Novel heterocyclic compound and light-emitting element including the same

Abstract

To provide a novel pyrene fused ring compound usable as a host material of a light-emitting layer in an organic light-emitting element.SOLUTION: The invention relates to pyrene heterocyclic compounds usable for an organic light-emitting element, and an organic light-emitting element including the same, and more specifically to compounds represented by the structural formulas in the figure and an organic light-emitting element including the same. In the formulas, Ar1 to Ar4 are each independently a substituent including a pyrene structure.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to novel heterocyclic compounds that can be used in organic light-emitting devices, and more particularly to heterocyclic compounds that can be used in organic light-emitting devices. It can be used as a host material for the light-emitting layer in the organic light-emitting device, resulting in high luminous efficiency and long life. Novel heterocyclic compound capable of realizing the above device characteristics, and organic light-emitting device including the same Regarding. [Background technology]

[0002] Organic light emitting diode (OLE) D) is a display that utilizes the self-luminous phenomenon, has a wide viewing angle, and is similar to a liquid crystal display. Compared to LEDs, they are lighter, thinner, and smaller, and have the advantage of fast response time. It is expected to be applied to full-color displays and lighting.

[0003] In general, organic light-emitting phenomena are those that convert electrical energy into light energy using organic materials. An organic light-emitting device that utilizes the organic light-emitting phenomenon usually consists of an anode, a cathode, and The organic layer has a structure including an organic material layer interposed between the organic material layers. To enhance the stability and durability, they often have a multi-layer structure made up of different materials, e.g. 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, etc. When a voltage is applied between the two electrodes in this structure of an organic light-emitting device, holes are generated at the anode and electrons are generated at the cathode. At the electrode, electrons are injected into the organic layer, and when the injected holes and electrons combine, excitons (e When this exciton falls back to the ground state, light is emitted. Such organic light-emitting devices have the following characteristics: self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high controllability. It is known to have properties such as durability and high-speed response.

[0004] The materials used in the organic layers of the organic light-emitting device are classified into two types depending on their functions: light-emitting material and electroluminescent material. Charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials The light-emitting materials can be classified into high molecular weight and low molecular weight types according to their molecular weight. By this mechanism, fluorescent materials derived from singlet excited states of electrons and triplet excited states of electrons are They can be classified as phosphorescent materials.

[0005] On the other hand, when only one substance is used as the luminescent material, the maximum The emission wavelength shifts to longer wavelengths, reducing color purity and decreasing the efficiency of the device due to the emission attenuation effect. Therefore, it is necessary to increase the color purity and improve the luminous efficiency by energy transfer. To increase the efficiency, a host-dopant system can be used as the emissive material. Cut.

[0006] The principle is to use a dopant with a smaller energy band gap than the host that forms the light-emitting layer. When mixed in a small amount into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, resulting in high efficiency. At this time, the wavelength of the host shifts to the wavelength band of the dopant, Light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] Recently, heterocyclic compounds have been studied as host compounds in such light-emitting layers. As related prior art, Korean Patent Publication No. 10-2017-0116843 The publication (October 20, 2017) describes a compound having a structure in which a nitrogen-containing heterocycle is fused to a benzofluorene ring. The present invention discloses a compound having the same structure and an organic light-emitting device containing the same. Publication No. 10-2017-0055743 (May 22, 2017) describes oxygen, nitrogen, Aryl or heteroaryl substituents on fused fluorene rings containing heteroatoms such as sulfur Compounds having attached groups and organic light-emitting devices containing them are disclosed.

[0008] However, including these conventional techniques, various types of organic light-emitting devices for use in the light-emitting layer of organic light-emitting devices have been developed. Although the compound has been produced in this state, it is still applicable to organic light-emitting devices and is stable. Development of a novel compound having stable, high efficiency and long life characteristics, and an organic light-emitting device containing the same There is a continuing need for development. Summary of the Invention [Problem to be solved by the invention]

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

[0010] Another object of the present invention is to apply the heterocyclic compound to a host material in an organic light emitting device. As a result, organic light-emitting devices with high luminous efficiency and long life are developed. The company aims to provide LEDs (light emitting diodes, OLEDs). [Means for solving the problem]

[0011] In order to achieve the above object, the present invention provides a compound represented by the following [Chemical Formula A] or [Chemical Formula B] Heterocyclic compounds are provided.

[0012] [Chemical formula A] JPEG2025148422000002.jpg64152

[0013] [Chemical formula B] JPEG2025148422000003.jpg84152

[0014] In the above [Chemical Formula A] and [Chemical Formula B], A1, A2, E and F are each independently may be the same or different, and each independently represent a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms. an aromatic hydrocarbon ring, Two adjacent carbon atoms in the aromatic ring of A1 and two adjacent carbon atoms in the aromatic ring of A2 The two carbon atoms form a five-membered ring with the carbon atoms connected to the substituents R1 and R2. and each of these forms a fused ring, The linking groups L1 to L4 may be the same or different from one another, and may each independently represent a single a bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, M is any one selected from N-R3, CR4R5, O, and S; M' is any one selected from N-R6, CR7R8, O, and S; The substituents R1 to R8, R 11 ~R 15 may be the same or different, and independently, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms; or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 3 carbon atoms alkylsilyl groups having 6 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, sialic acid is any one selected from the group consisting of a hydroxyl group, a nitro group, and a halogen group; The R1 and R2 may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. can be done, The s1 to s4 may be the same or different, and each independently represents an integer of 1 to 3. When each of these is two or more, the respective linking groups L1 to L4 are mutually may be the same or different, The x, y, z, and w may be the same or different, and each independently represents 0 or 1. is an integer, In chemical formula A, x+y+z=1 or x+y+z=2 is satisfied; In chemical formula B, x+y+z+w=1 or x+y+z+w=2 is satisfied; In the chemical formula A, two adjacent carbon atoms in the A2 ring are the same as * in the structural formula Q1. bonded to form a fused ring, In the chemical formula B, the two adjacent carbon atoms in the A1 ring are represented by the structural formula Q2 * to form a fused ring, and two adjacent carbon atoms in the A2 ring are It bonds with * in 1 to form a condensed ring, The Ar1 to Ar4 may be the same or different, and each independently represent the following: Represented by [Structural Formula C], [Structural formula C] JPEG2025148422000004.jpg4970R in the structural formula C 21 ~R 30 may be the same or different and are independent of each other. hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted substituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted Heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms arylsilyl group, substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, cyano group, nitro group, a tetrahydrogen group, a methyl group, or a halogen group; R 21 ~R 30 is a single bond bonded to linking groups L1 to L4, In the above [chemical formula A], [chemical formula B] and [structural formula C], the "substituted or unsubstituted The "substituted" in "substituted" includes deuterium, cyano group, halogen group, hydroxy group, nitro group, Alkyl groups having 1 to 24 carbon atoms, halogenated alkyl groups having 1 to 24 carbon atoms, and alkyl groups having 1 to 24 carbon atoms. an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 3 to 24 carbon atoms, Heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, and aryl groups having 7 to 24 carbon atoms. alkyl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, a aryl group, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, Alkylamino groups having 1 to 24 carbon atoms, diarylamino groups having 12 to 24 carbon atoms, and Diheteroarylamino groups with 7 to 24 carbon atoms, aryl (heteroaryl) amino groups with 7 to 24 carbon atoms alkylsilyl groups having 1 to 24 carbon atoms, arylsilyl groups having 6 to 24 carbon atoms, from the group consisting of an aryloxy group having 6 to 24 carbon atoms and an arylthionyl group having 6 to 24 carbon atoms; It means substituted with one or more selected substituents. [Effects of the Invention]

[0015] When the novel heterocyclic compound according to the present invention is used as a host material in an organic light-emitting device, The organic light emitting device exhibits improved efficiency and longevity compared to the organic light emitting device according to the prior art. A light emitting element can be provided. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a schematic diagram of an organic light-emitting device according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0017] The present invention will be described in more detail below. In each drawing of the present invention, the size or The dimensions are shown larger or smaller than actual dimensions for clarity of the present invention. The drawings are not intended to limit the scope of the present invention, but rather to illustrate the present invention by omitting known components so as to highlight the distinctive features of the present invention. stomach.

[0018] In addition, the size and thickness of each component shown in the drawings are shown arbitrarily for the convenience of explanation. The present invention is not necessarily limited to the illustrations shown, and the drawings may not clearly show multiple layers and regions. In the drawings, the thickness is enlarged for clarity. The thickness of layers and regions is exaggerated. Layers, films, regions, plates, etc. are shown "on" other parts. When there is a part, this does not only mean that it is "directly on top" of another part, but also that there is another part between them. This also includes cases where minutes are involved.

[0019] Also, throughout the specification, when a part "contains" a certain component, this means Unless specifically stated to the contrary, the term "inclusion" shall not be construed to exclude another element but to include another element. Also, throughout the specification, "on" means It means that the object is located above or below the target part, and does not necessarily have to be based on the direction of gravity. This does not mean that the device is located above the

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

[0021] [Chemical formula A] JPEG2025148422000005.jpg64143

[0022] [Chemical formula B] JPEG2025148422000006.jpg86143

[0023] In the above [Chemical Formula A] and [Chemical Formula B], A1, A2, E and F are each independently may be the same or different, and each independently represent a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms. an aromatic hydrocarbon ring, Two adjacent carbon atoms in the aromatic ring of A1 and two adjacent carbon atoms in the aromatic ring of A2 The two carbon atoms form a five-membered ring with the carbon atoms connected to the substituents R1 and R2. and each of these forms a fused ring, The linking groups L1 to L4 may be the same or different from one another, and may each independently represent a single a bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, M is any one selected from N-R3, CR4R5, O, and S; M' is any one selected from N-R6, CR7R8, O, and S; The substituents R1 to R8, R 11 ~R 15 may be the same or different from each other, each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted aryl groups having 3 to 30 carbon atoms a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; Substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted carbon atoms Alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms , a cyano group, a nitro group, or a halogen group; The R1 and R2 may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. can be done, The s1 to s4 may be the same or different, and each independently represents an integer of 1 to 3. When each of these is two or more, the respective linking groups L1 to L4 are mutually may be the same or different, The x, y, z, and w may be the same or different, and each independently represents 0 or 1. is an integer, In chemical formula A, x+y+z=1 or x+y+z=2 is satisfied; In chemical formula B, x+y+z+w=1 or x+y+z+w=2 is satisfied; In the chemical formula A, two adjacent carbon atoms in the A2 ring are the same as * in the structural formula Q1. bonded to form a fused ring, In the chemical formula B, the two adjacent carbon atoms in the A1 ring are represented by the structural formula Q2 * to form a fused ring, and two adjacent carbon atoms in the A2 ring are It bonds with * in 1 to form a condensed ring, The Ar1 to Ar4 may be the same or different, and each independently represent the following: Represented by [Structural Formula C], [Structural formula C] JPEG2025148422000007.jpg4973R in the structural formula C 21 ~R 30 may be the same or different and are independent of each other. hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, Substituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted cycloaryl groups having 3 to 30 carbon atoms alkyl groups, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, is one selected from a nitro group and a halogen group, R 21 ~R 30 is a single bond bonded to linking groups L1 to L4, In the above [chemical formula A], [chemical formula B] and [structural formula C], the "substituted or unsubstituted The "substituted" in "substituted" includes deuterium, cyano group, halogen group, hydroxy group, nitro group, Alkyl groups having 1 to 24 carbon atoms, halogenated alkyl groups having 1 to 24 carbon atoms, and alkyl groups having 1 to 24 carbon atoms. an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 3 to 24 carbon atoms, Heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, and aryl groups having 7 to 24 carbon atoms. alkyl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, a aryl group, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, Alkylamino groups having 1 to 24 carbon atoms, diarylamino groups having 12 to 24 carbon atoms, and Diheteroarylamino groups with 7 to 24 carbon atoms, aryl (heteroaryl) amino groups with 7 to 24 carbon atoms alkylsilyl groups having 1 to 24 carbon atoms, arylsilyl groups having 6 to 24 carbon atoms, from the group consisting of an aryloxy group having 6 to 24 carbon atoms and an arylthionyl group having 6 to 24 carbon atoms; It means substituted with one or more selected substituents.

[0024] On the other hand, the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and " The alkyl group or aryl group in the "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" Considering the range of the aryl group, the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms are The range of the carbon number of the aryl group is the range of the carbon number of the unsubstituted aryl group, without taking into consideration the portion substituted with the above-mentioned substituent. The total number of carbon atoms constituting the alkyl or aryl moiety when considered as a substituent. For example, a phenyl group substituted with a butyl group at the para position is substituted with a butyl group having four carbon atoms. It should be considered to be an aryl group having 6 carbon atoms.

[0025] The aryl group, which is a substituent used in the compounds of the present invention, can be converted to aromatic by removing one hydrogen atom. an organic radical derived from an aromatic hydrocarbon, wherein the aryl group has a substituent; In this case, adjacent substituents may be fused together to form a ring.

[0026] Specific examples of the aryl group include a phenyl group, an o-biphenyl group, and an m-biphenyl group. , p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, Naphthyl group, anthryl group, phenanthryl group, pyrenyl group, indenyl group, fluorenyl group aryl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl, fluoranyl group and aromatic groups such as phenyl and the like, wherein 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, The groups (-NH, -NH(R), -N(R')(R''), R' and R'' are independently and an alkyl group having 1 to 10 carbon atoms, in which case it is referred to as an "alkylamino group"); Amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphate group, Alkyl groups with 1 to 24 carbon atoms, halogenated alkyl groups with 1 to 24 carbon atoms, and alkyl groups with 2 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, Aryl groups having 6 to 24 carbon atoms, arylalkyl groups having 6 to 24 carbon atoms, It can be substituted with a heteroaryl group or a heteroarylalkyl group having 2 to 24 carbon atoms.

[0027] The heteroaryl group, which is a substituent used in the compounds of the present invention, is selected from the group consisting of N, O, P, Si, and S. , Ge, Se, Te, and the remaining ring It means a ring aromatic system having 2 to 24 carbon atoms, the atoms of which are carbon, and these rings are fused. d) can form a ring, and one or more hydrogen atoms in the heteroaryl group can be The atoms can be substituted with the same substituents as in the aryl group.

[0028] In the present invention, the aromatic heterocycle is an aromatic hydrocarbon ring in which an aromatic carbon atom is bonded to an aromatic hydrocarbon ring. The aromatic heterocycle preferably has one or more of the following substituents: The aromatic hydrocarbons have one to three aromatic carbon atoms, which are N, O, P, Si, S, Ge, Se, and T. e may be substituted with one or more heteroatoms selected from the group consisting of

[0029] The alkyl group used as a substituent in the present invention is a group consisting of an alkane and a hydroxyl group. It is a substituent in which hydrogen has been removed, and has a structure including a linear and branched structure. Specific examples include is methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert -butyl, pentyl, iso-amyl, hexyl, etc. One or more hydrogen atoms in the group can be substituted with the same substituents as in the aryl group. do.

[0030] The "cyclo" in the cycloalkyl group which is a substituent used in the compound of the present invention is means a substituent having a structure capable of forming a monocyclic or polycyclic structure of saturated hydrocarbon within the alkyl group; Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopropyl ... Pentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclo dicyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decyl Examples of such cyclohexyl groups include norbornyl, bornyl, and isobornyl. One or more hydrogen atoms in the alkyl group may be substituted with the same substituents as in the aryl group. It is Noh.

[0031] The alkoxy group, which is a substituent used in the compound of the present invention, is an alkyl group or a cycloalkoxy group. A substituent in which an oxygen atom is bonded to the end of an alkyl group, and specific examples thereof include methoxy, ethoxy, and ethoxy. Butyloxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isobutyloxy o-Amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, ada Mantanoxy, dicyclopentanoxy, bornyloxy, isobornyloxy, etc. In the case of the aryl group, one or more hydrogen atoms in the alkoxy group may be can be substituted with the same substituents as those shown in

[0032] Specific examples of the arylalkyl group that is a substituent used in the compound of the present invention include phenyl Nylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthyl and the like, wherein one or more hydrogen atoms in the arylalkyl group are The aryl group can be substituted with the same substituents as those for the aryl group.

[0033] Specific examples of the silyl group that is a substituent used in the compound of the present invention include trimethylsilyl. silyl, 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.

[0034] In the present invention, an alkenyl group is defined as a group consisting of two carbon atoms. Alkyl groups are defined as groups that contain one carbon-carbon double bond, and alkynyl groups are defined as groups that contain one carbon-carbon double bond. kynyl group contains one carbon-carbon triple bond formed by two carbon atoms It means an alkyl substituent.

[0035] The alkylene group used in the present invention may be a straight-chain or branched alkylene group. It is derived from the removal of two hydrogen atoms in the molecule of alkane, a saturated hydrocarbon. Specific examples of the alkylene group include a methylene group, an ethylene group, Propylene group, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group Examples of the alkyl group include an ethylene group, a pentylene group, an iso-amylene group, and a hexylene group. One or more hydrogen atoms in the alkylene group may be substituted with the same substituents as in the aryl group. can be replaced by

[0036] In addition, the diarylamino group in the present invention is a group consisting of the above-mentioned two identical or different aryl groups. In the present invention, the term "diheteroaryl" refers to an amine group in which a group is bonded to a nitrogen atom. The amino group refers to an amine group having two identical or different heteroaryl groups attached to the nitrogen atom. The aryl(heteroaryl)amino group is a group consisting of the aryl group and the heteroaryl group. Each represents an amine group bonded to a nitrogen atom.

[0037] On the other hand, the "substituted or unsubstituted" of [Chemical Formula A], [Chemical Formula B] and [Structural Formula C] More preferred examples of the "substitution" in "of" include deuterium, cyano group, halogen group, hydroxyl group, oxy group, nitro group, alkyl group having 1 to 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms alkenyl groups having 2 to 12 carbon atoms, alkynyl groups having 2 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, a heteroalkyl group having 6 to 18 carbon atoms, , an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, Heteroaryl groups having 2 to 18 carbon atoms, heteroarylalkyl groups having 2 to 18 carbon atoms, 12 alkoxy groups, alkylamino groups with 1 to 12 carbon atoms, diaryl groups with 12 to 18 carbon atoms C2-18 diheteroarylamino group, C7-18 aryl( Heteroaryl)amino group, alkylsilyl group having 1 to 12 carbon atoms, aryl group having 6 to 18 carbon atoms arylsilyl group, aryloxy group having 6 to 18 carbon atoms, and arylthio group having 6 to 18 carbon atoms and nyl groups.

[0038] In the present invention, the above-mentioned "R1 and R2 are linked to each other to form an alicyclic or aromatic single ring" is also applicable. In the case of "can form a ring or polycycle", this can be By removing one hydrogen radical from each of the groups and linking them together, a ring can be formed. This means that it is possible to

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

[0040] [Structural formula C] JPEG2025148422000008.jpg4973 A1, A2, E and F in the [Chemical Formula A] and [Chemical Formula B] according to the present invention are may be the same or different, and independently represent substituted or unsubstituted alkyl groups having 6 to 10 carbon atoms. 50 aromatic hydrocarbon ring, preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms. It is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 carbon atoms. The aromatic hydrocarbon ring may be an aromatic hydrocarbon ring.

[0041] As described above, A1, A2, E, and F in chemical formula A or chemical formula B are each the same. may be different, and may be independently substituted or unsubstituted aromatic hydrocarbons having 6 to 18 carbon atoms. When the aromatic hydrocarbon ring corresponds to a hydrogen ring, the aromatic hydrocarbon rings may be the same or different and may be independently In other words, it can be any one selected from [Structural Formula 10] to [Structural Formula 21].

[0042] JPEG2025148422000009.jpg131165

[0043] In the structural formulas 10 to 21, "-*" represents a bond between the substituents R1 and R2. forming a five-membered ring containing the carbon atom in the above structural formula Q1 and Q2, or means a bonding position for forming a five-membered ring, The aromatic hydrocarbon ring of the above [Structural Formula 10] to [Structural Formula 21] corresponds to the A1 ring or the A2 ring. When the compound is bonded to structural formula Q1 or structural formula Q2 while the compound is bonded to the compound, two adjacent compounds of the compound The carbon atom of is bonded to * in the structural formula Q1 or bonded to * in the structural formula Q2 to form a condensed Forming a ring, In [Structural Formula 10] to [Structural Formula 21], R is hydrogen, deuterium, substituted or unsubstituted C1-30 alkyl group, substituted or unsubstituted C6-20 aryl group, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 2 to 30 carbon atoms, 20 heteroaryl groups, substituted or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted arylsilyl groups with 6 to 30 carbon atoms, cyano groups, nitro groups, halogens is any one selected from the group The m is an integer of 1 to 8, and when m is 2 or more or when R is 2 or more, R may be the same or different.

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

[0045] JPEG2025148422000010.jpg65165 Hydrogen or deuterium can be bonded to the carbon of the aromatic ring in the linking group.

[0046] In one embodiment of the present invention, the compound represented by [Chemical Formula A] is A compound in which either A2 or E is bonded to a pyrene substituent represented by the following [Structural Formula C] wherein x is 1 and y and z are each 0, or wherein y is 1 and x and z are each 0. and z are each 0, or z is 1, and x and y are each 0. In the compound represented by the formula A, two of A1, A2, and E are A compound bonded to a pyrene substituent represented by the following structural formula C, where x and y are each each of x and z is 1 and y is 0; or each of x and z is 1 and y is 0; or a structure in which y and z are each 1 and x is 0, The compound represented by the formula (I) is such that any one of A1, A2, E and F is represented by the following [Structural Formula C] A structure binding to a pyrene substituent, where x is 1, and y, z, and w are each 0. Or, two of A1, A2, E and F are pyrene groups represented by the following structural formula C. A structure bonding to a substituent, where x and y are each 1, and z and w are 0. It could be.

[0047] In one embodiment of the present invention, the substituents R1 and R2 in the formula A or B are R and R2 may be the same or different and independently represent a substituted or unsubstituted carbon atom. alkyl groups having 1 to 10 prime numbers, which may be linked together to form a ring, It is also possible that the ring does not form a ring.

[0048] In one embodiment of the present invention, R in the pyrene structure of the structural formula C 21 ~R 23 Any of these may be a single bond that bonds to the linking groups L1 to L4.

[0049] In one embodiment of the present invention, R 21 ~R 30 are respectively may be the same or different, and may independently represent hydrogen, deuterium, substituted or unsubstituted Alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, or unsubstituted heteroaryl groups having 2 to 12 carbon atoms, In the structural formula C, R that is not connected to L1 to L4 21 ~R 30 At least one of substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 6 to 12 carbon atoms, an aryl group, a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms; It can be either:

[0050] In one embodiment of the present invention, the R 11 ~R 15 are the same but different may be each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, alkyl groups, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted carbon alkylsilyl groups having 1 to 15 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, The substituents may be selected from the group consisting of aryl, cyano, and halogen.

[0051] In addition, the compound represented by the formula A or B according to the present invention is a compound represented by the formula [H1] ~[H180] may be any one selected from.

[0052] JPEG2025148422000011.jpg220170JPEG2025148422000012.jpg228170JPEG2025148422000013.jpg227170 JPEG2025148422000014.jpg247170JPEG2025148422000015.jpg255168JPEG2025148422000016.jpg239170 JPEG2025148422000017.jpg244170JPEG2025148422000018.jpg231170JPEG2025148422000019.jpg249170 JPEG2025148422000020.jpg245170JPEG2025148422000021.jpg219170JPEG2025148422000022.jpg180170

[0053] The present invention also provides a semiconductor device comprising: a first electrode; a second electrode facing the first electrode; and the first electrode and an organic layer interposed between the second electrode and the organic layer; The present invention provides an organic light-emitting device comprising one or more compounds represented by [chemical formula A] or [chemical formula B].

[0054] On the other hand, in the present invention, "(the organic layer) contains one or more organic compounds" means "(the organic layer) However, one organic compound belonging to the category of the present invention, or a combination of the organic compounds belonging to the category of the present invention It can be interpreted as "the compound can contain two or more different compounds."

[0055] In this case, the organic layer in the organic light-emitting device of the present invention comprises a hole injection layer, a hole transport layer, ... transport layer, a hole injection layer, a hole transport layer, a hole injection layer, a hole transport layer, a hole transport layer, a hole injection layer, a hole transport layer, a hole transport layer, a hole injection functional layer having both an electron injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer It may contain at least one of them.

[0056] As a more preferred embodiment of the present invention, the present invention provides a method for manufacturing a semiconductor device comprising: The organic layer interposed therebetween includes a light-emitting layer, and the light-emitting layer comprises a host and a dopant. At least one of the compounds represented by [chemical formula A] or [chemical formula B] in It can be included as a host compound in the light-emitting layer.

[0057] In the present invention, the dopant compound used in the light-emitting layer may be the following [Chemical At least one compound represented by any one of formulas D1 to D10 It can include.

[0058] [Chemical formula D1] JPEG2025148422000023.jpg110170

[0059] [Chemical formula D2] JPEG2025148422000024.jpg124170

[0060] In the above [Chemical Formula D1] and [Chemical Formula D2], A 31 , A 32 , E1 and F1 are respectively may be the same or different, and each independently represents a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms. an aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle having 2 to 40 carbon atoms, The above A 31 and two adjacent carbon atoms in the aromatic ring of A 32 Next to the aromatic ring The two carbon atoms that meet are the substituents R 51 and R 52 carbon atoms connected to form a five-membered ring By combining the two, a fused ring is formed, The linking group L 21 ~L 32 may be the same or different and may be independently Bond, substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, substituted or unsubstituted carbon an alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, Substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, substituted or unsubstituted carbon heterocycloalkylene groups having 2 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R, The W and W' may be the same or different and independently represent NR 53 , CR 54 R 55 , SiR 56 R 57 , GeR 58 R 59 , O, S, Se either The substituent R 51 ~R 59 , Ar 21 ~Ar 28 may be the same or different , each independently represents hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted aryl groups having 2 to 3 carbon atoms 0 alkenyl group, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or Unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms chloroalkenyl group, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 1 carbon atom, alkoxy groups with up to 30 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkylthiol groups having 1 to 30 carbon atoms, substituted or unsubstituted alkylthiol groups having 5 carbon atoms Arylthioxy group having up to 30 carbon atoms, 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 carbon alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 5 to 30 carbon atoms group, substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, substituted or unsubstituted Substituted from arylgermanium groups with 1 to 30 carbon atoms, cyano groups, nitro groups, and halogen groups. Either one is selected, R 51 and R 52 are linked together to form an alicyclic or aromatic monocyclic or polycyclic ring. The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N, O, P, It can be substituted with at least one heteroatom selected from Si, S, Ge, Se, and 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 two or more, each linking group L 21 ~L 32 teeth, may be the same or different from each other, x1 is 1, and y1, z1, and z2 may be the same or different, are each independently an integer between 0 and 1, The Ar 21 and Ar 22 , Ar 23 and Ar 24 , Ar 25 and Ar 26 , and Ar 27 and Ar 28 can be linked to each other to form a ring, In the chemical formula D1, A 32 Two adjacent carbon atoms in the ring are represented by the formula Q 11 * combines with the to form a condensed ring, In the chemical formula D2, 31Two adjacent carbon atoms in the ring are represented by the formula Q 12 and * in the formula (I) to form a condensed ring, 32 Two adjacent carbon atoms in the ring are Structural formula Q 11 can be bonded to * to form a fused ring.

[0061] [Chemical Formula D3] JPEG2025148422000025.jpg50103

[0062] In the above [Chemical Formula D3], X1 is any one selected from B, P, and P=O, The T1 to T3 may be the same or different, and may be independently substituted or unsubstituted. or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic hydrocarbon ring having 2 to 50 carbon atoms ~40 aromatic heterocycles, wherein Y1 is NR 61 , C.R. 62 R 63 ,O,S,SiR 64 R 65 Selected from It can be either wherein Y2 is NR 66 , C.R. 66 R 68 ,O,S,SiR 69 R 70 Selected from It can be either R 61 ~R 70 may be the same or different, and may each independently represent 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 , a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted carbon an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, Substituted or unsubstituted alkylthiol groups having 1 to 30 carbon atoms, substituted or unsubstituted carbon an arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 5 to 30 carbon atoms, is any one selected from the group consisting of an alkyl group, a cyano group, and a halogen group, 61 ~R 70 each bonded to at least one ring selected from T1 to T3 to form an alicyclic or can further form an aromatic monocyclic or polycyclic ring.

[0063] JPEG2025148422000026.jpg65136

[0064] In the above [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], wherein Y4 is NR 61 , C.R. 62 R 63 ,O,S,SiR 64 R 65 Selected from It can be either wherein Y5 is NR 66 , C.R. 66 R 68 ,O,S,SiR 69 R 70 Selected from It can be either wherein Y6 is NR 71 , C.R. 72 R 73 ,O,S,SiR 74 R 75Selected from It can be either R 61 ~R 75 is the R in [Chemical Formula D3] 61 ~R 70 is the same as

[0065] JPEG2025148422000027.jpg59136

[0066] 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], wherein Y6 is NR 61 , C.R. 62 R 63 ,O,S,SiR 64 R 65 Selected from It can be either The substituent R 61 ~R 65 , R 71 ~R 72 are the above in [chemical formula D3], respectively. R 61 ~R 70 is identical to R 71 and R 72 are each connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. or by combining with the T7 ring or T9 ring to form an alicyclic or aromatic monocyclic or can further form polycyclic rings.

[0067] JPEG2025148422000028.jpg96130

[0068] In the above [Chemical Formula D8] to [Chemical Formula D10], X is any one selected from B, P, and P=O, 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. can be, The substituents R3 to R5 are each the R 61 ~R 70 Same as and The R3 to R5 are each bonded to the Q2 ring or the Q3 ring to form an alicyclic or aromatic monocyclic ring. or may further form polycyclic rings, The R4 and R5 may be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. can be further formed, The ring formed by Cy1 has a nitrogen (N) atom, a ring bonded to the nitrogen (N) atom, and a ring bonded to the nitrogen (N) atom. The aromatic carbon atom in the Q1 ring and the aromatic carbon atom in the Q1 ring bonded to Cy1 are excluded. For example, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, In the above chemical formula D9, The "Cy2" can be attached to the Cy1 to form a saturated hydrocarbon ring, and the C The ring formed by y2 may be substituted or unsubstituted except for the carbon atom contained in Cy1. is an alkylene group having 1 to 10 carbon atoms; In the above chemical formula D10, The ring formed by Cy3 is preferably an aromatic carbon atom in the ring Q3 bonded to Cy3. , an aromatic carbon atom in Q3 bonded to the nitrogen (N) atom, the nitrogen (N) atom, A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, excluding the carbon atom in Cy1 to which the atom is attached, is an alkylene group, Here, the "substituted or unsubstituted" in the [chemical formula D1] to [chemical formula D10] "Substitution" in "" means deuterium, cyano group, halogen group, hydroxy group, nitro group, carbon alkyl groups having 1 to 24 carbon atoms, halogenated alkyl groups having 1 to 24 carbon atoms, alkyl groups having 2 to 24 carbon atoms alkenyl groups, alkynyl groups having 2 to 24 carbon atoms, heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, arylalkyl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, an aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an oxy group, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, heteroarylamino groups having 1 to 24 carbon atoms, alkylsilyl groups having 6 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms; It means substituted with one or more substituents.

[0069] In addition, among the dopant compounds according to the present invention, the compounds represented by the formulas [Chemical Formula D3] to [Chemical Formula D10] In the case of a boron compound represented by any one of the following, the aromatic carbons T1 to T9 or Q1 to Q3 Substituents that can be substituted on the hydrogenocarbon ring or aromatic heterocycle include deuterium, alkylene having 1 to 24 carbon atoms, and alkyl groups, aryl groups having 6 to 24 carbon atoms, alkylamino groups having 1 to 24 carbon atoms, alkylamino groups having 6 to 24 carbon atoms 24 arylamino groups, wherein the alkylamino groups having 1 to 24 carbon atoms and and each alkyl group or aryl group in the arylamino group having 6 to 24 carbon atoms is More preferred substituents that can be linked to each other include alkyl groups having 1 to 12 carbon atoms, Aryl groups with 6 to 18 carbon atoms, alkylamino groups with 1 to 12 carbon atoms, aryl groups with 6 to 18 carbon atoms The amino group can be substituted, and the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms can be substituted. The alkyl or aryl groups in the alkylamino group can be linked to each other.

[0070] Meanwhile, 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 [Chemical Formula D1] to [Chemical Formula D2] include the following: <d1> ~ <d239>The compound may be a compound represented by any one of the following formulas:

[0071] JPEG2025148422000029.jpg226170JPEG2025148422000030.jpg220170JPEG2025148422000031.jpg212170JPEG2025148422000032.jpg21317 0JPEG2025148422000033.jpg220170JPEG2025148422000034.jpg244170JPEG2025148422000035.jpg228170JPEG2025148422000036.jpg23517 0JPEG2025148422000037.jpg216170JPEG2025148422000038.jpg225170JPEG2025148422000039.jpg239170JPEG2025148422000040.jpg22617 0JPEG2025148422000041.jpg251170JPEG2025148422000042.jpg227170JPEG2025148422000043.jpg239170JPEG2025148422000044.jpg89170

[0072] In the present invention, the dopant compound in the light-emitting layer is represented by [chemical formula D3]. The compounds to be treated are as follows: <d101> ~ <d130>It is represented by one of the following: It can be a compound.

[0073] JPEG2025148422000045.jpg245170JPEG2025148422000046.jpg202170

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

[0075] JPEG2025148422000047.jpg250170JPEG2025148422000048.jpg239170JPEG2025148422000049.jpg223170

[0076] In the present invention, the dopant compound in the light-emitting layer is selected from the group consisting of [Chemical Formula D6] and The compound represented by any one of the following formulas [Chemical Formula D7] <d301> ~ <d387>Among The compound may be a compound represented by any one of the following:

[0077] JPEG2025148422000050.jpg253170JPEG2025148422000051.jpg237170JPEG2025148422000052.jpg25516 9JPEG2025148422000053.jpg235170JPEG2025148422000054.jpg239170JPEG2025148422000055.jpg53170

[0078] In the present invention, the dopant compounds in the light-emitting layer are represented by the formulas [Chemical Formula D8] to [Chemical Formula D9]. The compound represented by any one of the following formulas [Chemical Formula D10] <d401> ~ <d532>of The compound may be any compound selected from the group consisting of:

[0079] JPEG2025148422000056.jpg224170JPEG2025148422000057.jpg221170JPEG202 5148422000058.jpg231170JPEG2025148422000059.jpg236170JPEG20251484220 00060.jpg231170JPEG2025148422000061.jpg229170JPEG2025148422000062.j pg242170JPEG2025148422000063.jpg248170JPEG2025148422000064.jpg190170

[0080] In addition, as one embodiment of the organic light-emitting device according to the present invention, the present invention provides a first electrode and a second electrode facing the first electrode; and a first electrode between the first electrode and the second electrode. a first emitting layer comprising a host and a first dopant; and a second emitting layer comprising a second host and a second dopant. an emitting layer; and at least one of the first host and the second host is Any one compound selected from the compounds represented by [chemical formula A] or [chemical formula B] and an organic light-emitting device comprising one or more of the following: The device can have high efficiency and long life characteristics.

[0081] In this case, the organic light emitting device has a hole transport layer and a hole transport layer between the first electrode and the first light emitting layer. At least one of the injection layer and the electron transport layer is provided between the second light-emitting layer and the second electrode. and at least one of an electron injection layer and an electron transport layer, preferably between the first electrode and the first light-emitting layer. a hole transport layer and a hole injection layer are provided in each of the first and second light emitting layers, and a hole transport layer is provided between the second light emitting layer and the second electrode. may each be provided with an electron transport layer and an electron injection layer.

[0082] In a preferred embodiment of the organic light-emitting device according to the present invention, the first light-emitting layer is Any compound selected from the compounds represented by [chemical formula A] or [chemical formula B] It may contain one or more of the following.

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

[0084] [Chemical formula E] JPEG2025148422000065.jpg59106

[0085] In the above [Chemical Formula E], The substituent R 41 ~R 48 may be the same or different and independently represent hydrogen, heavy water, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 6 carbon atoms aryl groups with up to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms, or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 3 carbon atoms alkylsilyl groups having 6 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, sialic acid is any one selected from the group consisting of a hydroxyl group, a nitro group, and a halogen group; The substituents Ar5 and Ar6 may be the same or different, and may be independently and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted a heteroaryl group having 2 to 50 prime numbers, The linking group L1 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. Or, The n is an integer of 1 to 2, and when n is 2 or more, each of the linking groups L1 is may be the same or different.

[0086] The "substituted" in the "substituted or unsubstituted" in the [chemical formula E] means deuterium. , cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, carbon halogenated alkyl groups having 1 to 24 carbon atoms, alkenyl groups having 2 to 24 carbon atoms, Alkynyl groups, heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a 4 heteroarylalkyl groups, alkoxy groups having 1 to 24 carbon atoms, alkoxy groups having 1 to 24 carbon atoms, arylamino group, arylamino group having 6 to 24 carbon atoms, heteroarylamino group having 1 to 24 carbon atoms amino group, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, substituted with one or more substituents selected from the group consisting of aryloxy groups having 6 to 24 This means that...

[0087] In a preferred embodiment of the organic light-emitting device according to the present invention, the second light-emitting layer is When the anthracene derivative represented by the formula E] is contained as a host, A more preferred structure of the anthracene derivative is the following [Chemical Formula E-1] or [Chemical Formula E-2]: Anthracene derivatives represented by the formula E-2 can be used.

[0088] [Chemical formula E-1] JPEG2025148422000066.jpg95106

[0089] [Chemical formula E-2] JPEG2025148422000067.jpg92106

[0090] In the above [Chemical Formula E-1] and [Chemical Formula E-2], The substituent R 41 ~R 48 , R 49 ~R 55 may be the same or different, each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted aryl groups having 3 to 30 carbon atoms Cycloalkyl groups, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 6 to 30 carbon atoms an arylsilyl group, a cyano group, a nitro group, or a halogen group; the law of nature, The substituent Ar5 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. or an unsubstituted heteroaryl group having 2 to 50 carbon atoms, The linking group L 11 represents 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. It is The k is an integer of 1 to 2, and when k is 2 or more, each linking group L 11 is mutual They may be the same or different, The "substituted or unsubstituted" in the [chemical formula E-1] and [chemical formula E-2] "Substitution" in the above is deuterium, cyano group, halogen group, hydroxy group, nitro group, carbon number 1 alkyl groups with carbon atoms of 1 to 24, halogenated alkyl groups with carbon atoms of 1 to 24, alkene groups with carbon atoms of 2 to 24 C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6 aryl groups with 7 to 24 carbon atoms, arylalkyl groups with 2 to 24 carbon atoms, heteroaryl groups with 2 to 24 carbon atoms, an aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms group, alkylamino group having 1 to 24 carbon atoms, arylamino group having 6 to 24 carbon atoms, Heteroarylamino groups with up to 24 carbon atoms, alkylsilyl groups with 1 to 24 carbon atoms, and alkylsilyl groups with 6 to 24 carbon atoms. an arylsilyl group having 6 to 24 carbon atoms; It means that the group is substituted with the above substituents.

[0091] Here, the compound represented by [Chemical Formula E-1] or [Chemical Formula E-2] is represented by the following formula 1 As shown in the figure, the 1st or 2nd position of either phenyl ring of dibenzofuran or dibenzo The 1'- or 2'-position of the other phenyl ring of the furan is an anthracenyl group or a linking group L 11 9 of It is characterized by binding to the position.

[0092] JPEG2025148422000068.jpg3773[Diagram 1]

[0093] On the other hand, in the present invention, the compounds represented by the formulas [Chemical Formula E], [Chemical Formula E-1] and [Chemical Formula E-2] The substituent Ar5 in the anthracene derivative represented by any one of these is represented by the following [Structural Formula C-1] It can be a substituent that is

[0094] [Structural formula C-1] JPEG2025148422000069.jpg4166

[0095] In this case, R in the [Structural Formula C-1] 61 ~R 65 may be the same or different Preferably, each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted aryl group having 7 carbon atoms Arylalkyl groups with up to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms , a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon is any one selected from an arylsilyl group having 6 to 30 carbon atoms and a halogen group, The "-*" in the [Structural Formula C-1] represents [Chemical Formula E], [Chemical Formula E-1], or [Chemical Formula This is the bonding position of the anthracenyl group at the 10-position in the formula E-2.

[0096] In one embodiment, a preferred example of the organic light-emitting device according to the present invention is an organic light-emitting device represented by the formula E -1] or the linking group L in [chemical formula E-2] 11 is a single bond, or is substituted or unsubstituted In this case, the k is an integer of 1 or 2. However, when the k is 2 or more, each L 13 may be the same or different from each other .

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

[0098] JPEG2025148422000070.jpg244170JPEG2025148422000071.jpg231170JPEG2025148422000072.jpg226170 JPEG2025148422000073.jpg216170JPEG2025148422000074.jpg232170JPEG2025148422000075.jpg186170

[0099] In another embodiment, the organic light-emitting device according to the present invention includes the compound represented by the formula E-1 and the compound represented by the formula E-2. Specific examples of anthracene derivatives represented by any one of the formulas E-2 are the following compounds 201. Compound 260 may be any one selected from the group consisting of:

[0100] JPEG2025148422000076.jpg227170JPEG2025148422000077.jpg254170JPEG20251484220 00078.jpg235170JPEG2025148422000079.jpg235168JPEG2025148422000080.jpg230170

[0101] As a more preferred embodiment of the present invention, the present invention provides a first electrode and a a second electrode having a first host and a first electrode; a first emitting layer including a dopant; and a second emitting layer including a second host and a second dopant. The first light-emitting layer comprises one compound represented by the formula A or B. The second light-emitting layer comprises the anthracene derivative represented by the chemical formula E as a host. When the first and second light-emitting layers contain the same or different light-emitting elements, One dopant compound independently selected from the chemical formulas D1 to D10 More than one can be used.

[0102] [Chemical formula D1] JPEG2025148422000081.jpg106167

[0103] [Chemical formula D2] JPEG2025148422000082.jpg119167

[0104] [Chemical Formula D3] JPEG2025148422000083.jpg4465

[0105] JPEG2025148422000084.jpg192146

[0106] In this case, the content of the dopant in the light-emitting layer is usually about 100 parts by weight of the host. The amount can be selected from the range of about 0.01 to about 20 parts by weight, but is not limited to this range.

[0107] In addition to the dopant and host, the light-emitting layer may contain various hosts and various dopants. The composition may further comprise a nutrient.

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

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

[0110] As shown in FIG. 1, the organic light-emitting device according to the embodiment of the present invention includes an anode 20, a hole transport layer 4, and a 0, a light-emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode 80, In the organic light-emitting device, the anode is a first electrode and the cathode is a second electrode, and the anode and the cathode are connected to each other. an organic light-emitting device including a hole transport layer between the light-emitting layer and the cathode, and an electron transport layer between the light-emitting layer and the cathode; This corresponds to the element.

[0111] In addition, in the organic light emitting device according to the embodiment of the present invention, between the anode 20 and the hole transport layer 40 a hole injection layer 30 between the electron transport layer 60 and the cathode 80; and an electron injection layer 70 between the electron transport layer 60 and the cathode 80. It can be enjoyed.

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

[0113] First, an anode material is coated on the upper surface of the substrate 10 to form the anode 20. Here, the substrate 10 is a substrate that is used in ordinary organic EL devices. , an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness The anode material is preferably indium oxide, which is transparent and has excellent conductivity. Tin (ITO), Indium Zinc Oxide (IZO), Tin Oxide (SnO2), Zinc Oxide (Z nO) etc.

[0114] A hole injection layer material is formed on the anode 20 by vacuum thermal deposition or spin coating. The hole injection layer 30 is formed. Then, a hole transport layer material is vacuum-insulated on the hole injection layer 30. The hole transport layer 40 is formed by thermal evaporation or spin coating.

[0115] There are no particular limitations on the material of the hole injection layer as long as it is one that is commonly used in the relevant field. It can be used without any modification, for example, 2-TNATA[4,4',4''-tris( 2-naphthylphenyl-phenylamino)-triphenyla mine], NPD[N,N'-di(1-naphthyl)-N,N'-diphe nylbenzidine)], TPD[N,N'-diphenyl-N,N'-bi s(3-methylphenyl)-1,1'-biphenyl-4,4'-dia mine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(p henyl-m-tolyl-amino)-phenyl]-biphenyl-4, However, the present invention does not necessarily require the use of such a compound. However, it is not limited to the above.

[0116] The material for the hole transport layer is not particularly limited as long as it is a material commonly used in the art. For example, but not limited to, N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1-biphenyl]-4,4'-diamine (TPD), or N,N'-di(naphthalene) Use N,N'-diphenylbenzidine (α-NPD) or similar. However, the present invention is not necessarily limited to this.

[0117] Meanwhile, in the present invention, an electron blocking layer may be further formed on the hole transport layer. The electron blocking layer prevents electrons injected from the electron injection layer from passing through the light emitting layer into the hole transport layer. This layer is for preventing the light-emitting layer from being oxidized, thereby improving the life and efficiency of the device. and the hole injection layer, and preferably, can be formed between

[0118] Then, the light-emitting layer 50 is formed on the hole transport layer 40 or the electron blocking layer by vacuum deposition or spin deposition. The lamination can be carried out by a coating method.

[0119] Here, the light-emitting layer can be composed of a host and a dopant. The same applies as described above.

[0120] The light-emitting layer includes a first light-emitting layer (not shown) and a second light-emitting layer (not shown), The same or different hosts and The first and second light-emitting layers can each be formed using a dopant material. .

[0121] More preferably, the first light-emitting layer contains a compound represented by the formula A or B as a fluorescent host. The second light-emitting layer contains one or more compounds represented by the formula E. The first and second light-emitting layers may contain one or more helical derivatives. The fluorescent dopants are each independently the same or different materials, Any material selected from the chemical formulas D1 to D10 can be used.

[0122] In addition, examples of host materials that can be used in the first and second light-emitting layers of the present invention include: The host material (BH1) used in the first light-emitting layer is the same as the host material used in the second light-emitting layer. The lowest unoccupied molecular orbital (LUMO) is lower than that of the hydroxyl group (BH2), and the highest occupied molecular orbital (LUMO) is By using a material with a higher orbital function (HOMO), the phosphorus used in the second emitting layer Compared to BH2, hole and / or electron injection is easier. It is preferable that the structure be simple.

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

[0124] Meanwhile, an electron transport layer 60 is formed on the light-emitting layer by vacuum deposition or spin coating. Vapor deposition.

[0125] On the other hand, in the present invention, the material of the electron transport layer is an electron injection electrode (cathode (C It functions to stably transport electrons injected from the athode. Known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives. Conductors, especially tris(8-quinolinolato)aluminum (Alq3), Liq, and TAZ , BAlq, beryllium bis(benzoquinolin-10-olate) bis(benzoquinolin-10-olate: Bebq2), compound 20 1. Compound 202, BCP, oxadiazole derivatives such as PBD, BMD, and BND The following materials can also be used, but are not limited to these.

[0126] JPEG2025148422000085.jpg161170

[0127] In addition, in the organic light-emitting device of the present invention, after forming the electron transport layer, On top of that, an electron injection layer (EIL) is formed, which is a material that facilitates the injection of electrons from the cathode. ) can be laminated. This does not particularly limit the material.

[0128] The electron injection layer forming material is an electron injection layer such as CsF, NaF, LiF, Li2O, or BaO. Any known material for forming an electron injection layer can be used. The deposition conditions for the hole injection layer are generally similar to those for the hole injection layer, although they vary depending on the compound used. You can select from a range of conditions.

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

[0130] In addition, in the present invention, the cathode is made of a material having a small work function for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys aluminum (Al), aluminum-lithium (Al-Li), magnesium Uses magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. Alternatively, a transmission cathode using ITO or IZO can be used.

[0131] The organic light-emitting element of the present invention emits light in the wavelength range of 380 nm to 800 nm. It may further comprise a light-emitting layer of a blue, green or red light-emitting material. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the light-emitting layer further comprises The blue, green or red light-emitting material may be a fluorescent material or a phosphorescent material.

[0132] In addition, in the present invention, one or more layers selected from the respective layers are monomolecular It can be formed by a vapor deposition process or a solution process.

[0133] Here, the vapor deposition step is carried out by using a material to form each of the layers. It means a method of forming a thin film by evaporating a substance under vacuum or low pressure by heating, etc. The solution process involves mixing the materials used to form each of the layers with a solvent. This can be done by inkjet printing, roll-to-roll coating, screen printing, By spray coating, dip coating, spin coating etc. It refers to a method for forming a thin film.

[0134] The organic light-emitting element of the present invention is also suitable for use in flat panel display devices, flexible displays, and the like. display devices, devices for lighting monochrome or white flat panels, and monochrome or white The flexible lighting device can be used in any of the devices selected from the flexible lighting devices.

[0135] The present invention will be described in more detail below with reference to preferred examples. The following examples are provided to more specifically illustrate the present invention. Therefore, it is obvious to a person skilled in the art that there is no limitation.

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

[0137] JPEG2025148422000086.jpg40165

[0138] A 500 mL round-bottom flask reactor was charged with methyl 2-bromobenzoate (30.0 g, 0.14 mL). 0 mol), 4-dibenzofuranboronic acid (32.5 g, 0.153 mol), tetrakis(2-methyl-4-benzofuran) Triphenylphosphine palladium (3.2 g, 3 mmol), potassium carbonate (3 8.6g, 0.279mol), 210mL of toluene, 90mL of methanol, and water 60 mL of the solution was added. The reactor was refluxed overnight with stirring. After the reaction was completed, the temperature of the reactor was reduced to room temperature. The mixture was cooled to room temperature, extracted with ethyl acetate, and the organic layer was separated. The product was separated by chromatography to obtain <1-a> (25.0 g, 59.1%).

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

[0140] JPEG2025148422000087.jpg37165

[0141] In a 500 ml round-bottom flask reactor, bromobenzene (28.6 g, 182 mmol) and 220 ml of tetrahydrofuran was added and cooled to -78°C in a nitrogen atmosphere. n-Butyllithium (104.6 ml, 167 mmol) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred for 2 hours, and then <1-a> (22.0 g, 73 mmol) was added little by little. After that, 50 ml of H2O was added to terminate the reaction, and ethyl acetate was added. The organic layer was separated and concentrated under reduced pressure to give <1-b>. (28 .0g, 90%)

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

[0143] JPEG2025148422000088.jpg37165

[0144] In a 500 ml round-bottom flask reactor, add 1-b (28.0 g, 66 mmol), acetic acid 3 10 ml of the mixture and 2 ml of hydrochloric acid were added and stirred under reflux for 1 hour. After confirming the completion of the reaction by chromatography, the mixture was cooled to room temperature. The resulting solid was filtered and diluted with H2O After washing with methanol, the product was dried to obtain <1-c> (22.3 g, 83.2%)

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

[0146] JPEG2025148422000089.jpg37165

[0147] In a 2 L round-bottom flask reactor, <1-c> (22.3 g, 55 mmol) and 500 mL Bromine (8.72 g, 55 mmol) was dissolved in 250 ml of salt. The mixture was mixed with methylene chloride and slowly added dropwise to the reactor, followed by stirring at room temperature for 3 hours. The reaction solution was washed with an aqueous solution of sodium bicarbonate. After filtering the solid, toluene and acetonitrile were added. The product was recrystallized in toluene to give <1-d> (25.0 g, 94%).

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

[0149] JPEG2025148422000090.jpg48156

[0150] A reaction vessel was charged with 10 g (0.021 mol) of <1-d> and pyrene-1-boronic acid (Pyre ne-1-boronic acid)6.1g(0.025mol), K2CO35. 7g (0.041mol), Pd(PPh3) 40.5g, toluene 40mL, ethanol After adding 30 mL of ethanol and 30 mL of distilled water and stirring under reflux for 6 hours, the reaction mixture was cooled and The mixture was slurried in toluene and then filtered. After that, [H1] (4 g, 32%) was synthesized by recrystallization from acetone. MS (MALDI-TOF): m / z 608.21 [M+]

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

[0152] JPEG2025148422000091.jpg41156

[0153] Add methyl 2-iodobenzoate (19.1 g, 73 mmHg) to a 500 mL round-bottom flask reactor. ol), 4-dibenzofuranboronic acid (18.7 g, 88 mmol), tetrakis(tri (phenylphosphine)palladium (1.7 g, 0.15 mmol), potassium carbonate (20 125 mL of toluene and 12 mL of tetrahydrofuran were added. The temperature of the reactor was raised to 80°C and the mixture was stirred for 10 hours. After the reaction was completed, the temperature of the reactor was lowered to room temperature, and the mixture was extracted with ethyl acetate and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <2-a>. 9.5g, 43%)

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

[0155] JPEG2025148422000092.jpg45156

[0156] A 2 L round-bottom flask reactor was charged with bromobenzene (13.2 g, 83.97 mmol), 2 50 ml of tetrahydrofuran was added and stirred in a low-temperature nitrogen atmosphere. Approximately 58 ml of n-butyllithium was slowly added dropwise over 2 hours, and then <2-a> (9.4 g, After the reaction was completed, 100 ml of water was added and stirred for 30 minutes. Extraction gave <2-b> (3.2g, 24%).

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

[0158] JPEG2025148422000093.jpg52140

[0159] In a 2 L round-bottom flask reactor, <2-b> (55.0 g, 129 mmol) and 500 mL of acetic acid were added. 10 ml of acetic acid and 10 ml of sulfuric acid were added and stirred under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and the resulting The solid was filtered and washed with methanol to give <2-c> (50g, 95% yield). )

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

[0161] JPEG2025148422000094.jpg49140

[0162] In a 2 L round-bottom flask reactor, <2-c> (50 g, 122 mmol) and 600 mL of distilled water were added. Chloromethane was charged and stirred at room temperature. Bromine (13.7 ml, 85 mmol) was added to 50 ml After diluting with 1 ml of dichloromethane and adding dropwise, the mixture was stirred for about 3 hours. <2-d> was obtained (45.6g, 66%).

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

[0164] JPEG2025148422000095.jpg52170

[0165] A reaction vessel was charged with 12.0 g (0.021 mol) of <2-d> and pyrene-1-boronic acid (Py rene-1-boronic acid)11.5g(0.047mol), K2CO 311.71g (0.085mol), Pd(PPh3) 40.98g, toluene 72m Add 36 mL of ethanol and 36 mL of distilled water and reflux overnight. After extraction with EA / distilled water, the extract was hot filtered using toluene. After column purification, it was recrystallized from toluene / acetone to give [H25] (7.8 g, 45%) was synthesized. MS (MALDI-TOF): m / z 810.29 [M+]

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

[0167] JPEG2025148422000096.jpg46141

[0168] Add 35 g (118 mm) of dibenzofuran-1-phoronic acid pinacol ester to a round-bottom flask. ol), methyl 5-bromo-2-iodobenzoate 40.5g (118mmol), tetra bistriphenylphosphinepalladium 2.7g (2.3mmol), potassium carbonate 33 g (237 mmol), toluene 200 ml, 1,4-dioxane 200 ml, water 100 ml was added under nitrogen atmosphere and refluxed for 12 hours. After the reaction was completed, the reaction mixture was separated into layers and the organic layer was The layer was concentrated under reduced pressure, separated by column chromatography, and dried. 33.5g was obtained (74% yield).

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

[0170] JPEG2025148422000097.jpg46141

[0171] Add 33.5g (110ml) of <3-a> to a round-bottom flask containing 150ml of tetrahydrofuran. mol), cooled to -10°C, and then 85 ml ( 254 mmol) was slowly added dropwise. Then, the mixture was heated to 40°C and stirred for 4 hours. After that, the temperature was cooled to -10°C, and 70 ml of 2N HCl was slowly added dropwise to the solution. After adding 70 ml of aqueous ammonium chloride solution, the temperature was raised to room temperature. After washing with water and extracting with ethyl acetate, the layers were separated and the organic layer was concentrated under reduced pressure. After separation by column chromatography and drying, 27 g of <3-b> was obtained (yield 8 0%)

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

[0173] JPEG2025148422000098.jpg42141

[0174] In a round-bottom flask, add 27 g (89.2 mmol) of <3-b> and 70 mL of After the reaction was completed, the mixture was extracted with ethyl acetate and water. After concentrating, separating by column chromatography and drying, 17.6 g of <3-c> was obtained. (Yield 70%)

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

[0176] JPEG2025148422000099.jpg39133

[0177] Place 17.6 g (48.4 mmol) of <3-c> in a round-bottom flask and 200 ml of tetrahydrofuran was added, the temperature was lowered to -78°C, and then 1.6 M n-butyl ether was added. 36.3 ml (58.1 mmol) of ethyllithium was slowly added dropwise. After 1 hour, 7.0 ml (62.9 mmol) of trimethyl nitrate was slowly added while keeping the temperature low. After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure. After that, the product was recrystallized from hexane and dried to obtain 33 g of <3-d> (yield 71%).

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

[0179] JPEG2025148422000100.jpg39151

[0180] A round-bottom flask was purged with nitrogen and 100 g (0.278 mol) of 1,6-dibromopyrene was added. , phenylboronic acid 33.9g (0.278mol), tetrakistriphenylphosphine 6.4g (0.006mol) of palladium (Pd[PPh3]4), 8g of sodium carbonate 8.3g (0.833mol), 1400ml of toluene and 420ml of water were added and the mixture was left for 9 hours. After the reaction is complete, the mixture is cooled to room temperature, and the resulting solid is filtered and discarded. The filtrate is extracted with ethyl acetate and water, and the organic layer is treated to remove water. After the treatment, the organic layer is concentrated under reduced pressure. After that, it was separated by column chromatography to obtain 45.4 g of <3-e> (yield 45. 7%).

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

[0182] JPEG2025148422000101.jpg50157

[0183] In a round-bottom flask, add 10 g (27.9 mmol) of intermediate <3-e> and 9 g of intermediate <3-d>. 2g (27.9mmol), tetrakistriphenylphosphine palladium 0.6g (0 0.5mmol), potassium carbonate 7.7g (55.9mmol), toluene 35ml, 1, 35 ml of 4-dioxane and 30 ml of water were charged under nitrogen atmosphere and refluxed for 12 hours. After completion of the reaction, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure and separated by column chromatography. After drying, 9.8 g of [H39] was obtained (yield 63%). MS (MALDI-TOF): m / z 560.21 [M+]

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

[0185] JPEG2025148422000102.jpg48101

[0186] Instead of methyl 5-bromo-2-iodobenzoate used in Synthesis Example 3-1, The synthesis was carried out in the same manner as in Synthesis Examples 3-1 to 3-3, except that methyl benzoate was used. This gave <4-a> (yield 60%).

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

[0188] JPEG2025148422000103.jpg40118

[0189] In a round-bottom flask, add 37.8 g (133 mmol) of 4-a and N-bromosuccinimide. 23.8g (133mmol) and 600mL of dimethylformamide were charged under nitrogen. After the reaction was completed, the organic layer was concentrated under reduced pressure and then subjected to column chromatography. After separation by roughing, 33.8g of <4-b> was obtained (70% yield).

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

[0191] JPEG2025148422000104.jpg47118

[0192] The same procedure was carried out as in Synthesis Example 3-4, except that <4-b> was used instead of <3-c>. <4-c> was obtained by the synthesis method (70% yield). Synthesis Example 4-(4): Synthesis of [H44]

[0193] JPEG2025148422000105.jpg48167

[0194] The same procedure was carried out as in Synthesis Example 3-6, except that <4-c> was used instead of <3-d>. [H44] was obtained by the synthesis method (70% yield). MS (MALDI-TOF): m / z 560.21 [M]+

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

[0196] JPEG2025148422000106.jpg40151

[0197] Instead of the dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, 9-phenylcarbazole-2-boronic acid was used to obtain 5-bromo-2-iodobenzoic acid The same procedure was used except that methyl 4-bromo-2-iodobenzoate was used instead of methyl <5-a> was obtained by synthesis (68% yield).

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

[0199] JPEG2025148422000107.jpg33144

[0200] The same procedure was carried out as in Synthesis Example 3-2, except that <5-a> was used instead of <3-a>. <5-b> was obtained by the synthesis method (yield 80%).

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

[0202] JPEG2025148422000108.jpg33144

[0203] The same procedure was carried out except that <5-b> was used instead of <3-b> used in Synthesis Example 3-3. The intermediate <5-c> was obtained by this method (yield 70%).

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

[0205] JPEG2025148422000109.jpg37144

[0206] The same procedure was carried out as in Synthesis Example 3-4, except that <5-c> was used instead of <3-c>. The intermediate <5-d> was obtained by the synthesis method (yield 72%).

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

[0208] JPEG2025148422000110.jpg57163

[0209] The same procedure was carried out as in Synthesis Example 3-6, except that <5-d> was used instead of <3-d>. [H58] was obtained by the synthesis method (70% yield). MS(MALDI-TOF): m / z 635.26[M]+

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

[0211] JPEG2025148422000111.jpg34148

[0212] In a round-bottom flask, 50 g (183 mmol) of 2-bromo-9,9-dimethylfluorene Sodium methoxide solution 59.3 g (1098 mmol), copper iodide 10.4 g (54 0.9 mmol) and 200 ml of methanol were charged under nitrogen atmosphere and refluxed for 12 hours. After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure and separated by column chromatography. After drying, 33.2 g of <6-a> was obtained (yield 81%).

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

[0214] JPEG2025148422000112.jpg34148

[0215] In a round-bottom flask, 30 g (133 mmol) of <6-a> and N-bromosuccinimide 23 0.8g (133mmol) and 600ml of dimethylformamide were charged under nitrogen atmosphere. The reaction mixture was stirred at 0°C for 12 hours. After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure. After separation by column chromatography and drying, 28 g of <6-b> was obtained (yield 70 %)

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

[0217] JPEG2025148422000113.jpg32148

[0218] The same procedure was carried out except that <6-b> was used instead of <3-c> used in Synthesis Example 3-4. <6-c> was obtained by this method (yield 72%).

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

[0220] JPEG2025148422000114.jpg43157

[0221] Instead of the dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, <6-c> was used, and 1-bromo-2-iodobenzoic acid methyl ester was used instead of 5-bromo-2-iodobenzoic acid methyl ester. 6-d was synthesized in a similar manner, except that 3-iodo-3-fluorobenzene was used. (Yield 70%)

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

[0223] JPEG2025148422000115.jpg48133

[0224] In a round-bottom flask, 30 g (85 mmol) of <6-d> and 300 ml of dichloromethane are added under nitrogen. After lowering the temperature to 0°C, 63.9g (255mmol) of boron tribromide was added. Dilute with 150 ml of dichloromethane and slowly add dropwise. Then, warm to room temperature. After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure and then column-cleaned. After separation by chromatography and drying, 21.3 g of <6-e> was obtained (yield 74 %)

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

[0226] JPEG2025148422000116.jpg40133

[0227] In a round-bottom flask, add 20 g (59 mmol) of <6-e> and 13 g (94.5 m mol) and 200 ml of 1-methyl-2-pyrrolidinone were charged under nitrogen atmosphere and stirred for 12 hours. The reaction mixture was stirred at 50°C. After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure and then purified by column chromatography. After separation by lithography and drying, 13.5 g of <6-f> was obtained (yield 72%).

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

[0229] JPEG2025148422000117.jpg42133

[0230] In a round-bottom flask, add 13 g (40.8 mmol) of <6-f> and bis(pinacolato)diborane. 12.4g (48.9mmol), tris(dibenzylideneacetone)palladium 2g (2.4 mmol), potassium acetate 11.6 g (122 mmol), tricyclohexyl 2.7 g (9.8 mmol) of phosphine and 150 ml of N-dimethylformamide were dissolved in nitrogen After the reaction was completed, the reaction mixture was separated into layers, and the organic layer was concentrated under reduced pressure. After separation by column chromatography and drying, 10.8 g of <6-g> was obtained. (Yield 65%)

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

[0232] JPEG2025148422000118.jpg54152

[0233] The same procedure was carried out except that <6-g> was used instead of <3-d> used in Synthesis Example 3-6. [H85] was obtained by this method (yield 65%). MS (MALDI-TOF): m / z 560.21 [M]+

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

[0235] JPEG2025148422000119.jpg38104

[0236] Instead of the dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, Dibenzofuran-3-boronic acid was used to synthesize methyl 5-bromo-2-iodobenzoate. Except for using methyl 1-iodobenzoate instead, Synthesis Examples 3-1 to 3-3 and Synthesis Example 3-4 were used. <7-a> was obtained by synthesis in the same manner as in Synthesis Examples 4-2 to 4-3 (yield 70%).

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

[0238] JPEG2025148422000120.jpg51104

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

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

[0241] JPEG2025148422000121.jpg39162

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

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

[0244] JPEG2025148422000122.jpg33162

[0245] The same procedure was carried out as in Synthesis Example 6-5, except that <8-a> was used instead of <6-d>. <8-b> was obtained by the synthesis method described above (yield 93.2%).

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

[0247] JPEG2025148422000123.jpg31162

[0248] The same procedure was carried out as in Synthesis Example 6-6, except that <8-b> was used instead of <6-e>. <8-c> was obtained by the synthesis method described above (yield 84.4%).

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

[0250] JPEG2025148422000124.jpg33162

[0251] In a round-bottom flask under nitrogen, add 19 g (0.063 mol) of <8-c> and pyridine 6. 5g (0.082mol) and 190ml of dichloromethane were added and cooled to below 0°C. , 19.6 g (0.070 mol) of trifluoromethanesulfonic anhydride is slowly added dropwise. After the dropwise addition, the reaction mixture is warmed to room temperature and stirred for 5 hours. Water is added to the liquid and stirred, then the layers are separated, the organic layer is treated to remove water, and then concentrated under reduced pressure. After that, separation by column chromatography gave 23 g of <8-d> (yield 84.1%).

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

[0253] JPEG2025148422000125.jpg39159

[0254] In a round-bottom flask, add 23 g (0.053 mol) of <8-d> and bis-pinacoldiboron-16. 0.2g (0.064mol), Bisdiphenylphospinoferrocene dichloropalladium 0 .9g (0.001mol), calcium acetate 13.1g (0.133mol), 1,4 230 ml of dioxane was added and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature. After cooling to room temperature, the mixture was filtered through Celite. The filtrate was concentrated and then purified by column chromatography. The product was separated using the method described above to obtain 17 g of <8-e> (yield 77.9%).

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

[0256] JPEG2025148422000126.jpg44170

[0257] The same procedure was carried out as in Synthesis Example 3-6, except that <8-e> was used instead of <3-d>. The synthesis of [H54] was carried out by the method described above, and 16 g of [H54] was obtained (yield 78.4%). MS (MALDI-TOF): m / z 560.21 [M]+

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

[0259] JPEG2025148422000127.jpg41170

[0260] Instead of the dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, 9-a was synthesized in a similar manner, except that dibenzofuran-4-boronic acid was used instead. 48g was obtained (74% yield)

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

[0262] JPEG2025148422000128.jpg44133

[0263] The same procedure was carried out as in Synthesis Example 3-2, except that <9-a> was used instead of <3-a>. 47g of <9-b> was obtained by the synthesis method (yield 97.9%).

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

[0265] JPEG2025148422000129.jpg44133

[0266] The same procedure was carried out as in Synthesis Example 3-3, except that <9-b> was used instead of <3-b>. 30g of <9-c> was obtained by the synthesis method (67.1% yield).

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

[0268] JPEG2025148422000130.jpg50133

[0269] The same procedure was carried out as in Synthesis Example 8-5, except that <9-c> was used instead of <8-d>. 27g of <9-d> was obtained by the method described above (yield 79.8%).

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

[0271] JPEG2025148422000131.jpg43170

[0272] The same procedure was carried out as in Synthesis Example 3-6, except that <9-d> was used instead of <3-d>. The synthesis of [H7] was carried out by the method described above, and 14 g of [H7] was obtained (yield 62.4%). MS (MALDI-TOF): m / z 560.21 [M]+

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

[0274] JPEG2025148422000132.jpg31162

[0275] Instead of <3-c> used in Synthesis Example 3-4, 6-bromo-1-methoxydibenzofuran was used. Using the same method, but using oran, 43 g of <10-a> was obtained (yield 95. 1%)

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

[0277] JPEG2025148422000133.jpg37164

[0278] Instead of the dibenzofuran-1-boronic acid pinacol ester used in Synthesis Example 3-1, Instead of methyl 5-bromo-2-iodobenzoate, <10-a> was used, and 2-bromo-2-iodobenzoate was used. 52g of <10-b> was obtained by synthesizing in the same manner except that methyl bromobenzoate was used. (Yield 96.1%)

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

[0280] JPEG2025148422000134.jpg40132

[0281] The same procedure as in Synthesis Example 3-2 was carried out except that <10-b> was used instead of <3-a>. By synthesizing the compound using the same method, 48g of <10-c> was obtained (yield 92.3%).

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

[0283] JPEG2025148422000135.jpg40132

[0284] The same procedure as in Synthesis Example 3-3 was carried out except that <10-c> was used instead of <3-b>. By synthesizing the compound using the same method, 38g of <10-d> was obtained (yield 83.8%).

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

[0286] JPEG2025148422000136.jpg40132

[0287] The same procedure as in Synthesis Example 6-5 was carried out except that <10-d> was used instead of <6-d>. By synthesizing the compound using the same method, 28g of <10-e> was obtained (yield 77.1%).

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

[0289] JPEG2025148422000137.jpg44132

[0290] The same procedure as in Synthesis Example 8-4 was carried out except that <10-e> was used instead of <8-c>. By synthesizing the compound using the same method, 35g of <10-f> was obtained (yield 87.5%).

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

[0292] JPEG2025148422000138.jpg54136

[0293] The same procedure as in Synthesis Example 8-5 was carried out except that <10-f> was used instead of <8-d>. The compound was synthesized using the same method and 26g of 10g was obtained (yield 78.3%).

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

[0295] JPEG2025148422000139.jpg46170

[0296] The same procedure as in Synthesis Example 3-6 was carried out except that <10-g> was used instead of <3-d>. By synthesizing the compound using the same method, 12 g of [H14] was obtained (yield 52.4%). MS (MALDI-TOF): m / z 560.21 [M]+

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

[0298] JPEG2025148422000140.jpg4671

[0299] In the above Synthesis Example 10-1, 2-bromo-1-methoxydibenzofuran was used instead of 6-bromo-1-methoxydibenzofuran. The same procedures as in Synthesis Examples 10-1 to 10-7 were carried out except that 3-3-methoxydibenzofuran was used. The compound <11-a> was synthesized by the same method and 23 g of <11-a> was obtained (yield 54.3%).

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

[0301] JPEG2025148422000141.jpg50170

[0302] The same procedure as in Synthesis Example 3-6 was carried out except that <11-a> was used instead of <3-d>. By synthesizing the compound using the same method, 16.7g of [H17] was obtained (yield 57.5%). MS (MALDI-TOF): m / z 560.21 [M]+

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

[0304] JPEG2025148422000142.jpg49170

[0305] Phenylboronic acid (D5) was used instead of the phenylboronic acid used in Synthesis Example 3-5. The synthesis was carried out in the same manner except for the above, and 46 g of <12-a> was obtained (yield 45.7%).

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

[0307] JPEG2025148422000143.jpg52170

[0308] The same procedure was carried out except that <12-a> was used instead of <3-e> used in Synthesis Example 6-8. Using this method, 8.7 g of [H90] was obtained (yield 68.7%). MS (MALDI-TOF): m / z 565.25 [M]+

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

[0310] JPEG2025148422000144.jpg62170

[0311] The same procedure was carried out except that <12-a> was used instead of <3-e> used in Synthesis Example 4-4. The synthesis yielded 12.4 g of [H51] (75% yield). MS (MALDI-TOF): m / z 565.25 [M]+

[0312] Examples 1 to 14: Fabrication of organic light-emitting devices After patterning the ITO glass so that the light-emitting area is 2mm x 2mm, After the ITO glass was installed in a vacuum chamber, the base pressure was 1×10 - 7 The pressure was adjusted to 700 Å torr, and then DNTPD (700 Å), α- As the light-emitting layer, a host compound according to the present invention and the following NPD (300 Å) were formed. After mixing with a dopant (BD) compound (1 wt%) and forming a film (200 Å), electron transport [E-1] and [ET5] were used as the layer with a thickness of 300 Å in a 1:1 ratio, and [E-1] was used as the electron injection layer. A film of 10 Å and a film of Al were sequentially formed to a thickness of 1000 Å to manufacture an organic light-emitting device. The light emitting characteristics were measured at 0.4 mA and are shown in Tables 1 and 2 below.

[0313] JPEG2025148422000145.jpg58170

[0314] JPEG2025148422000146.jpg48170

[0315] Comparative Examples 1 and 2 The organic light emitting device for the comparative example was fabricated using the same device structure as the example above as a host. Instead of the compound according to the present invention, the following compound 312 (Korean Patent Publication No. 10-2018- The same method was used except that [BH1] was used instead of [BH1] (which is compound 312 in No. 0077887). The light emitting characteristics of the organic light emitting device were measured at 0.4 mA and are shown in Table 1 and Table 2 below. and shown in Table 2.

[0316] (Compound 312 in Korean Patent Publication No. 2018-0077887) JPEG2025148422000147.jpg4171 JPEG2025148422000148.jpg4864

[0317] [Table 1]

[0318] As shown in Table 1, the organic light emitting device according to the present invention has a structure similar to that of the compound of Comparative Example 1 according to the prior art. By showing characteristics that are superior in luminous efficiency to organic light-emitting devices that use materials, It can be seen that there is a high possibility of application as

[0319] [Table 2]

[0320] As shown in Table 2, the organic light emitting device according to the present invention has a structure similar to that of the compound of Comparative Example 2 according to the prior art. By showing higher efficiency and longer life than organic light-emitting devices using organic compounds, It is clear that this has great potential for application as a child.

[0321] Examples 15 to 19: Preparation of organic light-emitting devices including a first light-emitting layer and a second light-emitting layer After patterning the ITO glass so that the light-emitting area is 2mm x 2mm, After the ITO glass was installed in the vacuum chamber, the base pressure was 1×10 -7 to Then, DNTPD (700 Å) and α-NPD were deposited on the ITO. The light-emitting layer according to the present invention is formed by sequentially depositing a first light-emitting layer and a second light-emitting layer. The first emitting layer is formed by mixing the host compound according to the present invention with the BD dopant compound (1 The second emitting layer was made of the following compound 313 (Korean Patent Publication No. Compound 313 in Patent No. 2018-0077887) and the BD dopant compound (1 wt%) was mixed and formed into a film (150 Å), and then [E-1] and [E T5] at a 1:1 ratio of 300 Å, [E-1] at 10 Å as an electron injection layer, and Al at 1000 The organic light emitting device was fabricated by sequentially depositing layers in the order of 0.4 mA. The results are shown in Table 3 below.

[0322] Comparative Example 3 The organic light-emitting device for the comparative example has the same device structure as that of Examples 1 to 14, but has the same structure as that of Examples 1 to 14. Instead of the compound according to the present invention, the following compound 313 (Korean Patent Publication No. 10-2 The compound was prepared in the same manner except that compound 313 in No. 018-0077887 was used. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA and are shown in Table 3 below. did.

[0323] (Compound 313 in Korean Patent Publication No. 2018-0077887) JPEG2025148422000151.jpg4668 JPEG2025148422000152.jpg4868

[0324] [Table 3]

[0325] As shown in Table 3, the host compounds according to the present invention and the host compounds used in the prior art The organic light-emitting device containing the compound in the first light-emitting layer and the compound in the second light-emitting layer, respectively, is a chemical compound according to the prior art. The organic light-emitting device exhibited superior luminous efficiency compared to the organic light-emitting device using only Compound 313 as the host material. By demonstrating this, we were able to confirm that the material has high applicability as an organic light-emitting device. In Table 3, two compounds containing a host represented by chemical formula A or chemical formula B according to the present invention are listed. In the case of an organic light-emitting device using a dual light-emitting layer, the Organic light-emitting devices using a single light-emitting layer containing a host represented by chemical formula A or chemical formula B It can be seen that higher efficiency can be achieved as the voltage drops compared to the conventional method. [Industrial Applicability]

[0326] The organic light-emitting device in which the light-emitting layer is manufactured using the compound according to the present invention has a higher Higher efficiency and longer life characteristics are achieved, resulting in improved properties when applied to organic light-emitting devices. The present invention has high industrial applicability in organic light-emitting devices and related industrial fields. stomach. < / d401> < / d301> < / 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], A １ , A ２ , E and F are mutually may be the same or different, and each independently represents a substituted or unsubstituted alkyl group having 6 to 50 carbon atoms. an aromatic hydrocarbon ring, The above A １ and two adjacent carbon atoms in the aromatic ring of A ２ Adjacent aromatic rings The two carbon atoms are the substituents R １ and R ２ and forming a five-membered ring with the carbon atom connected to and each of these forms a fused ring, The linking group L １ ~L ４ may be the same or different, and independently represent: a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, The M is N-R ３ , C.R. ４ R ５ , O, or S; The M' is N-R ６ , C.R. ７ R ８ , O, or S; The substituent R １ ~R ８ , R １１ ~R １５ may be the same or different from each other, each independently represents 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 aryl 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 heteroaryl group having 2 to 50 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; , a cyano group, a nitro group, or a halogen group; The R １ and R ２ are further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. can be done, The s1 to s4 may be the same or different, and each independently represents an integer of 1 to 3. and when each of these is two or more, each of the linking groups L １ ~L ４ are mutually may be the same or different, The x, y, z, and w may be the same or different, and each independently represents 0 or 1. is an integer, In chemical formula A, x + y + z = 1 or x + y + z = 2 is satisfied; In chemical formula B, x + y + z + w = ​​1 or x + y + z + w = ​​2 is satisfied; In the above chemical formula A, A ２ Two adjacent carbon atoms in the ring are represented by the formula Q １ * and bonded to form a fused ring, In the chemical formula B, １ Two adjacent carbon atoms in the ring are represented by the formula Q ２ of * to form a condensed ring, ２ Two adjacent carbon atoms in the ring are represented by the formula Q １ * to form a condensed ring, The Ar １ ~Ar ４ may be the same or different, and may be independently Represented by [Structural Formula C], [Structural formula C] R in the structural formula C ２１ ~R ３０ may be the same or different and are independent of each other. hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloaryl group having 3 to 30 carbon atoms, alkyl group, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, is one selected from a nitro group and a halogen group, The R ２１ ~R ３０ is a linking group L １ ~L ４ is a single bond that connects to In the above [chemical formula A], [chemical formula B] and [structural formula C], the “substituted or unsubstituted The "substituted" in "substituted" includes deuterium, cyano group, halogen group, hydroxy group, nitro group, Alkyl groups having 1 to 24 carbon atoms, halogenated alkyl groups having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms; an alkynyl group having 3 to 24 carbon atoms; heteroalkyl groups having 1 to 24 carbon atoms, aryl groups having 6 to 24 carbon atoms, aryl groups having 7 to 24 carbon atoms, alkylaryl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, a aryl group, 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, diheteroarylamino groups having 7 to 24 carbon atoms, aryl (heteroaryl)amino groups having 7 to 24 carbon atoms a C1-24 alkylsilyl group, a C6-24 arylsilyl group, a C6-24 arylsilyl group, from the group consisting of aryloxy groups having 6 to 24 carbon atoms and arylthionyl groups having 6 to 24 carbon atoms; It means that the group is substituted with one or more selected substituents.

2. A in the chemical formula A or B １ , A ２ , E and F may be the same or different. may be each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms. The compound according to claim 1, characterized in that

3. The substituted or unsubstituted aromatic hydrocarbon rings having 6 to 18 carbon atoms may be the same or different. Preferably, each independently is any one selected from [Structural Formula 10] to [Structural Formula 21]. The compound according to claim 2, characterized in that it is (In the above [Structural Formula 10] to [Structural Formula 21], "-*" represents the substituent R １ and R ２ or a five-membered ring containing the carbon atom linked to the structural formula Q １ and Q ２ in means a bonding position for forming a 5-membered ring containing M, The aromatic hydrocarbon rings of the above [Structural Formula 10] to [Structural Formula 21] are A １ Ring or A ２ It corresponds to the ring While structural formula Q １ or structural formula Q ２ When bonding with these, two adjacent carbon atoms The element atom is represented by the structural formula Q １ or structural formula Q ２ * to form a fused ring Formation In the structural formulas 10 to 21, R is R defined in claim 1. １ Reach BiR ２ and m is an integer of 1 to 8, and when m is 2 or more or when R is 2 or more, In some cases, each R may be the same or different from each other.

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

5. In the chemical formula A, x is 1, and y and z are each 0, or Alternatively, y is 1, and x and z are each 0; Alternatively, z is 1, and x and y are each 0; In the chemical formula B, x is 1, and y, z, and w are each 0, or Alternatively, claim 1 is characterized in that x and y are each 1, and z and w are 0.

1. The compound according to claim 1.

6. The substituent R in the chemical formula A or B １ and R ２ are the same but different may be each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. The compound according to claim 1, characterized in that

7. R in the structural formula C ２１ ~R ２３ is a linking group L １ ~L ４ one line that joins to is a combination, The R １１ ~R １５ may be the same or different, and independently represent hydrogen, Hydrogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms an aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, a substituted Alternatively, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a halogen group may be used. The compound according to claim 1, characterized in that the substituents are selected from the group consisting of:

8. R in the structural formula C ２１ ~R ３０ may be the same or different from each other, independently, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, represents an unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 12 carbon atoms, aryl groups, L in the structural formula C １ ~L ４ R not connected to ２１ ~R ３０ At least one of or an unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms; The compound according to claim 1, characterized in that it is either

9. The compound is any one selected from the group represented by the following [H1] to [H180]. The compound according to claim 1, characterized in that

10. 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 is 10. An organic light-emitting device comprising one or more compounds according to any one of claims 1 to 9.

11. The organic layer may be a hole injection layer, a hole transport layer, or a layer having both a hole injection function and a hole transport function. a functional layer, a light-emitting layer, an electron transport layer, and an electron injection layer. The organic light-emitting device according to claim 10 ,

12. The organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, and the light-emitting layer is a photoresist. and a dopant, wherein the compound is used as a host.

12. The organic light-emitting device according to claim 11.

13. The dopant is at least one selected from the following [Chemical Formula D1] to [Chemical Formula D10]. The organic light emitting device according to claim 12, wherein both of them are used. (In the above [Chemical Formula D1] and [Chemical Formula D2], A ３１ , A ３２ , E １ and F １ teeth may be the same or different, and each independently represents a substituted or unsubstituted group having 6 to 10 carbon atoms. 50 aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms. the law of nature, The above A ３１ and two adjacent carbon atoms in the aromatic ring of A ３２ Next to the aromatic ring The two carbon atoms that meet are the substituents R ５１ and R ５２ carbon atoms connected to form a five-membered ring By combining the two, a fused ring is formed, The linking group L ２１ ~L ３２ may be the same or different and may be independently a bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon 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 carbon a heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R, The W and W' are N-R ５３ , C.R. ５４ R ５５ , SiR ５６ R ５７ , GeR ５８ R ５ ９ , O, S, Se, The substituent R ５１ ~R ５９ , Ar ２１ ~Ar ２８ may be the same or different , each independently represents hydrogen, deuterium, or 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 aryl group having 2 to 3 carbon atoms a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms, a chloroalkenyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms; an alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or an unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 5 carbon atoms, an arylthioxy group having 1 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 carbon an 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 substituted arylgermanium groups having 1 to 30 carbon atoms, cyano groups, nitro groups, and halogen groups; Either one is selected, The R ５１ and R ５２ are linked together to form an alicyclic or aromatic monocyclic or polycyclic ring. The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N, O, P, It can be substituted with at least one heteroatom selected from Si, S, Ge, Se, and Te. 、 The p11 to p14, r11 to r14, and s11 to s14 are each an integer of 1 to 3. and when each of these is two or more, each linking group L ２１ ~L ３２ is mutual They may be the same or different, The x1 is 1, and y1, z1, and z2 may be the same or different, and may be mutually different. are each independently an integer from 0 to 1, The Ar ２１ and Ar ２２ , Ar ２３ and Ar ２４ , Ar ２５ and Ar ２６ , and Ar ２７ and Ar ２８ can be linked to each other to form a ring, In the above chemical formula D1, A ３２ Two adjacent carbon atoms in the ring are represented by the formula Q １１ * to form a condensed ring, In the chemical formula D2, the A ３１ Two adjacent carbon atoms in the ring are represented by the formula Q １２ and * in the formula (I) to form a condensed ring; ３２ Two adjacent carbon atoms in the ring are Structural formula Q １１ can bond with * to form a condensed ring.) [Chemical Formula D3] (In the above [Chemical Formula D3], The X １ is any one selected from B, P, and P=O, Said T １ ~T ３ may be the same or different from each other, and may be independently substituted or unsubstituted. or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic hydrocarbon ring having 2 carbon atoms an aromatic heterocycle of up to 40; The Y １ is N-R ６１ , C.R. ６２ R ６３ , O, S, SiR ６４ R ６５ Selected from It is either The Y ２ is N-R ６６ , C.R. ６６ R ６８ , O, S, SiR ６９ R ７０ Selected from It is either The R ６１ ~R ７０ may be the same or different, and may each independently represent water. hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted an aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; , a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted carbon an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon an arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms; a substituted or unsubstituted an alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, is any one selected from the group consisting of an alkyl group, a cyano group, and a halogen group, ６１ ~R ７０ are the T １ ~T ３ and bonded to at least one ring selected from the group consisting of an alicyclic or can further form an aromatic monocyclic or polycyclic ring. (In the above [Chemical Formula D4] and [Chemical Formula D5], The X ２ is any one selected from B, P, and P=O, Said T ４ ~T ６ is T in [Chemical Formula D3] １ ~T ３ is identical to The Y ４ is N-R ６１ , C.R. ６２ R ６３ , O, S, SiR ６４ R ６５ Selected from It is either The Y ５ is N-R ６６ , C.R. ６６ R ６８ , O, S, SiR ６９ R ７０ Selected from It is either The Y ６ is N-R ７１ , C.R. ７２ R ７３ , O, S, SiR ７４ R ７５ Selected from It is either The R ６１ ~R ７５ is the R in [Chemical Formula D3] ６１ ~R ７０ is the same as (The above X ３ is any one selected from B, P, and P=O, Said T ７ ~T ９ is T in [Chemical Formula D3] １ ~T ３ is identical to The Y ６ is N-R ６１ , C.R. ６２ R ６３ , O, S, SiR ６４ R ６５ Selected from It is either The substituent R ６１ ~R ６５ , R ７１ ~R ７２ are the above in [Chemical Formula D3], respectively. R ６１ ~R ７０ is identical to The R ７１ and R ７２ are each connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. or further forming the T ７ Ring or T ９ A monocyclic or aromatic ring bonded to the ring can further form polycyclic rings.) (In the above [Chemical Formula D8] to [Chemical Formula D10], X is any one selected from B, P, and P=O, Q １ ~Q ３ are the T in [Chemical Formula D3] １ ~T ３ is identical to The linking group Y is N—R ３ , C.R. ４ R ５ , O, S, Se can be, The substituent R ３ ~R ５ are the R in [Chemical Formula D3]. ６１ ~R ７０ Same as and The R ３ ~R ５ are the above Q ２ Ring or Q ３ Alicyclic or aromatic monocyclic rings bonded to the ring or may further form polycyclic rings, The R ４ and R ５ are each linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. can be further formed, The ring formed by Cy1 has a nitrogen (N) atom, a ring bonded to the nitrogen (N) atom, and a ring bonded to the nitrogen (N) atom. Q １ Aromatic carbon atoms in the ring and Q bonded to Cy1 １ Excluding aromatic carbon atoms in the ring For example, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, In the above chemical formula D9, The "Cy2" can be attached to the Cy1 to form a saturated hydrocarbon ring, and the C The ring formed by y2 may be substituted or unsubstituted except for the carbon atom contained in Cy1. is an alkylene group having 1 to 10 carbon atoms; In the above chemical formula D10, The ring formed by the Cy3 is ３ Aromatic carbon atoms in the ring , Q bonded to the nitrogen (N) atom ３ Aromatic carbon atoms, nitrogen (N) atoms, the nitrogen (N) A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, excluding the carbon atom in Cy1 to which the atom is bonded. is an alkylene group, Here, the "substituted or unsubstituted" in the [chemical formula D1] to [chemical formula D10] "Substitution" in "" means deuterium, cyano group, halogen group, hydroxy group, nitro group, carbon alkyl groups having 1 to 24 carbon atoms, halogenated alkyl groups having 1 to 24 carbon atoms, alkyl groups having 2 to 24 carbon atoms alkenyl group, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heterocyclic group having 2 to 24 carbon atoms, an aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms; an alkoxy group having 1 to 24 carbon atoms; an oxy group, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 6 to 14 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms; It means that it is substituted with one or more substituents.

14. A first electrode; a second electrode facing the first electrode, Between the first electrode and the second electrode, a first emitting layer containing a first host and a first dopant is disposed. a second light-emitting layer, and a second light-emitting layer comprising a second host and a second dopant; At least one of the first host and the second host is a host according to any one of claims 1 to 9.

1. An organic light-emitting device comprising one or more compounds according to claim 1.

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

16. The first light-emitting layer contains one or more compounds according to any one of claims 1 to 9. The organic light-emitting device according to claim 14 .

17. The second light-emitting layer uses an anthracene derivative represented by the following chemical formula E as a host. The organic light-emitting device according to claim 16 , [Chemical formula E] (In the above [Chemical Formula E], The substituent R ４１ ~R ４８ may be the same or different and independently represent hydrogen, heavy water, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 6 carbon atoms, aryl groups having 3 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 3 carbon atoms a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; is any one selected from the group consisting of a hydroxyl group, a nitro group, and a halogen group; The substituent Ar ５ and Ar ６ may be the same or different and are independent of each other. and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted a heteroaryl group having a prime number of 2 to 50, The linking group L １ represents a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms. Or, The n is an integer of 1 to 2, and when n is 2 or more, each linking group L １ are mutual may be the same as or different from The "substituted" in the "substituted or unsubstituted" in the [chemical formula E] means deuterium. , a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a carbon halogenated alkyl groups having 1 to 24 carbon atoms, alkenyl groups having 2 to 24 carbon atoms, an alkynyl group, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a carbon an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroaryl group having 2 to 2 carbon atoms; a heteroarylalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an amino group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, substituted with one or more substituents selected from the group consisting of aryloxy groups having 6 to 24 substituents; This means that

18. The anthracene derivative represented by the chemical formula E is represented by the following chemical formula E-1 or E- The organic light-emitting compound according to claim 17, wherein the anthracene compound is represented by the formula: element. [Chemical formula E-1] [Chemical formula E-2] (In the above [Chemical Formula E-1] and [Chemical Formula E-2], The substituent R ４１ ~R ４８ , R ４９ ~R ５５ may be the same or different, each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or an unsubstituted aryl group having 6 to 50 carbon atoms; a substituted or unsubstituted aryl group having 3 to 30 carbon atoms; a cycloalkyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 6 to 30 carbon atoms an arylsilyl group, a cyano group, a nitro group, or a halogen group; the law of nature, The substituent Ar ５ is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. or an unsubstituted heteroaryl group having 2 to 50 carbon atoms, The linking group L １１ represents 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. It is The k is an integer of 1 to 2, and when k is 2 or more, each linking group L １１ is mutual They may be the same or different, The "substituted or unsubstituted" in the [chemical formula E-1] and [chemical formula E-2] The "substitution" in the above is a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, a group having 1 carbon atom, alkyl groups having 1 to 24 carbon atoms, halogenated alkyl groups having 1 to 24 carbon atoms, alkene groups having 2 to 24 carbon atoms, an alkyl 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, and an alkyl group having 6 carbon atoms. aryl groups having 7 to 24 carbon atoms, arylalkyl groups having 7 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms, an aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms; group, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, heteroarylamino groups having 1 to 24 carbon atoms, alkylsilyl groups having 6 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms; It means that the group is substituted with the above substituents.

19. The first light-emitting layer and the second light-emitting layer may be the same or different and may each independently comprise the following: At least one selected from the chemical formulas D1 to D10 is used. The organic light-emitting device according to claim 17 . (The above [Chemical Formula D1] to [Chemical Formula D10] are the same as those described in claim 13, respectively.) It is one.)

20. One or more layers selected from the above layers are formed by a deposition process or a solution process. The organic light emitting device according to claim 11,

21. The organic light emitting device may be used in a flat panel display device, a flexible display device, or the like. for monochromatic or white flat panel lighting and for monochromatic or white flexible lighting The device according to claim 10, characterized in that it is used in any one of the devices selected from the group consisting of: The organic light-emitting element.

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