KR102899760B1 - Organic compounds and electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic compound represented by the following [chemical formula I] or [chemical formula II], which is employed as an organic layer material in an organic light-emitting device, preferably employed as a light-emitting layer host material, to realize excellent light-emitting characteristics such as light-emitting efficiency and quantum efficiency of the device, and to an organic light-emitting device comprising the same in an organic layer in the device.
[Chemical Formula I]

[Chemical Formula II]

Description

Organic compounds and electroluminescent devices comprising the same

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

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.

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.

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.

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.

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.

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

[Chemical Formula I]

[Chemical Formula II]

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

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 a high-efficiency organic light-emitting device having excellent device characteristics such as color purity, light-emitting efficiency, and quantum efficiency, and thus can be usefully utilized in various display devices such as lighting devices, flat panel, flexible, and wearable displays.

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

The present invention relates to a compound represented by the following [chemical formula I] or [chemical formula II], and due to the structural characteristics of the compound, it can be employed as a host material for a light-emitting layer in an organic light-emitting device, thereby realizing a high-efficiency organic light-emitting device having excellent device characteristics such as color purity, light-emitting efficiency, and quantum efficiency.

[Chemical Formula I]

[Chemical Formula II]

In the above [chemical formula Ⅰ] or [chemical formula Ⅱ],

R ₁ to R ₃ are the same or different from each other, and are each independently selected from 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, except when all of R ₁ to R ₃ have the same structure.

The compound of [Chemical Formula I] or [Chemical Formula II] according to the present invention is characterized in that when a silyl group substituted with R ₁ to R ₃ is introduced into a characteristic skeletal derivative, the structures of R ₁ to R ₃ are not all identical.

L ₁ is a divalent linker selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

L ₂ is a divalent linking group, which is a direct bond, or is the same as or different from each other, and is independently selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

P is an integer from 1 to 3, q is an integer from 0 to 3, and when p and q are 2 or more, a plurality of L ₁ and L ₂ are each the same or different from each other.

The compound of [Chemical Formula I] or [Chemical Formula II] according to the present invention is characterized in that the bicarbazole structure is a structure connected through a linking group (L ₂ ), and the introduced silyl group is introduced through the linking group (L ₁ ), and when p and q are 2 or more, a plurality of L ₁ and L ₂ are each the same or different from each other.

Ar ₁ is selected from 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.

R ₄ to R ₆ 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.

a, b and c are each integers from 0 to 4, and when a, b and c are each 2 or more, a plurality of R ₄ to R ₆ are each the same or different from each other.

D is deuterium, n means the number of hydrogens in the above [chemical formula I] or [chemical formula II] replaced with deuterium (D), and n is an integer from 0 to 80.

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

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%.

Meanwhile, in the definition of R ₁ to R ₆ , Ar ₁ , L ₁ and L ₂ in the above [Chemical Formula Ⅰ] or [Chemical Formula Ⅱ], 'substituted or unsubstituted' means that the R ₁ to R ₆ , Ar ₁ , L ₁ and L ₂ are each 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 are substituted with a substituent in which two or more of the substituents are connected, or do not have any substituents, and hydrogen in the substituents can be replaced with one or more deuterium, and two or more adjacent substituents are connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. Additional formations can be made.

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.

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'.

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.

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.

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.

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.

In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example, , , There is a back.

In the present invention, the fluorenyl group includes the structure of an open fluorenyl group, wherein the open fluorenyl group 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.

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.

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.

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.

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 cycloalkenes such as cyclohexene and cyclobutene.

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.

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.

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.

In the present invention, the germanium group (or germane group) may include -GeH ₃ , 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.

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.

In the present invention, the amine group may be -NH ₂ , 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.

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

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

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

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

In this way, the organic compound according to the present invention can synthesize compounds having various characteristics through a characteristic skeletal structure having unique characteristics and a 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.

The organic compound according to the present invention can be applied to an organic light-emitting device using a conventional manufacturing method.

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 organic compound according to the present invention is used in the organic layer of the device.

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.

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.

Therefore, in the organic light-emitting device according to the present invention, the organic layer may include a light-emitting layer, etc., and at least one of the layers may include an organic compound represented by [chemical formula I] or [chemical formula II] as a host material.

In addition, the organic light-emitting device according to the present invention can be composed of a plurality of host materials in the light-emitting layer, and at this time, in addition to the compound according to the present invention, one or more other compounds can be further included and formed by mixing or laminating them.

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.

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.

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.

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 SnO ₂ :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline.

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 LiO ₂ /Al.

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.

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.

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.

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.

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 (Alq ₃ ), 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.

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).

The electron transport layer is a material that can easily receive electrons from the cathode and transfer 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 Alq ₃ , organic radical compounds, and hydroxyflavone-metal complexes.

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.

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.

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.

Synthetic example 1: Synthesis of compound 6

(1) Manufacturing example 1: Synthesis of intermediate 6-1

3-Bromobiphenyl (10.0 g, 0.043 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (3.0 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. After that, dichlorodiphenylsilane (in THF) (14.1 g, 0.056 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 10.7 g (yield 67.2%) of <Intermediate 6-1>.

(2) Manufacturing example 2: Synthesis of intermediate 6-2

1,4-dibromobenzene (10.0 g, 0.042 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.9 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. Then, intermediate 6-1 (in THF) (20.4 g, 0.055 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 13.1 g (yield 62.9%) of <intermediate 6-2>.

(3) Manufacturing example 3: Synthesis of intermediate 6-3

Intermediate 6-2 (10.0 g, 0.020 mol), 3-Bromophenylboronic acid (4.9 g, 0.024 mol), K ₂ CO ₃ (8.4 g, 0.061 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 5.6 g (yield 60.7%) of <Intermediate 6-3>.

(4) Manufacturing example 4: Synthesis of compound 6

Intermediate 6-3 (10.0 g, 0.018 mol), 9-Phenyl-3,3'-bicarbazole (10.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 9.8 g (yield 62.1%) of <Compound 6>.

LC/MS: m/z=895[(M) ⁺ ]

Synthetic example 2: Synthesis of compound 31

(1) Manufacturing example 1: Synthesis of intermediate 31-1

4-Bromobiphenyl (10.0 g, 0.043 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (3.0 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. After that, dichlorodiphenylsilane (in THF) (14.1 g, 0.056 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 11.4 g (yield 71.6%) of <Intermediate 31-1>.

(2) Manufacturing example 2: Synthesis of intermediate 31-2

1,4-dibromobenzene (10.0 g, 0.042 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.9 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. Then, intermediate 31-1 (in THF) (20.4 g, 0.055 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 12.5 g (yield 60.0%) of <intermediate 31-2>.

(3) Manufacturing example 3: Synthesis of intermediate 31-3

Intermediate 31-2 (10.0 g, 0.020 mol), 3-Bromophenylboronic acid (4.9 g, 0.024 mol), K ₂ CO ₃ (8.4 g, 0.061 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 6.8 g (yield 58.9%) of <Intermediate 31-3>.

(4) Manufacturing example 4: Synthesis of compound 31

Intermediate 31-3 (10.0 g, 0.018 mol), 3-[4-(9H-Carbazol-3-yl)phenyl]-9-phenyl-9H-carbazole (12.8 g, 0.029 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 11.4 g (yield 66.6%) of <Compound 31>.

LC/MS: m/z=971[(M) ⁺ ]

Synthetic example 3: Synthesis of compound 47

(1) Manufacturing example 1: Synthesis of intermediate 47-1

2-Bromo-9,9'-dimethylfluorene (10.0 g, 0.037 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.5 g, 0.040 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. After that, dichlorodiphenylsilane (in THF) (12.0 g, 0.048 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 8.5 g (yield 56.5%) of <Intermediate 47-1>.

(2) Manufacturing example 2: Synthesis of intermediate 47-2

1,4-dibromobenzene (10.0 g, 0.042 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.9 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. Then, intermediate 47-1 (in THF) (22.6 g, 0.055 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 15.2 g (yield 67.5%) of <intermediate 47-2>.

(3) Manufacturing example 3: Synthesis of intermediate 47-3

Intermediate 47-2 (10.0 g, 0.019 mol), (4-Chlorophenyl)boronic acid (4.5 g, 0.023 mol), K ₂ CO ₃ (7.8 g, 0.056 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 6.6 g (yield 57.7%) of <Intermediate 47-3>.

(4) Manufacturing example 4: Synthesis of compound 47

Intermediate 47-3 (10.0 g, 0.017 mol), 9-Phenyl-3,3'-bicarbazole (10.1 g, 0.025 mol), NaOtBu (4.7 g, 0.049 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.3 mmol) were mixed with 150 mL of toluene 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 9.8 g (yield 63.7%) of <Compound 47>.

LC/MS: m/z=935[(M) ⁺ ]

Synthetic example 4: Synthesis of compound 75

(1) Manufacturing example 1: Synthesis of intermediate 75-1

1-Bromo-3,5-diphenylbenzene (10.0 g, 0.032 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.2 g, 0.035 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. After that, dichlorodiphenylsilane (in THF) (10.6 g, 0.042 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 9.7 g (yield 67.1%) of <Intermediate 75-1>.

(2) Manufacturing example 2: Synthesis of intermediate 75-2

1,4-dibromobenzene (10.0 g, 0.042 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.9 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. Then, intermediate 75-1 (in THF) (24.6 g, 0.055 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 16.8 g (yield 69.8%) of <intermediate 75-2>.

(3) Manufacturing example 3: Synthesis of intermediate 75-3

Intermediate 75-2 (10.0 g, 0.018 mol), (4-Bromophenyl)boronic acid (4.3 g, 0.021 mol), K ₂ CO ₃ (7.3 g, 0.053 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 6.3 g (yield 55.6%) of <Intermediate 75-3>.

(4) Manufacturing example 4: Synthesis of compound 75

Intermediate 75-3 (10.0 g, 0.016 mol), 9-[1,1'-biphenyl]-2-yl-3,3'-bi-9H-carbazole (11.3 g, 0.023 mol), NaOtBu (4.5 g, 0.047 mol), Pd(dba) ₂ (0.4 g, 0.6 mmol), t-Bu ₃ P (0.3 g, 1.2 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 9.4 g (yield 57.8%) of <Compound 75>.

LC/MS: m/z=1047[(M) ⁺ ]

Synthetic example 5: Synthesis of compound 96

(1) Manufacturing example 1: Synthesis of intermediate 96-1

3-Bromodibenzofuran (10.0 g, 0.041 mol) was dissolved in 100 mL of THF, and n-BuLi (2.8 M in hexane) (4.1 g, 0.044 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. After that, dichlorodiphenylsilane (in THF) (16.0 g, 0.085 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 9.9 g (yield 63.6%) of <Intermediate 96-1>.

(2) Manufacturing example 2: Synthesis of intermediate 96-2

1,4-dibromobenzene (10.0 g, 0.042 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.9 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. Then, intermediate 96-1 (in THF) (21.0 g, 0.055 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 15.1 g (yield 70.5%) of <intermediate 96-2>.

(3) Manufacturing example 3: Synthesis of intermediate 96-3

Intermediate 96-2 (10.0 g, 0.020 mol), (4-Bromophenyl)boronic acid (4.8 g, 0.024 mol), K ₂ CO ₃ (8.2 g, 0.059 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) were added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 7.2 g (yield 62.6%) of <Intermediate 96-3>.

(4) Manufacturing example 4: Synthesis of compound 96

Intermediate 96-3 (10.0 g, 0.017 mol), 9-[1,1'-biphenyl]-3-yl-3,3'-bi-9H-carbazole (12.5 g, 0.026 mol), NaOtBu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene 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 10.0 g (yield 59.0%) of <Compound 96>.

LC/MS: m/z=985[(M) ⁺ ]

Synthetic example 6: Synthesis of compound 106

(1) Manufacturing example 1: Synthesis of compound 106

Intermediate 6-3 (10.0 g, 0.018 mol), 9-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole (12.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 9.8 g (yield 57.3%) of <Compound 106>.

LC/MS: m/z=971[(M) ⁺ ]

Synthetic example 7: Synthesis of compound 107

(1) Manufacturing example 1: Synthesis of compound 107

Intermediate 31-3 (10.0 g, 0.018 mol), 9-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole (12.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 10.6 g (yield 61.9%) of <Compound 107>.

LC/MS: m/z=971[(M) ⁺ ]

Synthetic example 8: Synthesis of compound 121

(1) Manufacturing example 1: Synthesis of intermediate 121-1

Intermediate 31-2 (10.0 g, 0.020 mol), (4-Bromophenyl)boronic acid (4.9 g, 0.024 mol), K ₂ CO ₃ (8.4 g, 0.061 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) were added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 7.7 g (yield 66.7%) of <Intermediate 121-1>.

(2) Manufacturing example 2: Synthesis of compound 121

Intermediate 121-1 (10.0 g, 0.018 mol), 9-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole (12.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 11.1 g (yield 64.9%) of <Compound 121>.

LC/MS: m/z=971[(M) ⁺ ]

Synthetic example 9: Synthesis of compound 132

(1) Manufacturing example 1: Synthesis of intermediate 132-1

To 3-Bromo-9-[1,1':3',1"-terphenyl]-5'-yl-9H-carbazole (10.0 g, 0.021 mol), B-9H-Carbazol-3-ylboronic acid (5.3 g, 0.025 mol), K ₂ CO ₃ (8.7 g, 0.063 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 8.2 g (yield 69.4%) of <Intermediate 132-1>.

(2) Manufacturing example 2: Synthesis of compound 132

Intermediate 31-3 (10.0 g, 0.018 mol), Intermediate 132-1 (14.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were mixed with 150 mL of toluene 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 10.6 g (yield 57.4%) of <Compound 132>.

LC/MS: m/z=1046[(M) ⁺ ]

Synthetic example 10: Synthesis of compound 179

(1) Manufacturing example 1: Synthesis of intermediate 179-1

1,4-dibromobenzene (10.0 g, 0.042 mol) was dissolved in 100 mL of THF, and n-BuLi (2.5 M in hexane) (2.9 g, 0.046 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for 1 hour. Then, intermediate 6-1 (in THF) (20.4 g, 0.055 mol) was slowly added dropwise at -78 °C, and the mixture was stirred for another 12 hours at room temperature. After the reaction was completed, the mixture was extracted, concentrated, and purified by column chromatography to obtain 14.8 g (yield 71.0%) of <intermediate 179-1>.

(2) Manufacturing example 2: Synthesis of intermediate 179-2

Intermediate 179-1 (10.0 g, 0.020 mol), (4-Bromophenyl)boronic acid (4.9 g, 0.024 mol), K ₂ CO ₃ (8.4 g, 0.061 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 7.2 g (yield 62.3%) of <Intermediate 179-2>.

(3) Manufacturing example 3: Synthesis of compound 179

Intermediate 179-2 (10.0 g, 0.018 mol), 9-Phenyl-3,3'-bicarbazole (10.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene 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 9.4 g (yield 59.6%) of <Compound 179>.

LC/MS: m/z=894[(M) ⁺ ]

Synthetic example 11: Synthesis of compound 201

(1) Manufacturing example 1: Synthesis of compound 201

Intermediate 179-2 (10.0 g, 0.018 mol), 9-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole (12.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene 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 10.4 g (yield 60.8%) of <Compound 201>.

LC/MS: m/z=970[(M) ⁺ ]

Synthetic example 12: Synthesis of compound 208

(1) Manufacturing example 1: Synthesis of compound 208

Intermediate 31-3 (10.0 g, 0.018 mol), 9-Phenyl-2,3'-bi-9H-carbazol (10.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene and reacted by stirring at 70 °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 9.0 g (yield 57.1%) of <Compound 208>.

LC/MS: m/z=894[(M) ⁺ ]

Synthetic example 13: Synthesis of compound 268

(1) Manufacturing example 1: Synthesis of intermediate 268-1

9-[1,1'-Biphenyl]-3-yl-2-bromo-9H-carbazole (10.0 g, 0.025 mol), B-9H-Carbazol-2-ylboronic acid (6.4 g, 0.030 mol), K ₂ CO ₃ (10.4 g, 0.075 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol) were added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 8.1 g (yield 66.6%) of <Intermediate 268-1>.

(2) Manufacturing example 2: Synthesis of compound 268

Intermediate 179-2 (10.0 g, 0.018 mol), Intermediate 268-1 (12.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were mixed with 150 mL of toluene 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 10.5 g (yield 61.4%) of <Compound 268>.

LC/MS: m/z=970[(M) ⁺ ]

Synthetic example 14: Synthesis of compound 301

(1) Manufacturing example 1: Synthesis of compound 301

Intermediate 121-1 (10.0 g, 0.018 mol), 3,9'-bi-9H-carbazole (8.8 g, 0.026 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of toluene 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 9.5 g (yield 65.8%) of <Compound 301>.

LC/MS: m/z=818[(M) ⁺ ]

Synthetic example 15: Synthesis of compound 337

(1) Manufacturing example 1: Synthesis of intermediate 337-1

9-(3-Bromophenyl)-9H-carbazole (10.0 g, 0.031 mol), B-9H-Carbazol-3-ylboronic acid (7.8 g, 0.037 mol), K ₂ CO ₃ (12.9 g, 0.093 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol) were added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentrated, and then column chromatography was performed to obtain 7.8 g (yield 61.5%) of <Intermediate 337-1>.

(2) Manufacturing example 2: Synthesis of intermediate 337-2

Intermediate 75-2 (10.0 g, 0.018 mol), 3-Bromophenylboronic acid (4.3 g, 0.021 mol), K ₂ CO ₃ (7.3 g, 0.053 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 6.2 g (yield 54.7%) of <Intermediate 337-2>.

(3) Manufacturing example 3: Synthesis of compound 337

Intermediate 337-2 (10.0 g, 0.016 mol), Intermediate 337-1 (9.5 g, 0.023 mol), NaOtBu (4.5 g, 0.047 mol), Pd(dba) ₂ (0.4 g, 0.6 mmol), t-Bu ₃ P (0.3 g, 1.2 mmol) were mixed with 150 mL of toluene 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 8.1 g (yield 53.7%) of <Compound 337>.

LC/MS: m/z=970[(M) ⁺ ]

Synthetic example 16: Synthesis of compound 370

(1) Manufacturing example 1: Synthesis of intermediate 370-1

9-(4-Bromophenyl)-9H-carbazole (10.0 g, 0.031 mol), B-9H-Carbazol-3-ylboronic acid (7.8 g, 0.037 mol), K ₂ CO ₃ (12.9 g, 0.093 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol) were added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80 °C for 6 hours to react. After the reaction was completed, extraction was performed, concentration was performed, and column chromatography and recrystallization were performed to obtain 8.1 g (yield 63.9%) of <Intermediate 370-1>.

(2) Manufacturing example 2: Synthesis of compound 370

Intermediate 96-3 (10.0 g, 0.017 mol), Intermediate 370-1 (10.5 g, 0.026 mol), NaOtBu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) were mixed with 150 mL of toluene and reacted at 70°C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then column chromatographed and recrystallized to obtain 8.9 g (yield 56.9%) of <Compound 370>.

LC/MS: m/z=909[(M) ⁺ ]

element Example (Host)

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 thereto, so that the light-emitting area was 2 mm × 2 mm, and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure was made 1 × 10 ^-6 torr, and then an organic material and a metal were deposited on the ITO in the following structure.

element Example 1 to 41 (Green host)

The compound implemented according to the present invention was used as a host. An organic light-emitting device having the following device structure was fabricated, and its luminescence characteristics, including current efficiency, were measured.

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)

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 light-emitting layer was composed of a plurality of hosts, and at this time, the compound according to the present invention described in [Table 1] below was used as the first host, and the following [GH4] was used as the second host, mixed in a ratio of 6:4, 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 (50% doped with Liq of the following [ET1] compound) 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.

element Comparative example 1

The organic light-emitting device for Comparative Example 1 was manufactured in the same manner as the device structures of Examples 1 to 41, except that [GH1] was used instead of the compound according to the present invention as the first host.

element Comparative example 2

The organic light-emitting device for comparative example 2 was manufactured in the same manner as the device structures of Examples 1 to 41, except that [GH2] was used instead of the compound according to the present invention as the first host.

element Comparative example 3

The organic light-emitting device for comparative example 3 was manufactured in the same manner as the device structures of Examples 1 to 41, except that [GH3] was used instead of the compound according to the present invention as the first host.

Experimental example 1: Element Example Luminescence characteristics of 1 to 41

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 1,000 nit are as shown in [Table 1] below.

Example 1st host Second host V cd/A CIEx CIEy 1 Compound 6 GH4 3.68 52.11 0.325 0.610 2 Compound 9 3.74 51.88 0.324 0.623 3 Compound 19 3.80 53.46 0.328 0.616 4 Compound 31 3.62 54.16 0.326 0.612 5 Compound 34 3.77 52.63 0.322 0.617 6 Compound 47 3.53 53.01 0.321 0.615 7 Compound 52 3.60 51.05 0.325 0.618 8 Compound 66 3.51 53.08 0.320 0.612 9 Compound 75 3.71 52.10 0.326 0.614 10 Compound 84 3.66 50.77 0.324 0.611 11 Compound 85 3.72 50.54 0.321 0.615 12 Compound 96 3.56 51.22 0.318 0.611 13 Compound 99 3.62 50.88 0.323 0.613 14 Compound 106 3.50 53.91 0.322 0.609 15 Compound 107 3.57 53.76 0.312 0.620 16 Compound 111 3.61 49.91 0.323 0.615 17 Compound 116 3.57 53.76 0.312 0.620 18 Compound 121 3.77 53.43 0.318 0.621 19 Compound 122 3.69 54.53 0.325 0.614 20 Compound 132 3.58 53.39 0.323 0.617 21 Compound 138 3.62 51.31 0.323 0.616 22 Compound 144 3.55 50.92 0.317 0.611 23 Compound 165 3.48 52.13 0.324 0.607 24 Compound 169 3.61 51.80 0.320 0.613 25 Compound 179 3.64 52.52 0.328 0.622 26 Compound 186 3.64 52.52 0.328 0.622 27 Compound 195 3.52 54.69 0.325 0.615 28 Compound 201 3.47 51.58 0.321 0.615 29 Compound 208 3.74 54.84 0.316 0.620 30 Compound 222 3.54 53.10 0.322 0.622 31 Compound 236 3.56 52.92 0.328 0.611 32 Compound 268 3.49 53.35 0.321 0.615 33 Compound 274 3.68 53.08 0.325 0.614 34 Compound 290 3.55 52.24 0.326 0.620 35 Compound 301 3.51 53.92 0.326 0.611 36 Compound 314 3.44 54.07 0.327 0.614 37 Compound 337 3.46 53.30 0.320 0.615 38 Compound 344 3.55 53.10 0.326 0.621 39 Compound 370 3.58 52.52 0.322 0.618 40 Compound 389 3.47 51.17 0.325 0.614 41 Compound 405 3.73 52.34 0.320 0.614 Comparative Example 1 GH1 GH4 4.05 45.27 0.328 0.604 Comparative Example 2 GH2 GH4 3.91 43.69 0.323 0.608 Comparative Example 3 GH3 GH4 4.21 47.84 0.324 0.605

Looking at the results shown in [Table 1] above, when configuring a plurality of hosts for the light-emitting layer in an organic light-emitting device, and employing the compound according to the present invention as the first host of the light-emitting layer in the organic light-emitting device, it can be confirmed that the low-voltage driving characteristics and light-emitting characteristics are significantly superior to those of devices (Comparative Examples 1 to 3) employing conventional compounds (GH1 to GH3) that have structural characteristics contrasting with those of the compound according to the present invention.

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

[GH1] [GH2] [GH3] [GH4] [GD1]

element Example (Blue host)

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 thereto, so that the light-emitting area was 2 mm × 2 mm, and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure was made 1 × 10 ^-6 torr, and then an organic material and a metal were deposited on the ITO in the following structure.

element Example 42 to 82

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.

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)

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 light-emitting layer was composed of a plurality of hosts, and at this time, the compound according to the present invention described in [Table 2] below was used as the first host, and the second host was used by mixing [BH4] below in a 1:1 ratio. In addition, 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.

element Comparative example 4

The organic light-emitting device for Comparative Example 4 was manufactured in the same manner as the device structures of Examples 42 to 82, except that [BH1] was used instead of the compound according to the present invention as the first host.

element Comparative example 5

The organic light-emitting device for Comparative Example 5 was manufactured in the same manner as the device structures of Examples 42 to 82, except that [BH2] was used instead of the compound according to the present invention as the first host.

element Comparative example 6

The organic light-emitting device for comparative example 6 was manufactured in the same manner as the device structures of Examples 42 to 82, except that [BH3] was used instead of the compound according to the present invention as the first host.

Experimental example 2: Element Example Luminescence characteristics of 42 to 82

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 1,000 nit are as shown in [Table 2] below.

Example 1st host Second host V cd/A CIEx CIEy 42 Compound 6 BH4 5.22 22.84 0.161 0.293 43 Compound 9 5.11 24.33 0.159 0.290 44 Compound 19 5.15 25.61 0.158 0.284 45 Compound 31 5.18 23.96 0.162 0.288 46 Compound 34 5.12 23.38 0.163 0.289 47 Compound 47 5.04 26.24 0.154 0.290 48 Compound 52 5.25 24.80 0.160 0.293 49 Compound 66 5.04 27.04 0.155 0.288 50 Compound 75 5.20 25.58 0.161 0.289 51 Compound 84 5.18 27.11 0.158 0.292 52 Compound 85 5.22 26.44 0.163 0.289 53 Compound 96 5.06 25.88 0.162 0.286 54 Compound 99 5.21 22.53 0.155 0.294 55 Compound 106 5.19 22.91 0.160 0.287 56 Compound 107 5.21 24.35 0.163 0.294 57 Compound 111 5.25 23.62 0.159 0.293 58 Compound 116 5.21 24.35 0.163 0.294 59 Compound 121 5.24 21.62 0.156 0.290 60 Compound 122 5.19 24.83 0.157 0.292 61 Compound 132 5.17 27.47 0.163 0.293 62 Compound 138 5.12 25.22 0.160 0.292 63 Compound 144 5.25 24.17 0.156 0.289 64 Compound 165 5.22 21.78 0.159 0.291 65 Compound 169 5.15 26.31 0.164 0.285 66 Compound 179 5.26 26.87 0.159 0.296 67 Compound 186 5.26 26.87 0.159 0.296 68 Compound 195 5.04 24.56 0.155 0.292 69 Compound 201 5.27 27.02 0.159 0.284 70 Compound 208 5.25 25.26 0.157 0.287 71 Compound 222 5.11 24.88 0.160 0.290 72 Compound 236 5.24 22.97 0.160 0.289 73 Compound 268 5.12 26.64 0.158 0.294 74 Compound 274 5.18 22.38 0.164 0.294 75 Compound 290 5.22 27.53 0.160 0.285 76 Compound 301 5.19 25.85 0.163 0.288 77 Compound 314 5.08 23.59 0.157 0.291 78 Compound 337 5.20 26.43 0.160 0.289 79 Compound 344 5.14 25.20 0.164 0.286 80 Compound 370 5.21 25.36 0.166 0.295 81 Compound 389 5.16 23.42 0.164 0.289 82 Compound 405 5.11 24.16 0.158 0.294 Comparative Example 4 BH1 BH4 5.50 20.31 0.160 0.290 Comparative Example 5 BH2 BH4 5.48 20.55 0.163 0.292 Comparative Example 6 BH3 BH4 5.39 19.67 0.160 0.293

Looking at the results shown in the above [Table 2], 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 in the light-emitting layer, the light-emitting characteristics such as low-voltage driving characteristics and current efficiency are significantly superior to those of devices (Comparative Examples 4 to 6) employing compounds (BH1 to BH3) having a characteristic structure contrasting with that of the compound according to the present invention as the host.

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

[BH1] [BH2] [BH3] [BH4] [BD1]

Claims (11)

Organic compounds represented by the following [chemical formula Ⅰ] or [chemical formula Ⅱ]:
[Chemical Formula I]

[Chemical Formula II]

In the above [chemical formula Ⅰ] or [chemical formula Ⅱ],
R ₁ to R ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group (except when R ₁ to R ₃ are all the same structure),
L ₁ is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
L ₂ is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
p is an integer from 1 to 3, q is an integer from 0 to 3, and when p and q are 2 or more, a plurality of L ₁ and L ₂ are each the same or different from each other,
Ar ₁ 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 2 to 50 carbon atoms,
R ₄ to R ₆ are the same or different and are each independently any 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted halogen group, a cyano group and a halogen group.
a, b and c are each an integer from 0 to 4, and when a, b and c are each 2 or more, a plurality of R ₄ to R ₆ are each the same or different from each other,
D is deuterium, n means the number of hydrogens in the above [chemical formula Ⅰ] or [chemical formula Ⅱ] replaced with deuterium (D), and n is an integer from 0 to 80.
In the definition of R ₁ to R ₆ , Ar ₁ , L ₁ and L ₂ above, 'substituted or unsubstituted' means that R ₁ to R ₆ , Ar ₁ , L ₁ and L ₂ are each substituted with one or two or more substituents selected from deuterium, a cyano group, a halogen group, an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a cycloalkyl group, a phenyl group, a biphenyl group, an amino group, a silyl group and a cycloalkyl group, or are substituted with a substituent in which two or more of the above substituents are connected, or do not have any substituents. delete In the first paragraph,
The above [chemical formula Ⅰ] or [chemical formula Ⅱ] is an organic compound characterized in that the hydrogen present in [chemical formula Ⅰ] or [chemical formula Ⅱ] is partially substituted with deuterium (D), and the deuterium (D) substitution rate is 10 to 90%. In the third paragraph,
An organic compound characterized by a deuterium (D) substitution rate of 20 to 80%. In paragraph 4,
An organic compound characterized by a deuterium (D) substitution rate of 30 to 70%. In the first paragraph,
The above [chemical formula Ⅰ] or [chemical formula Ⅱ] is an organic compound characterized by being selected from the following compounds:




















































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] or [chemical formula Ⅱ] according to claim 1. 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] or [chemical formula Ⅱ]. In paragraph 8,
An organic light-emitting device characterized in that the light-emitting layer includes an organic compound represented by [chemical formula Ⅰ] or [chemical formula Ⅱ]. In paragraph 9,
An organic light-emitting device characterized in that the organic compound represented by the above [chemical formula Ⅰ] or [chemical formula Ⅱ] is a host material in the light-emitting layer. In Article 10,
An organic light-emitting device characterized in that the host material is composed of a plurality of compounds mixed or laminated, in addition to the organic compound represented by the above-described [chemical formula I] or [chemical formula II], and further includes at least one other compound.