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

Abstract

To provide a novel organic compound that can be used as a host material for an emission layer in an organic light-emitting device, and also to provide an organic light-emitting device that exhibits high efficiency, low driving voltage, and a long lifetime.SOLUTION: The present invention relates to a novel heterocyclic compound represented by [Chemical Formula B] that can be used in an organic light-emitting device, and to an organic light-emitting device comprising the same, wherein [Chemical Formula B] is as described in the detailed description of the invention.SELECTED DRAWING: None

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 device characteristics such as high luminous efficiency, low-voltage driving, and long lifetime, and an organic light-emitting device including the same.

Background Art

[0002] An organic light-emitting diode (OLED) is a display that utilizes the phenomenon of self-luminescence. 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. Therefore, it is expected to be applied to full-color (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 two electrodes in such a structure of an 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 has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, ​ It is known to have characteristics such as high response speed.

[0004] In an organic light-emitting device, the material used as the organic layer can be classified into a light-emitting material and an electric charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. The light-emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and according to the light-emitting mechanism, it can be classified into a fluorescent material derived from the singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons.

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

[0006] The principle is that when a dopant with an energy band gap smaller than that of the host forming the light-emitting layer is mixed in a small amount in 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, and as a related prior art, Korean Patent Publication No. 10-2016-0089693 (published on 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. In addition, Korean Patent Publication No. Publication No. 10-2017-0055743 (published on 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 lifetime, and organic light-emitting devices containing the same.

SUMMARY OF THE INVENTION

PROBLEM 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 a light-emitting layer in an organic light-emitting device.

[0010] Another object of the present invention is to provide an organic light-emitting device (organic light emitting diode, OLED) having high efficiency, low-voltage driving, and long lifetime by applying the organic compound to a host material in the organic light-emitting device.

MEANS FOR SOLVING THE PROBLEM

[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] JPEG2025109868000001.jpg65170

[0013] In the above [Chemical Formula A] and [Chemical Formula B], The above R1 to R 14 may be the same as or different from each other, and each independently is hydrogen, deuterium element, 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 carbon number 1 to 30 alkylsilyl group, a substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms group, a cyano group, a nitro group, or any one selected from halogen groups, The linking groups L1 and L2 may be the same as or different from each other, and are independent of each other , 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, and are selected from among them, The n1 and n2 may be the same as or different from each other, and are independently integers from 0 to 2 However, when each of these is 2, the respective linking groups L1 and L2 may be the same as or different from each other , The above R and R' may be the same as or different from each other, and are independent of each other, being 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, Substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number Alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms is any one selected from the group consisting of a cyano group, a nitro group, and a halogen group; The n3 and n4 may be the same or different, and each independently represents an integer of 1 to 9. However, when each of these is 2 or more, each R and R' are the same as each other. But it can be different, The "substituted" in the "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B] means , deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group with 1 to 24 carbon atoms group, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, Alkynyl groups with 3 to 24 carbon atoms, cycloalkyl groups with 3 to 24 carbon atoms, and heteroaryl groups with 1 to 24 carbon atoms. alkyl groups, aryl groups having 6 to 24 carbon atoms, arylalkyl groups having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, Heteroarylalkyl groups, alkoxy groups with 1 to 24 carbon atoms, alkyl groups with 1 to 24 carbon atoms Amino group, diarylamino group having 12 to 24 carbon atoms, diheteroaryl group having 2 to 24 carbon atoms Amino group, aryl (heteroaryl) amino group having 7 to 24 carbon atoms, aryl (heteroaryl) amino group having 1 to 24 carbon atoms Arylsilyl group, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms and one or more substituted aryl groups having 6 to 24 carbon atoms. It means that the substituted aryl group is substituted with a group. Effect of the Invention

[0014] The novel organic compound represented by the above chemical formula A or B according to the present invention is used for an organic light-emitting device. When used as a host material therein, an organic light-emitting device with higher efficiency, lower voltage driving, and longer lifespan compared to conventional organic light-emitting devices can be provided.

Brief Description of the Drawings

[0015]

Figure 1

Modes for Carrying Out the Invention

[0016] 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.

[0017] Also, the size and thickness of each illustrated configuration are arbitrarily shown for the sake of convenience of explanation, and the present invention is not necessarily limited to the illustration, and the thickness is enlarged in the drawings to clearly represent a plurality of layers and regions. And in the drawings, for the sake of convenience of explanation, the thickness of some layers and regions is exaggeratedly shown. When a part such as a layer, film, region, plate, etc. is said to be "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. When it is said that a certain part is "on" another part, this means that it is located above or below the target part, and it is not necessarily based on the direction of gravity.

[0018] Also, throughout the specification, when a certain part "includes" a certain component, this means that it does not exclude other components, but can further include other components unless otherwise stated to the contrary. Also, throughout the specification, "on ~" means being located above or below the target part, and it is not necessarily based on the direction of gravity. ​​It does not mean being located on the upper side.

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

[0020] JPEG2025109868000002.jpg65170

[0021] In the above [Chemical Formula A] and [Chemical Formula B], The above R1 to R 14 may be the same as or different from each other, and each independently 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 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 carbon number 1 to 30 alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms a cyano group, a nitro group, or any one selected from halogen groups, The linking groups L1 and L2 may be the same as or different from each other, and each independently is 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, and is selected from among them, The 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 these is 2, the respective linking groups L1 and L2 may be the same as or different from each other, The above R and R' may be the same as or different from each other, and each independently 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 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, or a halogen group, and is selected from any of them, wherein n3 and n4 may be the same or different from each other and are each independently an integer of 1 to 9 However, when each of these is 2 or more, each R and R' may be the same as or different from each other, and in the "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B], "substitution" means 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 A rucilsilyl group, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy having 6 to 24 carbon atoms group, and one or more substituents selected from the group consisting of an arylthionyl group having 6 to 24 carbon atoms means being substituted with.

[0022] On the other hand, 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, considering the range of the alkyl group or aryl group The range 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 is, respectively, without considering the portion substituted with the substituent It means the total number of carbon atoms constituting the alkyl part or aryl part when regarded as an unsubstituted one. 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. 。 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. 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 compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and when the aryl group has a substituent it can further form a ring by fusing with adjacent substituents. it can further form a ring by fusing with adjacent substituents.

[0024] Specific examples of the aryl group include a phenyl group, an o-biphenyl group, an m-biphenyl group , a p-biphenyl group, an o-terphenyl group, an m-terphenyl group, a p-terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyl group, a chrysenyl group, a naphthacenyl, a fluoranthene ntenyl group and other aromatic groups can be mentioned, and one or more hydrogen atoms in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH(R), -N(R’)(R’’), where R’ and R’’ are each independently an alkyl group having 1 to 10 carbon atoms, and in this case, it is called an “alkylamino group”). An amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

[0025] 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, Te, and the remaining ring atoms are carbon, meaning a ring aromatic system having 2 to 24 carbon atoms, and these rings can be fused (fuse d) 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] Also, in the present invention, the aromatic heterocyclic ring means one in which one or more of the aromatic carbons in the aromatic hydrocarbon ring are substituted with heteroatoms, and the aromatic heterocyclic ring is 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, T e.

[0027] The alkyl group, which is a substituent used in the present invention, is one obtained by removing one A substituent from which hydrogen has been removed, having a linear or branched structure, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert -butyl, pentyl, iso-amyl, hexyl, etc., and 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 , and for example, specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclo pentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclo pentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydro naphthyl, norbornyl, bornyl, isobornyl, etc., and one or more hydrogen atoms in the cyclo alkyl group can be substituted with the same substituents as in the case of the aryl group and are possible .

[0029] The alkoxy group which is a substituent used in the compound of the present invention is a substituent in which an oxygen atom is bonded to the end of an alkyl group or a cycloalkyl group, and specific examples thereof include methoxy, ethoxy , propoxy, isobutyloxy, sec-butyloxy, pentyloxy, is o-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantyloxy , dicyclopentaneoxy, bornyloxy, isobornyloxy, etc., and one or more hydrogen atoms in the alkoxy group are in the case of the aryl group and can be listed , and one or more hydrogen atoms in the alkoxy group are in the case of the aryl group It can be substituted with the same substituents.

[0030] Specific examples of the arylalkyl group, which is a substituent used in the compounds of the present invention, include phen ylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphth ylethyl, etc., and 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 trimethylsily l, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenyl silyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , dimethylfurylsilyl, etc., and 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 constituted by two carbon atoms, and an alkynyl (alkynyl) group means an alkyl substituent containing one carbon-carbon triple bond constituted by two carbon atoms.

[0033] Also, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens from an alkane molecule, which is a straight-chain 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-but ylene group, etc. ​Examples include a thylene group, a pentylene group, an iso-amyrene group, a hexylene group, etc., and one or more hydrogen atoms of the alkylene group can be substituted with the same substituents as in the case of the aryl group. It is possible.

[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, 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.

[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, a alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cyclo alkyl 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, a 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. It may be substituted with one or more substituents selected from the group consisting of

[0036] In the present invention, the organic compound represented by the above [Chemical Formula A] is a substituted or unsubstituted A linking group L1 is bonded to a specific position in the pyrene ring (see the following Structural Formula C), and the linking group L1 is characterized in that the 1-position of a substituted or unsubstituted dibenzofuran group is bonded thereto. Further, the organic compound represented by the above [Chemical Formula B] has a linking group L2 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, which is a technical feature. In the present invention, the organic compound represented by the above [Chemical Formula A] can contain at least one deuterium, and the organic compound represented by the above [Chemical Formula B] can contain at least one deuterium. More specifically, at least one of R1 to R7 in the above [Chemical Formula A] can be a substituent containing deuterium, and at least one of R8 to R

[0037] [Structural Formula C] JPEG2025109868000003.jpg29134

[0038] In the above [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. Furthermore, at least one of R1 to R7 in the above [Chemical Formula A] can be a substituent containing deuterium, and at least one of R8 to R can be a substituent containing deuterium.

[0039] More specifically, at least one of R1 to R7 in the above [Chemical Formula A] is a substituent containing deuterium, and at least one of R8 to R can be a substituent containing deuterium. 14 of which at least one can be a substituent containing deuterium.

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

[0041] Also, as an example of the present invention, the above R1 to R 14 , R, and R' may be the same or different from each other, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 1 0 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 alkyl silyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, a halo gen group, and may be a substituent selected from among them.

[0042] Also, as an example of the present invention, at least one of R1 to R7 in the above [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and the above [Chemical formula B] at least one of R8 to R 14 may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

[0043] As an example of the present invention, the linking groups L1 and L2 in the above chemical formula A and chemical formula B may each be a single bond or any one selected from the following [Structural Formula 1] to [Structural Formula 5].[[]END]] It may be.

[0044] JPEG2025109868000004.jpg57136

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

[0046] Also, as an example of the present invention, the linking groups L1 and L2 can each be a single bond.

[0047] Also, as an example of the present invention, n3 and n4 in the chemical formula A and the chemical formula B can each be 1. Also, as an example of 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] is , a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in this case, preferably, 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 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 the present invention, the organic compound represented by the [Chemical formula A] or [Chemical formula B] can be a compound represented by any of the following [Chemical formula A-1] or [Chemical formula B-1].

[0049] JPEG2025109868000005.jpg59170

[0050] At this time, in the [Chemical formula A-1] and [Chemical formula B-1], the substituents R1 to R1 4, the linking groups L1 and L2, 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 the present invention, in the chemical formula A and the chemical formula B, the n3 and n4 are each 1, and at least one of R1 to R7 and R in the [chemical formula A] is a deuterium-substituted aryl group having 6 to 18 carbon atoms, and in the [chemical formula B], at least one of R8 to R 14 and R' may be a deuterium-substituted aryl group having 6 to 18 carbon atoms.

[0052] Also, as an example of the present invention, in the chemical formula A and the chemical formula B, n3 and n4 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] Also, the compound represented by the [chemical formula A] or [chemical formula B] according to the present invention may be any compound selected from chemical formula 1 to chemical formula 240.

[0054] ​JPEG2025109868000006.jpg 222170 JPEG2025109868000007.jpg 225170 JPEG2025109868000008.jpg 229170 JPEG2025109868000009.jpg 209170 JPEG2025109868000010.jpg 217170 JPEG2025109868000011.jpg 210170 JPEG2025109868000012.jpg 231170 JPEG2025109868000013.jpg 223170 JPEG2025109868000014.jpg 234170 JPEG2025109868000015.jpg 216170 JPEG2025109868000016.jpg 222170 JPEG2025109868000017.jpg 223170 JPEG2025109868000018.jpg 229170 JPEG2025109868000019.jpg 233170 JPEG2025109868000020.jpg 227170 JPEG2025109868000021.jpg 238170

[0055] Further, the present invention includes a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, and the organic layer contains one or more compounds represented by the above [Chemical Formula A] or [Chemical Formula B] according to the present invention, and provides an organic light-emitting device thereof.

[0056] 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)".

[0057] At this time, the organic layer in the organic light-emitting device of the present invention includes 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 ​​​It can include at least one of them.

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

[0059] Further, 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] JPEG2025109868000022.jpg237165

[0061] 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 and two adjacent carbon atoms in the aromatic ring of the above A 31 form a condensed ring by forming a 5-membered ring with the carbon atoms to which the substituents R 32 and R are linked. 51 and R 52 The linking groups L 21 to L 32 may be the same or different from each other, and independently of each other, are a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number An 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, selected from wherein 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 , SiR 56 R 57 , GeR 58 R 59 , O, S, Se, and are any one selected from wherein the substituents 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 , 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, but is any one selected from among them, wherein said R 51 and R 52 are 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 among N, O, P, Si, S, Ge, Se, Te, , wherein said p11 to p14, r11 to r14 and s11 to s14 are each an integer of 1 to 3 but when each of these is 2 or more, each linking group L 21 ~L 32 is, may be the same or different from each other, wherein 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, wherein Ar 21 and Ar 22 , Ar 23 and Ar 24 , Ar 25 and Ar 26 , and Ar 27 and Ar 28 can each be linked to each other to form a ring, wherein two adjacent carbon atoms in the A ring in the chemical formula D1 are bonded to the * of the structural formula Q 32 to form a condensed ring, 11 wherein the A in the chemical formula D2 31 ​​​Two adjacent carbon atoms within the ring are bonded to the * in the structural formula Q1 to form a fused ring, and the A 32 Two adjacent carbon atoms within the ring are the structure formula Q 11 and can be bonded to the * to form a fused ring.)

[0062] JPEG2025109868000023.jpg48129

[0063] In the [Chemical formula D3], the X1 is any one selected from B, P, and P=O, the T1 to T3 may be the same as or different from each other, and independently of each other, are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted carbon atoms 2 to 40 aromatic heterocyclic rings, the Y1 is N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 and is any one selected therefrom , the Y2 is N- R66 , CR 67 R 68 , O, S, SiR 69 R 70 and is any one selected therefrom , the R 61 to R 70 may be the same as or different from each other, and independently of each other, are hydrogen , deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms , substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted carbon 1 to 30 alkoxy groups, substituted or unsubstituted aryloxy groups 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 each of R 61 ~R 70 is bonded to one or more rings selected from among the aforementioned T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0064] JPEG2025109868000024.jpg58129

[0065] In the aforementioned [Chemical Formula D4] and [Chemical Formula D5], X2 is any one selected from B, P, and P=O, T4 to T6 are the same as T1 to T3 in [Chemical Formula D3], Y4 is any one selected from N-R 61 , CR 62 R 63 , O, S, and SiR 64 R65, Y5 is any one selected from N-R , CR 66 , O, S, and SiR 67 R 68 , 69 R 70 Y6 is any one selected from N-R , CR , O, S, and SiR 71 , CR 72 R 73 , O, S, and SiR 74 R 75 , and each of R ~R 61 ~R 75is the same as the R in [Chemical Formula D3]. 61 ~R 70 is the same as that.

[0066] JPEG2025109868000025.jpg53129

[0067] The X3 is any one selected from B, P, and P=O. The T7 to T9 are the same as T1 to T3 in [Chemical Formula D3]. The Y6 is N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 and is any one selected therefrom. That is, any one of them can be selected. The substituent R 61 ~R 65 , R 71 ~R 72 are respectively the same as the R 61 ~R 70 in [Chemical Formula D3], but the R 71 and R 72 are each connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, or combine with the T7 ring or T9 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0068] JPEG2025109868000026.jpg92129

[0069] In the above [Chemical Formula D8] to [Chemical Formula D10], the X is any one selected from B, P, and P=O. The Q1 to Q3 are the same as T1 to T3 in [Chemical Formula D3] respectively. The linking group Y is any one selected from N-R3, CR4R5, O, S, and Se. That is, any one of them. The substituents R3 to R5 are respectively the same as the R in [Chemical Formula D3].61 ~R 70 is the same as but R3 to R5 are each bonded to the Q2 ring or Q3 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring, R4 and R5 are each connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring which can be formed, The ring formed by Cy1 is, excluding a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to which Cy1 is bonded, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, In the chemical formula D9, Cy2 can be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is, excluding the carbon atoms contained in Cy1, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, In the chemical formula D10, the ring formed by Cy3 is, excluding an aromatic carbon atom in the Q3 ring to which Cy3 is bonded, an aromatic carbon atom in the Q3 ring bonded to a nitrogen (N) atom, a nitrogen (N) atom, and a carbon atom in Cy1 to which the nitrogen (N) atom is bonded, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

[0070] Here, in the above [Chemical formula D1] to [Chemical formula D10], the "substituted or unsubstituted" in "substitution" refers to 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 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 ~24, etc. A lurkill group, 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, a carbon number of 1 ~ 24 alkylamino groups, diarylamino groups having 12 to 24 carbon atoms, and 2 to 24 carbon atoms Diheteroarylamino groups, aryl(heteroaryl)amino groups having 7 to 24 carbon atoms, carbon An alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and 6 to 24 carbon atoms Selected from the group consisting of aryloxy groups having 6 to 24 carbon atoms and arylthionyl groups having 6 to 24 carbon atoms. It means being substituted with one or more substituents, and more preferable examples include deuterium, a cyano group , a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 12 carbon atoms, and 1 to 12 carbon atoms Of the halogenated alkyl group, 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, and 6 carbon atoms ~ 18 aryl groups, arylalkyl groups having 7 to 20 carbon atoms, alkyls having 7 to 20 carbon atoms Aryl groups, heteroaryl groups having 2 to 18 carbon atoms, and heteroarylalkyl groups having 2 to 18 carbon atoms , an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, and 1 carbon atom 2 to 18 diarylamino groups, diheteroarylamino groups having 2 to 18 carbon atoms, and 7 carbon atoms ~ 18 aryl(heteroaryl)amino groups, alkylsilyl groups having 1 to 12 carbon atoms, and carbon Aryl silyl groups having 6 to 18 carbon atoms, aryloxy groups having 6 to 18 carbon atoms, and 6 to 18 carbon atoms Selected from the group consisting of arylthionyl groups, and being substituted with one or more substituents selected from the group consisting of It can be.

[0071] Among the dopant compounds according to the present invention, the above [Chemical Formula D3] to [Chemical Formula D10] In the case of a boron compound represented by any of the following, as substituents that can be substituted on the aromatic hydrocarbon ring or aromatic heterocyclic ring of 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 mentioned. Here, each 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. Each 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. 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>Compounds represented by any of the following are exemplified.

[0073] JPEG2025109868000027.jpg215170JPEG2025109868000028.jpg214170JPEG2025109868000029.jpg207170JPEG2025109868000030.jpg206170JPEG2025109868000031.jpg211170JPEG2025109868000032.jpg207170JPEG2025109868000033.jpg221170JPEG2025109868000034.jpg225170JPEG2025109868000035.jpg208170JPEG2025109868000036.jpg211170JPEG2025109868000037.jpg238170JPEG2025109868000038.jpg240170JPEG2025109868000039.jpg209170JPEG2025109868000040.jpg225170JPEG2025109868000041.jpg227170JPEG2025109868000042.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 described below <d101> ~ <d130>represented by any one selected from among can be a compound.

[0075] JPEG2025109868000043.jpg246170JPEG2025109868000044.jpg212170

[0076] Also, 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] JPEG2025109868000045.jpg223170JPEG2025109868000046.jpg223170JPEG2025109868000047.jpg238170JPEG2025109868000048.jpg240170JPEG2025109868000049.jpg243170JPEG2025109868000050.jpg232170JPEG2025109868000051.jpg236170JPEG2025109868000052.jpg238170JPEG2025109868000053.jpg227170JPEG2025109868000054.jpg213170JPEG2025109868000055.jpg220170JPEG2025109868000056.jpg239170JPEG2025109868000057.jpg255168JPEG2025109868000058.jpg226170

[0078] Also, 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 the following <d501> ~ <d587>from among and may be a compound represented by any one selected therefrom.

[0079] JPEG2025109868000059.jpg248170JPEG2025109868000060.jpg229170JPEG2025109868000061.jpg218170JPEG2025109868000062.jpg237170JPEG2025109868000063.jpg212170JPEG2025109868000064.jpg145170

[0080] At this time, the content of the dopant in the light-emitting layer is usually 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, and is not limited thereto. and is not limited thereto.

[0081] In addition to the dopant and the host, the light-emitting layer may further contain various host 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 includes an anode 20, a hole transport layer 40 , a light-emitting layer 50 containing a host and a dopant, an electron transport layer 60, and a cathode 80 in this order, and is an organic light-emitting device in which the anode is used as the first electrode and the cathode is used as the second electrode, and 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.

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

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

[0087] First, a substance for an anode electrode 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 an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used.

[0088] A positive hole injection layer material is vacuum thermally evaporated or spin-coated on the upper part of the anode 20 electrode to form the positive hole injection layer 30. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40.

[0089] The material of the positive 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 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 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 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 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 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 It is possible to use, for example, [[[1,1'-biphenyl]-4,4'-diamine]]. And 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 (α-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 vacuum evaporation or spin coating. 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 vacuum evaporation or spin coating. ​​​​​​​​

[0095] 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 (C athode)), and known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives , especially tris(8-quinolinolate)aluminum (Alq3), Liq, TAZ , BAlq, beryllium bis(benzoquinolin-10-olate)(beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 20 1, Compound 202, BCP, PBD which is an oxadiazole derivative, BMD, BND, etc . Although materials such as these can be used, it is not limited thereto.

[0096] JPEG2025109868000065.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 the 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 for this.

[0098] As the forming material of the electron injection layer, any substance known as the forming material of the electron injection layer such as CsF, NaF, LiF, Li2O, BaO, etc. can be used. The vapor deposition conditions of the electron injection layer vary depending on the compound used, but generally, they can be selected from within almost the same condition range as the formation of the hole injection layer. The thickness of the electron injection layer can be about 1 Å to about 100 Å, about 3 Å to about 90 Å. The electron

[0099] ​​​​​When the thickness of the sub-injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0100] In the present invention, the cathode can use a material with a small work function for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof such as aluminum (Al), aluminum-lithium (Al-Li), mag nesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. 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 formed in the further formed light-emitting layer can be a fluorescent material or a phosphorescent material.

[0102] In the present invention, one or more layers selected from 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 in a vacuum or a 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 this by methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc. ​ It means a method of forming a thin film.

[0104] In addition, the organic light-emitting device in the present invention can be used in any one of 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 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.

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

[0107] [Reaction formula 1] JPEG2025109868000066.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[PPh3]4) 6.4 g (0.006 mol), sodium carbonate 88.3 g (0.833 mol), 1400 ml of toluene and 420 ml of water were added and refluxed for 9 hours. After the reaction was completed, it was cooled to room temperature, and then the generated solid was filtered and discarded. The filtrate was extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. Then, it was concentrated under reduced pressure and separated by column chromatography to obtain 45.4 g (yield 45.7 %) of <1-a>.

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

[0110] [Reaction formula 2] JPEG2025109868000067.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), 1.8 g (0.002 mol) of tetrakis(triphenylphosphine)palladium (Pd[PPh3]4), 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 dried. After the organic layer was concentrated under reduced pressure, recrystallized from ethyl acetate and heptane to obtain 15.2 g (yield 75.4%) of <1-b>.

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

[0113] [Reaction formula 3] JPEG2025109868000068.jpg39144

[0114] A 500 ml round-bottom flask was purged with nitrogen, and 15.2 g (0.058 mol ) of <1-b>, 6 g (0.076 mol) of pyridine, and 150 ml of dichloromethane were added, and the temperature was cooled to 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 completed. After the reaction was completed, it was extracted with dichloromethane and water, the organic layer was dried, and then distilled under reduced pressure. ​Subsequently, it was separated by column chromatography to obtain 20 g (yield 87.3%).

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

[0116] [Reaction Formula 4] JPEG2025109868000069.jpg46144

[0117] A 300 ml round-bottom flask was purged with nitrogen, and 20 g (0.050 mol) of <1-c> bis(pinacolato)diboron 16.6 g (0.065 mol), bis(diphenylphosphino)ferrocene dichloropalladium 0.8 g (0.001 mol), calcium acetate 9.9 g ( 0.101 mol) and 200 ml of 1,4-dioxane were added, and the mixture was refluxed for 12 hours. After 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 14.8 g (yield 78.4%) of <1-d>.

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

[0119] [Reaction Formula 5] JPEG2025109868000070.jpg46170

[0120] A 300 ml round-bottom flask was purged with nitrogen, and 10.7 g (0.030 mol) of <1-a> and 13.7 g (0.036 mol) of <1-d>, tetrakis(triphenylphosphine)palladium 0.7 g (0.001 mol), potassium carbonate 7.4 g (0.053 mol), toluene 80 ml, ethanol 20 ml and water 26 ml 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 anhydrous treated, it was concentrated ​​, separated by column chromatography to obtain 8.4 g of [Chemical Formula 19] (yield 53.4%) obtained.

[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 Scheme 6] JPEG2025109868000071.jpg51170

[0124] Phenylboronic acid (D5) was used instead of phenylboronic acid used in Synthesis Example 1-1 and <2-a> (yield 79.3%) was obtained by synthesizing in the same manner except for this.

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

[0126] [Reaction Scheme 7] JPEG2025109868000072.jpg40170

[0127] 1,7-Dibromodibenzofuran was used instead of 6-bromo-1-dibenzofuranol used in Synthesis Example 1-2 and <2-b> (yield 54%) was obtained by synthesizing in the same manner except for this. obtained.

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

[0129] [Reaction Scheme 8] JPEG2025109868000073.jpg40170

[0130] <2-b> was used instead of <1-c> used in Synthesis Example 1-4 and <2-c> (yield 72.8%) was obtained by synthesizing in the same manner except for this.

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

[0132] [Reaction formula 9] JPEG2025109868000074.jpg46170

[0133] Using <2-a> instead of <1-a> used in Synthesis Examples 1-5 and <2-c> instead of <1-d>, it was synthesized in the same manner to obtain [Chemical formula 34] (yield 63.7 %).

[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] JPEG2025109868000075.jpg30170

[0137] Using 6-bromo-2-dibenzofuranol instead of 6-bromo-1-dibenzofuranol used in Synthesis Examples 1-2 and phenylboronic acid instead of phenylboronic acid (D5), it was synthesized in the same manner to obtain <3-a> (yield 72.0%).

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

[0139] [Reaction formula 11] JPEG2025109868000076.jpg30170

[0140] Using <3-a> instead of <1-b> used in Synthesis Example 1-3, it was synthesized in the same manner to obtain <3-b> (yield 85.2%). Synthesis Example 3-3. Synthesis of <3-c>

[0141] [Reaction Formula 12] JPEG2025109868000077.jpg30170

[0142] (Compound <3-b> was used instead of <1-c> in Synthesis Examples 1-4. Otherwise, the synthesis was carried out in the same way to obtain <3-c> (yield 76.8%).

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

[0144] [Reaction Formula 13] JPEG2025109868000078.jpg54170(Synthesis Example 2-4 was carried out in the same way except that <3-c> was used instead of <2-c>. As a result, [Chemical Formula 52] was obtained (yield 58.0%).

[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 Formula 14] JPEG2025109868000079.jpg48170

[0148] (Synthesis Example 2-4 was carried out in the same way except that 1-dibenzofuranboronic acid was used instead of <2-c>. As a result, [Chemical Formula 131] was obtained (yield 61.4%).

[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] JPEG2025109868000080.jpg38158

[0152] A 1000 ml round-bottom flask was purged with nitrogen, and 50 ml of a 30 wt% aqueous hydrogen peroxide solution ( 0.477 mol), 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) of iodine and 450 ml of water were added, and the mixture was stirred at 50 °C for 24 hours. When the reaction was completed, an aqueous sodium thiosulfate solution was added and stirred, and then the reaction solution was extracted with ethyl acetate and water. After that, it was anhydrous treated and concentrated under reduced pressure. After concentration, it was 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] JPEG2025109868000081.jpg40150

[0155] A 1000 ml round-bottom flask was 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 were added, and the mixture was refluxed for 8 hours. When the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. After the organic layer was concentrated under reduced pressure, it was 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] JPEG2025109868000082.jpg36147

[0158] Place 28.6 g (0.129 mol) of <5-b> and 44.5 g (0.322 mol) of potassium carbonate in a 500 ml round-bottom flask, and add 143 ml of 1-methyl-2-pyrrolidine. Reflux for 2 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. Place 28.6 g (0.129 mol) of <5-b> and 44.5 g (0.322 mol) of potassium carbonate in a 500 ml round-bottom flask, and add 143 ml of 1-methyl-2-pyrrolidine. Reflux for 2 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. 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 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. .

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

[0160] [Reaction Formula 18] JPEG2025109868000083.jpg34147

[0161] Place 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane in 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. Place 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane in 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 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 the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>. After the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>.

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

[0163] [Reaction Formula 19] JPEG2025109868000084.jpg34147

[0164] Purge a 500 ml round-bottom flask with nitrogen, and place 15.0 g (0.080 mol) of <5-d> ) 8.2 g (0.104 mol) of pyridine and 150 ml of dichloromethane were added, and 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. After the reaction was completed, it was extracted with dichloromethane and water, and then the organic layer was dehydrated treated, concentrated under reduced pressure, and separated by column chromatography to obtain 20 g (yield 78 .4%) of <5-e>.

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

[0166] [Reaction formula 20] JPEG2025109868000085.jpg45135

[0167] A 500 ml round-bottom flask was purged with nitrogen, and 20 g (0.062 mol) of <5-e>, 23.8 g (0.094 mol) of bis(pinacolato)diboron, 2.5 g (0.003 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 9.5 g of calcium acetate (0.125 mol), and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. After 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%) of <5-f>.

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

[0169] [Reaction formula 21] JPEG2025109868000086.jpg64165

[0170] <5-f> was used instead of <2-c> in Synthesis Example 2-4, and the synthesis was carried out in the same manner to obtain [Chemical Formula 136] (yield 60.3%).

[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] JPEG2025109868000087.jpg35165

[0174] Using phenylboronic acid instead of phenylboronic acid (D5) used in Synthesis Example 1-2 Except for this, it was synthesized in the same manner to obtain <6-a> (yield 57%).

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

[0176] [Reaction Formula 23] JPEG2025109868000088.jpg33150

[0177] Using <6-a> instead of <1-b> used in Synthesis Example 1-3, except for this, it was synthesized in the same manner to obtain <6-b> (yield 86.8%).

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

[0179] [Reaction Formula 24] JPEG2025109868000089.jpg42128

[0180] Using <6-b> instead of <1-c> used in Synthesis Example 1-4, except for this, it was synthesized in the same manner to obtain <6-c> (yield 79.2%).

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

[0182] [Reaction Formula 25] JPEG2025109868000090.jpg45153

[0183] Using 1-bromopyrene instead of <1-a> used in Synthesis Examples 1-5, and <6-c> instead of <1-d> except for using <6-c> instead of <1-d>, it was synthesized in the same manner to obtain [Chemical Formula 1] (yield 52 .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] JPEG2025109868000091.jpg50161

[0187] Except for using <6-c> instead of <1-d> used in Synthesis Examples 1-5, in the same manne r it was synthesized to obtain [Chemical Formula 23] (yield 53.8%).

[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] JPEG2025109868000092.jpg55170

[0191] Except for using <2-a> instead of <1-a> used in Synthesis Examples 1-5, in the same manne r it was synthesized to obtain [Chemical Formula 41] (yield 54.2%).

[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] JPEG2025109868000093.jpg45170

[0195] The compound <3-c> was used instead of <1-d> used in Synthesis Examples 1-5, and the synthesis was carried out in the same manner to obtain [Chemical formula 57] (yield 53.5%).

[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 becomes 2 mm × 2 mm in size, it was washed. After attaching the ITO glass to a vacuum chamber, the base pressure was 1×10 - 7 torr, and then DNTPD (700 Å) and α-NPD ( 300 Å) were deposited in this order on the ITO. As the light-emitting layer, the host compound according to the present invention and the following dopant (BD) (3 wt%) were mixed and deposited (300 Å). Then, as the electron transport layer, [E-1] and [E-2] were deposited (300 Å) in a ratio of (1:1), and as the electron injection layer, [E-2] (10 Å) and Al (1,000 Å) were deposited 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] JPEG2025109868000094.jpg109170

[0199] Comparative Examples 1 to 4 The organic light-emitting device for the comparative example was the same as the device structure of the example, except that the following [BH1] and [BH2] were used instead of the compound according to the present invention. The device was fabricated and tested in the same manner. 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] JPEG2025109868000095.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 has a lower driving 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, 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 lifespan than the organic light-emitting devices using the compounds of Comparative Examples 3 to 4 using BH1 or BH2, which are compounds having a pyrene group bonded to the 3-position or 4-position of the dibenzofuran group. From this, 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 using the compound according to the present invention, compared with the conventional compound, has improved characteristics such as higher efficiency, lower voltage driving, and longer lifespan, and thus when applied to an organic light-emitting device, it exhibits improved characteristics and has high industrial applicability in the organic light-emitting device and related industrial fields. It is highly useful. < / d501> < / d101> < / d1>

[0072]

[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, as specific examples of the compounds represented by any of the above [Chemical Formula D1] to [Chemical Formula D2], the following <d1> ~ <d239>Compounds represented by any of the following are exemplified.

[0073] JPEG2025109868000027.jpg215170JPEG2025109868000028.jpg214170JPEG2025109868000029.jpg207170JPEG2025109868000030.jpg206170JPEG2025109868000031.jpg211170JPEG2025109868000032.jpg207170JPEG2025109868000033.jpg221170JPEG2025109868000034.jpg225170JPEG2025109868000035.jpg208170JPEG2025109868000036.jpg211170JPEG2025109868000037.jpg238170JPEG2025109868000038.jpg240170JPEG2025109868000039.jpg209170JPEG2025109868000040.jpg225170JPEG2025109868000041.jpg227170JPEG2025109868000042.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 described below <d101> ~ <d130>represented by any one selected from among can be a compound.

[0075] JPEG2025109868000043.jpg246170JPEG2025109868000044.jpg212170

[0076] Also, 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] JPEG2025109868000045.jpg223170JPEG2025109868000046.jpg223170JPEG2025109868000047.jpg238170JPEG2025109868000048.jpg240170JPEG2025109868000049.jpg243170JPEG2025109868000050.jpg232170JPEG2025109868000051.jpg236170JPEG2025109868000052.jpg238170JPEG2025109868000053.jpg227170JPEG2025109868000054.jpg213170JPEG2025109868000055.jpg220170JPEG2025109868000056.jpg239170JPEG2025109868000057.jpg255168JPEG2025109868000058.jpg226170

[0078] Also, 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 the following <d501> ~ <d587>from among and may be a compound represented by any one selected therefrom.

[0079] JPEG2025109868000059.jpg248170JPEG2025109868000060.jpg229170JPEG2025109868000061.jpg218170JPEG2025109868000062.jpg237170JPEG2025109868000063.jpg212170JPEG2025109868000064.jpg145170

[0080] At this time, the content of the dopant in the light-emitting layer is usually 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, and is not limited thereto. and is not limited thereto.

[0081] In addition to the dopant and the host, the light-emitting layer may further contain various host 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 includes an anode 20, a hole transport layer 40 , a light-emitting layer 50 containing a host and a dopant, an electron transport layer 60, and a cathode 80 in this order, and is an organic light-emitting device in which the anode is used as the first electrode and the cathode is used as the second electrode, and 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.

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

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

[0087] First, a substance for an anode electrode 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 an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used.

[0088] A positive hole injection layer material is vacuum thermally evaporated or spin-coated on the upper part of the anode 20 electrode to form the positive hole injection layer 30. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40.

[0089] The material of the positive 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 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 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 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 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 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 It is possible to use, for example, [[[1,1'-biphenyl]-4,4'-diamine]]. And 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 (α-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 vacuum evaporation or spin coating. 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 vacuum evaporation or spin coating. ​​​​​​​​

[0095] 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 (C athode)), and known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives , especially tris(8-quinolinolate)aluminum (Alq3), Liq, TAZ , BAlq, beryllium bis(benzoquinolin-10-olate)(beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 20 1, Compound 202, BCP, PBD which is an oxadiazole derivative, BMD, BND, etc . Although materials such as these can be used, it is not limited thereto.

[0096] JPEG2025109868000065.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 the 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 for this.

[0098] As the forming material of the electron injection layer, any substance known as the forming material of the electron injection layer such as CsF, NaF, LiF, Li2O, BaO, etc. can be used. The vapor deposition conditions of the electron injection layer vary depending on the compound used, but generally, they can be selected from within almost the same condition range as the formation of the hole injection layer. The thickness of the electron injection layer can be about 1 Å to about 100 Å, about 3 Å to about 90 Å. The electron

[0099] ​​​​​When the thickness of the sub-injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0100] In the present invention, the cathode can use a material with a small work function for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof such as aluminum (Al), aluminum-lithium (Al-Li), mag nesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. 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 formed in the further formed light-emitting layer can be a fluorescent material or a phosphorescent material.

[0102] In the present invention, one or more layers selected from 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 in a vacuum or a 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 this by methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc. ​ It means a method of forming a thin film.

[0104] In addition, the organic light-emitting device in the present invention can be used in any one of 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 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.

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

[0107] [Reaction formula 1] JPEG2025109868000066.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[PPh3]4) 6.4 g (0.006 mol), sodium carbonate 88.3 g (0.833 mol), 1400 ml of toluene and 420 ml of water were added and refluxed for 9 hours. After the reaction was completed, it was cooled to room temperature, and then the generated solid was filtered and discarded. The filtrate was extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. Then, it was concentrated under reduced pressure and separated by column chromatography to obtain 45.4 g (yield 45.7 %) of <1-a>.

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

[0110] [Reaction formula 2] JPEG2025109868000067.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), 1.8 g (0.002 mol) of tetrakis(triphenylphosphine)palladium (Pd[PPh3]4), 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 dried. After the organic layer was concentrated under reduced pressure, recrystallized from ethyl acetate and heptane to obtain 15.2 g (yield 75.4%) of <1-b>.

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

[0113] [Reaction formula 3] JPEG2025109868000068.jpg39144

[0114] A 500 ml round-bottom flask was purged with nitrogen, and 15.2 g (0.058 mol ) of <1-b>, 6 g (0.076 mol) of pyridine, and 150 ml of dichloromethane were added, and the temperature was cooled to 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 completed. After the reaction was completed, it was extracted with dichloromethane and water, the organic layer was dried, and then distilled under reduced pressure. ​Subsequently, it was separated by column chromatography to obtain 20 g (yield 87.3%).

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

[0116] [Reaction Formula 4] JPEG2025109868000069.jpg46144

[0117] A 300 ml round-bottom flask was purged with nitrogen, and 20 g (0.050 mol) of <1-c> bis(pinacolato)diboron 16.6 g (0.065 mol), bis(diphenylphosphino)ferrocene dichloropalladium 0.8 g (0.001 mol), calcium acetate 9.9 g ( 0.101 mol) and 200 ml of 1,4-dioxane were added, and the mixture was refluxed for 12 hours. After 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 14.8 g (yield 78.4%) of <1-d>.

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

[0119] [Reaction Formula 5] JPEG2025109868000070.jpg46170

[0120] A 300 ml round-bottom flask was purged with nitrogen, and 10.7 g (0.030 mol) of <1-a> and 13.7 g (0.036 mol) of <1-d>, tetrakis(triphenylphosphine)palladium 0.7 g (0.001 mol), potassium carbonate 7.4 g (0.053 mol), toluene 80 ml, ethanol 20 ml and water 26 ml 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 anhydrous treated, it was concentrated ​​, separated by column chromatography to obtain 8.4 g of [Chemical Formula 19] (yield 53.4%) obtained.

[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 Scheme 6] JPEG2025109868000071.jpg51170

[0124] Phenylboronic acid (D5) was used instead of phenylboronic acid used in Synthesis Example 1-1 and <2-a> (yield 79.3%) was obtained by synthesizing in the same manner except for this.

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

[0126] [Reaction Scheme 7] JPEG2025109868000072.jpg40170

[0127] 1,7-Dibromodibenzofuran was used instead of 6-bromo-1-dibenzofuranol used in Synthesis Example 1-2 and <2-b> (yield 54%) was obtained by synthesizing in the same manner except for this. obtained.

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

[0129] [Reaction Scheme 8] JPEG2025109868000073.jpg40170

[0130] <2-b> was used instead of <1-c> used in Synthesis Example 1-4 and <2-c> (yield 72.8%) was obtained by synthesizing in the same manner except for this.

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

[0132] [Reaction formula 9] JPEG2025109868000074.jpg46170

[0133] Using <2-a> instead of <1-a> used in Synthesis Examples 1-5 and <2-c> instead of <1-d>, it was synthesized in the same manner to obtain [Chemical formula 34] (yield 63.7 %).

[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] JPEG2025109868000075.jpg30170

[0137] Using 6-bromo-2-dibenzofuranol instead of 6-bromo-1-dibenzofuranol used in Synthesis Examples 1-2 and phenylboronic acid instead of phenylboronic acid (D5), it was synthesized in the same manner to obtain <3-a> (yield 72.0%).

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

[0139] [Reaction formula 11] JPEG2025109868000076.jpg30170

[0140] Using <3-a> instead of <1-b> used in Synthesis Example 1-3, it was synthesized in the same manner to obtain <3-b> (yield 85.2%). Synthesis Example 3-3. Synthesis of <3-c>

[0141] [Reaction Formula 12] JPEG2025109868000077.jpg30170

[0142] (Compound <3-b> was used instead of <1-c> in Synthesis Examples 1-4. Otherwise, the synthesis was carried out in the same way to obtain <3-c> (yield 76.8%).

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

[0144] [Reaction Formula 13] JPEG2025109868000078.jpg54170(Synthesis Example 2-4 was carried out in the same way except that <3-c> was used instead of <2-c>. As a result, [Chemical Formula 52] was obtained (yield 58.0%).

[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 Formula 14] JPEG2025109868000079.jpg48170

[0148] (Synthesis Example 2-4 was carried out in the same way except that 1-dibenzofuranboronic acid was used instead of <2-c>. As a result, [Chemical Formula 131] was obtained (yield 61.4%).

[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] JPEG2025109868000080.jpg38158

[0152] A 1000 ml round-bottom flask was purged with nitrogen, and 50 ml of a 30 wt% aqueous hydrogen peroxide solution ( 0.477 mol), 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) of iodine and 450 ml of water were added, and the mixture was stirred at 50 °C for 24 hours. When the reaction was completed, an aqueous sodium thiosulfate solution was added and stirred, and then the reaction solution was extracted with ethyl acetate and water. After that, it was anhydrous treated and concentrated under reduced pressure. After concentration, it was 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] JPEG2025109868000081.jpg40150

[0155] A 1000 ml round-bottom flask was 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 were added, and the mixture was refluxed for 8 hours. When the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. After the organic layer was concentrated under reduced pressure, it was 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] JPEG2025109868000082.jpg36147

[0158] Place 28.6 g (0.129 mol) of <5-b> and 44.5 g (0.322 mol) of potassium carbonate in a 500 ml round-bottom flask, and add 143 ml of 1-methyl-2-pyrrolidine. Reflux for 2 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. Place 28.6 g (0.129 mol) of <5-b> and 44.5 g (0.322 mol) of potassium carbonate in a 500 ml round-bottom flask, and add 143 ml of 1-methyl-2-pyrrolidine. Reflux for 2 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. 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 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. .

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

[0160] [Reaction Formula 18] JPEG2025109868000083.jpg34147

[0161] Place 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane in 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. Place 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane in 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 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 the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>. After the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>.

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

[0163] [Reaction Formula 19] JPEG2025109868000084.jpg34147

[0164] Purge a 500 ml round-bottom flask with nitrogen, and place 15.0 g (0.080 mol) of <5-d> ) 8.2 g (0.104 mol) of pyridine and 150 ml of dichloromethane were added, and 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. After the reaction was completed, it was extracted with dichloromethane and water, and then the organic layer was dehydrated treated, concentrated under reduced pressure, and separated by column chromatography to obtain 20 g (yield 78 .4%) of <5-e>.

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

[0166] [Reaction formula 20] JPEG2025109868000085.jpg45135

[0167] A 500 ml round-bottom flask was purged with nitrogen, and 20 g (0.062 mol) of <5-e>, 23.8 g (0.094 mol) of bis(pinacolato)diboron, 2.5 g (0.003 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 9.5 g of calcium acetate (0.125 mol), and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. After 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%) of <5-f>.

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

[0169] [Reaction formula 21] JPEG2025109868000086.jpg64165

[0170] <5-f> was used instead of <2-c> in Synthesis Example 2-4, and the synthesis was carried out in the same manner to obtain [Chemical Formula 136] (yield 60.3%).

[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] JPEG2025109868000087.jpg35165

[0174] Using phenylboronic acid instead of phenylboronic acid (D5) used in Synthesis Example 1-2 Except for this, it was synthesized in the same manner to obtain <6-a> (yield 57%).

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

[0176] [Reaction Formula 23] JPEG2025109868000088.jpg33150

[0177] Using <6-a> instead of <1-b> used in Synthesis Example 1-3, except for this, it was synthesized in the same manner to obtain <6-b> (yield 86.8%).

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

[0179] [Reaction Formula 24] JPEG2025109868000089.jpg42128

[0180] Using <6-b> instead of <1-c> used in Synthesis Example 1-4, except for this, it was synthesized in the same manner to obtain <6-c> (yield 79.2%).

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

[0182] [Reaction Formula 25] JPEG2025109868000090.jpg45153

[0183] Using 1-bromopyrene instead of <1-a> used in Synthesis Examples 1-5, and <6-c> instead of <1-d> except for using <6-c> instead of <1-d>, it was synthesized in the same manner to obtain [Chemical Formula 1] (yield 52 .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] JPEG2025109868000091.jpg50161

[0187] Except for using <6-c> instead of <1-d> used in Synthesis Examples 1-5, in the same manne r it was synthesized to obtain [Chemical Formula 23] (yield 53.8%).

[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] JPEG2025109868000092.jpg55170

[0191] Except for using <2-a> instead of <1-a> used in Synthesis Examples 1-5, in the same manne r it was synthesized to obtain [Chemical Formula 41] (yield 54.2%).

[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] JPEG2025109868000093.jpg45170

[0195] The compound <3-c> was used instead of <1-d> used in Synthesis Examples 1-5, and the synthesis was carried out in the same manner to obtain [Chemical formula 57] (yield 53.5%).

[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 becomes 2 mm × 2 mm in size, it was washed. After attaching the ITO glass to a vacuum chamber, the base pressure was 1×10 - 7 torr, and then DNTPD (700 Å) and α-NPD ( 300 Å) were deposited in this order on the ITO. As the light-emitting layer, the host compound according to the present invention and the following dopant (BD) (3 wt%) were mixed and deposited (300 Å). Then, as the electron transport layer, [E-1] and [E-2] were deposited (300 Å) in a ratio of (1:1), and as the electron injection layer, [E-2] (10 Å) and Al (1,000 Å) were deposited 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] JPEG2025109868000094.jpg109170

[0199] Comparative Examples 1 to 4 The organic light-emitting device for the comparative example was the same as the device structure of the example, except that the following [BH1] and [BH2] were used instead of the compound according to the present invention. The device was fabricated and tested in the same manner. 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] JPEG2025109868000095.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 has a lower driving 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, 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 lifespan than the organic light-emitting devices using the compounds of Comparative Examples 3 to 4 using BH1 or BH2, which are compounds having a pyrene group bonded to the 3-position or 4-position of the dibenzofuran group. From this, 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 using the compound according to the present invention, compared with the conventional compound, has improved characteristics such as higher efficiency, lower voltage driving, and longer lifespan, and thus when applied to an organic light-emitting device, it exhibits improved characteristics and has high industrial applicability in the organic light-emitting device and related industrial fields. It is highly useful. < / d501> < / d101> < / d1> <d1> ~ <d239>Compounds represented by any of the following are exemplified.

[0073] JPEG2025109868000027.jpg215170JPEG2025109868000028.jpg214170JPEG2025109868000029.jpg207170JPEG2025109868000030.jpg206170JPEG2025109868000031.jpg211170JPEG2025109868000032.jpg207170JPEG2025109868000033.jpg221170JPEG2025109868000034.jpg225170JPEG2025109868000035.jpg208170JPEG2025109868000036.jpg211170JPEG2025109868000037.jpg238170JPEG2025109868000038.jpg240170JPEG2025109868000039.jpg209170JPEG2025109868000040.jpg225170JPEG2025109868000041.jpg227170JPEG2025109868000042.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 described below <d101> ~ <d130>represented by any one selected from among can be a compound.

[0075] JPEG2025109868000043.jpg246170JPEG2025109868000044.jpg212170

[0076] Also, 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] JPEG2025109868000045.jpg223170JPEG2025109868000046.jpg223170JPEG2025109868000047.jpg238170JPEG2025109868000048.jpg240170JPEG2025109868000049.jpg243170JPEG2025109868000050.jpg232170JPEG2025109868000051.jpg236170JPEG2025109868000052.jpg238170JPEG2025109868000053.jpg227170JPEG2025109868000054.jpg213170JPEG2025109868000055.jpg220170JPEG2025109868000056.jpg239170JPEG2025109868000057.jpg255168JPEG2025109868000058.jpg226170

[0078] Also, 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 the following <d501> ~ <d587>from among and may be a compound represented by any one selected therefrom.

[0079] JPEG2025109868000059.jpg248170JPEG2025109868000060.jpg229170JPEG2025109868000061.jpg218170JPEG2025109868000062.jpg237170JPEG2025109868000063.jpg212170JPEG2025109868000064.jpg145170

[0080] At this time, the content of the dopant in the light-emitting layer is usually 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, and is not limited thereto. and is not limited thereto.

[0081] In addition to the dopant and the host, the light-emitting layer may further contain various host 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 includes an anode 20, a hole transport layer 40 , a light-emitting layer 50 containing a host and a dopant, an electron transport layer 60, and a cathode 80 in this order, and is an organic light-emitting device in which the anode is used as the first electrode and the cathode is used as the second electrode, and 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.

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

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

[0087] First, a substance for an anode electrode 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 an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used. However, it is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness. And as the substance for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, are used.

[0088] A positive hole injection layer material is vacuum thermally evaporated or spin-coated on the upper part of the anode 20 electrode to form the positive hole injection layer 30. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40. Then, a positive hole transport layer material is vacuum thermally evaporated or spin-coated on the upper part of the positive hole injection layer 30 to form the positive hole transport layer 40.

[0089] The material of the positive 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 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 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 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 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 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 It is possible to use, for example, [[[1,1'-biphenyl]-4,4'-diamine]]. And 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 (α-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 vacuum evaporation or spin coating. 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 vacuum evaporation or spin coating. ​​​​​​​​

[0095] 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 (C athode)), and known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives , especially tris(8-quinolinolate)aluminum (Alq3), Liq, TAZ , BAlq, beryllium bis(benzoquinolin-10-olate)(beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 20 1, Compound 202, BCP, PBD which is an oxadiazole derivative, BMD, BND, etc . Although materials such as these can be used, it is not limited thereto.

[0096] JPEG2025109868000065.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 the 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 for this.

[0098] As the forming material of the electron injection layer, any substance known as the forming material of the electron injection layer such as CsF, NaF, LiF, Li2O, BaO, etc. can be used. The vapor deposition conditions of the electron injection layer vary depending on the compound used, but generally, they can be selected from within almost the same condition range as the formation of the hole injection layer. The thickness of the electron injection layer can be about 1 Å to about 100 Å, about 3 Å to about 90 Å. The electron

[0099] ​​​​​When the thickness of the sub-injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0100] In the present invention, the cathode can use a material with a small work function for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof such as aluminum (Al), aluminum-lithium (Al-Li), mag nesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. 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 formed in the further formed light-emitting layer can be a fluorescent material or a phosphorescent material.

[0102] In the present invention, one or more layers selected from 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 in a vacuum or a 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 this by methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc. ​ It means a method of forming a thin film.

[0104] In addition, the organic light-emitting device in the present invention can be used in any one of 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 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.

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

[0107] [Reaction formula 1] JPEG2025109868000066.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[PPh3]4) 6.4 g (0.006 mol), sodium carbonate 88.3 g (0.833 mol), 1400 ml of toluene and 420 ml of water were added and refluxed for 9 hours. After the reaction was completed, it was cooled to room temperature, and then the generated solid was filtered and discarded. The filtrate was extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. Then, it was concentrated under reduced pressure and separated by column chromatography to obtain 45.4 g (yield 45.7 %) of <1-a>.

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

[0110] [Reaction formula 2] JPEG2025109868000067.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), 1.8 g (0.002 mol) of tetrakis(triphenylphosphine)palladium (Pd[PPh3]4), 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 dried. After the organic layer was concentrated under reduced pressure, recrystallized from ethyl acetate and heptane to obtain 15.2 g (yield 75.4%) of <1-b>.

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

[0113] [Reaction formula 3] JPEG2025109868000068.jpg39144

[0114] A 500 ml round-bottom flask was purged with nitrogen, and 15.2 g (0.058 mol ) of <1-b>, 6 g (0.076 mol) of pyridine, and 150 ml of dichloromethane were added, and the temperature was cooled to 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 completed. After the reaction was completed, it was extracted with dichloromethane and water, the organic layer was dried, and then distilled under reduced pressure. ​Subsequently, it was separated by column chromatography to obtain 20 g (yield 87.3%).

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

[0116] [Reaction Formula 4] JPEG2025109868000069.jpg46144

[0117] A 300 ml round-bottom flask was purged with nitrogen, and 20 g (0.050 mol) of <1-c> bis(pinacolato)diboron 16.6 g (0.065 mol), bis(diphenylphosphino)ferrocene dichloropalladium 0.8 g (0.001 mol), calcium acetate 9.9 g ( 0.101 mol) and 200 ml of 1,4-dioxane were added, and the mixture was refluxed for 12 hours. After 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 14.8 g (yield 78.4%) of <1-d>.

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

[0119] [Reaction Formula 5] JPEG2025109868000070.jpg46170

[0120] A 300 ml round-bottom flask was purged with nitrogen, and 10.7 g (0.030 mol) of <1-a> and 13.7 g (0.036 mol) of <1-d>, tetrakis(triphenylphosphine)palladium 0.7 g (0.001 mol), potassium carbonate 7.4 g (0.053 mol), toluene 80 ml, ethanol 20 ml and water 26 ml 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 anhydrous treated, it was concentrated ​​, separated by column chromatography to obtain 8.4 g of [Chemical Formula 19] (yield 53.4%) obtained.

[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 Scheme 6] JPEG2025109868000071.jpg51170

[0124] Phenylboronic acid (D5) was used instead of phenylboronic acid used in Synthesis Example 1-1 and <2-a> (yield 79.3%) was obtained by synthesizing in the same manner except for this.

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

[0126] [Reaction Scheme 7] JPEG2025109868000072.jpg40170

[0127] 1,7-Dibromodibenzofuran was used instead of 6-bromo-1-dibenzofuranol used in Synthesis Example 1-2 and <2-b> (yield 54%) was obtained by synthesizing in the same manner except for this. obtained.

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

[0129] [Reaction Scheme 8] JPEG2025109868000073.jpg40170

[0130] <2-b> was used instead of <1-c> used in Synthesis Example 1-4 and <2-c> (yield 72.8%) was obtained by synthesizing in the same manner except for this.

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

[0132] [Reaction formula 9] JPEG2025109868000074.jpg46170

[0133] Using <2-a> instead of <1-a> used in Synthesis Examples 1-5 and <2-c> instead of <1-d>, it was synthesized in the same manner to obtain [Chemical formula 34] (yield 63.7 %).

[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] JPEG2025109868000075.jpg30170

[0137] Using 6-bromo-2-dibenzofuranol instead of 6-bromo-1-dibenzofuranol used in Synthesis Examples 1-2 and phenylboronic acid instead of phenylboronic acid (D5), it was synthesized in the same manner to obtain <3-a> (yield 72.0%).

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

[0139] [Reaction formula 11] JPEG2025109868000076.jpg30170

[0140] Using <3-a> instead of <1-b> used in Synthesis Example 1-3, it was synthesized in the same manner to obtain <3-b> (yield 85.2%). Synthesis Example 3-3. Synthesis of <3-c>

[0141] [Reaction Formula 12] JPEG2025109868000077.jpg30170

[0142] (Compound <3-b> was used instead of <1-c> in Synthesis Examples 1-4. Otherwise, the synthesis was carried out in the same way to obtain <3-c> (yield 76.8%).

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

[0144] [Reaction Formula 13] JPEG2025109868000078.jpg54170(Synthesis Example 2-4 was carried out in the same way except that <3-c> was used instead of <2-c>. As a result, [Chemical Formula 52] was obtained (yield 58.0%).

[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 Formula 14] JPEG2025109868000079.jpg48170

[0148] (Synthesis Example 2-4 was carried out in the same way except that 1-dibenzofuranboronic acid was used instead of <2-c>. As a result, [Chemical Formula 131] was obtained (yield 61.4%).

[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] JPEG2025109868000080.jpg38158

[0152] A 1000 ml round-bottom flask was purged with nitrogen, and 50 ml of a 30 wt% aqueous hydrogen peroxide solution ( 0.477 mol), 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) of iodine and 450 ml of water were added, and the mixture was stirred at 50 °C for 24 hours. When the reaction was completed, an aqueous sodium thiosulfate solution was added and stirred, and then the reaction solution was extracted with ethyl acetate and water. After that, it was anhydrous treated and concentrated under reduced pressure. After concentration, it was 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] JPEG2025109868000081.jpg40150

[0155] A 1000 ml round-bottom flask was 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 were added, and the mixture was refluxed for 8 hours. When the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. After the organic layer was concentrated under reduced pressure, it was 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] JPEG2025109868000082.jpg36147

[0158] Place 28.6 g (0.129 mol) of <5-b> and 44.5 g (0.322 mol) of potassium carbonate in a 500 ml round-bottom flask, and add 143 ml of 1-methyl-2-pyrrolidine. Reflux for 2 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. Place 28.6 g (0.129 mol) of <5-b> and 44.5 g (0.322 mol) of potassium carbonate in a 500 ml round-bottom flask, and add 143 ml of 1-methyl-2-pyrrolidine. Reflux for 2 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. 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 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. 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. Concentrate the organic layer and then separate by column chromatography to obtain 21 g (yield 80.7%) of <5-c>. .

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

[0160] [Reaction Formula 18] JPEG2025109868000083.jpg34147

[0161] Place 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane in 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. Place 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane in 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 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 the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>. After the reaction is completed, slowly add 100 ml of water to the reaction solution, and then stir well. Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>.

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

[0163] [Reaction Formula 19] JPEG2025109868000084.jpg34147

[0164] Purge a 500 ml round-bottom flask with nitrogen, and place 15.0 g (0.080 mol) of <5-d> ) 8.2 g (0.104 mol) of pyridine and 150 ml of dichloromethane were added, and 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. After the reaction was completed, it was extracted with dichloromethane and water, and then the organic layer was dehydrated treated, concentrated under reduced pressure, and separated by column chromatography to obtain 20 g (yield 78 .4%) of <5-e>.

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

[0166] [Reaction formula 20] JPEG2025109868000085.jpg45135

[0167] A 500 ml round-bottom flask was purged with nitrogen, and 20 g (0.062 mol) of <5-e>, 23.8 g (0.094 mol) of bis(pinacolato)diboron, 2.5 g (0.003 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 9.5 g of calcium acetate (0.125 mol), and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. After 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%) of <5-f>.

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

[0169] [Reaction formula 21] JPEG2025109868000086.jpg64165

[0170] <5-f> was used instead of <2-c> in Synthesis Example 2-4, and the synthesis was carried out in the same manner to obtain [Chemical Formula 136] (yield 60.3%).

[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] JPEG2025109868000087.jpg35165

[0174] Using phenylboronic acid instead of phenylboronic acid (D5) used in Synthesis Example 1-2 Except for this, it was synthesized in the same manner to obtain <6-a> (yield 57%).

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

[0176] [Reaction Formula 23] JPEG2025109868000088.jpg33150

[0177] Using <6-a> instead of <1-b> used in Synthesis Example 1-3, except for this, it was synthesized in the same manner to obtain <6-b> (yield 86.8%).

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

[0179] [Reaction Formula 24] JPEG2025109868000089.jpg42128

[0180] Using <6-b> instead of <1-c> used in Synthesis Example 1-4, except for this, it was synthesized in the same manner to obtain <6-c> (yield 79.2%).

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

[0182] [Reaction Formula 25] JPEG2025109868000090.jpg45153

[0183] Using 1-bromopyrene instead of <1-a> used in Synthesis Examples 1-5, and <6-c> instead of <1-d> except for using <6-c> instead of <1-d>, it was synthesized in the same manner to obtain [Chemical Formula 1] (yield 52 .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] JPEG2025109868000091.jpg50161

[0187] Except for using <6-c> instead of <1-d> used in Synthesis Examples 1-5, in the same manne r it was synthesized to obtain [Chemical Formula 23] (yield 53.8%).

[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] JPEG2025109868000092.jpg55170

[0191] Except for using <2-a> instead of <1-a> used in Synthesis Examples 1-5, in the same manne r it was synthesized to obtain [Chemical Formula 41] (yield 54.2%).

[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] JPEG2025109868000093.jpg45170

[0195] The compound <3-c> was used instead of <1-d> used in Synthesis Examples 1-5, and the synthesis was carried out in the same manner to obtain [Chemical formula 57] (yield 53.5%).

[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 becomes 2 mm × 2 mm in size, it was washed. After attaching the ITO glass to a vacuum chamber, the base pressure was 1×10 - 7 torr, and then DNTPD (700 Å) and α-NPD ( 300 Å) were deposited in this order on the ITO. As the light-emitting layer, the host compound according to the present invention and the following dopant (BD) (3 wt%) were mixed and deposited (300 Å). Then, as the electron transport layer, [E-1] and [E-2] were deposited (300 Å) in a ratio of (1:1), and as the electron injection layer, [E-2] (10 Å) and Al (1,000 Å) were deposited 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] JPEG2025109868000094.jpg109170

[0199] Comparative Examples 1 to 4 The organic light-emitting device for the comparative example was the same as the device structure of the example, except that the following [BH1] and [BH2] were used instead of the compound according to the present invention. The device was fabricated and tested in the same manner. 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] JPEG2025109868000095.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 has a lower driving 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, 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 lifespan than the organic light-emitting devices using the compounds of Comparative Examples 3 to 4 using BH1 or BH2, which are compounds having a pyrene group bonded to the 3-position or 4-position of the dibenzofuran group. From this, 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 using the compound according to the present invention, compared with the conventional compound, has improved characteristics such as higher efficiency, lower voltage driving, and longer lifespan, and thus when applied to an organic light-emitting device, it exhibits improved characteristics and has high industrial applicability in the organic light-emitting device and related industrial fields. It is highly useful. < / d501> < / d101> < / d1>

Claims

1. A compound represented by the following [Chemical Formula A] or [Chemical Formula B]. (In the above [Chemical Formula A] and [Chemical Formula B], Said R １ to R １４ may be the same as or different from each other, and each independently is hydrogen, heavy water element, 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, or any one selected from halogen groups, the linking group L １ and L ２ may be the same as or different from each other, and are independent of each other , 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, selected from among the n1 and n2 may be the same or different, and are each independently an integer of 0 to 2 However, when each of these is 2, each linking group L １ and L ２ are mutually may be the same or different, the R and R' may be the same or different, 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 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, or any one selected from halogen groups, the n3 and n4 may be the same or different, and are each independently an integer of 1 to 9 however, when each of these is 2 or more, the respective R and R' may be the same or different from each other, the "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B] is , 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, a carbon number of 1 an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkyl amino 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 a lkylsilyl 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, and is substituted with one or more substituents selected from the group consisting of ).

2. The compound represented by the chemical formula A contains at least one deuterium, The compound represented by the chemical formula B contains at least one deuterium, and is characterized by the compound according to claim 1.

3. and is a group, and is characterized by the compound according to claim 2.

4. At least one R in the [Chemical Formula A] is a substituent containing deuterium, At least one R' in the [Chemical Formula B] is a substituent containing deuterium, and is characterized by the compound according to claim 2.

5. R in the above [Chemical Formula A] １ ~R ７ At least one of them is a substituent containing deuterium is an aryl group having 6 to 18 carbon atoms, R in the above [Chemical Formula B] ８ ~R １４ At least one of which contains deuterium substitution and is an aryl group having 6 to 18 carbon atoms for substitution, and is characterized by the compound according to claim 1.

6. Or it is any one selected from the following [Structural Formula 1] to [Structural Formula 5], and is characterized by the compound according to claim 1. (Hydrogen or deuterium can be bonded to the carbon of the aromatic ring in the linking group.)

7. Compound. R in the above [Chemical Formula A] １ ~R ７ At least one of them is substituted or unsubstituted

8. R in the above [Chemical Formula B] ８ ~R １４ At least one of them is substituted or unsubstituted At least one R in the [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, At least one R' in the [Chemical Formula B] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and is characterized by the compound according to claim 1. The linking groups L in the chemical formula A and the chemical formula B １ and L ２ are each a single bond or

9. 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 aryl group having 6 to 18 carbon atoms, R' in the [Chemical Formula B] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms the linking group L １ and L ２ each being a single bond, according to claim 6 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ The compound according to claim 8, characterized in that it is as described.

10. The organic compound represented by the above [Chemical Formula A] or [Chemical Formula B] is one represented by any of the following [Chemical Formula A-1] or is a compound represented by [Chemical Formula B-1], characterized in that it is as described in claim 1 of the described compound. (In the above [Chemical Formula A-1] and [Chemical Formula B-1], the substituent R １ ~R １４ , the linking group L １ and L ２ , n1 and n2 are as defined in claim 1 is the same as defined by [Chemical Formula A] or [Chemical Formula B], The substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.)

11. In the above chemical formulas A and B, n3 and n4 are each 1, R in the above [Chemical Formula A] １ ~R ７ Among R, at least one is deuterium-substituted and are aryl groups having 6 to 18 carbon atoms, R in the above [Chemical Formula B] ８ ~R １４ At least one of R' is deuterium substitution The compound according to claim 1, characterized in that it is a substituted aryl group having 6 to 18 carbon atoms.

12. In the above chemical formulas A and B, n3 and n4 are each 1, R in the above [Chemical Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, R' in the above [Chemical Formula B] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, characterized in that it is a compound according to claim 1.

13. The compound is any one selected from the group represented by the following Chemical Formulas 1 to 240 characterized in that it is a compound according to claim 1.

14. 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 of the compounds according to any one of claims 1 to 13, an organic light-emitting device.

15. 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, characterized in that it is as described in claim 14 for the organic light-emitting device.

16. The organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, and the light-emitting layer consists of a host and a dopant, and the compound is used as a host, characterized in that it is as described in claim 15 for the organic light-emitting device.

17. One or more of the dopants are selected from the following [Chemical Formula D1] to [Chemical Formula D10], characterized in that it is as described in claim 16 for the organic light-emitting device. They may be the same or different from each other, and independently of each other, are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic heterocyclic rings having 2 to 40 carbon atoms, (In the above [Chemical Formula D1] and [Chemical Formula D2], A ３１ , A ３２ , E １ and F １ are each ​ ​ said A ３１ and two adjacent carbon atoms in the aromatic ring of said A ３２ adjacent within the aromatic ring of said A The two carbon atoms are the carbon atoms linked to the substituents R ５１ and R ５２ and form a 5-membered ring By forming, a condensed ring is formed respectively, The linking group L ２１ to L ３２ may be the same or different from each other, and are independently single bonds combined, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number 2 to 60 alkenylene groups, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a position substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 2 to 60 heterocycloalkylene groups, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms group, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, selected from among 、 Said W and W' are N-R ５３ , CR ５４ R ５５ , SiR ５６ R ５７ , GeR ５８ R ５ ９ , any one selected from O, S, and Se, The substituent R ５１ ~R ５９ , Ar ２１ ~Ar ２８ may be the same or different from each other , independently of each other, 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 3 0 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 group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted carbon number 1 to 30 alkylsilyl group, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms group, a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl germanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, a halogen group, selected from among any one of them, Said R ５１ and R ５２ are connected to each other to form an alicyclic, aromatic monocyclic or polycyclic ring it can be, and the formed alicyclic, aromatic monocyclic or polycyclic carbon atoms 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 However, when each of these is 2 or more, each linking group L ２１ ~L ３２ is and may be the same or different from each other, the x1 is 1, and y1, z1 and z2 may be the same or different from each other, and are each independently an integer of 0 to 1, the aforementioned Ar ２１ and Ar ２２ Ar ２３ and Ar ２４ Ar ２５ and Ar ２６ and ２７ Ar Ar ２８ can each be connected to one another to form a ring, A in the chemical formula D1 ３２ Two adjacent carbon atoms within the ring are the structural formula Q １１ of combines with * to form a condensed ring, The A in the chemical formula D2 ３１ Two adjacent carbon atoms within the ring are the structural formula Q １ ２ combines with the * to form a condensed ring, and the two adjacent carbon atoms in the A ３２ ring are the structure Formula Q １１ can combine with the * to form a condensed ring.) (in the said [Chemical formula D3], Said X １ is any one selected from B, P, and P=O, The T1 to T3 may be the same as or different from each other, and independently of each other, may be substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic heterocyclic rings having 2 to 40 carbon atoms, Said Y １ is selected from N-R ６１ , CR ６２ R ６３ , O, S, SiR ６４ R ６５ among them and any of them, Said Y ２ is selected from N-R ６６ , CR ６7 R ６８ , O, S, SiR ６９ R ７０ selected from among and any of them, Said R ６１ to R ７０ may be the same as or different from each other, and are independent of each other, water hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms , substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy groups having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy groups having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine groups having 1 to 30 carbon atoms, substituted or unsubstituted arylamine groups having 5 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 5 to 30 carbon atoms is, respectively, bonded to one or more rings selected from among the T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring. ( In the above [Chemical Formula D4] and [Chemical Formula D5], is any one selected from a ryl group, a cyano group, and a halogen group, and said R ６１ ~R ７０ the T4 to T6 are the same as T1 to T3 in [Chemical Formula D3], and any of them, and any of them, Said X ２ is any one selected from B, P, and P=O, and any of them, Said Y ４ is N-R ６１ , CR ６２ R ６３ , O, S, SiR ６４ R ６５ selected from among the T7 to T9 are the same as T1 to T3 in [Chemical Formula D3], Said Y ５ is selected from N-R ６６ CR ６7 R ６８ O, S, SiR ６９ R ７０ and selected from among them and any of them, Said Y ６ is selected from N-R ７１ , CR ７２ R ７３ , O, S, SiR ７４ R ７５ and selected from among them and can further form a ring, or can be bonded to the T7 ring or T9 ring to further form an alicyclic or aromatic monocyclic or The aforesaid R ６１ to R ７５ is the same as the aforesaid R ６１ to R ７０ in [Chemical Formula D3].) (wherein X ３ is any one selected from B, P, and P=O, polycyclic ring. ( Said Y ６ is selected from N-R ６１ , CR ６２ R ６３ , O, S, SiR ６４ R ６５ and is selected from among In the above [Chemical Formula D8] to [Chemical Formula D10], the substituent R ６１ ~R ６５ , R ７１ ~R ７２ are each the one in [[Chemical Formula D3]] R ６１ ~R ７０ is the same as, but Said R ７１ and R ７２ are each connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring the X is any one selected from B, P, and P=O, and any one, and can further form a ring, and can further form a ring, 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, Se, and is selected from any one of them the ring formed by the Cy1 is a nitrogen (N) atom, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms to which the nitrogen (N) atom is bonded, The substituent R ３ to R ５ are each the R ６１ to R ７０ in [Chemical Formula D3] and are identical in the above Chemical Formula D9, Said R ３ to R ５ each is bonded to said Q ２ ring or Q ３ ring to form an alicyclic or aromatic monocyclic ring the Cy2 can be added to the Cy1 to form a saturated hydrocarbon ring, and the ring formed by the Cy2 is, excluding the carbon atoms contained in the Cy1, a substituted or unsubstituted Said R ４ and R ５ are each connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring alkylene group having 1 to 10 carbon atoms, in the above Chemical Formula D10, Q １ An aromatic carbon atom in the ring and Q bonded to Cy1 １ Except for the aromatic carbon atom in the ring excluding the carbon atoms in the Cy1 to which the above is bonded, a substituted or unsubstituted alkylene having 1 to 10 carbon atoms ​ ​ ​ ​ ​ The ring formed by the Cy3 binds to the Q that binds to the Cy3 ３ aromatic carbon atoms within the ring, Q bonded to a nitrogen (N) atom ３ inner aromatic carbon atom, nitrogen (N) atom, the nitrogen (N) atom ​ is an N group.) (Here, the "substituted or unsubstituted" in the above [Chemical Formula D1] to [Chemical Formula D10] The "substitution" in means deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, a carbon number 1 to 24 alkyl group, 1 to 24 halogenated alkyl group, 2 to 24 alkenyl group, 2 to 24 alkynyl group, 3 to 24 cycloalkyl group, carbon number 1 to 24 heteroalkyl group, 6 to 24 aryl group, 7 to 24 arylalkyl group, 7 to 24 alkylaryl group, 2 to 24 heteroaryl group , 2 to 24 heteroarylalkyl group, 1 to 24 alkoxy group, 1 to 24 alkylamino group, 12 to 24 diarylamino group, 2 to 24 Diheteroarylamino group, 7 to 24 aryl(heteroaryl)amino group, 1 to 24 alkylsilyl group, 6 to 24 arylsilyl group, 6 to 2 4 aryloxy group, 6 to 24 arylthionyl group, and is substituted with one or more substituents selected from the group consisting of 1 to 24 alkyl group, 1 to 24 halogenated alkyl group, 2 to 24 alkenyl group, 2 to 24 alkynyl group, 3 to 24 cycloalkyl group, carbon number 1 to 24 heteroalkyl group, 6 to 24 aryl group, 7 to 24 arylalkyl group, 7 to 24 alkylaryl group, 2 to 24 heteroaryl group , 2 to 24 heteroarylalkyl group, 1 to 24 alkoxy group, 1 to 24 alkylamino group, 12 to 24 diarylamino group, 2 to 24 Diheteroarylamino group, 7 to 24 aryl(heteroaryl)amino group, 1 to 24 alkylsilyl group, 6 to 24 arylsilyl group, 6 to 2 4 aryloxy group, 6 to 24 arylthionyl group, and is substituted with one or more substituents selected from the group consisting of

18. One or more layers selected from each of the above layers are formed by a vapor deposition process or a solution process The organic light-emitting device according to claim 15, characterized in that

19. The organic light-emitting device is 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 The organic light-emitting device according to claim 14, characterized in that it is used in any one selected from the group consisting of device. The organic light-emitting device according to claim 14, characterized in that it is used in any one selected from the group consisting of

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