[0119] [Reaction formula 5] JPEG0007684399000070.jpg46170

[0120] A 300 ml round-bottom flask was purged with nitrogen, and <1-a> 10.7 g (0.030 mol), <1-d> 13.7 g (0.036 mol), 0.7 g (0.001 mol) of tetrakistriphenylphosphine palladium, 7.4 g (0.053 mol) of potassium carbonate, 80 ml of toluene, 20 ml of ethanol and 26 ml of water were added, and the mixture was refluxed for 4 hours. After the reaction was completed, it was cooled to room temperature and extracted with ethyl acetate and water. After the organic layer was dried, it was concentrated and separated by column chromatography to obtain 8.4 g (yield 53.4%) of [Chemical Formula 19].

[0121] MS (MALDI-TOF): m / z 525.21 [M] +

[0122] Synthesis Example 2. Synthesis of Chemical Formula 34 Synthesis Example 2-1. Synthesis of <2-a>

[0123] [Reaction Formula 6] JPEG0007684399000071.jpg51170

[0124] Compound <2-a> (yield 79.3%) was obtained in the same manner except that phenylboronic acid (D5) was used instead of the phenylboronic acid used in Synthesis Example 1-1.

[0125] Synthesis Example 2-2. Synthesis of <2-b>

[0126] [Reaction Formula 7] JPEG0007684399000072.jpg40170

[0127] Compound <2-b> (yield 54%) was obtained in the same manner except that 1,7-dibromodibenzofuran was used instead of 6-bromo-1-dibenzofuran used in Synthesis Example 1-2.

[0128] Synthesis Example 2-3. Synthesis of <2-c>_

[0129] [Reaction Formula 8] JPEG0007684399000073.jpg40170

[0130] Compound <2-c> (yield: 72.8%) was obtained in the same manner as in Synthesis Examples 1-4, except that <2-b> was used instead of <1-c>.

[0131] Synthesis Example 2-4. Synthesis of [Chemical Formula 34]

[0132] [Reaction Formula 9] JPEG0007684399000074.jpg46170

[0133] Compound [Chemical Formula 34] (yield: 63.7%) was obtained in the same manner as in Synthesis Example 1-5, except that <2-a> was used instead of <1-a> and <2-c> was used instead of <1-d>.

[0134] MS (MALDI-TOF): m / z 530.25 [M] +

[0135] Synthesis Example 3. Synthesis of Chemical Formula 52 Synthesis Example 3-1. Synthesis of <3-a>

[0136] [Reaction Formula 10] JPEG0007684399000075.jpg30170

[0137] Compound <3-a> (yield: 72.0%) was obtained in the same manner as in Synthesis Example 1-2, except that 6-bromo-2-dibenzofuranol was used instead of 6-bromo-1-dibenzofuranol and phenylboronic acid was used instead of phenylboronic acid (D5).

[0138] Synthesis Example 3-2. Synthesis of <3-b>_

[0139] [Reaction Formula 11] JPEG0007684399000076.jpg30170

[0140] Compound <3-b> (yield 85.2%) was obtained in the same manner as in Synthesis Examples 1-3, except that <3-a> was used instead of <1-b>. Synthesis Example 3-3. Synthesis of <3-c>

[0141] [Reaction Scheme 12] JPEG0007684399000077.jpg30170

[0142] Compound <3-c> (yield 76.8%) was obtained in the same manner as in Synthesis Examples 1-4, except that <3-b> was used instead of <1-c>.

[0143] Synthesis Example 3-4. Synthesis of [Chemical Formula 52]

[0144] [Reaction Scheme 13] JPEG0007684399000078.jpg54170Compound [Chemical Formula 52] (yield 58.0%) was obtained in the same manner as in Synthesis Example 2-4, except that <3-c> was used instead of <2-c>.

[0145] MS (MALDI-TOF): m / z 525.21 [M] +

[0146] Synthesis Example 4. Synthesis of Chemical Formula 131 Synthesis Example 4-1. Synthesis of [Chemical Formula 131]

[0147] [Reaction Scheme 14] JPEG0007684399000079.jpg48170

[0148] Compound [Chemical Formula 131] (yield 61.4%) was obtained in the same manner as in Synthesis Example 2-4, except that 1-dibenzofuranboronic acid was used instead of <2-c>.

[0149] MS (MALDI-TOF): m / z 449.18 [M] +

[0150] Synthesis Example 5. Synthesis of Chemical Formula 136 Synthesis Example 5-1. Synthesis of <5-a>

[0151] [Reaction Formula 15] JPEG0007684399000080.jpg38158

[0152] A 1000 ml round-bottom flask is purged with nitrogen, and 50 ml (0.477 mol) of a 30 wt% aqueous hydrogen peroxide solution, 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) of iodine, and 450 ml of water are added, followed by stirring at 50 °C for 24 hours. After the reaction is completed, an aqueous sodium thiosulfate solution is added and stirred, and then the reaction solution is extracted with ethyl acetate and water. Thereafter, it is anhydrous treated and concentrated under reduced pressure. After concentration, it is separated by column chromatography to obtain 45 g (yield 44.3%) of <5-a>.

[0153] Synthesis Example 5-2. Synthesis of <5-b>

[0154] [Reaction Formula 16] JPEG0007684399000081.jpg40150

[0155] A 1000 ml round-bottom flask is purged with nitrogen, and 45 g (0.201 mol) of <5-a>, 41 g (0.241 mol) of 2-fluoro-6-methoxyphenylboronic acid, 7 g (0.006 mol) of tetrakis(triphenylphosphine)palladium, 47.2 g (0.341 mol) of potassium carbonate, 315 ml of toluene, 80 ml of ethanol, and 170 ml of water are added, followed by refluxing for 8 hours. After the reaction is completed, it is cooled to room temperature, extracted with ethyl acetate and water, and then the organic layer is anhydrous treated. After the organic layer is concentrated under reduced pressure, it is separated by column chromatography to obtain 28.6 g (yield 64.1%) of <5-b>.

[0156] Synthesis Example 5-3. Synthesis of <5-c>

[0157] [Reaction Formula 17] JPEG0007684399000082.jpg36147

[0158] Place <5-b> 28.6 g (0.129 mol), 44.5 g (0.322 mol) of potassium carbonate, and 143 ml of 1-methyl-2-pyrrolidine into a 500 ml round-bottom flask and reflux for 12 hours. After the reaction is completed, cool the temperature to room temperature, then slowly add 200 ml of 2N hydrochloric acid aqueous solution, stir well, and extract with ethyl acetate and water. After concentrating the organic layer, separate by column chromatography to obtain <5-c> 21 g (yield 80.7%).

[0159] Synthesis Example 5-4. Synthesis of <5-d>

[0160] [Reaction Formula 18] JPEG0007684399000083.jpg34147

[0161] Place <5-c> 21 g (0.104 mol) and 120 ml of dichloromethane into a 500 ml round-bottom flask, and cool the reaction solution to 0 °C or below. Slowly add 52 g (0.208 mol) of boron tribromide while paying attention to the temperature. After the addition, warm the reaction solution to room temperature and stir until the reaction is completed. After the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. After extracting the reaction solution with dichloromethane and water, perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain <5-d> 15 g (yield 76.8%).

[0162] Synthesis Example 5-5. Synthesis of <5-e>

[0163] [Reaction Formula 19] JPEG0007684399000084.jpg34147

[0164] A 500 ml round-bottom flask was purged with nitrogen, and 15.0 g (0.080 mol), 8.2 g (0.104 mol) of pyridine and 150 ml of dichloromethane were added, and the temperature of the reaction solution was cooled to 0 °C or lower. After cooling, 24.7 g (0.088 mol) of trifluoromethanesulfonic anhydride was slowly added dropwise. After the addition, the reaction solution was warmed to room temperature and stirred until the reaction was completed. When the reaction was completed, it was extracted with dichloromethane and water, the organic layer was dehydrated, concentrated under reduced pressure, and then separated by column chromatography to obtain 20 g (yield 78.4%).

[0165] Synthesis Example 5-6. Synthesis of <5-f>

[0166] [Reaction Formula 20] JPEG0007684399000085.jpg45135

[0167] A 500 ml round-bottom flask was purged with nitrogen, and 20 g (0.062 mol), 23.8 g (0.094 mol) of bis(pinacolato)diboron, 2.5 g (0.003 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 9.5 g (0.125 mol) of calcium acetate and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, filtered through celite, the filtrate was concentrated, and then separated by column chromatography to obtain 15 g (yield 80.6%).

[0168] Synthesis Example 5-7. Synthesis of [Chemical Formula 136]

[0169] [Reaction Formula 21] JPEG0007684399000086.jpg64165

[0170] Compound [Chemical Formula 136] (yield 60.3%) was obtained by synthesizing in the same manner except that <5-f> was used instead of <2-c> in Synthesis Example 2-4.

[0171] MS (MALDI-TOF): m / z 453.21 [M] +

[0172] Synthesis Example 6. Synthesis of Chemical Formula 1 Synthesis Example 6-1. Synthesis of <6-a>_

[0173] [Reaction formula 22] JPEG0007684399000087.jpg35165

[0174] Compound <6-a> (yield 57%) was obtained by synthesis in the same manner except that phenylboronic acid was used instead of phenylboronic acid (D5) used in Synthesis Example 1-2.

[0175] Synthesis Example 6-2. Synthesis of <6-b>

[0176] [Reaction formula 23] JPEG0007684399000088.jpg33150

[0177] Compound <6-b> (yield 86.8%) was obtained by synthesis in the same manner except that <6-a> was used instead of <1-b> used in Synthesis Example 1-3.

[0178] Synthesis Example 6-3. Synthesis of <6-c>_

[0179] [Reaction formula 24] JPEG0007684399000089.jpg42128

[0180] Compound <6-c> (yield 79.2%) was obtained by synthesis in the same manner except that <6-b> was used instead of <1-c> used in Synthesis Example 1-4.

[0181] Synthesis Example 6-4. Synthesis of [Chemical Formula 1]

[0182] [Reaction formula 25] JPEG0007684399000090.jpg45153

[0183] Compound [Chemical Formula 1] (yield 52.5%) was obtained in the same manner except that 1-bromopyrene was used instead of <1-a> and <6-c> was used instead of <1-d> as used in Synthesis Examples 1-5.

[0184] MS (MALDI-TOF): m / z 444.15 [M] +

[0185] Synthesis Example 7. Synthesis of Chemical Formula 23 Synthesis Example 7-1. Synthesis of [Chemical Formula 23]

[0186] [Reaction Formula 26] JPEG0007684399000091.jpg50161

[0187] Compound [Chemical Formula 23] (yield 53.8%) was obtained in the same manner except that <6-c> was used instead of <1-d> as used in Synthesis Examples 1-5.

[0188] MS (MALDI-TOF): m / z 520.18 [M] +

[0189] Synthesis Example 8. Synthesis of Chemical Formula 41 Synthesis Example 8-1. Synthesis of [Chemical Formula 41]

[0190] [Reaction Formula 27] JPEG0007684399000092.jpg55170

[0191] Compound [Chemical Formula 41] (yield 54.2%) was obtained in the same manner except that <2-a> was used instead of <1-a> as used in Synthesis Examples 1-5.

[0192] MS (MALDI-TOF): m / z 530.25 [M] +

[0193] Synthesis Example 9. Synthesis of Chemical Formula 57 Synthesis Example 9-1. Synthesis of [Chemical Formula 57]

[0194] [Reaction Formula 28] JPEG0007684399000093.jpg45170

[0195] Compound [Chemical formula 57] (yield 53.5%) was obtained by synthesis in the same manner except that <3-c> was used instead of <1-d> used in Synthesis Examples 1-5.

[0196] MS (MALDI-TOF): m / z 520.18 [M] +

[0197] Examples 1 to 13: Fabrication of Organic Light-Emitting Devices After patterning the ITO glass so that the light-emitting area became 2 mm × 2 mm in size, it was washed. After attaching the ITO glass to a vacuum chamber, after setting the base pressure to 1×10 -7 torr, films of DNTPD (700 Å) and α-NPD (300 Å) were formed on the ITO in this order. As the light-emitting layer, after mixing the host compound according to the present invention and the following dopant (BD) (3 wt%) and forming a film (300 Å), then, as the electron transport layer, [E-1] and [E-2] were formed in a ratio of (1:1) (300 Å), as the electron injection layer, [E-2] (10 Å), and Al (1,000 Å) were formed in this order to fabricate an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0198] JPEG0007684399000094.jpg109170

[0199] Comparative Examples 1 to 4 For the organic light-emitting device for the comparative example, experiments were conducted in the same manner except that the following [BH1] and [BH2] were used instead of the compound according to the present invention used as the host in the device structure of the above example. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA. The structures of the above [BH1] and [BH2] are as follows.

[0200] JPEG0007684399000095.jpg56170

[0201]

Table 1

[0202]

Table 2

[0203] As shown in Table 1 above, the organic light-emitting device using the compound having a pyrene group bonded to the 1-position or 2-position of the dibenzofuran group according to the present invention can be driven at a lower voltage than the organic light-emitting devices in Comparative Examples 1 to 2 using BH1 or BH2, which is a compound having a pyrene group bonded to the 3-position or 4-position of the dibenzofuran group, in the light-emitting layer, and exhibits excellent characteristics in terms of luminous efficiency. Also, in Table 2, the organic light-emitting device using the compound having a pyrene group bonded to the 1-position or 2-position of the dibenzofuran group according to the present invention exhibits excellent characteristics of longer lifetime than the organic light-emitting devices using the compounds of Comparative Examples 3 to 4 using BH1 or BH2, which is a compound having a pyrene group bonded to the 3-position or 4-position of the dibenzofuran group, in the light-emitting layer. Thus, it can be seen that the organic light-emitting device according to the present invention has high application potential.

Industrial Applicability

[0204] The organic light-emitting device manufactured with the light-emitting layer using the compound according to the present invention exhibits improved characteristics when applied to an organic light-emitting device because it has higher efficiency, lower voltage driving, and improved long-lifetime characteristics compared to conventional compounds, and thus has high industrial applicability in the field of organic light-emitting devices and related industries. < / d501> < / d101> < / d1>

Claims

1. A compound represented by the following [Chemical Formula A]. (In the above [Chemical Formula A], Said R 1 ~R7 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 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 cyano group, and a halogen group. R in the above [Chemical Formula A] 1 ~R 7 At least one of them is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, the linking group L1 is a single bond or any one selected from the following [Structural Formula 1] to [Structural Formula 2], in the linking group, hydrogen or deuterium can be bonded to the carbon of the aromatic ring, n1 is 0 or 1, 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 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a cyano group, and a halogen group, n3 is an integer of 1 to 9, and when each of these is 2 or more, the respective Rs may be the same as or different from each other, "substituted or unsubstituted" in the above [Chemical Formula A] means substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen 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. The compound represented by the above [Chemical Formula A] is characterized by containing at least one deuterium, and is the compound according to Claim 1.

3.

4. R in the above [Chemical Formula A] 1 ~R 7 The compound according to claim 2, characterized in that at least one of them is a substituent containing deuterium. The compound according to Claim 2, wherein at least one R in the above [Chemical Formula A] is a substituent containing deuterium.

5. The compound according to Claim 1, wherein the linking group L1 is a single bond.

6. The compound according to Claim 1, wherein at least one R in the above [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

7. In the above [Chemical Formula A], n3 is 1, and R in the above [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and is the compound according to Claim 6.

8. The organic compound represented by the above [Chemical Formula A] is a compound represented by the following [Chemical Formula A-1], and is the compound according to Claim 1. In the above [Chemical Formula A-1], the substituent R is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.) The substituent R 1 ~R 7, the linking group L 1, and n1 are the same as defined in [Chemical Formula A] according to claim 1,

9. In the above [Chemical Formula A], n3 is 1,

10. R in the above [Chemical Formula A] 1 ~R 7 The compound according to claim 1, wherein at least one of R, R is an aryl group having 6 to 18 carbon atoms substituted with deuterium. ​ The compound is any one selected from the group represented by the following Chemical Formulas 1 to 11, Chemical Formulas 19 to 26, Chemical Formulas 30 to 32, Chemical Formulas 34 to 36, Chemical Formulas 38 to 43, Chemical Formula 45, Chemical Formula 46, Chemical Formulas 73 to 75, Chemical Formulas 79 to 81, Chemical Formula 83, Chemical Formula 84, Chemical Formula 91, Chemical Formula 93, Chemical Formulas 96 to 104, Chemical Formulas 107 to 111, and Chemical Formulas 144 to 237, and is the compound according to Claim 1.

11. A first electrode, A second electrode facing the first electrode, An organic layer interposed between the first electrode and the second electrode, and the organic layer contains one or more of the compounds according to any one of Claims 1 to 10, an organic light-emitting device.

12. 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, and is the organic light-emitting device according to Claim 11.

13. 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, and is the organic light-emitting device according to Claim 12.

14. One or more selected from the following [Chemical Formulas D1] to [Chemical Formulas D10] are used as the dopant, and is the organic light-emitting device according to Claim 13. (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 and two adjacent carbon atoms within the aromatic ring of said A 51 and the substituents R 52 and R are each linked to a carbon atom to form a five-membered ring, thereby forming a fused ring The linking group L 21 to L 32 may be the same or different from each other, and are independently 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 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 are 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 are each independently 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, provided that 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 one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, Te. The p11 to p14, r11 to r14, and s11 to s14 are each an integer of 1 to 3. 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, y1, z1, and z2 may be the same or different from each other, and are each independently an integer of 0 to 1, The foregoing 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, A in the chemical formula D1 32 Two adjacent carbon atoms within the ring are bonded to the * of the structural formula Q 11 to form a condensed ring The A in the chemical formula D2 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 are bonded to the * of the structural formula Q 11 to be able to form a condensed ring. ) (In the [Chemical Formula D3], Said X 1 is any one selected from B, P, and P=O, The 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, 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, The aforementioned Y 2 is any one selected from N-R 66 CR 67 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 one or more rings selected from said T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring. ) (In the [Chemical Formulas D4] and [Chemical Formulas D5], Said X 2 is any one selected from B, P, and P=O, The T4 to T6 are the same as T1 to T3 in the [Chemical Formula D3], 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 any one selected from N-R 66 , CR 67 R 68 , O, S, SiR 69 R 70 and is any one selected therefrom. 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 T7 to T9 are the same as T1 to T3 in the [Chemical Formula D3], 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 same as the R 61 ~R 70 in [Chemical Formula D3], but Said R 71 and R 72 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, or may be combined with the T7 ring or T9 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring. (In the [Chemical Formulas D8] to [Chemical Formulas D10], The X is any one selected from B, P, and P=O, Said Q 1 to Q 3 are the same as T1 to T3 in [Chemical Formula D3], respectively, The linking group Y is N—R 3 , CR 4 R 5 , O, S, or Se, and is any one selected therefrom The substituent R 3 to R 5 are each the R 61 to R 70 in [Chemical Formula D3], and are the same, but Said R 3 to 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 an alkylene group having 1 to 10 carbon atoms, which is substituted or unsubstituted, excluding the carbon atoms contained in the Cy1. In the chemical formula D10, The ring formed by the Cy3 binds to the Cy3 and is Q 3 Q binds to the aromatic carbon atom and nitrogen (N) atom within the ring 3 Except for the aromatic carbon atom, nitrogen (N) atom, and the carbon atom within Cy1 to which the nitrogen (N) atom is bound, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.) (Here, the "substitution" in the "substituted or unsubstituted" in the [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, 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.)

15. The organic light-emitting device according to claim 12, wherein one or more layers selected from the respective layers are formed by a vapor deposition process or a solution process.

16. The organic light-emitting device according to claim 11, wherein the organic light-emitting device is used in any one 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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