Organic compound and organic light-emitting device comprising same

Abstract

The present invention relates to an organic compound and an organic light-emitting device employing same and, more specifically, to an organic compound which is employed as an organic layer material in an organic light-emitting device, preferably as a host material of a light-emitting layer, to enable excellent light-emitting and quantum efficiency in the organic light-emitting device and which can be usefully employed in various displays, lighting devices, and the like.

Description

Organic compounds and organic light-emitting diodes containing the same

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

[0002] Organic light-emitting diodes (OLEDs) can be formed on transparent substrates, and compared to plasma display panels or inorganic light-emitting diode (EL) displays, they have the advantages of being able to operate at a low voltage of 10 V or less, consuming relatively little power, and having excellent color quality, and can display three colors of green, blue, and red, so they have recently become the subject of much interest as next-generation display devices.

[0003] However, for such organic light-emitting diodes to exhibit the characteristics described above, it is necessary for the materials constituting the organic layer within the device—such as the hole injection layer, hole transport layer, hole blocking layer, emissive layer host and dopant, electron blocking layer, electron transport layer, and electron injection layer—to be supported by stable and efficient materials; yet, the development of stable and efficient organic layer materials for organic light-emitting diodes has not yet been sufficiently achieved.

[0004] Therefore, in order to realize more stable organic light-emitting diodes and to achieve high efficiency, long lifespan, and large scale, further improvements in efficiency and lifespan characteristics are required; in particular, there is an urgent need for the development of materials constituting each organic layer of the organic light-emitting diode.

[0005] In particular, to obtain maximum efficiency in the emissive layer, the energy band gaps of the host and the dopant must be in a suitable combination 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 capable of realizing excellent characteristics in terms of color purity, luminous efficiency, and quantum efficiency when employed as a host material for the light-emitting layer in an organic light-emitting device, and an organic light-emitting device containing the same.

[0007] 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 comprising 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 by it, as well as the definitions of each substituent, will be described later.

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

[0012] The present invention will be described in more detail below.

[0013] The present invention relates to an organic compound represented by the following [Chemical Formula I], which is employed as a host material for the light-emitting layer in an organic light-emitting device due to the characteristics of its characteristic skeletal structure and the moiety structure introduced therein. Furthermore, according to one embodiment of the present invention, 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], thereby enabling the realization of an organic light-emitting device having excellent device characteristics in terms of color purity, luminous efficiency, and quantum efficiency.

[0014] [Chemical Formula I]

[0015]

[0016] In the above [Chemical Formula I],

[0017] L1 and L2 are identical or different from each other and are each independently selected from arylene groups having 6 to 30 carbon atoms that are directly bonded, substituted, or unsubstituted.

[0018] n and m are integers from 0 to 2, and when n and m are 2, multiple L1 and L2 are each the same or different from each other.

[0019] R1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

[0020] R2 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0021]

[0022] According to one embodiment of the present invention, the R1 may be any one selected from the following [Structural Formula 1].

[0023] [Structural Formula 1]

[0024]

[0025] In the above [Structural Formula 1],

[0026] X1 is O, S, NR3, CR4R5.

[0027] The above R3 and R5 are identical or different from each other and are each independently selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0028] In addition, the above R4 and R5 can combine with each other to form a monocyclic or polycyclic ring of alicyclic or aromatic groups.

[0029] '*' is the part connected to the above L1.

[0030]

[0031] In addition, according to one embodiment of the present invention, R2 may be any one selected from among a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophen group and a substituted or unsubstituted dibenzofuranyl group.

[0032]

[0033] Meanwhile, in the present invention, the term "substituted or unsubstituted" as described above means that each of the substituents defined above is substituted with one or more substituents selected from deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, halogenated alkyl group, alkoxy group, halogenated alkoxy group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, amine group, silyl group, and germanium group, or is substituted with a substituent in which two or more of the substituents are connected, or has no substituents at all.

[0034] In addition, the hydrogen within the further substituted substituent can be substituted with one or more deuterium, and two or more adjacent substituents can be connected to each other to additionally form a monocyclic or polycyclic ring of alicyclic or aromatic.

[0035] For specific examples, the term "substituted aryl group" means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, anthracenyl group, etc., are substituted with other substituents such as deuterium, and the term "substituted heteroaryl group" means that 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., are also substituted with other substituents such as deuterium.

[0036]

[0037] In addition, the meaning of forming an additional ring by connecting to each other or adjacent groups in the present invention means that adjacent substituents among each specified substituent may combine with each other, or a specified substituent and another adjacent group may combine with each other to form a substituted or unsubstituted alicyclic or aromatic ring, and 'adjacent group' may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in stereostructure, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as 'adjacent groups' to each other.

[0038]

[0039] In the present invention, the alkyl group may be a straight chain or a branched chain, and specific examples 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 cycloheptylmethyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group. There are, but are not limited to, 2-propylpentyl groups, n-nonyl groups, 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc.

[0040] In the present invention, the alkoxy group may be a straight chain or a branched chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 20, which is within the range that does not cause steric interference. 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.

[0041] In the present invention, the alkyl group and the alkoxy group may each be a deuterated alkyl group or alkoxy group, a halogenated alkyl group or alkoxy group, and the alkyl group or alkoxy group means an alkyl group or alkoxy group substituted with a deuterated or halogen group.

[0042] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and polycyclic means a group that is directly connected to or condensed with another ring group, and the other ring group may be an aromatic hydrocarbon ring, but may also be other types of ring groups, such as an aliphatic heterocycle, an aliphatic hydrocarbon ring, an aromatic heterocycle, etc. Examples of monocyclic aryl groups include phenyl groups, biphenyl groups, terphenyl groups, etc., and examples of polycyclic aryl groups include naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, perylenyl groups, tetracenyl groups, chrysenyl groups, fluorenyl groups, acenaphthacenyl groups, triphenylene groups, fluoranthene groups, etc., but the scope of the present invention is not limited only to these examples.

[0043] In the present invention, the fluorene in the fluorenyl group or fluorene moiety, etc., is a structure in which two ring organic compounds are connected through one atom, and examples include , , There are others.

[0044] In addition, it includes open fluorene structures, where open fluorene is a structure in which the connection of one ring compound is broken in a structure in which two ring organic compounds are connected through one atom, examples include , There are others.

[0045] In addition, the carbon atoms of the above ring may be substituted with one or more heteroatoms selected from N, S, and O, examples include , , , There are others. In the present invention, the fluorene in the fluorenyl group or fluorene moiety, etc., is a structure in which two ring organic compounds are connected through one atom, and examples include , , There are others.

[0046] In addition, in the present invention, the fluorenyl group may be a structure in which a monocyclic or polycyclic aromatic ring and a monocyclic or polycyclic alicyclic ring, etc. are further condensed into the above-mentioned connected structure or open structure.

[0047] In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring comprising one or more heteroatoms, 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 acryl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazolin group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl 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 benzothiophen group, a dibenzothiophen group. There are benzofuranyl groups, dibenzofuranyl groups, phenanthroline groups, thiazolyl groups, isooxazolyl groups, oxadiazoyl groups, thiadiazolyl groups, benzothiazoyl groups, phenothiazinyl groups, etc., but are not limited to these.

[0048] In the present invention, an aliphatic hydrocarbon ring or a cycloalkyl group refers to a ring that is not aromatic and consists only of carbon and hydrogen atoms, and includes, as examples, a monocyclic or polycyclic group, and may be further substituted by other substituents, and a polycyclic group refers to 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 other types of ring groups, such as an aliphatic heterocyclic ring, an aromatic hydrocarbon ring, an aromatic heterocyclic ring, etc. Specifically, it includes, but is not limited to, cycloalkyls such as cyclopropyl group, cyclobutyl group, cyclopentyl group, adamantyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., cycloalkanes such as cyclohexane, cyclopentane, etc., and cyclocycloalkenes such as cyclohexene, cyclobutene, etc.

[0049] In the present invention, an aliphatic heterocycle or a heterocycloalkyl group refers to an aliphatic ring comprising one or more heteroatoms, and includes heteroatoms such as O, S, Se, N, or Si, and also includes a monocyclic or polycyclic group, and may be further substituted by other substituents, and polycyclic refers to a group in which a heterocycloalkyl, a heterocycloalkane, etc. is directly connected or condensed with another ring group, and the other ring group may be an aliphatic heterocycle, but may also be a different type of ring group, such as an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aromatic heterocycle, etc.

[0050] 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. Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.

[0051] In the present invention, the germanium group (or germane group) may include -GeH3, alkyl germanium group, aryl germanium group, heteroaryl germanium group, alkylaryl germanium group, alkyl heteroaryl germanium group, aryl heteroaryl germanium group, etc., and their definitions may be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) instead of a silicon atom (Si) in the silyl group.

[0052] In addition, specific examples of the germanium group include trimethylgermaine, triethylgermaine, triphenylgermaine, trimethoxygermaine, dimethoxyphenylgermaine, diphenylmethylgermaine, diphenylvinylgermaine, methylcyclobutylgermaine, dimethylfurylgermaine, etc., and one or more hydrogen atoms of the germanium group can be substituted with substituents similar to those in the case of the aryl group.

[0053] In the present invention, the amine group may be -NH2, an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., and the arylamine group refers to an amine substituted with an aryl group, the alkylamine group refers to an amine substituted with an alkyl group, and the arylheteroarylamine group refers to an amine substituted with an aryl and a heteroaryl group. Examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group and heteroaryl group among the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group, a polycyclic heteroaryl group. The arylamine group and arylheteroarylamine group comprising two or more aryl groups and heteroaryl groups may be a monocyclic aryl group (heteroaryl group). It may include a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group) and a polycyclic aryl group (heteroaryl group) simultaneously. Additionally, the aryl group and heteroaryl group among the arylamine group and the arylheteroarylamine group may be selected from the examples of aryl groups and heteroaryl groups described above.

[0054] Specific examples of halogen groups used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), etc.

[0055] In addition, various specific examples of substituents according to the present invention can be clearly identified in the specific compounds described below.

[0056]

[0057] The organic compound according to the present invention represented by [Chemical Formula I] above can be used as an organic layer of an organic light-emitting diode due to the structural peculiarities of the skeletal structure and the introduced moiety as described above, and more specifically, can be used as a host material for the light-emitting layer within the organic layer.

[0058] Preferred embodiments of the compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited thereto.

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] As such, the organic compound according to the present invention can synthesize compounds having various characteristics through a characteristic skeletal structure and a moiety having unique characteristics introduced therein, and as a result, when the organic compound according to the present invention is applied as a various organic layer material such as a light-emitting layer, the luminescence characteristics such as the luminescence efficiency of the device can be further improved, and preferably, an organic light-emitting device having excellent luminescence characteristics can be realized by using it as a light-emitting layer host material.

[0099]

[0100] 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, wherein the organic layers preferably comprise a host, a compound of [Chemical Formula I] according to the present invention as defined above, within a light-emitting layer comprising a host and a dopant.

[0101] [Chemical Formula I]

[0102]

[0103]

[0104] In addition, the light-emitting layer has a structure composed of a host and a dopant, and the light-emitting layer may further include a dopant material, wherein the content of the dopant can typically be selected in 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.

[0105] In addition, the light-emitting layer may further include various hosts and various dopant materials in addition to the host and dopant compounds according to the present invention, and accordingly, among the light-emitting layers, one or more different compounds as well as dopant materials may be mixed or laminated.

[0106]

[0107] The organic layer of the organic light-emitting diode according to the present invention may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are stacked. 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.

[0108] Accordingly, an 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.

[0109]

[0110] In addition, according to one embodiment of the organic light-emitting diode according to the present invention, the dopant may include at least one organometallic compound, and may also be configured to include a thermally activated delayed fluorescence (TADF) material in addition to the organometallic compound, and in this case, the dopant material may also be used by mixing or stacking.

[0111] Accordingly, in an organic light-emitting device according to one embodiment of the present invention, the light-emitting layer may be composed of a first host, a second host, an organometallic compound, and a thermally activated delayed fluorescence (TADF) material, and in this case, an organic compound represented by [Chemical Formula I] according to the present invention may be used as the host material.

[0112] In this case, the organometallic compound functions as a sensorizer and the TADF material functions as a luminescent dopant, so that the sensorizer compound can receive excitons from the first host and the second host and transfer them to the luminescent dopant.

[0113] Accordingly, excitons from the sensorizer are transferred to a luminescent dopant compound through a dexter energy transfer (DET) or Forster resonance transfer (FRET) mechanism, and the exciton energy transferred to the luminescent dopant compound can emit light as it transitions to the ground state. At this time, the excitons of the sensorizer may be formed by being transferred from the first host and the second host via the FRET mechanism, or by excitons generated from the host being transferred via the DET mechanism.

[0114] Accordingly, energy transfer by FRET and DET mechanisms between the sensorizer and the light-emitting dopant is facilitated, and triplet-triplet extinction is suppressed, making it possible to fabricate high-efficiency organic light-emitting diodes.

[0115] In addition, the delayed fluorescent emitter enables Forster energy transfer from the triplet of the phosphorescence sensitizer to the singlet of the delayed fluorescent emitter, thereby reducing the number of long-life triplet excitons involved in device degradation and improving the lifespan.

[0116] 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 multiple resonance effects, which increases color purity.

[0117]

[0118] An organic compound represented by [Chemical Formula I] according to the present invention can be applied to an organic light-emitting diode according to a conventional manufacturing method.

[0119] An organic light-emitting device according to one embodiment of the present invention may be formed with a structure including a first electrode, a second electrode, and an organic layer disposed between them, and may be manufactured using conventional manufacturing methods and materials for devices, except that a compound according to the present invention is used in the organic layer of the device.

[0120] The structure of the organic layer of a preferred organic light-emitting diode according to the present invention will be explained in more detail in the embodiments described below.

[0121]

[0122] In addition, the organic light-emitting diode according to the present invention can be manufactured by using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, 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, and an electron blocking layer on the anode, and then depositing a material that can be used as a cathode on the anode.

[0123] In addition to the above method, an organic light-emitting diode can also be fabricated 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 emitting layer, an electron blocking layer, an electron transport layer, and an electron blocking layer, but is not limited thereto and may have a single-layer structure. Furthermore, the organic layer can be manufactured with fewer layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0124]

[0125] The anode is typically an organic layer, and a material with a high work function is preferred to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include 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, but are not limited to these.

[0126] The cathode is typically an organic layer, and it is desirable that the material has a small work function to facilitate electron injection. Specific examples of cathode materials include 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, but are not limited to these.

[0127] The hole injection layer is a material capable of effectively receiving holes from the anode at low voltage, and it is desirable 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 metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited to these.

[0128] The hole transport layer is a material capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer; materials with high hole mobility are suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0129] The electron blocking layer is a layer that blocks the movement of electrons and can be formed on a hole transport layer, and as the electron blocking layer, a material capable of blocking the movement of electrons without affecting the transport of holes can be used. 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.

[0130] The hole blocking layer may be capable of blocking the movement of holes without affecting electron transport, 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), etc. ...and is not limited to this.

[0131] The emissive layer is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material with good quantum efficiency for fluorescence or phosphorescence is preferred. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene.

[0132] The electron injection layer can be one that has a high electron injection efficiency transferred from the cathode. Examples of such electron injection layers include lithium quinoleate (Liq), but are not limited thereto.

[0133] The electron transport layer is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes, but are not limited to these.

[0134]

[0135] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0136] In addition, the organic compound according to the present invention can also function in organic electronic devices, including organic solar cells, organic photosensitive materials, and organic transistors, using a principle similar to that applied to organic light-emitting diodes.

[0137] The present invention will be described in more detail below with reference to preferred embodiments. However, these embodiments are intended to explain the invention more specifically, and the scope of the invention is not limited by them. It will be obvious to those skilled in the art that various changes and modifications are possible within the scope and spirit of the invention.

[0138]

[0139] Synthesis Example 1: Synthesis of Compound 1

[0140] (1) Preparation Example 1: Synthesis of Intermediate 1-1

[0141]

[0142] 200 mL of dioxane was added to 2-bromo-4,6-diphenyldibenzo[b,d]furan (10.0 g, 0.025 mol), Bis(pinacolato)diboron (7.6 g, 0.030 mol), KOAc (10.38 g, 0.0751 mol), and Pd(dppf)Cl2 (0.92 g, 0.0013 mol), and the mixture was reacted by stirring at 100 ℃ for 12 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.6 g (yield 68%) of <Intermediate 1-1>.

[0143]

[0144] (2) Preparation Example 2: Synthesis of Intermediate 1-2

[0145]

[0146] 800 mL of THF and 200 mL of H2O were added to cyanuric chloride (10.0 g, 0.0542 mol), intermediate 1-1 (29.05 g, 0.0651 mol), K2CO3 (22.49 g, 0.1627 mol), and Pd(PPh3)4 (1.25 g, 0.0011 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 12.2 g (yield 48%) of <intermediate 1-2>.

[0147]

[0148] (3) Preparation Example 3: Synthesis of Intermediates 1-3

[0149]

[0150] 300 mL of THF and 75 mL of H2O were added to intermediate 1-2 (10.0 g, 0.0214 mol), (9-phenyl-9H-carbazol-2-yl)boronic acid (7.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8.94 g (yield 62%) of <intermediate 1-3>.

[0151]

[0152] (4) Preparation Example 4: Synthesis of Compound 1

[0153]

[0154] 7H-benzofuro[2,3-b]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediates 1-3 (10 g, 0.0148 mol) were added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 9.1 g (yield 68.6%) of <Compound 1>.

[0155] LC / MS: m / z=896[(M)+]

[0156]

[0157] Synthesis Example 2: Synthesis of Compound 3

[0158] (1) Preparation Example 1: Synthesis of Intermediate 3-1

[0159]

[0160] Intermediate 1-2 (10.0 g, 0.0214 mol), (9-phenyl-9H-carbazol-3-yl)boronic acid (7.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol) were mixed with 300 mL of THF and 75 mL of H2O and reacted at 100 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8.2 g of <Intermediate 3-1> (yield 56.88%).

[0161]

[0162] (2) Preparation Example 2: Synthesis of Compound 3

[0163]

[0164] 7H-benzofuro[2,3-b]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediates 1-3 (10 g, 0.0148 mol) were added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.4 g (yield 63.3%) of <Compound 3>.

[0165] LC / MS: m / z=896[(M)+]

[0166]

[0167] Synthesis Example 3: Synthesis of Compound 9

[0168] (1) Preparation Example 1: Synthesis of Compound 9

[0169]

[0170] 11H-benzofuro[3,2-b]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 1-3 (10 g, 0.0148 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.8 g (yield 66.3%) of <Compound 9>.

[0171] LC / MS: m / z=896[(M)+]

[0172]

[0173] Synthesis Example 4: Synthesis of Compound 10

[0174] (1) Preparation Example 1: Synthesis of Compound 10

[0175]

[0176] 5H-benzofuro[3,2-c]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 1-3 (10 g, 0.0148 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.33 g (yield 62.7%) of <Compound 10>.

[0177] LC / MS: m / z=896[(M)+]

[0178]

[0179] Synthesis Example 5: Synthesis of Compound 13

[0180] (1) Preparation Example 1: Synthesis of Compound 13

[0181]

[0182] 8H-benzofuro[2,3-c]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 1-3 (10 g, 0.0148 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.42 g (yield 63.4%) of <Compound 13>.

[0183] LC / MS: m / z=896[(M)+]

[0184]

[0185] Synthesis Example 6: Synthesis of Compound 18

[0186] (1) Preparation Example 1: Synthesis of Intermediate 18-1

[0187]

[0188] 300 mL of THF and 75 mL of H2O were added to intermediate 1-2 (10.0 g, 0.0214 mol), [1,1'-biphenyl]-3-ylboronic acid (5.1 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.6 g (yield 60.4%) of <intermediate 18-1>.

[0189]

[0190] (2) Preparation Example 2: Synthesis of Compound 18

[0191]

[0192] 7H-benzofuro[2,3-b]carbazole (5.27 g, 0.0205 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.5 mL, 0.0188 mol) was added and stirred for 30 minutes. Subsequently, intermediate 18-1 (10 g, 0.0171 mol) was added dropwise, and the reaction was carried out by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.9 g (yield 64.6%) of <Compound 18>.

[0193] LC / MS: m / z=807[(M)+]

[0194]

[0195] Synthesis Example 7: Synthesis of Compound 21

[0196] (1) Preparation Example 1: Synthesis of Compound 21

[0197]

[0198] 11H-benzofuro[3,2-b]carbazole (5.27 g, 0.0205 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.5 mL, 0.0188 mol) was added and stirred for 30 minutes. Subsequently, intermediate 18-1 (10 g, 0.0171 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.47 g (yield 61.5%) of <Compound 21>.

[0199] LC / MS: m / z=807[(M)+]

[0200]

[0201] Synthesis Example 8: Synthesis of Compound 32

[0202] (1) Preparation Example 1: Synthesis of Intermediate 32-1

[0203]

[0204] 300 mL of THF and 75 mL of H2O were added to intermediate 1-2 (10.0 g, 0.0214 mol), naphthalen-2-ylboronic acid (4.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.1 g (yield 59.3%) of <intermediate 32-1>.

[0205]

[0206] (2) Preparation Example 2: Synthesis of Compound 32

[0207]

[0208] 5H-benzofuro[3,2-c]carbazole (5.51 g, 0.0214 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.9 mL, 0.0196 mol) was added and stirred for 30 minutes. Subsequently, intermediate 18-1 (10 g, 0.0179 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.18 g (yield 58.6%) of <Compound 32>.

[0209] LC / MS: m / z=781[(M)+]

[0210]

[0211] Synthesis Example 9: Synthesis of Compound 39

[0212] (1) Preparation Example 1: Synthesis of Intermediate 39-1

[0213]

[0214] 300 mL of THF and 75 mL of H2O were added to intermediate 1-2 (10.0 g, 0.0214 mol), dibenzo[b,d]furan-3-ylboronic acid (5.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.3 g (yield 57%) of <intermediate 39-1>.

[0215]

[0216] (2) Preparation Example 2: Synthesis of Compound 39

[0217]

[0218] 7H-benzofuro[2,3-b]carbazole (5.15 g, 0.0200 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.3 mL, 0.0183 mol) was added and stirred for 30 minutes. Subsequently, intermediate 39-1 (10 g, 0.0167 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 7.96 g (yield 58%) of <Compound 39>.

[0219] LC / MS: m / z=821[(M)+]

[0220]

[0221] Synthesis Example 10: Synthesis of Compound 43

[0222] (1) Preparation Example 1: Synthesis of Intermediate 43-1

[0223]

[0224] Intermediate 1-2 (10.0 g, 0.0214 mol), (4-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid (7.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol) were mixed with 300 mL of THF and 75 mL of H2O and reacted at 100 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.63 g (yield 52.85%) of <Intermediate 43-1>.

[0225]

[0226] (2) Preparation Example 2: Synthesis of Compound 43

[0227]

[0228] 7H-benzofuro[2,3-b]carbazole (4.57 g, 0.0177 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 43-1 (10 g, 0.0167 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 7.61 g (yield 57.3%) of <Compound 43>.

[0229] LC / MS: m / z=897[(M)+]

[0230]

[0231] Synthesis Example 11: Synthesis of Compound 45

[0232] (1) Preparation Example 1: Synthesis of Intermediate 45-1

[0233]

[0234] 300 mL of THF and 75 mL of H2O were added to intermediate 1-2 (10.0 g, 0.0214 mol), dibenzo[b,d]thiophen-3-ylboronic acid (5.8 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8 g of <intermediate 45-1> (yield 60.8%).

[0235]

[0236] (2) Preparation Example 2: Synthesis of Compound 45

[0237]

[0238] 7H-benzofuro[2,3-b]carbazole (5.01 g, 0.0195 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.1 mL, 0.0183 mol) was added and stirred for 30 minutes. Subsequently, intermediate 39-1 (10 g, 0.0162 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 9.13 g (yield 67.2%) of <Compound 45>.

[0239] LC / MS: m / z=837[(M)+]

[0240]

[0241] Synthesis Example 12: Synthesis of Compound 51

[0242] (1) Preparation Example 1: Synthesis of Intermediate 51-1

[0243]

[0244] 300 mL of THF and 75 mL of H2O were added to intermediate 1-2 (10.0 g, 0.0214 mol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (6.1 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.63 g (yield 52.85%) of <intermediate 51-1>.

[0245]

[0246] (2) Preparation Example 2: Synthesis of Compound 51

[0247]

[0248] 7H-benzofuro[2,3-b]carbazole (4.93 g, 0.0192 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7 mL, 0.0176 mol) was added and stirred for 30 minutes. Subsequently, intermediate 51-1 (10 g, 0.0160 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.8 g (yield 65%) of <Compound 51>.

[0249] LC / MS: m / z=847[(M)+]

[0250]

[0251] Synthesis Example 13: Synthesis of Compound 77

[0252] (1) Preparation Example 1: Synthesis of Intermediate 77-1

[0253]

[0254] 200 mL of dioxane was added to 1-chloro-4,6-diphenyldibenzo[b,d]furan (10.0 g, 0.0282 mol), Bis(pinacolato)diboron (8.6 g, 0.0338 mol), KOAc (8.3 g, 0.0845 mol), and Pd(dppf)Cl2 (1.03 g, 0.0014 mol), and the mixture was reacted by stirring at 100 ℃ for 12 hours. After the reaction was complete, the mixture was extracted, concentrated, and then column-processed to obtain 7.46 g (yield 59.3%) of <Intermediate 7-1>.

[0255]

[0256] (2) Preparation Example 2: Synthesis of Intermediate 77-2

[0257]

[0258] 800 mL of THF and 200 mL of H2O were added to cyanuric chloride (10.0 g, 0.0542 mol), intermediate 77-1 (22.49 g, 0.0651 mol), K2CO3 (22.49 g, 0.1627 mol), and Pd(PPh3)4 (1.25 g, 0.0011 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 11.5 g (yield 45.2%) of <intermediate 77-2>.

[0259]

[0260] (3) Preparation Example 3: Synthesis of Intermediate 77-3

[0261]

[0262] 300 mL of THF and 75 mL of H2O were added to intermediate 77-2 (10.0 g, 0.0214 mol), (9-phenyl-9H-carbazol-2-yl)boronic acid (7.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8.65 g (yield 60%) of <intermediate 77-3>.

[0263]

[0264] (4) Preparation Example 4: Synthesis of Compound 77

[0265]

[0266] 7H-benzofuro[2,3-b]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 77-3 (10 g, 0.0148 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.5 g (yield 64.2%) of <compound 77>.

[0267] LC / MS: m / z=896[(M)+]

[0268]

[0269] Synthesis Example 14: Synthesis of Compound 82

[0270] (1) Preparation Example 1: Synthesis of Compound 82

[0271]

[0272] 8H-benzofuro[2,3-c]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 77-3 (10 g, 0.0148 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.3 g (yield 62.6%) of <Compound 82>.

[0273] LC / MS: m / z=896[(M)+]

[0274]

[0275] Synthesis Example 15: Synthesis of Compound 85

[0276] (1) Preparation Example 1: Synthesis of Compound 85

[0277]

[0278] 5H-benzofuro[3,2-c]carbazole (4.57 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 6.5 mL, 0.0163 mol) was added and stirred for 30 minutes. Subsequently, intermediate 77-3 (10 g, 0.0148 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.3 g (yield 62.6%) of <Compound 85>.

[0279] LC / MS: m / z=896[(M)+]

[0280]

[0281] Synthesis Example 16: Synthesis of Compound 108

[0282] (1) Preparation Example 1: Synthesis of Intermediate 108-1

[0283]

[0284] 300 mL of THF and 75 mL of H2O were added to intermediate 77-2 (10.0 g, 0.0214 mol), naphthalen-2-ylboronic acid (4.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.34 g (yield 61.3%) of <intermediate 108-1>.

[0285]

[0286] (2) Preparation Example 2: Synthesis of Compound 108

[0287]

[0288] 7H-benzofuro[2,3-b]carbazole (5.51 g, 0.0178 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.9 mL, 0.0196 mol) was added and stirred for 30 minutes. Subsequently, intermediate 108-1 (10 g, 0.0179 mol) was added dropwise and reacted by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.5 g (yield 61.1%) of <compound 108>.

[0289] LC / MS: m / z=781[(M)+]

[0290]

[0291] Synthesis Example 17: Synthesis of Compound 119

[0292] (1) Preparation Example 1: Synthesis of Intermediate 119-1

[0293]

[0294] 300 mL of THF and 75 mL of H2O were added to intermediate 77-2 (10.0 g, 0.0214 mol), dibenzo[b,d]furan-2-ylboronic acid (5.4 g, 0.0256 mol), K2CO3 (8.85 g, 0.0641 mol), and Pd(PPh3)4 (0.49 g, 0.0004 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8 g of <intermediate 119-1> (yield 62.7%).

[0295]

[0296] (2) Preparation Example 2: Synthesis of Compound 119

[0297]

[0298] 7H-benzofuro[2,3-b]carbazole (5.15 g, 0.02 mol) was dissolved in THF (100 mL) and cooled to 0 °C. Then, nBuLi (2.5 M in hexane, 7.3 ml, 0.0183 mol) was added and stirred for 30 minutes. Subsequently, intermediate 108-1 (10 g, 0.0167 mol) was added dropwise, and the reaction was carried out by stirring at 70 °C for 15 hours. After the reaction was completed, the mixture was column-recrystallized to obtain 8.9 g (yield 65%) of <compound 108>.

[0299] LC / MS: m / z=821[(M)+]

[0300]

[0301] Device Example (Blue host)

[0302] In an embodiment according to the present invention, an ITO transparent electrode was patterned on a 25 mm × 25 mm × 0.7 mm glass substrate using an ITO glass substrate with an attached ITO transparent electrode to have a light-emitting area of ​​2 mm × 2 mm, and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 -6 After making the torr, the organic material and metal were deposited on the above ITO in the following structure.

[0303]

[0304] Device Examples 1 to 32

[0305] After fabricating an organic light-emitting diode having the following device structure by employing a compound implemented according to the present invention as a host compound for the light-emitting layer, luminescence characteristics including current efficiency were measured.

[0306]

[0307] ITO / Hole injection layer (HAT-CN, 5 nm) / Hole transport layer (HT1, 100 nm) / Electron blocking layer (EB1, 10 nm) / Emitting layer (1st host : 2nd host : BD1, 30 nm) / Electron transport layer (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)

[0308]

[0309] To form a hole injection layer on top of an ITO transparent electrode, the following [HAT-CN] was deposited to a thickness of 5 nm, and subsequently, a hole transport layer was deposited to a thickness of 100 nm using the following [HT1]. An electron blocking layer was deposited to a thickness of 10 nm using the following [EB1]. In addition, for the emissive layer, a mixed host was used by mixing the compounds according to the present invention listed in [Table 1] below as the first host compound and the second host compound in a 6:4 ratio, and the dopant was co-deposited to a thickness of 30 nm by doping with 10% of the following [BD1]. Additionally, an electron transport layer (doped with 50% Liq of the following [ET1] compound) was deposited to a thickness of 30 nm, LiF was deposited as the electron injection layer to a thickness of 1 nm, and finally, Al was deposited to a thickness of 100 nm to fabricate an organic light-emitting diode.

[0310]

[0311] Device Comparison Example 1

[0312] The organic light-emitting diode for Comparative Example 1 was fabricated in the same manner as the device structures of Examples 1 to 32, except that [BH1] was used as the first host instead of the compound according to the present invention, and [BH2] was used as the second host instead of the compound according to the present invention.

[0313]

[0314] Device Comparison Example 2

[0315] The organic light-emitting diode for Comparative Example 2 was fabricated in the same manner as the device structures of Examples 1 to 32, except that [BH1] was used as the first host instead of the compound according to the present invention, and [BH2-1] was used as the second host instead of the compound according to the present invention.

[0316]

[0317] Experimental Example 1: Luminescence characteristics of device Examples 1 to 32

[0318] For the organic light-emitting diodes manufactured according to the above examples and comparisons, 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 1,000 nit are as shown in [Table 1] below.

[0319] Example 1 Host 2 Host Vcd / ACIExCIEy1BH1 Compound 14.7327.470.13470.13112 Compound 35.0325.580.13320.13313 Compound 94.7126.720.13790.12914 Compound 104.8027.250.13430.13135 Compound 135.0425.130.13570.13066 Compound 154.7627.580.13550.13087 Compound 185.0225.780.13280.13368 Compound 215.1325.940.13380.13149 Compound 334.9426.680.13210.135710 Compound 395.0425.370.13200.135911 Compound 434.9727.310.12990.138212 Compound 454.9326.820.13190.136013 Compound 514.8927.380.13070.137814 Compound 775.2326.740.13250.134715 Compound 824.8429.850.13170.136816 Compound 854.7925.240.13350.132617 Compound 1084.8527.710.13270.134118 Compound 1194.9027.040.13370.132519 Compound 1234.8826.460.13140.137320 Compound 1274.9726.250.13120.137521 Compound 1335.0227.180.13110.137722 Compound 1344.9926.070.13050.137923 Compound 1464.7526.510.13260.134224 Compound 1504.8127.070.13220.135425 Compound 1624.8730.530.13720.130026 Compound 1735.1327.750.13260.134527 Compound 1804.9025.140.13160.137028 Compound 2024.8627.620.13180.136529 Compound 2674.9126.960.12900.139130 Compound 3005.0225.680.13770.129531 Compound 3214.9826.140.12930.138532 Compound 3404.8224.950.13330.1328 Comparative Example 1BH1BH25.6322.410.14300.2010 Comparative Example 2BH1BH2-15.8121.520.14500.1940.

[0320] Looking at the results shown in [Table 1] above, it can be confirmed that when a compound according to the present invention is used as a first host or second host in an organic light-emitting device having a light-emitting layer composed of a plurality of host compounds, the light-emitting characteristics, such as low-voltage driving characteristics and current efficiency, are significantly superior compared to devices (Comparative Examples 1 and 2) that use a compound as a host that is contrasted with the characteristic structure of the compound used as a conventional host compound or the compound according to the present invention.

[0321] [HAT-CN] [HT1] [EB1] [ET1]

[0322]

[0323] [BH1] [BH2] [BD1] [BH2-1]

[0324]

[0325] The present invention relates to an organic compound that is employed as an organic layer material within an organic light-emitting diode, preferably as a host material for a light-emitting layer, and is capable of realizing excellent luminescence characteristics such as luminescence efficiency and quantum efficiency of the organic light-emitting diode, and can be industrially usefully utilized in various display and lighting devices.

Claims

1. Organic compounds represented by the following [Chemical Formula I]: [Chemical Formula I] In the above [Chemical Formula I], L1 and L2 are identical or different from each other and are each independently selected from directly bonded, substituted, or unsubstituted arylene groups having 6 to 30 carbon atoms, and n and m are each integers from 0 to 2, and when n and m are 2, a plurality of L1 and L2 are each identical or different from each other, and R1 is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, and R2 is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

2. In Paragraph 1, An organic compound characterized in that the above R1 is any one selected from the following [Structural Formula 1]: [Structural Formula 1] In the above [Structural Formula 1], X1 is O, S, NR3, CR4R5, and The above R3 and R5 are identical or different from each other and are each independently selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, and substituted or unsubstituted C3 to C30 heteroaryl group. The above R4 and R5 can combine with each other to form a monocyclic or polycyclic ring of alicyclic or aromatic groups, and '*' is the part connected to the above L1.

3. In Paragraph 1, An organic compound characterized in that the above R2 is any one selected from a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophen group, and a substituted or unsubstituted dibenzofuranyl group.

4. In any one of paragraphs 1 through 3, An organic compound in which each substituent defined in claims 1 and 3 is substituted with one or more substituents selected from deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, halogenated alkyl group, alkoxy group, halogenated alkoxy group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, amine group, silyl group, and germanium group, or is substituted with a substituent in which two or more of the said substituents are connected, or has no substituents at all.

5. In Paragraph 1, An organic compound characterized in that the above [Chemical Formula I] is any one selected from [Compound 1] to [Compound 341] below:

6. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, An organic light-emitting diode in which at least one of the above organic layers comprises an organic compound of [Chemical Formula I] according to claim 1.

7. In Paragraph 6, The above organic layer comprises one or more layers 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, and An organic light-emitting diode characterized in that at least one of the above layers comprises an organic compound represented by [Chemical Formula I].

8. In Paragraph 7, An organic light-emitting device characterized by including an organic compound represented by [Chemical Formula I] in the light-emitting layer.

9. In Paragraph 8, An organic light-emitting diode characterized in that the organic compound represented by the above [Chemical Formula I] is a host material within the light-emitting layer.

10. In Paragraph 9, An organic light-emitting diode characterized in that the above host material employs one or more organic compounds represented by [Chemical Formula I], or is composed of a plurality of materials mixed or stacked together with one or more other compounds along with the organic compound represented by [Chemical Formula I].

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