Polycyclic aromatic derivative compound and organic light-emitting device using the same

Abstract

The present invention relates to a polycyclic aromatic derivative compound and an organic light-emitting device including the same. According to the present invention, an organic light-emitting device having a high efficiency and a long lifespan with significantly improved luminous efficiency can be realized, and thus can be industrially usefully used in flat display devices, flexible display devices, monochrome or white flat lighting devices, monochrome or white flexible lighting devices, etc.

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic derivative compound and an organic light-emitting device using the compound, which has a significantly improved luminous efficiency and a long life. [Background technology]

[0002] An organic light-emitting device is a self-emitting device in which electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in the light-emitting layer to form excitons, which then emit light while releasing energy. Such organic light-emitting devices have the advantages of low driving voltage, high brightness, wide viewing angle, and fast response speed, and are applicable to full-color flat panel light-emitting displays, and are therefore in the spotlight as a next-generation light source.

[0003] In order for such an organic light emitting device to exhibit the above-mentioned characteristics, it is necessary to optimize the structure of the organic layers in the device and ensure that the materials constituting each organic layer, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and an electron blocking material, are supported by stable and efficient materials. However, there is still a need to continue developing stable and efficient organic layer structures and materials for organic light emitting devices.

[0004] As described above, there is a continuing demand for development of element structures capable of improving the light-emitting characteristics of organic light-emitting elements, and new materials that support such structures. Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, the present invention provides a polycyclic aromatic derivative compound that can be used in an organic layer of a device to realize an organic light emitting device with high efficiency and long life, and an organic light emitting device including the same. [Means for solving the problem]

[0006] In order to solve the above problems, the present invention provides a polycyclic aromatic derivative compound represented by the following chemical formula A.

[0007] [ka]

[0008] The structure of the formula A, specific compounds that can be realized, and the definitions of the rings Q1 to Q3, X, Y1 and Y2 will be described later.

[0009] The present invention also provides an organic light-emitting device comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, the organic layer comprising one or more specific polycyclic aromatic derivative compounds represented by Chemical Formula A. Effect of the Invention

[0010] The polycyclic aromatic derivative compound according to the present invention can be used in an organic layer in a device to realize an organic light-emitting device with high efficiency and long life. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The present invention will now be described in further detail.

[0012] The present invention relates to a polycyclic aromatic derivative compound included in an organic light-emitting device and represented by the following chemical formula A, which is characterized in that it can realize an organic light-emitting device with high efficiency and long life.

[0013] [ka]

[0014] In the above chemical formula A, Q1 is selected from a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 50 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic aliphatic heterocycle having 2 to 50 carbon atoms.

[0015] Q2 and Q3 are the same or different and are each independently selected from a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms and a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 50 carbon atoms.

[0016] X is any one selected from B, P, P=O, P=S and Al.

[0017] Y1 and Y2 are the same or different and each independently represents a single bond; or JPEG0007650961000003.jpg1554-O-, -S-, or -Se-.

[0018] The R1 to R5 are the same or different and each independently represent any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl 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 alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, and a halogen group.

[0019] The R1 to R5 can be bonded to the Q1 to Q3 rings to form an alicyclic or aromatic monocyclic or polycyclic ring, respectively, and the R2 and R3, and the R4 and R5 can be bonded to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, respectively.

[0020] Thus, the specific structure of the formula A according to the present invention and the structure forming the additional ring, which are realized according to the definition of the substituents, can be confirmed from the specific compounds described below.

[0021] On the other hand, in the present invention, the term "substituted or unsubstituted" means that the rings Q1 to Q3, R1 to R5, etc. are each substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, halogenated alkyl group, cycloalkyl group, alkenyl group, alkynyl group, heteroalkyl group, aryl group, arylalkyl group, alkylaryl group, heteroaryl group, heteroarylalkyl group, alkoxy group, amine group, silyl group, aryloxy group, and aliphatic aromatic mixed ring group, are substituted with a substituent in which two or more of the above substituents are linked, or have no substituents.

[0022] In addition, the range of the carbon number 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 6 to 50 carbon atoms" and the like means the total number of carbon atoms constituting the alkyl portion or aryl portion when considered as unsubstituted without taking into account the portion substituted with the substituent. For example, a phenyl group substituted with a butyl group at the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0023] In addition, in the present invention, the meaning of bonding with adjacent groups to form a ring means that the adjacent groups can bond with each other to form a substituted or unsubstituted alicyclic or aromatic ring, and "adjacent substituents" can mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent positioned closest to the substituent in terms of the stereostructure, or another substituent substituted on an atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent substituents" to each other.

[0024] In the present invention, the alkyl group may be a straight chain or a branched chain, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethyl Examples of aryl groups include, but are not limited to, arylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0025] In the present invention, the alkenyl group includes a straight chain or a branched chain and may be further substituted by other substituents, and specifically includes, but is not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0026] In the present invention, alkynyl groups also include straight or branched chains and may be further substituted with other substituents, including, but not limited to, ethynyl, 2-propynyl, and the like.

[0027] In the present invention, the cycloalkyl group includes a single ring or multiple rings, and may be further substituted with other substituents, and the multiple rings refer to a group in which the cycloalkyl group is directly linked or condensed with another ring group, and the other ring group may be a cycloalkyl group, but may also be other types of ring groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an adamantyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0028] In the present invention, a heterocycloalkyl group contains a heteroatom such as O, S, Se, N or Si, and also includes a single ring or multiple rings, which may be further substituted by other substituents. The multiple rings refer to a group in which a heterocycloalkyl group is directly linked or condensed with another ring group, which may be a heterocycloalkyl group, but may also be other types of ring groups, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0029] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, a chrysenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluoranthene group, but the scope of the present invention is not limited to these examples.

[0030] In the present invention, an aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, Examples of such groups include, but are not limited to, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, and a phenothiazinyl group.

[0031] In the present invention, the aliphatic hydrocarbon ring means a ring that is not aromatic and consists only of carbon and hydrogen atoms, examples of which include a monocyclic or polycyclic ring, which may be further substituted with other substituents, and the polycyclic ring means a group directly linked or condensed with another ring group, and the other ring group may be an aliphatic hydrocarbon ring, but may also be other types of ring groups, for example, an aliphatic heterocyclic ring, an aryl group, a heteroaryl group, etc. Specifically, it includes cycloalkyl such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an adamantyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc., cycloalkanes such as cyclohexane and cyclopentane, and cycloalkenes such as cyclohexene and cyclobutene, but is not limited thereto.

[0032] In the present invention, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms, such as O, S, Se, N, or Si, which also includes a monocycle or polycycle and may be further substituted with other substituents. The term "polycycle" refers to a group in which a heterocycloalkyl, heterocycloalkane, or heterocycloalkene group is directly linked or condensed with another ring group, and the other ring group may be an aliphatic heterocycle, but may also be another type of ring group, such as an aliphatic hydrocarbon ring, an aryl group, or a heteroaryl group.

[0033] In the present invention, the aliphatic aromatic mixed ring refers to a ring in which two or more rings are connected and fused to each other, and an aliphatic ring and an aromatic ring are fused to have non-aromaticity as a whole. In addition, in a polycyclic aliphatic aromatic mixed ring, in addition to C, a heteroatom selected from N, O, P, and S may be included.

[0034] In the present invention, the alkoxy group may specifically be methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited to these.

[0035] In the present invention, the silyl group may be -SiH, an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, or the like. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like.

[0036] In the present invention, the amine group may be -NH, an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., the arylamine group means an amine substituted with an aryl, the alkylamine group means an amine substituted with an alkyl, and the arylheteroarylamine group means an amine substituted with an aryl and a heteroaryl group. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl and heteroaryl groups in the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group, and the arylamine group and the arylheteroarylamine group containing two or more aryl groups and two or more heteroaryl groups may contain a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group) and a polycyclic aryl group (heteroaryl group) at the same time. The aryl group and heteroaryl group in the arylamine group and arylheteroarylamine group may be selected from the examples of the aryl group and heteroaryl group given above.

[0037] In the present invention, the aryl group in the aryloxy group and the arylthioxy group is the same as the above-mentioned aryl group examples. Specifically, the aryloxy group includes a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, and the like. The arylthioxy group includes a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, but is not limited thereto.

[0038] In the present invention, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0039] More specifically, the polycyclic aromatic derivative compound represented by the chemical formula A according to the present invention may be any one selected from the following compounds, through which the specific substituents can be clearly identified, however, the scope of the chemical formula A according to the present invention is not limited thereto.

[0040] JPEG0007650961000004.jpg178150 JPEG0007650961000005.jpg193150 JPEG0007650961000006.jpg180150 JPEG0007650961000007.jpg185150 JPEG0007650961000008.jpg159150

[0041] As can be seen from the above specific compounds, a polycyclic aromatic structure can be formed by including B, P, P=O, P=S, Al, etc., and a substituent can be introduced into the polycyclic aromatic structure to synthesize an organic light-emitting material having the inherent properties of the substituent. For example, by introducing a substituent used in the materials of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc., used in the manufacture of an organic light-emitting device into the above structure, a material that satisfies the requirements of each organic layer can be manufactured, thereby realizing a highly efficient organic light-emitting device.

[0042] Another aspect of the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, and the organic layer may contain at least one organic light-emitting compound according to the present invention represented by chemical formula A.

[0043] That is, the organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode, a second electrode, and an organic layer disposed therebetween, and may be manufactured using a conventional device manufacturing method and materials in the art, except that the organic light emitting compound of Formula A according to the present invention is used in the organic layer of the device.

[0044] The organic layer of the organic light emitting device according to the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic layers are laminated. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. However, it is not limited thereto, and it may have a smaller or larger number of organic layers. The structure of the organic layer of the preferred organic light emitting device according to the present invention will be described in more detail in the examples below.

[0045] The organic light-emitting device according to the present invention includes an anode, a hole transport layer, an emission layer, an electron transport layer, and a cathode, and may further include a hole injection layer between the anode and the hole transport layer, and may further include an electron injection layer between the electron transport layer and the cathode, and may further include one or two intermediate layers, or may further include a hole blocking layer or an electron blocking layer.

[0046] As a preferred embodiment of the present invention, the organic layer interposed between the first electrode and the second electrode includes an emitting layer, the emitting layer includes a host and a dopant, and the compound represented by the chemical formula A according to the present invention may be included as a dopant in the emitting layer.

[0047] In this case, the content of the dopant in the light emitting layer may be selected from the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0048] In addition, in one embodiment of the present invention, the host in the light-emitting layer may be an anthracene derivative compound represented by the following chemical formula C:

[0049] [ka]

[0050] In the above chemical formula C, R 21 ~R 28 are the same or different and are the same as defined for R in the above chemical formula A.

[0051] Ar9 and Ar 10are each the same or different 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a halogen group, a substituted or unsubstituted amine group, and a substituted or unsubstituted silyl group.

[0052] L 13 is a single bond or is selected from 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.

[0053] k is an integer of 1 to 3, and when k is 2 or more, each L 13 are the same or different from each other.

[0054] According to an embodiment of the present invention, Ar9 in Formula C may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0055] The host represented by formula C according to an embodiment of the present invention may be any one selected from the following formulae C1 to C69, but the scope is not limited thereto.

[0056] JPEG0007650961000010.jpg188150 JPEG0007650961000011.jpg194150 JPEG0007650961000012.jpg185150 JPEG0007650961000013.jpg99150 JPEG0007650961000014.jpg37150

[0057] Meanwhile, a specific structure of the organic light emitting device according to an embodiment of the present invention, a manufacturing method thereof, and materials of each organic layer will be described as follows.

[0058] First, an anode is formed by coating an anode material on the upper part of a substrate. The substrate is a substrate used in a typical organic light emitting device, and is preferably an organic substrate or a transparent plastic substrate, which has excellent transparency, surface smoothness, ease of handling, and water resistance. The anode material is transparent and highly conductive, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc.

[0059] A hole injection layer is formed on the anode electrode by vacuum thermal deposition or spin coating of a hole injection layer material, and then a hole transport layer is formed on the hole injection layer by vacuum thermal deposition or spin coating of a hole transport layer material.

[0060] The material for the hole injection layer is not particularly limited as long as it is a material commonly used in the art. Specific examples thereof include 2-TNATA [4,4',4''-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'- diamine] (N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine), DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine] (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile] (1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile), and the like can be used.

[0061] The material of the hole transport layer is not particularly limited as long as it is a material commonly used in the art, and for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) can be used.

[0062] Then, a hole auxiliary layer and an emitting layer are laminated on the hole transport layer, and a hole blocking layer can be selectively formed as a thin film on the emitting layer by a vacuum deposition method or a spin coating method. The hole blocking layer plays a role in preventing a problem in which the life and efficiency of the device are reduced when holes pass through the organic emitting layer and flow into the cathode, by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level. The hole blocking material used here is not particularly limited, but should have an electron transport ability and a higher ionization potential than the emitting compound, and representative examples include BAlq, BCP, and TPBI.

[0063] The material used for the hole blocking layer may be, but is not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq, etc.

[0064] An electron transport layer is deposited on the hole blocking layer by vacuum deposition or spin coating, and then an electron injection layer is formed. A metal for forming a cathode is then vacuum thermally deposited on the top of the electron injection layer to form a cathode electrode, thereby completing an organic light emitting device according to an embodiment of the present invention.

[0065] Here, examples of metals that can be used for forming the cathode include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In order to obtain a front-emitting element, a transmissive cathode using ITO or IZO can be used.

[0066] The material of the electron transport layer may be a known electron transport material that stably transports electrons injected from the cathode. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolato)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), and oxadiazole derivatives such as PBD, BMD, and BND.

[0067] In addition, each of the organic layers may be formed by a monomolecular deposition method or a solution process, where the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers by heating under a vacuum or low pressure condition, and the solution process refers to a method of mixing a material 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.

[0068] In addition, the organic light emitting device according to the present invention may be used in a device selected from a flat display device, a flexible display device, a monochrome or white flat lighting device, and a monochrome or white flexible lighting device. EXAMPLES

[0069] The present invention will be described in more detail below with reference to preferred examples. However, it will be obvious to those skilled in the art that these examples are provided to more specifically explain the present invention and do not limit the scope of the present invention.

[0070] Synthesis Example 1. Preparation of Compound 64 Synthesis Example 1-1. Synthesis of Intermediate A-1 JPEG0007650961000015.jpg28133A-1a A-1b A-1c A-1

[0071] Using A-1a and A-1b, A-1c was synthesized with reference to the literature (Tetrahedron Letters, 2011, vol. 52, #11, p. 1161-1164), and A-1 was synthesized with reference to the synthetic method in the literature (Dyes and Pigments, 2016, vol. 133, p. 114-119). (37.3 g, 83.2%)

[0072] MS (ESI) calculation for Chemical Formula: C 18 H 18 BrClN(Pos)362.03,found 362.0

[0073] Synthesis Example 1-2. Synthesis of Intermediate A-2 JPEG0007650961000016.jpg44121A-1 A-2a A-2

[0074] A-2 was synthesized from A-1 and A-2a synthesized with reference to the literature (US Patent Publication 2020 / 172558A1) with reference to the synthesis method of the literature (Korean Patent Publication 2017 / 52777A). (15.3g, yield 91.1%)

[0075] MS (ESI) calcd for Chemical Formula:C 38 H 43 Cl2N2(Pos)597.28,found 597.2

[0076] Synthesis Example 1-3. Synthesis of Intermediate A-3 JPEG0007650961000017.jpg43122A-2 A-3a A-3

[0077] A-2 (21.7 g), A-3a (6.65 g), bis(tri-tert-butylphosphine)palladium(0) (0.56 g), sodium tert-butoxide (10.5 g), and xylene (200 mL) were added to a reactor and refluxed and stirred for 24 hours. After cooling to room temperature, water (200 mL) was added. The organic layer was extracted with ethyl acetate and concentrated under reduced pressure, and then A-3 was isolated by silica gel column chromatography (6.0 g, yield 23.3%).

[0078] MS (ESI) calcd for Chemical Formula:C 50 H 50 N3O (Pos) 708.40, found 708.4

[0079] Synthesis Example 1-4. Synthesis of Compound 64 JPEG0007650961000018.jpg36104A-3 64

[0080] A-3 (13.6 g) and dichlorobenzene (140 mL) were added to a reactor, and boron tribromide (1.8 mL) was added dropwise at room temperature, followed by reflux and stirring for 16 hours. After cooling to room temperature, water (60 mL) and sodium acetate (4.7 g) were added. The organic layer was extracted with ethyl acetate and concentrated under reduced pressure. Compound 64 was isolated by silica gel column chromatography and purified by recrystallization. (1.40 g, yield 10.2%)

[0081] MS (ESI) calcd for Chemical Formula:C 50 H 47 BN3O (Pos) 716.38, found 716.3

[0082] Synthesis Example 2. Synthesis of Compound 65 Synthesis Example 2-1. Synthesis of Intermediate B-1 JPEG0007650961000019.jpg39153B-1a B-1b B-1c B-1d B-1

[0083] Intermediate B-1 was obtained from intermediate B-1c obtained from intermediate B-1a by the same synthesis method as in Synthesis Example 1. (88.1%)

[0084] MS (ESI) calcd for Chemical Formula:C 46 H 43 Cl2N2(Pos)693.28,found 693.2

[0085] Synthesis Example 2-2. Synthesis of Compound 65 JPEG0007650961000020.jpg39151B-2a B-2b B-2c 65

[0086] Compound 65 was obtained from intermediate B-2c obtained from intermediate B-2a in the same manner as in Synthesis Example 1. (9.4%)

[0087] MS (ESI) calcd for Chemical Formula:C 62 H 57 BN3(Pos)854.47,found 854.4

[0088] Synthesis Example 3: Synthesis of Compound 66 Synthesis Example 3-1. Synthesis of Intermediate C-1 JPEG0007650961000021.jpg27149C-1a C-1b C-1c C-1d C-1

[0089] Intermediate C-1 was obtained from intermediate C-1c obtained from intermediate C-1a by the same synthesis method as in Synthesis Example 1. (90.1%)

[0090] MS (ESI) calcd for Chemical Formula:C 56 H 56 Cl2N3(Pos)840.39,found 840.3

[0091] Synthesis Example 3-2. Synthesis of Compound 66 JPEG0007650961000022.jpg30146C-2a C-2b C-2c 66

[0092] Compound 66 was obtained from intermediate C-2c obtained from intermediate C-2a in the same manner as in Synthesis Example 1. (14.1%)

[0093] MS (ESI) calcd for Chemical Formula:C 68 H 62 BN4(Pos)945.51,found 945.5

[0094] Synthesis Example 4. Synthesis of Compound 67 Synthesis Example 4-1. Synthesis of Intermediate D-1 JPEG0007650961000023.jpg33146D-1a D-1b D-1c D-1d D-1

[0095] Intermediate D-1 was obtained from intermediate D-1c obtained from intermediate D-1a by the same synthesis method as in Synthesis Example 1. (81.2%)

[0096] MS (ESI) calcd for Chemical Formula:C 54 H 42 Cl2N3O (Pos)834.25,found 834.2

[0097] Synthesis Example 4-2. Synthesis of Compound 67 JPEG0007650961000024.jpg34146D-2a D-2b D-2c 67

[0098] Compound 67 was obtained from intermediate D-2c obtained from intermediate D-2a in the same manner as in Synthesis Example 1. (9.3%)

[0099] MS (ESI) calcd for Chemical Formula:C 64 H 52 BN4S (Pos) 919.40, found 919.4

[0100] Synthesis Example 5. Synthesis of Compound 68 Synthesis Example 5-1. Synthesis of Intermediate E-1 JPEG0007650961000025.jpg34146E-1a E-1b E-1c E-1d E-1

[0101] Intermediate E-1 was obtained from intermediate E-1c obtained from intermediate E-1a by the same synthesis method as in Synthesis Example 1. (76.5%)

[0102] MS (ESI) calcd for Chemical Formula:C 44 H 47 Cl2N2(Pos)673.31,found 673.3

[0103] Synthesis Example 5-2. Synthesis of Compound 68 JPEG0007650961000026.jpg31146E-2a E-2b E-2c 68

[0104] Compound 68 was obtained from intermediate E-2c obtained from intermediate E-2a in the same manner as in Synthesis Example 1. (8.9%)

[0105] MS (ESI) calcd for Chemical Formula:C 60 H 61 BN3(Pos)834.50,found 834.5

[0106] Synthesis Example 6. Synthesis of Compound 69 Synthesis Example 6-1. Synthesis of Intermediate F-1 JPEG0007650961000027.jpg27146F-1a F-1b F-1c F-1d F-1

[0107] Intermediate F-1 was obtained from intermediate F-1c obtained from intermediate F-1a by the same synthesis method as in Synthesis Example 1. (72.4%)

[0108] MS (ESI) calcd for Chemical Formula:C 54 H 56 Cl2N3(Pos)816.39,found 816.3

[0109] Synthesis Example 6-2. Synthesis of Compound 69 JPEG0007650961000028.jpg31146F-2a F-2b F-2c 69

[0110] Compound 69 was obtained from intermediate F-2c obtained from intermediate F-2a in the same manner as in Synthesis Example 1. (8.5%)

[0111] MS (ESI) calcd for Chemical Formula:C 72 H 66 BN4(Pos)997.54,found 997.5

[0112] Examples 1 to 10: Fabrication of organic light-emitting devices The ITO glass was patterned so that the light-emitting area of ​​the glass was 2 mm × 2 mm, and then washed. The ITO glass was placed in a vacuum chamber, and the base pressure was 1 × 10 -7 After adjusting the pressure to torr, DNTPD (700 Å) and a compound of formula H (250 Å) were deposited on the ITO in this order. The light-emitting layer was formed by mixing the host (BH1) described below and the compound of the present invention (3 wt%) to form a film (250 Å), and then, as an electron transport layer, a film of formula E-1 and a film of formula E-2 were deposited in a ratio of 1:1 to 300 Å, and as an electron injection layer, a film of formula E-1 was deposited in 5 Å and Al (1000 Å) was deposited in this order to manufacture an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0113] JPEG0007650961000029.jpg92149

[0114] Comparative Example 1 An organic light-emitting device was produced in the same manner as in Example 1, except that BD1 was used instead of the compound used in Example 1, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0115] [BD1] JPEG0007650961000030.jpg3749

[0116] The external quantum efficiency and lifetime of the organic light emitting devices manufactured in Examples 1 to 10 and Comparative Example 1 were measured, and the results are shown in Table 1 below.

[0117] [Table 1]

[0118] As can be seen from Table 1, the organic light emitting device using the compound according to the present invention exhibits higher quantum efficiency and longer life than the organic light emitting device using the compound according to Comparative Example 1. [Industrial Applicability]

[0119] The present invention relates to a polycyclic aromatic derivative compound, which can be used to realize an organic light-emitting device with high efficiency and long life with significantly improved luminous efficiency, and can be industrially usefully used in flat display devices, flexible display devices, monochrome or white flat lighting devices, and monochrome or white flexible lighting devices.

Claims

1. An organic compound represented by the following chemical formula A. 【Chemistry A】 (In the above chemical formula A, Q １ is selected from a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 50 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic aliphatic heterocycle having 2 to 50 carbon atoms; Q ２ and Q. ３ are the same or different and are each independently selected from a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms and a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 50 carbon atoms; X is B, Y １ and Y ２ are the same or different from each other, and each independently represents 【change】 and R1 is any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl 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 alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, and a halogen group; The R1 is the Q １ ~Q ３ can further combine with to form an alicyclic or aromatic monocyclic or polycyclic ring.

2. The organic compound according to claim 1 , wherein the chemical formula A is any one selected from the following compounds:

3. a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode; An organic light-emitting device, wherein the organic layer comprises one or more organic compounds represented by the chemical formula A according to claim 1 .

4. the organic layer includes one or more of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer; The organic light-emitting device of claim 3 , wherein one or more of the layers comprises the organic compound represented by Formula A.

5. The organic light-emitting device according to claim 4 , wherein the light-emitting layer is composed of a host and a dopant, and the organic compound represented by the chemical formula A is the dopant in the light-emitting layer.

6. The organic light emitting device according to claim 5 , wherein the host is an anthracene derivative represented by the following chemical formula C: 【Chemical C】 (In the above chemical formula C, R ２１ ~R ２８ are the same or different and are the same as any one selected from the various functional groups defined as R1 in the above chemical formula A; Ar ９ and Ar １０ are each the same or different and independently represent any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a halogen group, a substituted or unsubstituted amine group, and a substituted or unsubstituted silyl group; L １３ represents a single bond or any one selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms; k is an integer of 1 to 3, and when k is 2 or more, each L １３ are the same or different.)

7. Ar of the above formula C ９ The organic light-emitting device according to claim 6 , wherein is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

8. The organic light emitting device according to claim 6, wherein the formula C is any one selected from the following formulas C1 to C69:

9. The organic light emitting device according to claim 3, wherein the organic light emitting device is used in any one selected from the group consisting of a flat display device, a flexible display device, a monochrome or white flat lighting device, and a monochrome or white flexible lighting device.

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