Organic light-emitting device including novel organic compound in light-emitting layer

Abstract

To provide an organic light emitting device (OLED) with high efficiency, low driving voltage and long life by using a novel organic compound that can be used as a host material of a light emitting layer in an organic light emitting device.SOLUTION: The present invention relates to an organic light-emitting device including an organic compound represented by [Chemical Formula A] or [Chemical Formula B], and more specifically, to an organic light-emitting device including two light-emitting layers between a first electrode and a second electrode, at least one of the two light-emitting layers using the organic compound represented by [Chemical Formula A] or [Chemical Formula B], and [Chemical Formula A] and [Chemical Formula B] are the same as those described in the detailed description of the present invention.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organic light-emitting device that contains a novel compound in a light-emitting layer. More specifically, the present invention includes two light-emitting layers between a first electrode and a second electrode, and the two light-emitting layers By introducing the novel organic compound into at least one of the above, high luminous efficiency, The present invention relates to an organic light-emitting device that can achieve low-voltage driving and long-life device characteristics. [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 as light-emitting as a liquid crystal display. Compared to LEDs, it is lighter, thinner, and smaller, and has the advantage of a faster response time. It is expected that this technology will be useful for full-color displays and lighting applications.

[0003] In general, organic light-emitting phenomenon refers to the conversion of electrical energy into light energy using organic materials. The 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 layer between the organic layers. Here, the organic layer is a layer that improves the efficiency and stability of the organic light-emitting device. In order to enhance the performance, they often have a multi-layer structure consisting of multiple different materials. For example, The layer 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 such an organic light-emitting device, holes are generated at the anode and electrons are generated at the cathode. When electrons are injected into the organic layer and combine with the injected holes, they become excitons. On) is generated, and when this exciton falls back to the ground state, light is emitted. The light-emitting element is known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

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

[0005] On the other hand, when only one substance is used as the light-emitting material, due to the intermolecular interaction, the maximum emission wavelength moves to a longer wavelength, the color purity decreases, and problems such as a decrease in the efficiency of the element due to the emission attenuation effect occur. Therefore, in order to increase the color purity and the emission efficiency due to energy transfer, a host-dopant system can be used as the light-emitting material. The principle is that when a dopant having an energy band gap smaller than that of the host forming the light-emitting layer is

[0006] mixed in a small amount in the light-emitting layer, the excitons generated from the light-emitting layer are transported to the dopant and emit highly efficient light. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

[0007] Recently, research has been conducted on heterocyclic compounds as host compounds in such light-emitting layers, and as a related prior art, Korean Patent Publication No. 10-2016-0089693 (published on July 28, 2016) discloses a structure in which a dibenzofuran ring is bonded to an anthracene ring The compound and an organic light-emitting device including the same are described in Korean Patent Publication No. Publication No. 10-2017-0055743 (May 22, 2017) states that oxygen, nitrogen, sulfur Aryl or heteroaryl substituents on fused fluorene rings containing heteroatoms such as yellow and an organic light-emitting device including the same.

[0008] However, including these conventional techniques, various forms of organic light-emitting devices for use in the light-emitting layer have been developed. Although the compound has been produced in the form of a fluorine-containing compound, it is still applicable to organic light-emitting devices and has high There is a continuing need to develop novel organic light-emitting devices that have the device characteristics of high efficiency, low voltage operation, and long life. It is continually being demanded. Summary of the Invention [Problem to be solved by the invention]

[0009] It is therefore an object of the present invention to provide a method for producing a compound which can be used as a host material for the light-emitting layer in an organic light-emitting device. Using novel organic compounds, we have developed organic light-emitting devices with high efficiency, low voltage operation, and long life. The company's objective is to provide LEDs (integrated light emitting diodes, OLEDs). [Means for solving the problem]

[0010] In order to achieve the above object, the present invention provides a semiconductor device comprising a first electrode and a second electrode facing the first electrode. and a first host and a first dopant are disposed between the first electrode and the second electrode. and a second emitting layer comprising a second host and a second dopant, At least one of the first host and the second host is represented by the following [Chemical Formula A] or [Chemical Formula B The present invention provides an organic light-emitting device, comprising one or more compounds represented by the formula:

[0011] JPEG2025084936000001.jpg65170

[0012] In the above [Chemical formula A] and [Chemical formula B], the above R 1 ~R 14 may be the same as or different from each other, and each independently is hydrogen, deuterium element, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms , a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number 1 to 30 alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or any one selected from halogen groups, the linking group L 1 and L 2 may be the same as or different from each other, and are independent of each other , a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, and are selected from among them, the above n1 and n2 may be the same as or different from each other, and are independently integers from 0 to 2 However, when each of these is 2, each of the linking groups L 1 and L 2 may be the same as or different from each other, and the above R and R’ may be the same as or different from each other, and are independent of each other, and are hydrogen, deuterium , a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 6 to a 50-carbon aryl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group, and n3 and n4 may be the same or different and are each independently an integer from 1 to 9, but when each of these is 2 or more, each R and R’ may be the same as or different from each other, and in the “substituted or unsubstituted” in the [Chemical Formula A] and [Chemical Formula B], the “substitution” is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl(heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having One or more substituents selected from the group consisting of a base and an arylthionyl group having 6 to 24 carbon atoms It means being substituted with a group.

Advantages of the Invention

[0013] In the case of an organic light-emitting device according to the present invention, which has two light-emitting layers in the organic light-emitting device, and an organic compound represented by the above chemical formula A or chemical formula B is introduced into at least one of these light-emitting layers, compared with an organic light-emitting device according to the prior art, an organic light-emitting device that exhibits higher efficiency, lower voltage driving, and longer life can be provided.

Brief Description of the Drawings

[0014]

Figure 1

Modes for Carrying Out the Invention

[0015] Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimension of the structure is shown enlarged or reduced compared to the actual size for the sake of clarity of the present invention, and known configurations are omitted from the illustration so that characteristic configurations appear, and thus the present invention is not limited to the drawings.

[0016] In addition, the size and thickness of each illustrated configuration are arbitrarily shown for the sake of convenience of explanation, and the present invention is not necessarily limited to the illustration. Also, in the drawings, the thickness is enlarged to clearly show a plurality of layers and regions, and for the sake of convenience of explanation, the thickness of some layers and regions is exaggerated. When a part such as a layer, film, region, or plate is said to be "on" another part, this includes not only the case where it is "directly on" another part, but also the case where another part is interposed between them. is interposed between them. is included.

[0017] ​ Also, throughout the specification, when a certain part “includes” a certain component, this means that, unless otherwise stated to the contrary, it does not exclude other components, but rather means that other components can be further included. Also, throughout the specification, “on” means being located above or below the target part, and does not necessarily mean being located on the upper side with reference to the direction of gravity.

[0018] The present invention includes a first electrode and a second electrode facing the first electrode, and between the first electrode and the second electrode, there are sequentially included a first light-emitting layer including a first host and a first dopant, and a second light-emitting layer including a second host and a second dopant. At least one of the first host and the second host contains one or more compounds represented by the following [Chemical Formula A] or [Chemical Formula B], and provides an organic light-emitting device. Among the above-mentioned [Chemical Formula A] and [Chemical Formula B],

[0019] JPEG2025084936000002.jpg65170

[0020] In the above-mentioned [Chemical Formula A] and [Chemical Formula B], the R 1 ~R 14 may be the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon An alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms is any one selected from a cyano group, a nitro group, and a halogen group, said linking group L 1 and L 2 may be the same as or different from each other, and are independent of each other and are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, wherein said n1 and n2 may be the same as or different from each other, and are independent of each other and are integers from 0 to 2 However, when each of these is 2, each of the linking groups L and L 1 and L 2 may be the same as or different from each other, wherein said R and R’ may be the same as or different from each other, and are independent of each other and are hydrogen, deuterium , a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms , a cyano group, a nitro group, and a halogen group, and are any one selected therefrom, wherein said n3 and n4 may be the same as or different from each other, and are independent of each other and are integers from 1 to 9 However, when each of these is 2 or more, each of the R and R’ may be the same as or different from each other, wherein said n3 and n4 may be the same as or different from each other, and are independent of each other and are integers from 1 to 9 However, when each of these is 2 or more, each of the R and R’ may be the same as or different from each other, wherein said n3 and n4 may be the same as or different from each other, and are independent of each other and are integers from 1 to 9 The "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B] means deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, a carbon number of 1 to 24 alkynyl groups, cycloalkyl groups having 3 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, carbon numbers 7 to 24 alkylaryl groups, heteroaryl groups having 2 to 24 carbon atoms, carbon numbers of 2 to 24 heteroarylalkyl groups, alkoxy groups having 1 to 24 carbon atoms, alkyl amino groups having 1 to 24 carbon atoms, diarylamino groups having 12 to 24 carbon atoms, diheteroaryl amino groups having 2 to 24 carbon atoms, aryl(heteroaryl)amino groups having 7 to 24 carbon atoms, alkyl silyl groups having 1 to 24 carbon atoms, arylsilyl groups having 6 to 24 carbon atoms, aryloxy groups having 6 to 24 carbon atoms, and arylthionyl groups having 6 to 24 carbon atoms, and is substituted with one or more substituents selected from the group consisting of groups.

[0021] On the other hand, considering the ranges of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", " substituted or unsubstituted aryl group having 5 to 50 carbon atoms", etc. in the present invention, the ranges of the carbon numbers of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms are, respectively, without considering the substituted portions of the substituents, the total number of carbon atoms constituting the alkyl portion or aryl portion when regarded as unsubstituted . For example, a phenyl group substituted with a butyl group at the para position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms. . For example, a phenyl group substituted with a butyl group at the para position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms. ​​

[0022] The aryl group, which is a substituent used in the compounds of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen, and when the aryl group has a substituent, it can further form a ring by fusing with adjacent substituents.

[0023] Specific examples of the aryl group include phenyl group, o-biphenyl group, m-biphenyl group , p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl, fluoranthen enyl group and other aromatic groups. One or more hydrogen atoms in the aryl group can be deuterium atom, halogen atom, hydroxy group, nitro group, cyano group, silyl group, amino group (-NH 2 , -NH(R), -N(R’)(R’’), where R’ and R’’ are independently alkyl groups having 1 to 10 carbon atoms, and in this case, it is called an "alkylamino group".), amidinogroup, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, or heteroarylalkyl group having 2 to 24 carbon atoms.

[0024] The heteroaryl group, which is a substituent used in the compounds of the present invention, contains N, O, P, Si, S 、containing one, two or three heteroatoms selected from Ge, Se, Te, and the remaining ring atoms are carbon atoms, which means a cyclic aromatic system having 2 to 24 carbon atoms. These rings can be fused d) to form rings. And one or more hydrogen atoms in the heteroaryl group can be substituted with the same substituents as in the case of the aryl group.

[0025] Also, in the present invention, the aromatic heterocyclic ring means a ring in which one or more of the aromatic carbons in the aromatic hydrocarbon ring are substituted with heteroatoms. The aromatic heterocyclic ring is preferably one to three of the aromatic carbons in the aromatic hydrocarbon can be substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, T e.

[0026] The alkyl group, which is a substituent used in the present invention, is a substituent obtained by removing one hydrogen from an alkane, and has a structure including linear and branched forms. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert -butyl, pentyl, iso-amyl, hexyl, etc. One or more hydrogen atoms in the alkyl group can be substituted with the same substituents as in the case of the aryl group .

[0027] The "cyclo" in the cycloalkyl group, which is a substituent used in the compounds of the present invention, means a substituent having a structure capable of forming a monocyclic or polycyclic saturated hydrocarbon within the alkyl group . For example, specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclo pentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclo pentyl, etc. ​Ropentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydro Examples include ronaphthyl, norbornyl, bornyl, isobornyl, etc. Among them, one or more hydrogen atoms in the cycloalkyl group can be substituted with the same substituents as in the case of the aryl group. It is possible.

[0028] The alkoxy group, which is a substituent used in the compounds of the present invention, is a substituent in which an oxygen atom is bonded to the end of an alkyl group or a cycloalkyl group. Specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, is o-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, ada mantanoxy, dicyclopentanoxy, bornyloxy, isobornyloxy, etc. Among them, one or more hydrogen atoms in the alkoxy group can be substituted with the same substituents as in the case of the aryl group. It is possible. It is possible. It is possible.

[0029] Specific examples of the arylalkyl group, which is a substituent used in the compounds of the present invention, include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphth ylethyl, etc. Among them, one or more hydrogen atoms in the arylalkyl group can be substituted with the same substituents as in the case of the aryl group. It is possible. It is possible.

[0030] Specific examples of the silyl group, which is a substituent used in the compounds of the present invention, include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenyl silyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl Examples include dimethylfurylsilyl, etc. Among them, one or more hydrogen atoms in the silyl group It can be substituted with the same substituents as in the case of the aryl group.

[0031] In the present invention, an alkenyl group means an alkyl substituent containing one carbon-carbon double bond constituted by two carbon atoms, and an alkynyl (alkynyl) group means an alkyl substituent containing one carbon-carbon triple bond constituted by two carbon atoms. (alkynyl) group means an alkyl substituent containing one carbon-carbon triple bond constituted by two carbon atoms. is meant.

[0032] In addition, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens in an alkane molecule which is a linear or branched saturated hydrocarbon. Specific examples of the alkylene group include a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, a sec-butylene group, a tert-but ylene group, a pentylene group, an iso-amylene group, a hexylene group, etc. One or more hydrogen atoms in the alk ylene group can be substituted with the same substituents as in the case of the aryl group. ylene group can be substituted with the same substituents as in the case of the aryl group. able.

[0033] In addition, the diarylamino group in the present invention means an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom. The diheteroarylamino group in the present invention means an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom, and the aryl(heteroaryl)amino group means an amine group in which the aryl group and the heteroaryl group are each bonded to a nitrogen atom.

[0034] On the other hand, in the "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B], More preferred examples of the "substitution" include deuterium, cyano group, halogen group, hydroxy group , nitro group, alkyl group having 1 to 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, car bon atoms 2 to 12 alkenyl group, carbon atoms 2 to 12 alkynyl group, carbon atoms 3 to 12 cyclo alkyl group, heteroalkyl group having 1 to 12 carbon atoms, aryl group having 6 to 18 carbon atoms, carbon atoms 7 to 20 arylalkyl group, alkylaryl group having 7 to 20 carbon atoms, carbon atoms 2 to 18 heteroaryl group, heteroarylalkyl group having 2 to 18 carbon atoms, alkoxy group having 1 to 12 carbon atoms, alkylamino group having 1 to 12 carbon atoms, diarylamino group having 12 to 18 carbon atoms, diheteroarylamino group having 2 to 18 carbon atoms, aryl(heteroary l)amino group having 7 to 18 carbon atoms, alkylsilyl group having 1 to 12 carbon atoms, arylsily l group having 6 to 18 carbon atoms, aryloxy group having 6 to 18 carbon atoms, and arylthionyl group having 6 to 18 carbon atoms, and may be substituted with one or more substituents selected from the group consisting of .

[0035] In the present invention, the organic compounds represented by the above [Chemical Formula A] and [Chemical Formula B] are compounds used as hosts in the light-emitting layer. The organic compound represented by the above [Chemical Formula A] is , a linking group L1 is bonded to a specific position in the substituted or unsubstituted pyrene ring (see the following Structural Formula C), and the 1-position of the substituted or unsubstituted dibenzofuran group is bonded to the linking group L1 , which is a technical feature. Further, the organic compound represented by the above [Chemical Formula B] has a linking group L2 bonded to a specific position in the substituted or unsubstituted pyrene ring (see the following Structural Formula C), and the 2-position of the substituted or unsubstituted dibenzofuran group is bonded to the linking group L2, which is a technical feature. feature. ​​​

[0036] [Structural formula C] JPEG2025084936000003.jpg31140

[0037] In the [Chemical formula A] and [Chemical formula B] in the organic light-emitting device according to the present invention, the chemical compound represented by formula A can contain at least one deuterium, and the compound represented by formula B can contain at least one deuterium.

[0038] More specifically, at least one of R 1 ~R 7 in the [Chemical formula A] is a substituent containing deuterium, and at least one of R ~R 8 ~R 14 in the [Chemical formula B] can be a substituent containing deuterium.

[0039] Also, in the organic light-emitting device according to the present invention, when the compound represented by formula A can contain at least one deuterium and the compound represented by formula B can contain at least one deuterium, at least one R in the [Chemical formula A] is a substituent containing deuterium, and at least one R' in the [Chemical formula B] can be a substituent containing deuterium.

[0040] Also, as an embodiment according to the present invention, R 1 ~R 14 , R, and R' can be the same or different from each other, and independently of each other, are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 1 0 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, a substituted or unsubstituted cyclo group having 3 to 18 carbon atoms ​An alkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a halogen group can be a substituent selected from among them.

[0041] Also, as an example of the present invention, at least one of R 1 ~R 7 in the above [Chemical Formula A] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and at least one of R ~R in the above [Chemical Formula B] can be a substituted or unsubstituted aryl group having 6 8 ~18 carbon atoms. 14

[0042] As an example of the present invention, the linking groups L 1 and L 2 in the above Chemical Formula A and Chemical Formula B can each be a single bond or any one selected from the following [Structural Formula 1] to [Structural Formula 5].

[0043] JPEG2025084936000004.jpg58140

[0044] Hydrogen or deuterium can be bonded to the carbon atoms of the aromatic ring in the above [Structural Formula 1] to [Structural Formula 5].

[0045] Also, as an example of the present invention, the linking groups L 1 and L 2 can each be a single bond.

[0046] Also, as an example of the present invention, n3 and n4 in the above Chemical Formula A and Chemical Formula B can each be 1.

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

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

[0049] JPEG2025084936000005.jpg65165

[0050] At this time, in the above [Chemical Formula A-1] and [Chemical Formula B-1], the substituents R 1 ~R 1 4 , the linking groups L 1 and L 2 , n1 and n2 are the same as those defined above in [Chemical Formula A] or [Chemical Formula B], and the substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

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

[0052] Also, as an example of the present invention, n3 and n4 in the above Chemical Formula A and Chemical Formula B are each 1, R in the above [Chemical Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, and R’ in the above [Chemical Formula B] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms. It may be a heteroaryl group.

[0053] Also, the compound represented by the above [Chemical Formula A] or [Chemical Formula B] according to the present invention may be any compound selected from Chemical Formula 1 to Chemical Formula 240.

[0054] JPEG2025084936000006.jpg 221170 JPEG2025084936000007.jpg 225170 JPEG2025084936000008.jpg 222170 JPEG2025084936000009.jpg 205170 JPEG2025084936000010.jpg 220170 JPEG2025084936000011.jpg 208170 JPEG2025084936000012.jpg 217170 JPEG2025084936000013.jpg 216170 JPEG2025084936000014.jpg 223170 JPEG2025084936000015.jpg 207170 JPEG2025084936000016.jpg 212170 JPEG2025084936000017.jpg 221170 JPEG2025084936000018.jpg 224170 JPEG2025084936000019.jpg 221170 JPEG2025084936000020.jpg 222170 JPEG2025084936000021.jpg 234170

[0055] On the other hand, in the present invention, “(the organic layer) contains one or more organic compounds” can be interpreted as “(the organic layer can) contain one kind of organic compound belonging to the scope of the present invention or two or more different compounds belonging to the scope of the organic compound”.

[0056] At this time, the organic layer in the organic light-emitting device of the present invention can include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0057] Further, in the present invention, at least one of a hole transport layer and a hole injection layer is provided between the first electrode and the first light-emitting layer, and at least one of an electron transport layer and an electron injection layer is provided between the second light-emitting layer and the second electrode. Preferably, between the first electrode and the first light-emitting layer ​​​​​ A hole transport layer and a hole injection layer are respectively provided therebetween, and between the second light-emitting layer and the second electrode An electron transport layer and an electron injection layer are respectively provided, and an organic light-emitting device can be provided. It is possible.

[0058] In addition, in the organic light-emitting device according to the present invention, at least one of the first dopant in the first light-emitting layer or the second dopant in the second light-emitting layer can contain at least one compound represented by any one of the following [Chemical Formula D1] to [Chemical Formula D10 , and preferably, both the first dopant in the first light-emitting layer and the second dopant in the second light-emitting layer may be the same or different from each other, and one or more compounds selected from the [Chemical Formula D1] to [Chemical Formula D10] can be used.

[0059] JPEG2025084936000022.jpg226170

[0060] In the [Chemical Formula D1] and [Chemical Formula D2], A 31 , A 32 , E 1 and F 1 may be the same or different from each other, and independently of each other, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms, 31 32 51 52 Two adjacent carbon atoms in the aromatic ring of A 51 and two adjacent carbon atoms in the aromatic ring of A 52 form a condensed ring by forming a 5-membered ring with the carbon atoms to which the substituents R and R are attached, 21 ~L 32 may be the same or different from each other, and independently of each other, a single bond A combined, substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, selected from among; Said W and W' may be the same or different from each other, and independently of each other, N-R 53 , CR 54 R 55 R, SiR 56 R 57 R, GeR 58 R 59 R, and is selected from among O, S, and Se; wherein; Said substituents R 51 ~R 59 and Ar 21 ~Ar 28 may be the same or different from each other , and independently of each other, are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted chloroalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or An arylthioxy group of 1 to 30, a substituted or unsubstituted alkylamine group of 1 to 30 carbon atoms , a substituted or unsubstituted arylamine group of 5 to 30 carbon atoms, a substituted or unsubstituted carbon An alkylsilyl group of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl Group, a substituted or unsubstituted alkylgermanium group of 1 to 30 carbon atoms, a substituted or unsubstituted An arylgermanium group of 1 to 30 carbon atoms, a cyano group, a nitro group, a halogen group, among which Any one selected, but Said R 51 And R 52 Are connected to each other to form an alicyclic, aromatic monocyclic or polycyclic ring And the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring can be substituted with at least one heteroatom selected from N, O, P, Si, S, Ge, Se, Te , Said p11 to p14, r11 to r14 and s11 to s14 are each an integer of 1 to 3 However, when each of these is 2 or more, each linking group L 21 ~L 32 Is May be the same or different from each other, Said x1 is 1, y1, z1 and z2 may be the same or different from each other, and are each independently an integer of 0 to 1 , Said Ar 21 And Ar 22 , Ar 23 And Ar 24 , Ar 25 And Ar 26 , and Ar 27 And Ar 28 Can be connected to each other to form a ring Two adjacent carbon atoms in the A ring in the chemical formula D1 are the structural formula Q 32 Of 11 Of Combine with * to form a condensed ring, the A in the chemical formula D2 31 Two adjacent carbon atoms in the ring are the structural formula Q 1 2 Combine with * of to form a condensed ring, the A 32 Two adjacent carbon atoms in the ring are the struct ural formula Q 11 Can combine with * of to form a condensed ring.)

[0061] JPEG2025084936000023.jpg49128

[0062] In the [chemical formula D3], the X 1 is any one selected from B, P, and P=O, The T1 to T3 may be the same or different from each other, and independently of each other, are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted carbon numbers 2 to 40 aromatic heterocyclic rings, the Y 1 is N-R 61 、CR 62 R 63 、O、S、SiR 64 R 65 Selected from among any one of them, the Y 2 is N-R 66 、CR 67 R 68 、O、S、SiR 69 R 70 Selected from among any one of them, the R 61 ~R 70 may be the same or different from each other, and independently of each other, are water element, 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 number 1 to 30 alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 5 to 30 arylthioxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, or a halogen group, and any one selected from the group consisting of 61 R 70 is bonded to one or more rings selected from the above T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0063] JPEG2025084936000024.jpg58128

[0064] In the above [Chemical Formula D4] and [Chemical Formula D5], the X 2 is any one selected from B, P, and P=O, the T4 to T6 are the same as T1 to T3 in [Chemical Formula D3], the Y 4 is N-R 61 , CR 62 R 63 , O, S, SiR 64 R 65 selected from among any one of them, the Y 5 is N-R 66 , CR 66 R 68 , O, S, SiR 69 R 70 selected from among any one of them, the Y6 is N-R 71 CR 72 R 73 O, S, SiR 74 R 75 selected from any of them and said R 61 ~R 75 is the same as said R 61 ~R 70 in [Chemical formula D3].

[0065] JPEG2025084936000025.jpg50128

[0066] Said X 3 is selected from any of B, P, P=O and said T7~T9 are the same as T1~T3 in [Chemical formula D3], said Y 6 is N-R 61 CR 62 R 63 O, S, SiR 64 R 65 selected from any of them and said substituents R 61 ~R 65 R 71 ~R 72 are respectively the same as said R 61 ~R 70 in [Chemical formula D3], but said R 71 and R 72 are respectively connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, or combined with said T7 ring or T9 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0067] JPEG2025084936000026.jpg92132

[0068] Among said [Chemical formula D8]~[Chemical formula D10], Said X is any one selected from B, P, and P=O, said Q 1 ~Q 3 is the same as T1 to T3 in [Chemical Formula D3], respectively, said linking group Y is N-R 3 , CR 4 R 5 and is any one selected from O, S, and Se, and is one of them, said substituent R 3 ~R 5 is the same as said R 61 ~R 70 in [Chemical Formula D3], respectively, but said R 3 ~R 5 is respectively bonded to said Q 2 ring or Q 3 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring, said R 4 and R 5 can be respectively connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and can further form an alicyclic or aromatic monocyclic or polycyclic ring, the ring formed by said Cy1 is, excluding a nitrogen (N) atom, an aromatic carbon atom in the Q ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q ring bonded to said Cy1, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, 1 in said Chemical Formula D9, 1 said Cy2 can be added to said Cy1 to form a saturated hydrocarbon ring, and the ring formed by said Cy2 is, excluding the carbon atoms contained in Cy1, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, in said Chemical Formula D10, the ring formed by said Cy3 is an aromatic carbon atom in the Q ring bonded to said Cy3, a nitrogen (N) atom, and a nitrogen (N) atom-bonded Q ring, in said Chemical Formula D10, the ring formed by said Cy3 is an aromatic carbon atom in the Q ring bonded to said Cy3, 3 and a nitrogen (N) atom-bonded Q3 excluding the internal aromatic carbon atom, nitrogen (N) atom, and Cy1 internal carbon atom to which the nitrogen (N) atom is bonded, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms group.

[0069] Here, the "substituted or unsubstituted" in the above [Chemical Formula D1] to [Chemical Formula D10] wherein "substituted" means substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheteroarylamino group having 2 to 24 carbon atoms, aryl(heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms, arylthionyl group having 6 to 24 carbon atoms, and more preferred examples include deuterium, cyano group , halogen group, hydroxy group, nitro group, alkyl group having 1 to 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, heteroalkyl group having 1 to 12 carbon atoms, aryl group having 6 to 18 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, alkyl aryl group having 7 to 20 carbon atoms. , halogen group, hydroxy group, nitro group, alkyl group having 1 to 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, heteroalkyl group having 1 to 12 carbon atoms, aryl group having 6 to 18 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, alkyl aryl group having 7 to 20 carbon atoms, ​​An aryl group, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 2 to 18 carbon atoms, a diheteroarylamino group having 2 to 18 carbon atoms, a carbon number of 7 to 18 aryl(heteroaryl)amino group, an alkylsilyl group having 1 to 12 carbon atoms, carbon a number of 6 to 18 arylsilyl group, an aryloxy group having 6 to 18 carbon atoms, a carbon number of 6 to 18 It may be substituted with one or more substituents selected from the group consisting of an arylthionyl group.

[0070] Further, among the dopant compounds according to the present invention, in the case of the boron compound represented by any one of the above [Chemical Formula D3] to [Chemical Formula D10] , as a substituent capable of substituting the aromatic hydrocarbon ring or aromatic heterocyclic ring of the above T1 to T9 or Q 1 ~Q 3 , deuterium, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a carbon number of 6 to 24 arylamino groups are mentioned, and here, each alkyl group or aryl group in the alkylamino group having 1 to 24 carbon atoms and the arylamino group having 6 to 24 carbon atoms can be linked to each other, and more preferable substituents include an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a carbon number of 6 to 1 8 arylamino groups are mentioned, and each alkyl group or aryl group in the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms can be linked to each other.

[0071] ​On the one hand, among the dopant compounds used in the light-emitting layer in the organic light-emitting device according to the present invention, the former Specific examples of the compound represented by any of the following [Chemical Formula D1] to [Chemical Formula D2] are as follows <d1> ~ <d239>Compounds represented by any of the following are exemplified.

[0072] JPEG2025084936000027.jpg213170JPEG2025084936000028.jpg210170JPEG2025084936000029.jpg207170JPEG2025084936000030.jpg195170JPEG2025084936000031.jpg206170JPEG2025084936000032.jpg200170JPEG2025084936000033.jpg214170JPEG2025084936000034.jpg228170JPEG2025084936000035.jpg203170JPEG2025084936000036.jpg201170JPEG2025084936000037.jpg230170JPEG2025084936000038.jpg233170JPEG2025084936000039.jpg233170JPEG2025084936000040.jpg206170JPEG2025084936000041.jpg201170JPEG2025084936000042.jpg123170

[0073] In the present invention, among the dopant compounds in the light-emitting layer, the compound represented by [Chemical Formula D3] is as follows <d101> ~ <d130>represented by any one selected from among may be a compound.

[0074] JPEG2025084936000043.jpg253170JPEG2025084936000044.jpg204170

[0075] In the present invention, among the dopant compounds in the light-emitting layer, the compound represented by the above [Chemical Formula D4], Chemical Formula D5], or any one of [Chemical Formula D8] to [Chemical Formula D10] may be a compound represented by any one selected from the following [D201] to [D476].

[0076] JPEG2025084936000045.jpg219170JPEG2025084936000046.jpg216170JPEG2025084936000047.jpg208170JPEG2025084936000048.jpg208170JPEG2025084936000049.jpg225170JPEG2025084936000050.jpg212170JPEG2025084936000051.jpg207170JPEG2025084936000052.jpg235170JPEG2025084936000053.jpg243170JPEG2025084936000054.jpg217170JPEG2025084936000055.jpg240170JPEG2025084936000056.jpg213170JPEG2025084936000057.jpg239170JPEG2025084936000058.jpg166170

[0077] In the present invention, among the dopant compounds in the light-emitting layer, the compound represented by either [Chemical Formula D6] or [Chemical Formula D7] is the following <d501> ~ <d587>from among It may be a compound represented by any one selected therefrom.

[0078] JPEG2025084936000059.jpg248170JPEG2025084936000060.jpg225170JPEG2025084936000061.jpg216170JPEG2025084936000062.jpg234170JPEG2025084936000063.jpg200170JPEG2025084936000064.jpg139170

[0079] At this time, the content of the dopant in the light-emitting layer is usually selected from the range of about 0.01 to about 20 parts by weight with respect to about 100 parts by weight of the host, and is not limited thereto. It can be selected from the range of about 0.01 to about 20 parts by weight with respect to about 100 parts by weight of the host, and is not limited thereto.

[0080] In addition, the light-emitting layer can further contain various host and various dopant substances in addition to the dopant and the host. It can further contain various host and various dopant substances in addition to the dopant and the host.

[0081] Also, as one embodiment of the organic light-emitting device according to the present invention, the first light-emitting layer is selected from among the compounds represented by either one of the compounds represented by [Chemical formula A] or [Chemical formula B] can contain one or more of them.

[0082] Here, when the first light-emitting layer in the organic light-emitting device according to the present invention contains any one of the compounds represented by [Chemical formula A] or [Chemical formula B] in the second light-emitting layer an anthracene derivative represented by the following [Chemical formula E] can be used as the host.

[0083] [Chemical formula E] JPEG2025084936000065.jpg71128

[0084] In the above [Chemical formula E], the substituent R 41 ~R 56 may be the same or different, and are independent of each other, being hydrogen, heavy water element, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 3 0 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group, and is selected from any of them, wherein the substituent Ar 5 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, wherein the linking group L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and either a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, and wherein n is an integer of 1 to 2, and when n is 2 or more, each linking group L 1 may be the same or different from each other, and in the "substituted or unsubstituted" in the [Chemical Formula E], the "substitution" means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, carbon number 1 to 24 halogenated alkyl groups, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, carbon number 6 to 24 aryl group, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms A linear alkyl group, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diaryl amino group having 12 to 24 carbon atoms, a diheteroaryl amino group having 2 to 24 carbon atoms, a aryl(heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, a arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and is substituted with one or more substituents selected from the group consisting of the following.

[0085] In addition, the anthracene derivative represented by Chemical Formula E in the second light-emitting layer in the present invention can contain at least one deuterium. In this case, the substituent R ~R 41 ~R 56 or at least one of Ar5 can be an aryl group having 6 to 18 carbon atoms substituted with deuterium atoms.

[0086] In addition, as a preferred example of the organic light-emitting device according to the present invention, when the second light-emitting layer contains the anthracene derivative represented by the above [Chemical Formula E] as a host, a more preferred structure of the anthracene derivative represented by the above [Chemical Formula E] is the following [Chemical Formula E-1] or the anthracene derivative represented by [Chemical Formula E-2] can be used.

[0087] [Chemical Formula E-1] JPEG2025084936000066.jpg84129[Chemical Formula E-2] JPEG2025084936000067.jpg79129

[0088] In the above [Chemical Formula E-1] and [Chemical Formula E-2], the substituents R 41 ~R 48 and R 49 ~R 55 may be the same or different from each other and are independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, or a halogen group, wherein, the substituent Ar 5 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, the linking group L 11 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, wherein, k is an integer from 1 to 2, and when k is 2 or more, each linking group L 11 may be the same or different from each other, wherein, in the said "[Formula E-1]" and "[Formula E-2]", the "substituted or unsubstituted" "substitution" means deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 2 4 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 2 4 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkoxy group having 1 to 2 A C4 alkylamino group, a C12-24 diarylamino group, a C2-24 diheteroaryl arylamino group, a C7-24 aryl(heteroaryl)amino group, a C1-24 alkylsilyl group, a C6-24 arylsilyl group, a C6-24 aryloxy group, and a C6-24 arylthionyl group, meaning that it is substituted with one or more substituents selected from the group consisting of them.

[0089] Also, more preferred examples of the "substituted or unsubstituted" in the above [Chemical Formula E], [Chemical Formula E-1], and [Chemical Formula E-2] for "substituted" are deuterium, a cyano group, a halo gen group, a hydroxy group, a nitro group, a C1-12 alkyl group, a C1-12 halo alkyl group, a C2-12 alkenyl group, a C2-12 alkynyl group, a C3-12 cycloalkyl group, a C1-12 heteroalkyl group, a C6-18 aryl group, a C7-20 arylalkyl group, a C7-20 alkylaryl group, a C2-18 heteroaryl group, a C2-18 heteroarylalkyl group a C1-12 alkoxy group, a C1-12 alkylamino group, a C12-18 diarylamino group, a C2-18 diheteroarylamino group, a C7-18 aryl(heteroaryl)amino group, a C1-12 alkylsilyl group, a C6-18 arylsilyl group, a C6-18 aryloxy group, a C6-18 aryl thionyl group, and being substituted with one or more substituents selected from the group consisting of them. Here, the compound represented by the above [Chemical Formula E-1] or [Chemical Formula E-2] is the following [Formula ~18 aryloxyl group, a C6-18 arylthionyl group, and being substituted with one or more substituents selected from the group consisting of them. .

[0090] Here, the compound represented by the above [Chemical Formula E-1] or [Chemical Formula E-2] is the following [Formula As shown in [1], the 1-position or 2-position of one of the phenyl rings of dibenzofuran or the 1'-position or 2'-position of the other phenyl ring of dibenzofuran is bonded to the 9-position of an anthracenyl group or a linking group L. 11 It is characterized in that.

[0091] [Formula 1] JPEG2025084936000068.jpg35129

[0092] On the other hand, in the present invention, the substituent Ar in the anthracene derivative represented by any of the following [Chemical Formula E], [Chemical Formula E-1], and [Chemical Formula E-2] may be a substituent represented by the following [Structural Formula C-1]. 5 is represented by the substituent represented.

[0093] [Structural Formula C-1] JPEG2025084936000069.jpg40129

[0094] At this time, R in the following [Structural Formula C-1] 61 ~R 65 may be the same or different well, independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, or any one selected from halogen groups, and "-*" in the following [Structural Formula C-1] is a bonding site bonded to the 10-position of the anthracenyl group in [Chemical Formula E], [Chemical Formula E-1], or [Chemical Formula E-2].

[0095] In one embodiment, as a preferred example of the organic light-emitting device according to the present invention, the above-mentioned [Chemical formula E- 1] or the linking group L in [Chemical formula E-2] 11 is a single bond, or may be a substituted or unsubstituted arylene group having 6 to 14 carbon atoms. At this time, the above-mentioned k is an integer of 1 to 2 However, when the above-mentioned k is 2 or more, each L 13 may be the same as or different from each other .

[0096] Also, as one embodiment according to the present invention, in the above-mentioned Chemical formula E, Ar5 is a substituent containing at least 1 deuterium, preferably an aryl group having 6 to 50 carbon atoms containing at least 1 deuterium, more preferably an aryl group having 6 to 40 carbon atoms containing deuterium and even more preferably an aryl group having 6 to 30 carbon atoms containing deuterium, and even more preferably an aryl group having 6 to 24 carbon atoms containing deuterium, and even more preferably an aryl group having 6 to 18 carbon atoms containing deuterium, and most preferably a deuterium-substituted phenyl group. It may be.

[0097] Also, as one embodiment according to the present invention, at least 41 one of R 48 to R in the following Chemical formula E may be deuterium, preferably at least 2, more preferably at least 4, and even more preferably all 8 may be deuterium.

[0098] Also, as one embodiment according to the present invention, at least 49 one of R 56 to R in the following Chemical formula E may be a substituent containing deuterium, preferably a carbon number containing deuterium It may be an aryl group having 6 to 50 carbon atoms, more preferably an aryl group having 6 to 40 carbon atoms and containing deuterium, still more preferably an aryl group having 6 to 30 carbon atoms and containing deuterium, even more preferably an aryl group having 6 to 24 carbon atoms and containing deuterium, still even more preferably an aryl group having 6 to 18 carbon atoms and containing deuterium, and most preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium. Among them, it may be an aryl group having 6 to 30 carbon atoms and containing deuterium, more preferably an aryl group having 6 to 24 carbon atoms and containing deuterium, still more preferably an aryl group having 6 to 18 carbon atoms and containing deuterium, and most preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium. Among them, it may be an aryl group having 6 to 24 carbon atoms and containing deuterium, more preferably an aryl group having 6 to 18 carbon atoms and containing deuterium, still more preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium. Among them, it may be an aryl group having 6 to 18 carbon atoms and containing deuterium, and most preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium. Among them, it may be an aryl group having 6 to 18 carbon atoms and containing deuterium, and most preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium. 49 ~R 56 Among them, it may be an aryl group having 6 to 18 carbon atoms and containing deuterium, and most preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium. Among them, it may be an aryl group having 6 to 18 carbon atoms and containing deuterium, and most preferably, one or two of R~R in the following chemical formula E are aryl groups having 6 to 18 carbon atoms substituted with deuterium.

[0099] Also, as an example of the present invention, the anthracene derivative represented by the chemical formula E may have a degree of deuteration of 20% or more, preferably 30% or more, more preferably 35% or more, still more preferably 40% or more, even more preferably 45% or more, and still even more preferably 50% or more. Also, as an example of the present invention, the anthracene derivative represented by the chemical formula E may have a degree of deuteration of 20% or more, preferably 30% or more, more preferably 35% or more, still more preferably 40% or more, even more preferably 45% or more, and still even more preferably 50% or more. Also, as an example of the present invention, the anthracene derivative represented by the chemical formula E may have a degree of deuteration of 20% or more, preferably 30% or more, more preferably 35% or more, still more preferably 40% or more, even more preferably 45% or more, and still even more preferably 50% or more. Also, as an example of the present invention, the anthracene derivative represented by the chemical formula E may have a degree of deuteration of 20% or more, preferably 30% or more, more preferably 35% or more, still more preferably 40% or more, even more preferably 45% or more, and still even more preferably 50% or more. Also, as an example of the present invention, the anthracene derivative represented by the chemical formula E may have a degree of deuteration of 20% or more, preferably 30% or more, more preferably 35% or more, still more preferably 40% or more, even more preferably 45% or more, and still even more preferably 50% or more.

[0100] On the other hand, looking specifically at the degree of deuteration used in this specification, generally, the "deuterated derivative" of compound X has the same structure as compound X, but means that it is accompanied by at least one deuterium (D) that replaces a hydrogen atom (H) bonded to a carbon atom, nitrogen atom, or oxygen atom in compound X. On the other hand, looking specifically at the degree of deuteration used in this specification, generally, the "deuterated derivative" of compound X has the same structure as compound X, but means that it is accompanied by at least one deuterium (D) that replaces a hydrogen atom (H) bonded to a carbon atom, nitrogen atom, or oxygen atom in compound X. On the other hand, looking specifically at the degree of deuteration used in this specification, generally, the "deuterated derivative" of compound X has the same structure as compound X, but means that it is accompanied by at least one deuterium (D) that replaces a hydrogen atom (H) bonded to a carbon atom, nitrogen atom, or oxygen atom in compound X. On the other hand, looking specifically at the degree of deuteration used in this specification, generally, the "deuterated derivative" of compound X has the same structure as compound X, but means that it is accompanied by at least one deuterium (D) that replaces a hydrogen atom (H) bonded to a carbon atom, nitrogen atom, or oxygen atom in compound X.

[0101] Here, the term "yy% deuterated" or "yy% deuteration" refers to the ratio of deuterium to the sum of all hydrogen and deuterium directly bonded to carbon atoms, nitrogen atoms, or oxygen atoms in compound X, expressed as a percentage. Here, the term "yy% deuterated" or "yy% deuteration" refers to the ratio of deuterium to the sum of all hydrogen and deuterium directly bonded to carbon atoms, nitrogen atoms, or oxygen atoms in compound X, expressed as a percentage. Here, the term "yy% deuterated" or "yy% deuteration" refers to the ratio of deuterium to the sum of all hydrogen and deuterium directly bonded to carbon atoms, nitrogen atoms, or oxygen atoms in compound X, expressed as a percentage.

[0102] Therefore, when 2 of the 6 hydrogens in benzene are deuterated, the compound C6H4D The degree of deuteration in 2 can be regarded as 2 / (4 + 2)×100 = 33% deuteration. It is possible.

[0103] When deuterium is substituted in the anthracene derivative compound of the present invention, the degree of deuteration means the percentage of all deuteriums directly bonded to carbon atoms in the anthracene derivative with respect to the sum of all hydrogens directly bonded to carbon atoms in the anthracene derivative and all deuteriums directly bonded to carbon atoms in the anthracene derivative. That is, it is expressed as a percentage of the ratio of all deuteriums directly bonded to carbon atoms in the anthracene derivative to the sum of all hydrogens directly bonded to carbon atoms in the anthracene derivative and all deuteriums directly bonded to carbon atoms in the anthracene derivative. For example, in the case of an anthracene derivative represented by the following compound Z, there are 5 deuteriums in the phenyl group bonded to the anthracene group and 5 deuteriums in the phenyl group bonded to dibenzofuran, so there are a total of 10 deuteriums. There are 8 hydrogen atoms in the anthracene group and 6 hydrogen atoms bonded to the aromatic carbon atoms in both 6-membered rings of dibenzofuran. The degree of deuteration

[0104] For example, in the case of an anthracene derivative represented by the following compound Z, since there are 5 deuteriums in the phenyl group bonded to the anthracene group and 5 deuteriums in the phenyl group bonded to dibenzofuran, there are a total of 10 deuteriums. There are 8 hydrogen atoms in the anthracene group and 6 hydrogen atoms bonded to the aromatic carbon atoms in both 6-membered rings of dibenzofuran. The degree of deuteration is 100×10 / (10 + 8 + 6) = 41.7%. can be expressed as In the case of an anthracene derivative represented by the following compound Z, there are 5 deuteriums in the phenyl group bonded to the anthracene group and 5 deuteriums in the phenyl group bonded to dibenzofuran, so there are a total of 10 deuteriums. There are 8 hydrogen atoms in the anthracene group and 6 hydrogen atoms bonded to the aromatic carbon atoms in both 6-membered rings of dibenzofuran. The degree of deuteration is 100×10 / (10 + 8 + 6) = 41.7%.

[0105] JPEG2025084936000070.jpg59130

[0106] On the other hand, in the case of specific substituents, the degree of deuteration may vary for each individual substituent. Therefore, the degree of deuteration can be indicated by obtaining the average degree of substitution. Since there is a possibility of variation, the degree of deuteration can be indicated by determining the average degree of substitution. It is possible.

[0107] As an example, considering the case of an anthracene group with partial deuterium substitution, depending on the reaction conditions, an anthracene derivative in which deuterium is bonded to all carbon atoms can be produced and used as an anthracene group with deuterium substitution. However, depending on the reaction conditions, at specific positions depending on the reaction conditions, an anthracene derivative in which deuterium is bonded to all carbon atoms can be produced and used as an anthracene group with deuterium substitution. However, depending on the reaction conditions, at specific positions depending on the reaction conditions, an anthracene derivative in which deuterium is bonded to all carbon atoms can be produced and used as an anthracene group with deuterium substitution. However, depending on the reaction conditions, at specific positions A product in which a compound having hydrogen bonded to a carbon atom of a moiety and a compound having deuterium bonded thereto are present in a mixed form is obtained, and it may be very difficult to separate them. In this case, the degree of deuterium substitution on average can be determined and the degree of deuteration can be calculated according to the overall structural formula with reference to this. It may be difficult, and in this case, the degree of deuterium substitution on average is determined, and the degree of deuteration can be calculated according to the overall structural formula with reference to this. In the present invention, among the anthracene derivatives represented by the following [Chemical Formula E], by using an anthracene derivative in which deuterium is substituted as described above, the lifetime of the organic light-emitting device can be further improved.

[0108] In the present invention, among the anthracene derivatives represented by the following [Chemical Formula E], as described above by using an anthracene derivative in which deuterium is substituted, the lifetime of the organic light-emitting device can be further improved.

[0109] The anthracene derivative represented by the following [Chemical Formula E] in the organic light-emitting device according to the present invention is as follows described <c201> ~ <c506>It can be any one selected from among them.

[0110] JPEG2025084936000071.jpg219170JPEG2025084936000072.jpg232170JPEG2025084936000073.jpg231170JPEG2025084936000074.jpg237170JPEG2025084936000075.jpg234170JPEG2025084936000076.jpg219170JPEG2025084936000077.jpg231170JPEG2025084936000078.jpg225170JPEG2025084936000079.jpg246170JPEG2025084936000080.jpg248170JPEG2025084936000081.jpg245170JPEG2025084936000082.jpg230170JPEG2025084936000083.jpg231170JPEG2025084936000084.jpg225170JPEG2025084936000085.jpg218170JPEG2025084936000086.jpg237170JPEG2025084936000087.jpg249170JPEG2025084936000088.jpg242170JPEG2025084936000089.jpg212170JPEG2025084936000090.jpg238170JPEG2025084936000091.jpg234170JPEG2025084936000092.jpg240170JPEG2025084936000093.jpg232170JPEG2025084936000094.jpg141170

[0111] Hereinafter, an organic light-emitting element according to an embodiment of the present invention will be described with reference to the drawings.

[0112] FIG. 1 is a diagram showing the structure of an organic light-emitting element according to an embodiment of the present invention.

[0113] As shown in FIG. 1, the organic light-emitting element according to the embodiment of the present invention includes an anode 20 and a hole transport layer 40 A first light-emitting layer 50-A and a second light-emitting layer 50-B including a host and a dopant, and an electron transport layer 60 and a cathode 80, which is an organic light-emitting device that sequentially includes an anode as a first electrode and a cathode as a second electrode, includes a hole transport layer between the anode and the light-emitting layer, and includes an electron transport layer between the light-emitting layer and the cathode, corresponding to an organic light-emitting device. Further, in the organic light-emitting device according to an embodiment of the present invention, a hole injection layer 30 may be included between the anode 20 and the hole transport layer 40, and an electron injection layer 70 may be included between the electron transport layer 60 and the cathode 80. Next, with reference to FIG. 1, the organic light-emitting device and its manufacturing method according to the present invention will be described.

[0114] First, a substance for an anode (anode) electrode is coated on the upper part of the substrate 10 to form the anode 20. Here, as the substrate 10, a substrate usually used in a normal organic EL device is used, but it is preferably an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. And, as the anode electrode substance, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used. A hole injection layer 30 is formed by vacuum thermal evaporation or spin coating of a hole injection layer substance on the upper part of the anode 20 electrode. Then, a hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of a hole transport layer substance on the upper part of the hole injection layer 30.

[0115] The material of the hole injection layer is not particularly limited as long as it is commonly used in the art and can be used

[0116] First, a substance for an anode (anode) electrode is coated on the upper part of the substrate 10 to form the anode 20. Here, as the substrate 10, a substrate usually used in a normal organic EL device is used, but it is preferably an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. And, as the anode electrode substance, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used. Preferably, it is an organic substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofness. And, as the anode electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used. ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used. 2 ) ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

[0117] A hole injection layer substance is vacuum thermally evaporated or spin-coated on the upper part of the anode 20 electrode to form a hole injection layer 30. Then, a hole transport layer substance is vacuum thermally evaporated or spin-coated on the upper part of the hole injection layer 30 to form a hole transport layer 40. Thereafter, a hole transport layer substance is vacuum thermally evaporated or spin-coated on the upper part of the hole injection layer 30 to form a hole transport layer 40. The hole injection layer substance is vacuum thermally evaporated or spin-coated on the upper part of the anode 20 electrode to form a hole injection layer 30. Then, a hole transport layer substance is vacuum thermally evaporated or spin-coated on the upper part of the hole injection layer 30 to form a hole transport layer 40.

[0118] The material of the hole injection layer is not particularly limited as long as it is commonly used in the art and can be used can be used, for example, 2-TNATA [4,4’,4’’-tris(2-naphthyl phenyl-phenylamino)-triphenylamine], NPD [N,N’-di(1-naph thyl)-N,N’-diphenylbenzidine)], TPD [N,N’-diphenyl-N,N ’-bis(3-methylphenyl)-1,1’-biphenyl-4,4’-diamine], DN TPD [N,N’-diphenyl-N,N’-bis-[4-(phenyl-m-tolyl-amino)- phenyl]-biphenyl-4,4’-diamine], etc. can be used. However, the present invention is not necessarily limited thereto.

[0119] Also, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N,N’-bis(3-methylphenyl)-N,N’-diphenyl- 1,1-biphenyl]-4,4’-diamine (TPD) or N,N’-di(naphthalene- 1-yl)-N,N’-diphenylbenzidine (α-NPD), etc. can be used. However, the present invention is not necessarily limited thereto.

[0120] On the other hand, the present invention can further form an electron blocking layer on the hole transport layer. The above-mentioned electron blocking layer is a layer for preventing the electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole transport layer, thereby improving the lifetime and efficiency of the device. It can be formed at an appropriate position between the light-emitting layer and the hole injection layer, preferably, it can be formed between the light-emitting layer and the hole transport layer.

[0121] Next, on the hole transport layer 40 or the electron blocking layer, the first light-emitting layer 50-A and the second light-emitting The layers 50-B may be deposited in sequence by vacuum deposition or spin coating.

[0122] Here, each of the first and second emitting layers is composed of a host and a dopant. The materials constituting these are as described above.

[0123] That is, the light emitting layers are respectively designated as a first light emitting layer 50-A and a second light emitting layer 50-B. The same or different hosts and dopants are deposited by separate deposition or coating processes. The first and second light-emitting layers can each be formed using a light-emitting material.

[0124] More preferably, the first light-emitting layer contains, as a fluorescent host, a compound represented by the formula A or the formula B. The second light-emitting layer contains one or more compounds represented by the chemical 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, and are as follows: At least one material selected from among the materials of the chemical formulas D1 to D10 can be used.

[0125] In addition, a host material that can be used in the first light-emitting layer and the second light-emitting layer in the present invention is The host material (BH1) used in the first light-emitting layer is the same as the host material (BH2) used in the second light-emitting layer. The lowest unoccupied molecular orbital (LUMO) is higher than that of the material (BH2). d molecular orbital is even lower, and the highest occupied molecular orbital (HOMO , the highest occupied molecular orbital) By using a material with a high hole emission rate compared to the host (BH2) used in the second emitting layer, It is preferable to have a structure that facilitates the injection of (holes) and / or electrons. This is preferable.

[0126] Also, according to a specific example of the present invention, the thickness of each of the light-emitting layers is preferably 50 to 2000 Å. This is preferable.

[0127] In addition, in the present invention, the deposition thickness ratio of the first light-emitting layer (including a compound represented by Chemical Formula A or Chemical Formula B) to the second light-emitting layer (including an anthracene derivative represented by Chemical Formula E) is such that when the sum of the thicknesses of the first light-emitting layer and the second light-emitting layer is 100, the thickness of the first light-emitting layer is preferably 10% to 70%, and more preferably can be in the range of 20% to 50%. ) and the second light-emitting layer (including an anthracene derivative represented by Chemical Formula E) is When the sum of the thicknesses of the first light-emitting layer and the second light-emitting layer is 100, the thickness of the first light-emitting layer is preferably 10 % to 70%, and more preferably can be in the range of 20% to 50%.

[0128] On the other hand, an electron transport layer 60 is deposited on the light-emitting layer by a vacuum evaporation method or a spin coating method. Deposit.

[0129] On the other hand, in the present invention, as the material of the electron transport layer, it is a material that functions to stably transport electrons injected from an electron injection electrode (cathode), and known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq athode)), Liq, TAZ , BAlq, beryllium bis(benzoquinolin-10-olate) (beryllium bis(benzoquinolin-10-olate: Bebq 3 ), E201, , E202, BCP, materials such as PBD, BMD, and BND which are oxadiazole derivatives can also be used, but it is not limited thereto. 2 ) can also be used, but it is not limited thereto. be used, but it is not limited thereto.

[0130] JPEG2025084936000095.jpg168169

[0131] In addition, in the organic light-emitting device of the present invention, after forming the electron transport layer, an electron injection layer (EIL), which is a substance having a function of facilitating the injection of electrons from the cathode, can be laminated thereon. There is no particular limitation on the material.

[0132] As the material for forming the electron injection layer, any substance known as a material for forming an electron injection layer, such as CsF, NaF, LiF, Li 2 O, BaO, etc., can be used. The vapor deposition conditions of the electron injection layer vary depending on the compound used, but generally, they can be selected from substantially the same condition range as that for forming the hole injection layer. The thickness of the electron injection layer can be about 1 Å to about 100 Å, preferably about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0133]

[0134] In the present invention, for the cathode, a substance with a small work function can be used for easy electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or alloys thereof such as aluminum (Al), aluminum-lithium (Al-Li), mag nesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used, or a transmissive cathode using ITO or IZO can be used.

[0135] In addition, the organic light-emitting device of the present invention emits light in the wavelength range of 380 nm to 800 nm. It can further include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the further formed light-emitting layer can be a fluorescent material or a phosphorescent material.

[0136] In addition, in the present invention, one or more layers selected from the respective layers can be formed by a single-molecule vapor deposition process or a solution process.

[0137] Here, the vapor deposition process means a method of forming a thin film by evaporating a substance used as a material for forming each of the layers by heating in a vacuum or a low-pressure state, and the solution process means a method of mixing a substance used as a material for forming each of the layers with a solvent and forming a thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc. In addition, the organic light-emitting device in the present invention can be used in any one of a flat panel display device, a flexible

[0138] display device, a single-color or white flat panel lighting device, and a single-color or white flexible lighting device.

[0139] Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are for more specifically explaining the present invention. It is self-evident to those having ordinary knowledge in the art that the scope of the present invention is not limited by these examples.

[0140] (Example) <Production of Host Compound> Synthesis Example 1. Synthesis of Chemical Formula 19 Synthesis Example 1-1. Synthesis of <1-a>

[0141] [Reaction Formula 1] JPEG2025084936000096.jpg40156

[0142] A 3000 ml round-bottom flask was purged with nitrogen, and 100 g (0. 278 mol) of 1,6-dibromopyrene, 33.9 g (0.278 mol) of phenylboronic acid, tetrakis triphenylphosphine palladium (Pd[PPh 3 ) 4 6.4 g (0.006 mol), 88.3 g (0.833 mol) of sodium carbonate, 1400 ml of toluene and 420 ml of water were added and refluxed for 9 hours. After the reaction was completed, it was cooled to room temperature, and the resulting solid was filtered and discarded. The filtrate was extracted with ethyl acetate and water, and then the organic layer was anhydrous treated. Then, under reduced pressure After concentration, it was separated by column chromatography to obtain 45.4 g of <1-a> (yield 45.7 %). Synthesis Example 1-2. Synthesis of <1-b>

[0143] [Reaction Formula 2] JPEG2025084936000097.jpg44156

[0144] A 500 ml round-bottom flask was purged with nitrogen, and 20 g (0.076 mol) of 6-bromo-1-dibenzofuranol, 11.6 g (0.091 mol) of phenylboronic acid (D5), tetrakis triphenylphosphine palladium (Pd[PPh 3 ) 4 1.8 g (0.0 02 mol), 17.9 g (0.129 mol) of potassium carbonate, 140 ml of toluene, and e ​Add 35 ml of tannol and 65 ml of water and reflux for 5 hours. After the reaction is completed, cool to room temperature, extract with ethyl acetate and water, and anhydrous treat the organic layer. After concentrating the organic layer under reduced pressure, recrystallize with ethyl acetate and heptane to obtain 15.2 g (yield 75.4%) of <1-b>. After cooling, extract with ethyl acetate and water, and anhydrous treat the organic layer. After concentrating the organic layer under reduced pressure, recrystallize with ethyl acetate and heptane to obtain 15.2 g (yield 75.4%) of <1-b>.

[0145] Synthesis Example 1-3. Synthesis of <1-c>

[0146] [Reaction formula 3] JPEG2025084936000098.jpg38156

[0147] Purge a 500 ml round-bottom flask with nitrogen, add 15.2 g (0.058 mol ) of <1-b>, 6 g (0.076 mol) of pyridine, and 150 ml of dichloromethane, and cool the temperature to 0 °C or lower. After cooling, slowly add dropwise 18.1 g (0.064 mol) of trifluoromethanesulfonic anhydride. After the dropwise addition, warm the reaction solution to room temperature and stir until the reaction is completed . After the reaction is completed, extract with dichloromethane and water, anhydrous treat the organic layer, then distill under reduced pressure and separate by column chromatography to obtain 20 g (yield 87.3%) of <1-c>.

[0148] Synthesis Example 1-4. Synthesis of <1-d>

[0149] [Reaction formula 4] JPEG2025084936000099.jpg48162

[0150] Purge a 300 ml round-bottom flask with nitrogen, add 20 g (0.050 mol) of <1-c>, 16.6 g (0.065 mol) of bis(pinacolato)diboron, 0.8 g (0.001 mol) of bis(diphenylphosphino)ferrocene dichloropalladium, 9.9 g of calcium acetate( ), Add 0.101 mol and 200 ml of 1,4-dioxane and reflux for 12 hours. The reaction After completion, cool the reaction solution to room temperature, filter through celite, concentrate the filtrate, and then perform column chromatography to separate and obtain 14.8 g (yield 78.4%) of <1-d>.

[0151] Synthesis Example 1-5. Synthesis of [Chemical Formula 19]

[0152] [Reaction formula 5] JPEG2025084936000100.jpg50170

[0153] Purge a 300 ml round-bottom flask with nitrogen, add 10.7 g (0.030 mol ) of <1-a>, 13.7 g (0.036 mol) of <1-d>, 0.7 g (0.001 mol) of tetrakistriphenylphosphine palladium, 7.4 g (0.053 mol) of potassium carbonate, 80 ml of toluene, 20 ml of ethanol and 26 ml of water, and reflux for 4 hours. After the reaction is completed, cool to room temperature and extract with ethyl acetate and water. After anhydrous treatment of the organic layer, concentrate and separate by column chromatography to obtain 8.4 g (yield 53.4%) of [Chemical formula 19]. Obtained.

[0154] MS (MALDI-TOF): m / z 525.21 [M] +

[0155] Synthesis Example 2. Synthesis of Chemical Formula 34 Synthesis Example 2-1. Synthesis of <2-a>

[0156] [Reaction formula 6] JPEG2025084936000101.jpg48170

[0157] Use phenylboronic acid (D5) instead of phenylboronic acid used in Synthesis Example 1-1 ​Except for the following, it was synthesized in the same manner to obtain <2-a> (yield 79.3%). Synthesis Example 2-2. Synthesis of <2-b>

[0158] [Reaction Scheme 7] JPEG2025084936000102.jpg35169

[0159] Except for using 1,7-dibromo dibenzofuran instead of 6-bromo-1-dibenzofuranol used in Synthesis Example 1-2, it was synthesized in the same manner to obtain <2-b> (yield 54%)

[0160] Synthesis Example 2-3. Synthesis of <2-c>_

[0161] [Reaction Scheme 8] JPEG2025084936000103.jpg37169

[0162] Except for using <2-b> instead of <1-c> used in Synthesis Example 1-4, it was synthesized in the same manner to obtain <2-c> (yield 72.8%).

[0163] Synthesis Example 2-4. Synthesis of [Chemical Formula 34]

[0164] [Reaction Scheme 9] JPEG2025084936000104.jpg48170

[0165] Except for using <2-a> instead of <1-a> and <2-c> instead of <1-d> used in Synthesis Example 1-5, it was synthesized in the same manner to obtain [Chemical Formula 34] (yield 63.7 %)

[0166] MS (MALDI-TOF): m / z 530.25 [M] +

[0167] Synthesis Example 3. Synthesis of Chemical Formula 52 Synthesis Example 3-1. Synthesis of <3-a> ​​​​

[0168] [Reaction formula 10] JPEG2025084936000105.jpg28170

[0169] Instead of 6-bromo-1-dibenzofuranol used in Synthesis Example 1-2, 6-bromo- 2-dibenzofuranol was used, and instead of phenylboronic acid (D5), phenylboron acid was used. Compound <3-a> (yield 72.0%) was obtained by synthesis in the same manner.

[0170] Synthesis Example 3-2. Synthesis of <3-b>_

[0171] [Reaction formula 11] JPEG2025084936000106.jpg33164

[0172] Compound <3-b> (yield 85.2%) was obtained by synthesis in the same manner, except that <3-a> was used instead of <1-b> used in Synthesis Example 1-3.

[0173] Synthesis Example 3-3. Synthesis of <3-c>

[0174] [Reaction formula 12] JPEG2025084936000107.jpg30164

[0175] Compound <3-c> (yield 76.8%) was obtained by synthesis in the same manner, except that <3-b> was used instead of <1-c> used in Synthesis Example 1-4.

[0176] Synthesis Example 3-4. Synthesis of [Chemical Formula 52]

[0177] [Reaction formula 13] JPEG2025084936000108.jpg57170

[0178] Compound was synthesized in the same manner, except that <3-c> was used instead of <2-c> in Synthesis Example 2-4.​​ to obtain [Chemical Formula 52] (yield 58.0%).

[0179] MS (MALDI-TOF): m / z 525.21 [M] +

[0180] Synthesis Example 4. Synthesis of Chemical Formula 131 Synthesis Example 4-1. Synthesis of [Chemical Formula 131]

[0181] [Reaction Formula 14] JPEG2025084936000109.jpg49170

[0182] Except that 1-dibenzofuranboronic acid was used instead of <2-c> in Synthesis Example 2-4, it was synthesized in the same manner to obtain [Chemical Formula 131] (yield 61.4%).

[0183] MS (MALDI-TOF): m / z 449.18 [M] +

[0184] Synthesis Example 5. Synthesis of Chemical Formula 136 Synthesis Example 5-1. Synthesis of <5-a>

[0185] [Reaction Formula 15] JPEG2025084936000110.jpg35161

[0186] A 1000 ml round-bottom flask was purged with nitrogen, and 50 ml of 30 wt% aqueous hydrogen peroxide solution ( 0.477 mol), 45 g (0.454 mol) of phenol (D5), 57.6 g (0.227 mol) of iodine and 450 ml of water were added, and the mixture was stirred at 50 °C for 24 hours. After the reaction was completed, an aqueous sodium thiosulfate solution was added and stirred, and then the reaction solution was extracted with ethyl acetate and water, then anhydrous treated and concentrated under reduced pressure. After concentration, it was separated by column chromatography to obtain 45 g (yield 44.3%) of <5-a>.

[0187] Synthesis Example 5-2. Synthesis of <5-b>_

[0188] [Reaction formula 16] JPEG2025084936000111.jpg35161

[0189] A 1000 ml round-bottom flask was purged with nitrogen, and <5-a> 45 g (0.201 mol) , 41 g (0.241 mol) of 2-fluoro-6-methoxyphenylboronic acid, and tetra phenylphosphine palladium 7 g (0.006 mol), potassium carbonate 47.2 g (0.341 mol), 315 ml of toluene, 80 ml of ethanol and 170 ml of water were added and refluxed for 8 hours. After the reaction was completed, it was cooled to room temperature, extracted with ethyl acetate and water, and then , the organic layer was anhydrous treated. After the organic layer was concentrated under reduced pressure, it was separated by column chromatography to obtain <5-b> 28.6 g (yield 64.1%).

[0190] Synthesis Example 5-3. Synthesis of <5-c>

[0191] [Reaction formula 17] JPEG2025084936000112.jpg35161

[0192] <5-b> 28.6 g (0.129 mol), potassium carbonate 44.5 g (0.322 mol), and 143 ml of 1-methyl-2-pyrrolidine were placed in a 500 ml round-bottom flask and refluxed for 1 2 hours. After the reaction was completed, the temperature was cooled to room temperature, and then 200 ml of 2N hydrochloric acid aqueous solution was slowly added. After sufficient stirring, it was extracted with ethyl acetate and water. The organic layer was concentrated and then separated by column chromatography to obtain <5-c> 21 g (yield 80.7%). .

[0193] Synthesis Example 5-4. Synthesis of <5-d>

[0194] [Reaction Formula 18] JPEG2025084936000113.jpg31128

[0195] Add 21 g (0.104 mol) of <5-c> and 120 ml of dichloromethane to a 500-ml round-bottom flask, and cool the reaction solution to 0 °C or lower. Slowly add 52 g (0.208 mo l) of boron tribromide dropwise with attention to the temperature. After the dropwise addition, warm the reaction solution to room temperature and stir until the reaction is complete . After the reaction is complete, slowly add 100 ml of water to the reaction solution, and then stir well . Extract the reaction solution with dichloromethane and water, and then perform anhydrous treatment. After concentration under reduced pressure, separate by column chromatography to obtain 15 g (yield 76.8%) of <5-d>.

[0196] Synthesis Example 5-5. Synthesis of <5-e>

[0197] [Reaction Formula 19] JPEG2025084936000114.jpg31128

[0198] Purge a 500-ml round-bottom flask with nitrogen, add 15.0 g (0.080 mol ) of <5-d>, 8.2 g (0.104 mol) of pyridine, and 150 ml of dichloromethane, and cool the temperature of the reaction solution to 0 °C or lower. After cooling, slowly add 24.7 g (0.088 mol) of trifluoromethanesulfonic anhydride dropwise. After the dropwise addition, warm the reaction solution to room temperature and stir until the reaction is complete. After the reaction is complete, extract with dichloromethane and water, then treat the organic layer anhydrously , concentrate under reduced pressure, and separate by column chromatography to obtain 20 g (yield 78 .4%) of <5-e>.

[0199] Synthesis Example 5-6. Synthesis of <5-f>

[0200] ​ [Reaction Scheme 20] JPEG2025084936000115.jpg40128

[0201] In a 500 ml round-bottom flask purged with nitrogen, add 20 g (0.062 mol) of <5-e>, Bispinacole diboron 23.8g (0.094mol), bisdiphenylphosphino 2.5g (0.003mol) of palladium dichlorosulfate, 9.5g of calcium acetate ( 0.125 mol) and 200 ml of 1,4-dioxane and reflux for 12 hours. After the reaction is completed, the reaction mixture is cooled to room temperature, filtered through Celite, and the filtrate is concentrated and then passed through a column. After separation by chromatography, 15 g of <5-f> was obtained (yield 80.6%).

[0202] Synthesis Example 5-7. Synthesis of [Chemical Formula 136]

[0203] [Reaction Scheme 21] JPEG2025084936000116.jpg62159

[0204] Synthesize in the same manner as in Synthesis Example 2-4, except that <5-f> was used instead of <2-c>. As a result, [chemical formula 136] was obtained (yield 60.3%).

[0205] MS(MALDI-TOF): m / z 453.21[M] +

[0206] Synthesis Example 6. Synthesis of Chemical Formula 41 Synthesis Example 6-1. Synthesis of [Chemical Formula 41]

[0207] [Reaction Scheme 22] JPEG2025084936000117.jpg49170

[0208] The same procedure was carried out except that <2-a> was used instead of <1-a> used in Synthesis Example 1-5. It was synthesized by a method to obtain [Chemical Formula 41] (yield 54.2%).

[0209] MS (MALDI-TOF): m / z 530.25 [M] +

[0210] Synthesis Example 7. Synthesis of Chemical Formula 57 Synthesis Example 7-1. Synthesis of [Chemical Formula 57]

[0211] [Reaction Formula 23] JPEG2025084936000118.jpg49170

[0212] Except for using <3-c> instead of <1-d> used in Synthesis Examples 1-5, in the same manner It was synthesized by a method to obtain [Chemical Formula 57] (yield 53.5%).

[0213] MS (MALDI-TOF): m / z 520.18 [M] +

[0214] <Production of Dopant Compound> Synthesis Example 8. Synthesis of D202 Synthesis Example 8-1. Synthesis of <8-a>_

[0215] [Reaction Formula 24] JPEG2025084936000119.jpg29165

[0216] Charge 3.1 g (16 mmol) of 1-bromo-3-chlorobenzene, a niline 5.8 g (16 mmol), palladium acetate 0.1 g (1 mmol), sodium tert-butoxide 3 g (32 mmol), bis(diphenylphosphino)-1,1’ -binaphthyl 0.2 g (1 mmol), and 45 mL of toluene into a 100 mL reactor, and reflux and stir for 24 hours After completion of the reaction, filter, concentrate the filtrate, and separate by column chromatography to obtain 5.2 g of <8-a>. (Yield 82%)

[0217] Synthesis Example 8-2. Synthesis of <8-b>

[0218] [Reaction formula 25] JPEG2025084936000120.jpg34137

[0219] Charge 20 g (98 mmol) of <8-a>, 20.9 g (98 mmol) of 3-bromobenzothiophene, 0.5 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine, and 200 mL of toluene into a 250 mL reactor, and reflux and stir for 5 hours. After the reaction is completed, filter, concentrate the filtrate, and separate by column chromatography to obtain 24.7 g of <8-b>. (Yield 75%)

[0220] Synthesis Example 8-3. Synthesis of <8-c>_

[0221] [Reaction formula 26] JPEG2025084936000121.jpg33145

[0222] Charge 5.4 g (16 mmol) of <8-b>, 5.8 g (16 mmol) of aniline, 0.1 g (1 mmol) of palladium acetate, 3 g (32 mmol) of sodium tert-butoxide, 0.2 g (1 mmol) of bis(diphenylphosphino)-1,1'-binaphthyl, and 45 mL of toluene into a 100 mL reactor, and reflux and stir for 24 hours. After the reaction is completed, filter, concentrate the filtrate, and separate by column chromatography to obtain 4.6 g of <8-c>. (Yield 73%)

[0223] Synthesis Example 8-4. Synthesis of <8-d>_

[0224] [Reaction formula 27] JPEG2025084936000122.jpg38145

[0225] Using <8-c> instead of <8-a> used in Synthesis Example 8-2, 3-bromobenzene Except for using 1-bromo-2-iodobenzene instead of thiophene, in the same way Synthesis was carried out to obtain <8-d>. (Yield 77%)

[0226] Synthesis Example 8-5. <d202>Synthesis of < / d202>

[0227] [Reaction Formula 28] JPEG2025084936000123.jpg32145

[0228] Into a 300 mL reactor, charge 12.6 g (23 mmol) of <8-d> and 120 mL of tert-butylbenzene Dropwise add 42.5 mL (68 mmol) of n-butyllithium at -78 °C After the dropwise addition, stir at 60 °C for 3 hours. Then, blow nitrogen at 60 °C to remove heptane Dropwise add 11.3 g (45 mmol) of boron tribromide at -78 °C. After the dropwise addition Stir at room temperature for 1 hour, and dropwise add 5.9 g (45 mmol) of N,N-diisopropylethylamine at 0 °C After the dropwise addition, stir at 120 °C for 2 hours. After the reaction is completed, add an aqueous ethyl acetate solution at room temperature and stir. Extract with ethyl acetate, concentrate the organic layer, and separate by column chromatography to obtain <d202>Obtained 1.1g (yield 10%)

[0229] MS(MALDI-TOF): m / z 476.15[M + ]

[0230] Synthesis Example 9. Synthesis of D265 Synthesis Example 9-1. Synthesis of <9-a>

[0231] [Reaction Scheme 29] JPEG2025084936000124.jpg25135

[0232] In the synthesis example 8-1, 1-bromo-2,3-dichlorobenzene was used instead of 1-bromo-3-chlorobenzene. Except for using chlorobenzene, the synthesis was carried out in the same manner to obtain <9-a> (yield 71%). )

[0233] Synthesis Example 9-2. Synthesis of <9-b>

[0234] [Reaction Scheme 30] JPEG2025084936000125.jpg34135

[0235] Instead of <8-a> used in Synthesis Example 8-2, diphenylamine was used, and 1-bromo The same procedure was used, except that 1-bromo-3-iodobenzene was used instead of -3-chlorobenzene. The compound was synthesized in the same manner to obtain <9-b> (yield 77%).

[0236] Synthesis Example 9-3. Synthesis of <9-c>_

[0237] [Reaction Scheme 31] JPEG2025084936000126.jpg42135

[0238] Using <9-a> instead of <8-a> used in Synthesis Example 8-2, 1-bromo-3- Except for using <9-b> instead of chlorobenzene, <9-c> was obtained in the same manner (yield 75%).

[0239] Synthesis Example 9-4. Synthesis of <9-d>_

[0240] [Reaction Formula 32] JPEG2025084936000127.jpg27135

[0241] Charge 30 g (174 mmol) of 3-bromoaniline, 25 .5 g (209 mmol) of phenylboronic acid, 4 g (3 mmol) of tetrakis(triphenylphosphine)palladium, 48.2 g (349 mmol) of potassium carbonate, 150 m L of 1,4-dioxane, 150 mL of toluene, and 90 mL of distilled water into a 1 L reactor, and reflux and stir for 4 hours. After the reaction is completed , separate the layers at room temperature, concentrate the organic layer under reduced pressure, and then separate by column chromatography to obtain <9 -d> 24 g. (Yield 80%)

[0242] Synthesis Example 9-5. Synthesis of <9-e>_

[0243] [Reaction Formula 33] JPEG2025084936000128.jpg36136

[0244] Synthesize in the same manner as in Synthesis Example 8-1, except that 3-bromobenzofuran is used instead of 1-bromo-3-chlorobenzene and <9-d> is used instead of aniline to obtain <9- e>. (Yield 68%) e> was obtained. (Yield 68%)

[0245] Synthesis Example 9-6. Synthesis of <9-f>_

[0246] [Reaction Formula 34] JPEG2025084936000129.jpg43147

[0247] Use <9-c> instead of <8-a> used in Synthesis Example 8-2, and 1-bromo-3- <9-f> was obtained in the same manner except that <9-e> was used instead of chlorobenzene. (Yield 68%)

[0248] Synthesis Example 9-7 <d265>Synthesis of < / d265>

[0249] [Reaction formula 35] JPEG2025084936000130.jpg43147

[0250] Charge 21 g (37 mmol) of <9-f> and tert-butylrubenzene into a 250 mL reactor. Dropwise add 42.4 mL (74 mmol) of tert-butyllithium at -78 °C. After the dropwise addition, stir at 60 °C for 3 hours. Then, blow nitrogen at 60 °C to remove pentane. Dropwise add 7.1 mL (74 mmol) of boron tribromide at -78 °C. After the dropwise addition, stir at room temperature for 1 hour and add 6 g (74 mmol) of N,N-diisopropylethylamine at 0 °C. After the dropwise addition, stir at 120 °C for 2 hours. After completion of the reaction, add an aqueous ethyl acetate solution at room temperature and stir. Extract with ethyl acetate, concentrate the organic layer, and separate by column chromatography and separate by column chromatography <d265>2.0 g was obtained. (Yield 17%)

[0251] MS (MALDI-TOF): m / z 703.28 [M +

[0252] Synthesis Example 10. Synthesis of Chemical Formula D459 Synthesis Example 10-1. Synthesis of <10-a>_

[0253] [Reaction Scheme 36] JPEG2025084936000131.jpg35147

[0254] Instead of <8-a> used in Synthesis Example 8-2, 4a,9a-dimethyl-2,3,4,4 a,9,9a-hexahydro-1H-carbazole was used, and <10-a> was obtained in the same manner except that 1-bromo-2,3-dichloro-5-methylbenzene was used instead of 3-bromobenzothiophene. (Yield 32%)

[0255] Synthesis Example 10-2. Synthesis of <10-b>

[0256] [Reaction Scheme 37] JPEG2025084936000132.jpg36130

[0257] Instead of 1-bromo-3-chlorobenzene in Synthesis Example 8-1, 3-(1-naphthyl)-1 -bromobenzene was used, and <10-b> was obtained in the same manner. (Yield 77%)

[0258] Synthesis Example 10-3. Synthesis of <10-c>

[0259] [Reaction Scheme 38] JPEG2025084936000133.jpg41130 Instead of <8-a> used in Synthesis Example 8-2, <10-b> was used, and 3-bromobenzo ​Except for using 1-bromo-3-iodobenzene instead of thiophene, it was synthesized in the same manner to obtain <10-c>. (Yield 64%)

[0260] Synthesis Example 10-4. Synthesis of <10-d>

[0261] [Reaction Formula 39] JPEG2025084936000134.jpg46135

[0262] Except for using <10-c> instead of 1-bromo-3-chlorobenzene in Synthesis Example 8-1 it was synthesized in the same manner to obtain <10-d>. (Yield 75%)

[0263] Synthesis Example 10-5. Synthesis of <10-e>

[0264] [Reaction Formula 40] JPEG2025084936000135.jpg49166

[0265] Using <10-d> instead of <8-a> used in Synthesis Example 8-2, and except for using <10-a> instead of 3-bromobenzothiophene it was synthesized in the same manner to obtain <10- e>. (Yield 65%)

[0266] Synthesis Example 10-6. <d459>Synthesis of < / d459>

[0267] [Reaction Formula 41] JPEG2025084936000136.jpg49166

[0268] Except for using <10-e> instead of <9-f> used in Synthesis Example 9-7 it was synthesized in the same manner <d459>was obtained. (Yield 11%)

[0269] MS (MALDI-TOF): m / z 759.38 [M +

[0270] Examples 1 to 46: Fabrication of Organic Light-Emitting Devices Containing a First Light-Emitting Layer and a Second Light-Emitting Layer After patterning so that the light-emitting area of the ITO glass becomes 2 mm × 2 mm in size, it was washed. After attaching the ITO glass to a vacuum chamber, after setting the base pressure to 1×10 - 7 torr, DNTPD (700 Å) and α-NPD ( 300 Å) were sequentially deposited on the ITO. As the light-emitting layer, a first light-emitting layer and a second light-emitting layer are sequentially formed, wherein the first light-emitting layer is formed by mixing a pyrene compound (a compound represented by Chemical Formula A or Chemical Formula B) according to the present invention with the following BD dopant compound (1 wt%) and depositing a film (50 Å), and the second light-emitting layer is formed by mixing an anthracene compound (a compound represented by Chemical Formula E) according to the present invention with the following BD dopant compound (1 wt%) and depositing a film (150 Å), and then [E-1 and [E-2] are deposited in a ratio of (1:1) (300 Å) as the electron transport layer, and [E-2] (10 Å ) and Al (1,000 Å) are deposited in this order to fabricate an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0271] JPEG2025084936000137.jpg102169

[0272]

Table 1

[0273] Comparative Examples 1 to 18 ​For Comparative Examples 1 to 18, the organic light-emitting devices were the same except that the compounds described in the following table were used instead of the compounds used in the first light-emitting layer and the second light-emitting layer of Examples 1 to 46. The light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA. Except for using the compounds described in the following table in addition to the compounds used in the first light-emitting layer and the second light-emitting layer, the organic light-emitting devices were fabricated in the same manner. The light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA. Except for using the compounds described in the following table in addition to the compounds used in the first light-emitting layer and the second light-emitting layer, the organic light-emitting devices were fabricated in the same manner. The light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA.

[0274]

Table 2

[0275] JPEG2025084936000141.jpg54138

[0276] As shown in Tables 1 and 2 above, the organic light-emitting devices according to the present invention are superior in luminous efficiency to the organic light-emitting devices using the compounds of the prior art comparative examples, and also exhibit characteristics of low-voltage driving and long life, indicating high applicability as organic light-emitting devices. As shown in Tables 1 and 2 above, the organic light-emitting devices according to the present invention are superior in luminous efficiency to the organic light-emitting devices using the compounds of the prior art comparative examples, and also exhibit characteristics of low-voltage driving and long life, indicating high applicability as organic light-emitting devices. As shown in Tables 1 and 2 above, the organic light-emitting devices according to the present invention are superior in luminous efficiency to the organic light-emitting devices using the compounds of the prior art comparative examples, and also exhibit characteristics of low-voltage driving and long life, indicating high applicability as organic light-emitting devices.

Industrial Applicability

[0277] The organic light-emitting devices fabricated using the compounds according to the present invention show improved characteristics of higher efficiency, low-voltage driving, and longer life compared to conventional compounds. Therefore, when applied to organic light-emitting devices, they exhibit improved characteristics and have high industrial applicability in the field of organic light-emitting devices and related industries. The organic light-emitting devices fabricated using the compounds according to the present invention show improved characteristics of higher efficiency, low-voltage driving, and longer life compared to conventional compounds. Therefore, when applied to organic light-emitting devices, they exhibit improved characteristics and have high industrial applicability in the field of organic light-emitting devices and related industries. The organic light-emitting devices fabricated using the compounds according to the present invention show improved characteristics of higher efficiency, low-voltage driving, and longer life compared to conventional compounds. Therefore, when applied to organic light-emitting devices, they exhibit improved characteristics and have high industrial applicability in the field of organic light-emitting devices and related industries. The organic light-emitting devices fabricated using the compounds according to the present invention show improved characteristics of higher efficiency, low-voltage driving, and longer life compared to conventional compounds. Therefore, when applied to organic light-emitting devices, they exhibit improved characteristics and have high industrial applicability in the field of organic light-emitting devices and related industries. ​​ ​ < / c201> < / d501> < / d101> < / d1>

Claims

1. A first electrode; a second electrode facing the first electrode; A first light-emitting layer including a first host and a first dopant is disposed between the first electrode and the second electrode. a second emissive layer comprising a second host and a second dopant; At least one of the first host and the second host is represented by the following formula A or formula B: and wherein the organic light-emitting element comprises at least one compound represented by the formula B. (In the above [Chemical Formula A] and [Chemical Formula B], The R １ ~R １４ may be the same or different, and each independently represents hydrogen, heavy water, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkyl group having 6 aryl groups having 3 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms; A heteroaryl group having 2 to 50 carbon atoms, or a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms. a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; an alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; is any one selected from the group consisting of a cyclic group, a cyano group, a nitro group, and a halogen group; The linking group L １ and L ２ may be the same or different, and are each independently , a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted is selected from the group consisting of heteroarylene groups having 2 to 20 carbon atoms, The n1 and n2 may be the same or different, and each independently represents an integer of 0 to 2. However, when each of these is 2, each linking group L １ and L ２ are mutually may be the same or different, The R and R' may be the same or different, and each independently represents hydrogen, deuterium, , a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 6 to 30 carbon atoms, aryl group having 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms; a heteroaryl group having from 1 to 50 carbon atoms, a substituted or unsubstituted alkylamine group having from 1 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; is any one selected from the group consisting of a cyano group, a nitro group, and a halogen group; The n3 and n4 may be the same or different, and each independently represents an integer of 1 to 9. However, when each of these is 2 or more, each R and R' are the same as each other. But it can be different, The "substituted" in the "substituted or unsubstituted" in the above [Chemical Formula A] and [Chemical Formula B] means , deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms group, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, alkynyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 24 carbon atoms, and heteroaryl groups having 1 to 24 carbon atoms. alkyl group, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms; a heteroaryl group having 2 to 24 carbon atoms; Heteroarylalkyl group, alkoxy group having 1 to 24 carbon atoms, alkyl group having 1 to 24 carbon atoms Amino group, diarylamino group having 12 to 24 carbon atoms, diheteroaryl group having 2 to 24 carbon atoms Amino group, aryl (heteroaryl) amino group having 7 to 24 carbon atoms, aryl (heteroaryl) amino group having 1 to 24 carbon atoms arylsilyl group, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms and one or more substituted aryl groups selected from the group consisting of aryl groups having 6 to 24 carbon atoms. It means that it is substituted with a group.)

2. The compound represented by formula A contains at least one deuterium atom, The compound represented by the chemical formula B is characterized in that it contains at least one deuterium. The organic light-emitting device according to claim 1 .

3. R in the above [Chemical Formula A] １ ~R ７ At least one of the substituents is a deuterium-containing substituent. and R in the above [Chemical Formula B] ８ ~R １４ At least one of the substitutions contains deuterium. The organic light-emitting element according to claim 2 , wherein the R 1 -R 2 -R 3 group is a R 2 -R 3 group.

4. At least one R in the above [Chemical Formula A] is a substituent containing deuterium, At least one R' in the [chemical formula B] is a substituent containing deuterium. The organic light-emitting device according to claim 2 .

5. R in the above [Chemical Formula A] １ ~R ７ At least one of the carbon atoms is a substituted or unsubstituted carbon atom. an aryl group having a number of 6 to 18; R in the above [Chemical Formula B] ８ ~R １４ At least one of the carbon atoms is a substituted or unsubstituted carbon atom.

2. The organic light-emitting device according to claim 1, wherein the aryl group has 6 to 18 prime numbers.

6. The linking group L in the above formula A and formula B １ and L ２ are each a single bond or Alternatively, it is characterized in that it is any one selected from the following [Structural Formula 1] to [Structural Formula 5]. The organic light-emitting device according to claim 1 . (Hydrogen or deuterium can be bonded to the carbon of the aromatic ring in the linking group. ）

7. The linking group L １ and L ２ Each of the formulas according to claim 6 is a single bond. Organic light-emitting device.

8. At least one R in the above [chemical formula A] is a substituted or unsubstituted group having 6 to 1 carbon atoms. 8 aryl group, At least one R' in the above [chemical formula B] is a substituted or unsubstituted group having 6 to 6 carbon atoms. The organic light-emitting element according to claim 1 , wherein the aryl group is 18.

9. In the chemical formula A and the chemical formula B, n3 and n4 are each 1; In the above [chemical formula A], R is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. can be, In the above [chemical formula B], R' is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. The organic light-emitting device according to claim 8 ,

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

11. In the chemical formula A and the chemical formula B, n3 and n4 are each 1; R in the above [Chemical Formula A] １ ~R ７ At least one of R is deuterium substituted. an aryl group having 6 to 18 carbon atoms, R in the above [Chemical Formula B] ８ ~R １４ At least one of R' is deuterium substituted. The organic light-emitting device according to claim 1, characterized in that the aryl group is an aryl group having 6 to 18 carbon atoms. element.

12. In the chemical formula A and the chemical formula B, n3 and n4 are each 1; In the above [chemical formula A], R is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms. is a aryl group, In the above [chemical formula B], R' is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms. The organic light-emitting element according to claim 1 , wherein the alkyl group is a aryl group.

13. The compound is any one selected from the group represented by the following formulas 1 to 240: The organic light-emitting device according to claim 1 .

14. 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. Between the second light-emitting layer and the second electrode, an electron transport layer and an electron injection layer are provided. The organic light emitting device according to claim 1 , comprising at least one of the above.

15. At least one of the first dopant in the first light-emitting layer or the second dopant in the second light-emitting layer At least one of the following [Chemical Formula D1] to [Chemical Formula D10] is selected from 2. The organic light-emitting device according to claim 1, characterized in that a compound of the formula: (In the above [Chemical Formula D1] and [Chemical Formula D2], A ３１ , A ３２ , E １ and F １ Is that Each 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 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 Adjacent in the aromatic ring of The two carbon atoms connected to each other are the substituents R ５１ and R ５２ A carbon atom connected to the five-membered ring By forming the rings, a condensed ring is formed, The linking group L ２１ ~L ３２ may be the same or different, and each independently represents a single bond. In the case of substituted or unsubstituted alkylene groups having 1 to 60 carbon atoms, 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 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; 、 The W and W' are N-R ５３ , C.R. ５４ R ５５ , SiR ５６ R ５７ , GeR ５８ R ５ ９ , O, S, or 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 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, 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, or an unsubstituted alkylthio group having 1 to 30 carbon atoms; an arylthioxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms; a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms; an alkylsilyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms; a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms; The substituted aryl group having 1 to 30 carbon atoms, the cyano group, the nitro group, and the halogen group However, 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 selected from the group consisting of N, O, P, may be substituted with one or more heteroatoms 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. When each of these is two or more, each of the linking groups L ２１ ~L ３２ teeth, may be the same or different, The x1 is 1, and y1, z1 and z2 may be the same or different, and each may be are 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, A in the above-mentioned chemical formula D1 ３２ Two adjacent carbon atoms in the ring are represented by the formula Q １１ of * forms a condensed ring, The A in the chemical formula D2 ３１ Two adjacent carbon atoms in the ring are represented by the formula Q １ ２ and * in the formula (I) form a condensed ring; ３２ Two adjacent carbon atoms in the ring are Form Q １１ can bond with * to form a condensed ring.) (In the above [Chemical Formula D3], The X １ is any one selected from B, P, and P=O, The T1 to T3 may be the same or different, and each independently represents a substituent. or an unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms 2 to 40 aromatic heterocycles; The Y １ is N-R ６１ , C.R. ６２ R ６３ , O, S, SiR ６４ R ６５ Selected from Either The Y ２ is N-R ６６ , C.R. ６7 R ６８ , O, S, SiR ６９ R ７０ Selected from Either The R ６１ ~R ７０ may be the same or different, and each independently represents 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 arylthiooxy 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; an alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, R is any one selected from the group consisting of an alkyl group, a cyano group, and a halogen group. ６１ ~R ７０ each of which is bonded to one or more rings selected from T1 to T3 to form an alicyclic or aromatic ring; It is possible to further form a monocyclic or polycyclic ring of the group. (In the above [Chemical Formula D4] and [Chemical Formula D5], The X ２ is any one selected from B, P, and P=O, The T4 to T6 are the same as T1 to T3 in [Chemical Formula D3], The Y ４ is N-R ６１ , C.R. ６２ R ６３ , O, S, SiR ６４ R ６５ Selected from Either The Y ５ is N-R ６６ , C.R. ６６ R ６８ , O, S, SiR ６９ R ７０ Selected from Either The Y ６ is N-R ７１ , C.R. ７２ R ７３ , O, S, SiR ７４ R ７５ Selected from 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, The T7 to T9 are the same as T1 to T3 in [Chemical Formula D3], The Y ６ is N-R ６１ , C.R. ６２ R ６３ , O, S, SiR ６４ R ６５ Selected from Either The substituent R ６１ ~R ６５ , R ７１ ~R ７２ are the above in [Chemical Formula D3] R ６１ ~R ７０ is the same as, The R ７１ and R ７２ are each linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. or further form an alicyclic or aromatic monocyclic or 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 same as T1 to T3 in [Chemical Formula D3], The linking group Y is N-R ３ , C.R. ４ R ５ , O, S, Se It is one The substituent R ３ ~R ５ Each of the R in [Chemical Formula D3] ６１ ~R ７０ Same as However, The R ３ ~R ５ are the above Q ２ Ring or Q ３ A monocyclic alicyclic or aromatic ring bound to the ring or polycyclic rings may be formed, The R ４ and R ５ are each linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. It can be further formed, The ring formed by the Cy1 may be a nitrogen (N) atom, Q １ Aromatic carbon atom in the ring and Q bonded to Cy1 １ Excluding the aromatic carbon atom in the ring, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, In the above chemical formula D9, The Cy2 can be added to the Cy1 to form a saturated hydrocarbon ring, The ring formed by the above formula (I) is a substituted or unsubstituted carbon atom except for the carbon atom contained in Cy1. an alkylene group having a prime number of 1 to 10, In the above chemical formula D10, The ring formed by the Cy3 has Q bonded to the Cy3. ３ Aromatic ring carbon atom, Q bonded to nitrogen (N) atom ３ Aromatic carbon atom, nitrogen (N) atom, said nitrogen (N) atom A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, excluding the carbon atom in Cy1 to which It is a phenyl group.) (Here, the “substituted or unsubstituted” in the above [Chemical Formula D1] to [Chemical Formula D10] The "substitution" in the formula is deuterium, cyano group, halogen group, hydroxyl group, nitro group, carbon number, an alkyl group having 1 to 24 carbon atoms; a halogenated alkyl group having 1 to 24 carbon atoms; an alkynyl group having 2 to 24 carbon atoms; a cycloalkyl 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 group, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms , a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 7 to 24 carbon atoms; An alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 4 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms; It means that it is substituted with one or more substituents.

16. The first light-emitting layer contains one or more compounds represented by Chemical Formula A or Chemical Formula B, 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 1 , [Chemical formula E] (In the above [Chemical Formula E], The substituent R ４１ ~R ５６ may be the same or different, and each independently represents hydrogen, heavy water, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkyl group having 6 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, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; is any one selected from the group consisting of a nitro group and a halogen group; The substituent Ar ５ is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or or an unsubstituted heteroaryl group having 2 to 50 carbon atoms, 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. and The n is an integer of 1 to 2, and when n is 2 or more, each linking group L １ is mutual They may be the same or different, The "substitution" in the "substituted or unsubstituted" in the [chemical formula E] is deuterium. , a cyano group, a halogen group, a hydroxyl 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; Alkynyl group, cycloalkyl group having 3 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, an alkylaryl group having 2 to 24 carbon atoms; a heteroaryl group having 2 to 24 carbon atoms; Arylalkyl group, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms , a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms aryl (heteroaryl) amino groups having 7 to 24 carbon atoms, alkyl groups having 1 to 24 carbon atoms an aryl group, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and Substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms This means that

17. The anthracene derivative represented by the chemical formula E is represented by the following chemical formula E-1 or E-2 The organic light-emitting device according to claim 16, which is an anthracene compound represented by the formula: child. [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 represents 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 cycloalkyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, or an unsubstituted alkylsilyl group having 1 to 30 carbon atoms; The aryl group is selected from the group consisting of an arylsilyl group, a cyano group, a nitro group, and 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 or an unsubstituted heteroaryl group having 2 to 50 carbon atoms, The linking group L １１ represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; and any one selected from the group consisting of substituted or unsubstituted heteroarylene groups having 2 to 20 carbon atoms. Or The k is an integer of 1 to 2, and when k is 2 or more, each linking group L １１ are mutual may be the same or different, In the above [chemical formula E-1] and [chemical formula E-2], the term "substituted or unsubstituted" The "substitution" is a deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, a 1-2 carbon atom group, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, group, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 4 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkyl group having 7 to 24 carbon atoms; an alkylaryl group having 2 to 24 carbon atoms; a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 4 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a dihetero group having 2 to 24 carbon atoms, Heteroarylamino group, aryl (heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group, and an arylthionyl group having 6 to 24 carbon atoms; It means that the group is substituted with one or more substituents.

18. The anthracene derivative represented by the chemical formula E in the second light-emitting layer is a compound represented by the chemical formula E. The organic light-emitting device according to claim 16, comprising:

19. R in the following chemical formula E ４１ ~R ４８ At least one of the following is deuterium:

17. The compound according to claim 16.

20. Ar in the above formula E ５ is preferably a substituent containing at least one deuterium. The compound according to claim 16,

21. R in the following chemical formula E ４９ ~R ５６ At least one of the substituents is a deuterium-containing substituent.

17. The compound according to claim 16, characterized in that it is

22. The compound according to claim 16, wherein the compound of formula E has a deuteration degree of 20% or more. Compound.

23. The first dopant in the first light-emitting layer and the second dopant in the second light-emitting layer are the same. At least one selected from the above [Chemical Formula D1] to [Chemical Formula D10] may be one or different.

16. The organic light-emitting device according to claim 15, wherein at least one compound is used.

24. 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 14, characterized in that it is used in any one of the following devices: Organic light-emitting device.

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