Organic compound and organic light-emitting device comprising same

Abstract

The present invention relates to an organic compound that can be used as a host material of a light-emitting layer in an organic light-emitting device. When used as a host material of a light-emitting layer, an organic light-emitting device having excellent device characteristics such as color purity, luminous efficiency and quantum efficiency can be implemented by means of the characteristics of a specific polycyclic skeleton and a moiety structure introduced thereto, and thus can be effectively used in various displays and lighting devices.

Description

Organic compounds and organic light-emitting devices containing the same

[0001] The present invention relates to a compound employed in an organic layer within an organic light-emitting device, and more specifically, to a compound employed as a host material for a light-emitting layer within an organic light-emitting device due to structural characteristics of the compound, and to an organic light-emitting device employing the compound, in which device characteristics such as color purity, luminous efficiency, and quantum efficiency are significantly improved.

[0002] Organic light-emitting diodes can be formed on transparent substrates, and compared to plasma display panels or inorganic electroluminescent (EL) displays, they can be driven at a low voltage of less than 10 V, consume relatively little power, have excellent color reproduction, and can display three colors: green, blue, and red, so they have recently become the subject of much interest as next-generation display devices.

[0003] However, in order for these organic light-emitting devices to exhibit the characteristics described above, the materials that make up the organic layers within the device, such as the hole injection layer, hole transport layer, hole blocking layer, light-emitting layer host and dopant, electron blocking layer, electron transport layer, and electron injection layer, must first be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic light-emitting devices has not yet been sufficiently accomplished.

[0004] Therefore, in order to realize more stable organic light-emitting devices and to achieve high efficiency, long life, and large size of the devices, additional improvements in efficiency and life characteristics are required, and in particular, development of materials that make up each organic layer of the organic light-emitting device is urgently needed.

[0005] In particular, to obtain maximum efficiency in the light-emitting layer, the energy band gaps of the host and dopant must be appropriately combined so that holes and electrons can move to the dopant through stable electrochemical pathways to form excitons.

[0006] Accordingly, the present invention aims to provide an organic compound that can be employed as a host material for a light-emitting layer in an organic light-emitting device and exhibit excellent characteristics in terms of color purity, light-emitting efficiency, quantum efficiency, etc., and an organic light-emitting device comprising the same.

[0007] In order to solve the above problem, the present invention provides an organic compound represented by the following [chemical formula Ⅰ] and an organic light-emitting device including the same as a light-emitting layer host material.

[0008] [Chemical Formula I]

[0009]

[0010] The characteristic structure of the above [Chemical Formula I] and the specific compounds realized thereby and the definition of each substituent will be described later.

[0011] The organic compound according to the present invention can be used as a host material for a light-emitting layer in an organic light-emitting device to realize excellent device characteristics such as color purity, luminous efficiency, and quantum efficiency, and thus can be usefully utilized in various displays and lighting devices.

[0012] Hereinafter, the present invention will be described in more detail.

[0013] The present invention relates to an organic compound represented by the following [Chemical Formula Ⅰ], which is employed as a host material for a light-emitting layer in an organic light-emitting device due to the characteristics of a polycyclic ring skeleton structure and an introduced moiety structure, and further, according to one embodiment of the present invention, when the light-emitting layer host is composed of a mixed host, and one of the host materials is employed as a compound represented by the following [Chemical Formula Ⅰ], an organic light-emitting device having excellent device characteristics such as color purity, luminous efficiency, and quantum efficiency can be implemented.

[0014] [Chemical Formula I]

[0015]

[0016] In the above [chemical formula Ⅰ],

[0017] R1 to R4 are the same or different, and are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a cyano group, and a halogen group.

[0018] o and p are each an integer from 0 to 3, q ​​is an integer from 0 to 4, s is an integer from 0 to 2, and when o, p, q and s are 2 or more, a plurality of R1 to R4 are each the same or different from each other.

[0019]

[0020] X1 and X2 are the same or different and are each independently selected from O, S, CR5R6, NR7 and SiR8R9, and Y1 is O, S, CR 10 R 11 , NR 12 and SiR 13 R 14 One of the following is selected.

[0021] Above R5 to R 14 are the same or different from each other, and are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

[0022] Also, the above R5 and R6; R8 and R9; R 10 and R 11 ; and R13 and R 14 ; can be linked to each other to form a monocyclic or polycyclic ring of alicyclic or aromatic group.

[0023]

[0024] D is deuterium, n means the number of hydrogen atoms in the above [chemical formula Ⅰ] replaced with deuterium (D), and n is an integer from 0 to 60.

[0025] According to one embodiment of the present invention, the compound represented by the above-mentioned [chemical formula Ⅰ] is characterized in that the skeleton as well as the hydrogen present in the substituents defined in the structure of the [chemical formula Ⅰ] are each partially substituted with deuterium (D), and accordingly, an organic light-emitting device having superior luminescence efficiency and significantly improved lifespan characteristics can be implemented.

[0026] According to one embodiment of the present invention, the deuterium (D) substitution rate may be 10 to 90%, and in a preferred embodiment, the deuterium (D) substitution rate may be 20 to 80%, and in a more preferred embodiment, the deuterium (D) substitution rate may be 30 to 70%.

[0027]

[0028] Meanwhile, in the definition of the above [Chemical Formula Ⅰ], ‘substituted or unsubstituted’ means R1 to R defined in [Chemical Formula Ⅰ]. 14It means that each of the above substituents is substituted with one or more substituents selected from among deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aliphatic aromatic mixed ring group, an amine group, a silyl group, and a germanium group, or two or more of the above substituents are substituted with a linked substituent, or has no substituent, and hydrogen in the above substituents can be replaced with one or more deuterium, and two or more adjacent substituents can be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0029] For example, a substituted aryl group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc., substituted with another substituent such as deuterium, and a substituted heteroaryl group means a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and condensed heterocyclic groups thereof, such as a benzquinoline group, a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, etc., substituted with another substituent such as deuterium.

[0030]

[0031] In addition, in the present invention, the meaning of forming an additional ring by being connected to each other or to adjacent groups means that adjacent substituents among the specified substituents can be connected to each other, or a specified substituent and another adjacent group can be connected to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and the 'adjacent group' may mean a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent positioned closest to the substituent in terms of steric structure, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as 'adjacent groups'.

[0032]

[0033] In the present invention, the alkyl group may be straight-chain or branched, 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-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohectylmethyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, Examples thereof include, but are not limited to, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0034] In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20, which is a range that does not cause steric hindrance. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0035] In the present invention, the alkyl group and the alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group or alkoxy group, respectively, and the alkyl group or alkoxy group means an alkyl group or alkoxy group substituted with a deuterium or halogen group.

[0036] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and polycyclic means a group directly connected to or condensed with another ring group, and the other ring group may be an aromatic hydrocarbon ring, but may also be another type of ring group, for example, an aliphatic heterocycle, an aliphatic hydrocarbon ring, an aromatic heterocycle, etc. Examples of monocyclic aryl groups include a phenyl group, a biphenyl group, a terphenyl group, etc., and examples of polycyclic aryl groups include a naphthyl group, 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, a fluoranthene group, etc., but the scope of the present invention is not limited to these examples.

[0037] In the present invention, fluorene in the fluorenyl group or fluorene moiety, etc., is a structure in which two ring organic compounds are connected through one atom, for example, , , There is a back.

[0038] Also, it includes an open fluorene structure, where the open fluorene is a structure in which two ring organic compounds are connected through one atom, and one of the ring compounds is disconnected, for example. , There is a back.

[0039] Additionally, the carbon atoms of the above ring may be substituted with one or more heteroatoms selected from N, S and O, for example, , , , There is a back.

[0040] In addition, in the present invention, the fluorenyl group may have a structure in which a monocyclic or polycyclic aromatic ring and a monocyclic or polycyclic alicyclic ring are further condensed in the above-mentioned connected structure or open structure.

[0041] In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing at least one heteroatom, 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 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 pyrido pyrimidinyl group, a pyrido pyrazinyl group, a pyrazino pyrazinyl group, an isoquinoline group, an indole group, a carbazole group, an indolocarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, Examples thereof include, but are not limited to, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, and phenothiazinyl group.

[0042] In the present invention, an aliphatic hydrocarbon ring or cycloalkyl group means a ring that is not aromatic and is composed only of carbon and hydrogen atoms, and includes, for example, a monocyclic ring or a polycyclic ring, and may be further substituted by another substituent. A polycyclic ring means a group that is directly connected to or condensed with another ring group, and the other ring group may be an aliphatic hydrocarbon ring, but may also be another type of ring group, such as an aliphatic heterocycle, an aromatic hydrocarbon ring, an aromatic heterocycle, etc. Specifically, it includes, but is not limited to, cycloalkyl groups 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, and a cyclooctyl group, and cycloalkanes such as cyclohexane and cyclopentane, and cyclocycloalkenes such as cyclohexene and cyclobutene.

[0043] In the present invention, an aliphatic heterocycle or heterocycloalkyl group means an aliphatic ring containing at least one heteroatom, and includes a heteroatom such as O, S, Se, N or Si, and also includes a monocyclic ring or a polycyclic ring, and may be further substituted by another substituent, and a polycyclic ring means a group in which a heterocycloalkyl or a heterocycloalkane is directly connected to 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 aromatic hydrocarbon ring, an aromatic heterocycle, etc.

[0044] In the present invention, the aliphatic aromatic mixed ring (group) means a ring in which two or more rings are connected and condensed with each other, and in which the aliphatic ring and the aromatic ring are condensed to have non-aromaticity as a whole, and more specifically, it may be an aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring condensed with an aliphatic heterocycle, an aromatic heterocycle condensed with an aliphatic heterocycle, an aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring, an aromatic heterocycle condensed with an aliphatic heterocycle, an aromatic heterocycle condensed with an aliphatic heterocycle, etc. Additionally, the polycyclic aliphatic aromatic mixed ring may include heteroatoms such as N, O, S, Si, Ge, and P in addition to carbon.

[0045] In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of such silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc.

[0046] In the present invention, the germanium group (or germane group) may include -GeH3, an alkylgermanium group, an arylgermanium group, a heteroarylgermanium group, an alkylarylgermanium group, an alkylheteroarylgermanium group, an arylheteroarylgermanium group, etc., and the definitions of these are as described for the silyl group, but may be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) for a silicon atom (Si) in the silyl group.

[0047] In addition, specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, etc., and one or more hydrogen atoms of the germanium group can be substituted with a substituent similar to that of the aryl group.

[0048] In the present invention, the amine group may be -NH2, an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., and the arylamine group means an amine substituted with aryl, the alkylamine group means an amine substituted with alkyl, and the arylheteroarylamine group means an amine substituted with aryl and heteroaryl groups, and 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, and the aryl group and heteroaryl group 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 including two or more aryl groups and heteroaryl groups may be a monocyclic It may include an aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or both a monocyclic aryl group (heteroaryl group) and a polycyclic aryl group (heteroaryl group). In addition, the aryl group and heteroaryl group among the arylamine group and arylheteroarylamine group may be selected from the examples of the above-mentioned aryl group and heteroaryl group.

[0049] Specific examples of halogen groups used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), etc.

[0050] Additionally, various specific examples of substituents according to the present invention can be clearly identified in the specific compounds described below.

[0051]

[0052] The organic compound according to the present invention represented by the above [chemical formula Ⅰ] can be used as an organic layer of an organic light-emitting device due to the structural specificity of the skeletal structure and the introduced moiety as described above, and more specifically, can be used as a host material for a light-emitting layer in the organic layer.

[0053] Preferred specific examples of the compound represented by [Chemical Formula Ⅰ] according to the present invention include, but are not limited to, the following compounds.

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] In this way, the organic compound according to the present invention can synthesize compounds having various characteristics through the characteristic skeleton of a polycyclic ring structure and the moiety having unique characteristics introduced thereto, and as a result, when the organic compound according to the present invention is applied to various organic layer materials such as a light-emitting layer, the light-emitting characteristics such as the light-emitting efficiency of the device can be further improved, and preferably, when used as a light-emitting layer host material, an organic light-emitting device having excellent light-emitting characteristics can be implemented.

[0067]

[0068] Another aspect of the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer comprises a compound of [chemical formula I] according to the present invention defined above as a host, preferably in a light-emitting layer comprising a host and a dopant.

[0069] [Chemical Formula I]

[0070]

[0071]

[0072] In addition, the light-emitting layer is a structure composed of a host and a dopant, and the light-emitting layer may further include a dopant material. At this time, the content of the dopant may be typically selected in a 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.

[0073] In addition, the light-emitting layer may additionally include various hosts and various dopant materials in addition to the host and dopant compounds according to the present invention, and accordingly, in the light-emitting layer, not only the host but also the dopant material may be used by mixing or laminating one or more different compounds.

[0074]

[0075] The organic layer of the organic light-emitting device according to the present invention may be formed as a single-layer structure, but may also be formed as 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 light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, etc. However, it is not limited thereto and may include a smaller or larger number of organic layers.

[0076] In this way, the organic light-emitting device according to one embodiment of the present invention may include a hole injection layer, a hole transport layer, a light-emitting layer, etc. formed on an anode, and may also include a hole blocking layer, an electron injection layer, an electron transport layer, an electron blocking layer, a light-emitting auxiliary layer, etc., but is not limited thereto.

[0077]

[0078] In addition, according to one embodiment of the present invention, the dopant may include at least one organometallic compound, and may further include a thermally activated delayed fluorescence (TADF) material in addition to the organometallic compound. In this case, the dopant material may also be used by mixing or layering.

[0079] Accordingly, in an organic light-emitting device according to one embodiment of the present invention, the light-emitting layer may be configured to include a first host, a second host, an organometallic compound, and a thermally activated delayed fluorescence (TADF) material, and at this time, an organic compound represented by [chemical formula I] according to the present invention may be used as a host material.

[0080] In this case, the organometallic compound functions as a sensitizer, and the TADF material functions as a luminescent dopant, such that the sensitizer compound can receive excitons from the first host and the second host and transfer them to the luminescent dopant.

[0081] Accordingly, excitons from the sensitizer are transferred to the light-emitting dopant compound through the Dexter energy transfer (DET) or Forster resonance transfer (FRET) mechanism, and the exciton energy transferred to the light-emitting dopant compound can emit light while being transferred to the ground state. At this time, the excitons of the sensitizer can be transferred from the first host and the second host through the FRET mechanism, or can be formed by the transfer of excitons generated from the host through the DET mechanism.

[0082] Accordingly, energy transfer through FRET and DET mechanisms between the sensor and the light-emitting dopant is facilitated, and triplet-triplet annihilation is suppressed, enabling the production of a high-efficiency organic light-emitting device.

[0083] Additionally, the delayed fluorescent emitter at this time can improve the lifespan by enabling Förster energy transfer from the triplet of the phosphorescence sensitizer to the singlet of the delayed fluorescent emitter, thereby reducing the number of long-lived triplet excitons involved in device degradation.

[0084] In addition, because it has a high molar extinction coefficient, the efficiency and lifespan can be improved due to effects such as an increase in the rate of fluorescence resonance energy transfer from the phosphorescence sensitizer to the emitter and a narrowing of the emission spectrum due to the multiple resonance effect, thereby increasing color purity.

[0085]

[0086] The organic compound represented by [Chemical Formula Ⅰ] according to the present invention can be applied to an organic light-emitting device according to a conventional manufacturing method.

[0087] An organic light-emitting device according to one 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, except that the compound according to the present invention is used in the organic layer of the device.

[0088] The organic layer structure, etc. of the preferred organic light-emitting device according to the present invention will be described in more detail in the examples described below.

[0089]

[0090] In addition, the organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer 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 blocking layer, etc., thereon, and then depositing a material that can be used as a cathode thereon.

[0091] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole blocking layer, an emission layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc., but is not limited thereto and may have a single layer structure. In addition, the organic layer can be manufactured with a smaller number of layers using various polymer materials by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0092]

[0093] The anode is preferably a material having a high work function to facilitate hole injection into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline.

[0094] The cathode is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayer materials such as LiF / Al or LiO2 / Al.

[0095] The hole injection layer is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0096] The hole transport layer is a material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer. Suitable materials should have high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0097] An electron blocking layer is a layer that blocks the movement of electrons and can be formed on a hole transport layer. The electron blocking layer can be a layer that blocks the movement of electrons without affecting the transport of holes. In addition, a light-emitting layer can be formed on the electron blocking layer, and a hole blocking layer, an electron transport layer, and an electron injection layer can be formed.

[0098] The hole-blocking layer can be used to block the movement of holes without affecting the transport of electrons, and examples of such hole-blocking layers include TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP (2,9-dimethyl4,7-diphenyl-1,10-phenanthroline), CBP (4,4-bis(N-carbazolyl)-1,1'-biphenyl), PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole), PTCBI (bisbenzimidazo[2,1-a:1',2-b']anthra[2,1,9-def:6,5,10-d'e'f']diisoguinoline-10,21-dione) or BPhen. (4,7-diphenyl-1,10-phenanthroline), but are not limited thereto.

[0099] The light-emitting layer is a material that can emit light in the visible range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them. A material with good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3), carbazole series compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzo quinoline-metal compounds, benzoxazole, benzthiazole and benzimidazole series compounds, poly(p-phenylenevinylene) (PPV) series polymers, spiro compounds, polyfluorene, rubrene, etc.

[0100] The electron injection layer can be a material with high electron injection efficiency from the cathode. Examples of such electron injection layers include, but are not limited to, lithium quinolate (Liq).

[0101] The electron transport layer is a material capable of receiving electrons from the cathode and transporting them to the light-emitting layer. A material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes.

[0102]

[0103] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided light-emitting device depending on the material used.

[0104] In addition, the organic compound according to the present invention can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., using a principle similar to that applied to organic light-emitting devices.

[0105] Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these embodiments are intended to illustrate the present invention more specifically, and the scope of the present invention is not limited thereby. It will be apparent to those skilled in the art that various changes and modifications are possible within the scope and technical spirit of the present invention.

[0106]

[0107] Synthesis Example 1: Synthesis of Compound 3

[0108] (1) Manufacturing Example 1: Synthesis of Intermediate 3-1

[0109]

[0110] To a solution of B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.0 g, 0.035 mol), 3-Bromo-4-nitrobenzenamine (9.1 g, 0.042 mol), K2CO3 (14.4 g, 0.105 mol), and Pd(PPh3)4 (0.8 g, 0.7 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added and stirred at 80 °C for 6 hours. After the reaction was completed, the mixture was extracted, concentrated, and then purified by column chromatography to obtain 7.7 g (yield 58.3%) of <Intermediate 3-1>.

[0111]

[0112] (2) Manufacturing Example 2: Synthesis of Intermediate 3-2

[0113]

[0114] Intermediate 3-1 (10.0 g, 0.026 mol), 1-Bromo-2-chlorobenzene (7.6 g, 0.040 mol), NaOtBu (7.6 g, 0.079 mol), Pd(dba)2 (0.6 g, 1.1 mmol), t-Bu3P (0.4 g, 2.1 mmol) was added to 150 mL of xylene and reacted by stirring at 70°C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then purified by column chromatography to obtain 8.9 g (yield 68.9%) of <Intermediate 3-2>.

[0115]

[0116] (3) Manufacturing Example 3: Synthesis of Intermediate 3-3

[0117]

[0118] Intermediate 3-2 (10.0 g, 0.020 mol), Cs2CO3 (20.0 g, 0.061 mol), PCy3HBF4 (0.8 g, 2.0 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), and 500 mL of DMAC were added and stirred at 130°C for 5 hours to allow the reaction. After the reaction, the product was extracted, concentrated, and then purified by column chromatography to obtain 7.1 g (yield 76.7%) of <Intermediate 3-3>.

[0119]

[0120] (4) Manufacturing Example 4: Synthesis of Intermediate 3-4

[0121]

[0122] Intermediate 3-3 (10.0 g, 0.022 mol), Fluorobenzene (2.5 g, 0.027 mol), Cs2CO3 (4.6 g, 0.033 mol) were added to 500 mL of DMF and reacted by refluxing at 150 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then purified by column chromatography to obtain 7.9 g (yield 67.7%) of <Intermediate 3-4>.

[0123]

[0124] (5) Manufacturing Example 5: Synthesis of Intermediate 3-5

[0125]

[0126] Intermediate 3-4 (10.0 g, 0.019 mol), PPh3 (12.4 g, 0.047 mol), and 350 mL of DCB were added and reacted by reflux stirring at 180°C for 3 hours. After the reaction, the mixture was extracted, concentrated, and then column chromatographed and recrystallized to obtain 5.8 g (yield 61.7%) of <Intermediate 3-5>.

[0127]

[0128] (6) Manufacturing Example 6: Synthesis of Compound 3

[0129]

[0130] Intermediate 3-5 (10.0 g, 0.020 mol), 4-Bromobiphenyl (7.0 g, 0.030 mol), NaOtBu (5.8 g, 0.060 mol), Pd(dba)2 (0.5 g, 0.8 mmol), t-Bu3P (0.5 g, 2.4 mmol) were added to 150 mL of xylene and reacted by stirring at 70°C for 4 hours. After completion of the reaction, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 9.2 g (yield 70.5%) of <Compound 3>.

[0131] LC / MS: m / z=649[(M) + ]

[0132]

[0133] Synthesis Example 2: Synthesis of Compound 12

[0134] (1) Manufacturing Example 1: Synthesis of Compound 12

[0135]

[0136] Intermediate 3-5 (10.0 g, 0.020 mol), 4-Bromo-9-phenyl-9H-carbazole (9.7 g, 0.030 mol), NaOtBu (5.8 g, 0.060 mol), Pd(dba)2 (0.5 g, 0.8 mmol), t-Bu3P (0.3 g, 1.6 mmol) were mixed with 150 mL of xylene and reacted at 70°C for 4 hours. After completion of the reaction, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 9.7 g (yield 65.3%) of <Compound 12>.

[0137] LC / MS: m / z=738[(M) + ]

[0138]

[0139] Synthesis Example 3: Synthesis of Compound 16

[0140] (1) Manufacturing Example 1: Synthesis of Compound 16

[0141]

[0142] Intermediate 3-5 (10.0 g, 0.020 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.1 g, 0.030 mol), NaOtBu (5.8 g, 0.060 mol), Pd(dba)2 (0.5 g, 0.8 mmol), t-Bu3P (0.3 g, 1.6 mmol) were added to 150 mL of xylene and reacted by stirring at 120 °C for 4 hours. After completion of the reaction, extraction was performed, concentration was performed, and then column chromatography and recrystallization were performed to obtain 8.9 g (yield 60.8%) of <Compound 16>.

[0143] LC / MS: m / z=728[(M) + ]

[0144]

[0145] Synthesis Example 4: Synthesis of Compound 45

[0146] (1) Manufacturing Example 1: Synthesis of intermediate 45-1

[0147]

[0148] To a solution of B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.0 g, 0.035 mol), 3-Bromo-4-methoxybenzenamine (8.4 g, 0.042 mol), K2CO3 (14.4 g, 0.105 mol), and Pd(PPh3)4 (0.8 g, 0.7 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added and stirred at 80 °C for 6 hours to react. After the reaction was completed, the mixture was extracted, concentrated, and then purified by column chromatography to obtain 7.4 g (yield 58.3%) of <Intermediate 45-1>.

[0149]

[0150] (2) Manufacturing Example 2: Synthesis of Intermediate 45-2

[0151]

[0152] Intermediate 45-1 (10.0 g, 0.027 mol), 1-Bromo-2-chlorobenzene (7.9 g, 0.041 mol), NaOtBu (7.9 g, 0.082 mol), Pd(dba)2 (0.6 g, 1.1 mmol), t-Bu3P (0.4 g, 2.2 mmol) was added to 150 mL of xylene and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then purified by column chromatography to obtain 8.3 g (yield 63.7%) of <Intermediate 45-2>.

[0153]

[0154] (3) Manufacturing Example 3: Synthesis of Intermediate 45-3

[0155]

[0156] Intermediate 45-2 (10.0 g, 0.021 mol), Cs2CO3 (20.6 g, 0.063 mol), PCy3HBF4 (0.8 g, 2.1 mmol), Pd(OAc)2 (0.2 g, 1.1 mmol), and 500 mL of DMAC were added and reacted by stirring at 130°C for 5 hours. After the reaction, the product was extracted, concentrated, and then purified by column chromatography to obtain 6.6 g (yield 71.5%) of <Intermediate 45-3>.

[0157]

[0158] (4) Manufacturing Example 4: Synthesis of intermediate 45-4

[0159]

[0160] Intermediate 45-3 (10.0 g, 0.023 mol), Fluorobenzene (2.6 g, 0.027 mol), Cs2CO3 (4.7 g, 0.034 mol) were added to 500 mL of DMF and reacted by refluxing at 150 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then purified by column chromatography to obtain 7.4 g (yield 63.1%) of <Intermediate 45-4>.

[0161]

[0162] (5) Manufacturing Example 5: Synthesis of Intermediate 45-5

[0163]

[0164] Intermediate 45-4 (10.0 g, 0.019 mol) was dissolved in 60 mL of anhydrous DCM. Then, BBr3 (in DCM, 12.2 g, 0.049 mol) was added dropwise while maintaining the temperature at 0°C, and the mixture was stirred at 25°C for 16 hours to allow the reaction. After completion of the reaction, the mixture was extracted, concentrated, and then column chromatographed and recrystallized to obtain 7.4 g (yield 76.1%) of <Intermediate 45-5>.

[0165]

[0166] (6) Manufacturing Example 6: Synthesis of Compound 45

[0167]

[0168] Intermediate 45-5 (10.0 g, 0.020 mol), Pd(OAc)2 (0.4 g, 2.0 mmol), and 3-nitropyridine (0.2 g, 2.0 mmol) were dissolved in C6F6 and DMI, and TBPB (7.8 g, 0.040 mol) was added and stirred at 90°C to react. After completion of the reaction, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 7.4 g (yield 74.3%) of <Compound 45>.

[0169] LC / MS: m / z=498[(M) + ]

[0170]

[0171] Component Example (Green Host)

[0172] In an embodiment according to the present invention, an ITO transparent electrode was patterned on a glass substrate measuring 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate with an ITO transparent electrode attached, so that the light-emitting area was 2 mm × 2 mm, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 -6 After making it torr, the organic material and metal were deposited on the ITO in the following structure.

[0173]

[0174] Device Examples 1 to 15

[0175] An organic light-emitting device having the following device structure was manufactured by employing a compound implemented according to the present invention as a host, and the light-emitting characteristics including current efficiency were measured.

[0176]

[0177] ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (HT1, 100 nm) / electron blocking layer (EB1, 10 nm) / emitting layer (first host: second host: Ir(ppy)3, 30 nm) / electron transport layer (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)

[0178]

[0179] In order to form a hole injection layer on top of an ITO transparent electrode, [HAT-CN] was deposited with a thickness of 5 nm, and then a hole transport layer was deposited with a thickness of 100 nm using [HT1]. A hole blocking layer was deposited with a thickness of 10 nm using [EB1]. In addition, the host for the light-emitting layer was composed of a first host and a second host using the compounds according to the present invention described in [Table 1] below, mixed in a ratio of 6:4 to use a mixed host, and the dopant was doped with Ir(ppy)3 and co-deposited with a thickness of 30 nm. Additionally, a 30 nm thick electron transport layer (doped with 50% Liq of the [ET1] compound below) was deposited. Then, LiF was deposited with a thickness of 1 nm as an electron injection layer, and then 100 nm of Al was deposited to manufacture an organic light-emitting device.

[0180]

[0181] Component Comparison Example 1

[0182] The organic light-emitting device for Comparative Example 1 was manufactured in the same manner as in Examples 1 to 15 except that the compound according to the present invention was replaced with [GH1] as the first host.

[0183]

[0184] Experimental Example 1: Luminescence characteristics of device examples 1 to 15

[0185] For the organic light-emitting devices manufactured according to the above examples and comparative examples, the driving voltage, current efficiency, and color coordinates were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the results based on 10,000 nit are as shown in [Table 1] below.

[0186] Example 1 Host 2 Host Vcd / ACIExCIEy1 Compound 3GH2 3.575 3.47 0.321 0.6152 Compound 53.64 54.07 0.320 0.6203 Compound 73.58 53.42 0.325 0.6174 Compound 123.52 53.59 0.321 0.6235 Compound 163.60 52.98 0.323 0.6186 Compound 223.65 53.82 0.317 0.6157 Compound 353.59 54.84 0.326 0.6208 Compound 423.57 53.47 0.321 0.6159 Compound Compound 453.6852.350.3240.60810 Compound 483.6352.560.3170.61111 Compound 743.6750.940.3210.61712 Compound 943.7151.710.3140.60913 Compound 1053.6852.110.3180.61314 Compound 1113.7251.820.3230.61815 Compound 1303.6652.540.3250.615 Comparative Example 1GH1GH24.0545.270.3280.604

[0187] Looking at the results shown in [Table 1] above, it can be confirmed that in an organic light-emitting device employing a light-emitting layer composed of a plurality of host compounds, when the compound according to the present invention is employed as the first host or the second host in the light-emitting layer, the light-emitting characteristics such as low-voltage driving characteristics and current efficiency are significantly superior to a device (Comparative Example 1) employing a compound used as a conventional host compound as a host.

[0188]

[0189] [HAT-CN] [HT1] [EB1] [ET1]

[0190]

[0191] [GH1] [GH2] [Ir(ppy)3]

[0192]

[0193] Component Example (Blue Host)

[0194] In an embodiment according to the present invention, an ITO transparent electrode was patterned on a glass substrate measuring 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate with an ITO transparent electrode attached, so that the light-emitting area was 2 mm × 2 mm, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 -6 After making it torr, the organic material and metal were deposited on the ITO in the following structure.

[0195]

[0196] Element Examples 16 to 30

[0197] After fabricating an organic light-emitting device having the following device structure by employing the compound implemented according to the present invention as a light-emitting layer host compound, the light-emitting characteristics including current efficiency were measured.

[0198]

[0199] ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (HT1, 100 nm) / electron blocking layer (EB1, 10 nm) / emitting layer (first host: second host: BD1, 30 nm) / electron transport layer (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)

[0200]

[0201] In order to form a hole injection layer on top of an ITO transparent electrode, [HAT-CN] below was deposited with a thickness of 5 nm, and then a hole transport layer was deposited with a thickness of 100 nm using [HT1] below. An electron blocking layer was deposited with a thickness of 10 nm using [EB1] below. In addition, the host for the light-emitting layer was composed of a first host and a second host using the compounds according to the present invention described in [Table 2] below, mixed in a 1:1 ratio to use a mixed host, and the dopant was doped with 10% of [BD1] below and co-deposited with a thickness of 30 nm. In addition, a 30 nm thick electron transport layer (50% doped with Liq of the [ET1] compound below) was deposited, and a 1 nm thick LiF was deposited as an electron injection layer, and finally, 100 nm of Al was deposited to manufacture an organic light-emitting device.

[0202]

[0203] Component Comparison Example 2

[0204] The organic light-emitting device for device comparison example 2 was manufactured in the same manner as in the device structures of Examples 16 to 30, except that the following [BH1] was used instead of the compound according to the present invention as the first host.

[0205]

[0206] Experimental Example 2: Luminescence characteristics of device examples 16 to 30

[0207] The driving voltage, current efficiency, and color coordinates of the organic light-emitting device manufactured according to the above examples and comparisons were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the results based on 1,000 nit are as shown in [Table 2] below.

[0208] Example 1 Host 2 Host Vcd / ACIExCIEy16 Compound 3BH2 5.24 23.0 20.155 0.297 17 Compound 55.30 23.56 0.162 0.280 18 Compound 75.18 22.87 0.163 0.286 19 Compound 125.31 23.86 0.160 0.288 20 Compound 165.27 24.9 40.154 0.290 21 Compound 225.20 23.52 0.158 0.293 22 Compound 355.17 24.08 0.160 0.288 23 Compound 425.24 24.0 20.155 0.297 24 Compound Compound 455.1623.990.1570.28425 Compound 485.2523.170.1650.29226 Compound 745.3123.220.1610.28627 Compound 945.2722.280.1610.29028 Compound 1055.2223.500.1560.28929 Compound 1115.2622.160.1570.29330 Compound 1305.2322.380.1630.296 Comparative Example 2BH1BH25.5020.310.1600.290

[0209] Looking at the results shown in [Table 2] above, it can be confirmed that in an organic light-emitting device employing a light-emitting layer composed of a plurality of host compounds, when the compound according to the present invention is employed as the first host or the second host in the light-emitting layer, the light-emitting characteristics such as low-voltage driving characteristics and current efficiency are significantly superior to a device (Comparative Example 2) employing a compound used as a conventional host compound as a host.

[0210]

[0211] [HAT-CN] [HT1] [EB1] [ET1]

[0212]

[0213] [BH1] [BH2] [BD1]

[0214] The organic compound according to the present invention can be used as a host material for a light-emitting layer in an organic light-emitting device due to its characteristic polycyclic ring skeleton and the characteristics of the moiety structure introduced therein, thereby realizing an organic light-emitting device having excellent device characteristics such as color purity, light-emitting efficiency, and quantum efficiency, and thus can be usefully utilized industrially in various displays and lighting devices.

Claims

1. Organic compound represented by the following [chemical formula Ⅰ]: [Chemical Formula I] In the above [chemical formula Ⅰ], R1 to R4 are the same or different, and each independently represent one selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a cyano group, and a halogen group. o and p are each an integer from 0 to 3, q ​​is an integer from 0 to 4, s is an integer from 0 to 2, and when o, p, q and s are 2 or more, a plurality of R1 to R4 are each the same or different from each other, X1 and X2 are the same or different and are each independently selected from O, S, CR5R6, NR7 and SiR8R9, Y1 is O, S, CR 10 R 11 , NR 12 and SiR 13 R 14 One of the following is selected: Above R5 to R 14 are the same or different from each other, and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, The above R5 and R6; R8 and R9; R 10 and R 11 ; and R 13 and R 14 ; can be connected to each other to form a monocyclic or polycyclic ring of alicyclic or aromatic group, D is deuterium, n means the number of hydrogen atoms in the above [chemical formula Ⅰ] replaced with deuterium (D), and n is an integer from 0 to 60.

2. In paragraph 1, R1 to R in the above [chemical formula Ⅰ] 14 In the definition of 'substituted or unsubstituted' means R1 to R 14 An organic compound which is substituted with one or two or more substituents selected from among deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aliphatic aromatic mixed ring group, an amine group, a silyl group, and a germanium group, or wherein two or more of the above substituents are substituted with a linked substituent, or has no substituent.

3. In paragraph 1, The above [chemical formula Ⅰ] is an organic compound characterized in that each hydrogen present in [chemical formula Ⅰ] is partially substituted with deuterium (D), and the deuterium (D) substitution rate is 10 to 90%.

4. In paragraph 3, An organic compound characterized by a deuterium (D) substitution rate of 20 to 80%.

5. In paragraph 4, An organic compound characterized by a deuterium (D) substitution rate of 30 to 70%.

6. In paragraph 1, The above [chemical formula Ⅰ] is an organic compound characterized by being any one selected from the following [compound 1] to [compound 130]:

7. An organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises an organic compound of [chemical formula Ⅰ] according to claim 1.

8. In paragraph 7, The above organic layer includes at least one layer among 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, An organic light-emitting device characterized in that at least one of the above layers comprises an organic compound represented by the above [chemical formula Ⅰ].

9. In paragraph 8, An organic light-emitting device characterized in that the light-emitting layer includes an organic compound represented by the above-described [chemical formula Ⅰ].

10. In paragraph 9, An organic light-emitting device characterized in that the organic compound represented by the above [chemical formula Ⅰ] is a host material in the light-emitting layer.

11. In paragraph 10, An organic light-emitting device characterized in that the host material is composed of a plurality of compounds mixed or laminated, including at least one compound other than the organic compound represented by the above-mentioned [chemical formula Ⅰ].

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