WO2021040467A1 - Novel heterocyclic compound and organic light-emitting device using same - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light-emitting device using same.

Description

Novel heterocyclic compound and organic light emitting device using same

Cross-reference with related application(s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0105959 filed on August 28, 2019 and Korean Patent Application No. 10-2020-0109034 filed on August 28, 2020. All contents disclosed in the literature are included as part of this specification.

The present invention relates to a novel heterocyclic compound and an organic light emitting device including the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light-emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

Development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Prior art literature

Patent Literature

(Patent Document 0001) Korean Patent Publication No. 10-2013-073537

The present invention relates to a novel heterocyclic compound and an organic light emitting device including the same.

The present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X ₁ to X ₃ are each independently CH; Or N, provided that at least one of _{X 1} to X _{3 is N,}

Ar is substituted or unsubstituted C _6-60 aryl,

R ₁ and R ₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

Each R ₅ is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

n1 and n2 are each independently an integer of 0 to 8,

n3 is an integer from 0 to 2.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of the present invention.

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device comprising the cathode 4 is shown.

Hereinafter, it will be described in more detail to aid the understanding of the present invention.

(Explanation of terms)

In this specification,

And

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium (D); Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Can be, etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidine group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the description of the aforementioned heterocyclic group may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are bonded to each other and formed.

(compound)

The present invention provides a compound represented by Chemical Formula 1. The compound represented by Formula 1 is a compound in which two carbazole groups, triazine groups, and aryl groups are simultaneously substituted on a benzene ring, and two carbazole groups and aryl groups are substituted at the ortho position to improve electronic stability, and accordingly, an organic light-emitting device When employed as a light emitting layer compound, characteristics of low driving voltage, high efficiency, and long life can be realized. The compound represented by Formula 1 is specifically as follows:

[Formula 1]

In Formula 1,

X ₁ to X ₃ are each independently CH; Or N, provided that at least one of _{X 1} to X _{3 is N,}

Ar is substituted or unsubstituted C _6-60 aryl,

R ₁ and R ₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

Each R ₅ is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

n1 and n2 are each independently an integer of 0 to 8,

n3 is an integer from 0 to 2.

Preferably, all of X ₁ to X ₃ are N.

Preferably, R ₁ and R ₂ are each independently phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Dibenzothiophenyl; Carbazole-9-yl; 9-phenyl-9H-carbazolyl; Or 9H-carbazol-9-yl-N-phenyl,

Each of these is independently substituted or unsubstituted with one or more deuterium.

Preferably, R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Or diphenylfluorenyl,

The phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; And diphenylfluorenyl are each independently substituted or unsubstituted with one or more deuterium.

More preferably, R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Phenyl or phenyl substituted with one or more deuterium.

Preferably, _{each R 5} is independently hydrogen; heavy hydrogen; Phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Dibenzothiophenyl; Carbazole-9-yl; Or 9-phenyl-9H-carbazolyl,

The phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Dibenzothiophenyl; Carbazole-9-yl; And 9-phenyl-9H-carbazolyl are each independently substituted or unsubstituted with one or more deuterium.

More preferably, _{each R 5} is independently hydrogen; Phenyl; It is carbazole-9-yl.

Preferably Ar is phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Or diphenylfluorenyl; and,

Each independently, deuterium; C _1-60 alkyl; C _6-60 aryl; And C _6-60 aralkyl substituted or unsubstituted with one or more substituents selected from the group consisting of.

Preferably, the compound represented by Formula 1 is any one selected from the group consisting of:

.

The compound represented by Formula 1 can be prepared by a manufacturing method such as the following Scheme 1:

[Scheme 1]

In the above formula, X ₁ and X ₂ are each independently halogen, bromo, chloro or fluoro, more preferably X ₁ is chloro and X ₂ is fluoro. In addition, the definition of other substituents is as described above.

Reaction Scheme 1 is a Suzuki-coupling reaction, and is preferably carried out in the presence of a palladium catalyst and a base. In addition, the reactor for the Suzuki-coupling reaction may be appropriately changed. The method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.

(Organic Light-Emitting Element)

In addition, the present invention provides an organic light-emitting device including the compound represented by Formula 1 above. For example, the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention 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, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Including the indicated compound.

In addition, the organic material layer may include an emission layer, and the emission layer includes a compound represented by Formula 1 above.

In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer for simultaneous electron transport and electron injection, and the electron transport layer, an electron injection layer, or a layer for simultaneous electron transport and electron injection is represented by Formula 1 It includes a compound represented by.

In addition, the organic material layer includes a hole injection layer, a hole transport layer, an electron blocking layer, and an emission layer, and at least one selected from the group consisting of the hole injection layer, the hole transport layer, and the electron blocking layer is a compound represented by Formula 1 above. Can include.

In addition, the organic material layer may include an emission layer and an electron transport layer, and the electron transport layer may include a compound represented by Formula 1 above.

In addition, the organic light-emitting device according to the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In such a structure, the compound represented by Formula 1 may be included in the emission layer.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device comprising the cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the electron suppression layer, the light-emitting layer, the electron transport layer, and the electron injection layer.

The organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

For example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material 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 SNO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.As a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron blocking layer (or electron suppressing layer) is a layer between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being recombined in the light emitting layer and passing to the hole transport layer, and is called an electron suppressing layer. Also do. The electron blocking layer is preferably a material having less electron affinity than the electron transport layer.

As the light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable. Specific examples of 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of injecting electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The organic light-emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Preparation of the compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Synthesis Example 1-1: Preparation of compound sub 1-2

1) Preparation of compound sub 1-1

2-chloro-4,6-diphenyl-1,3,5-triazine (50 g, 187.2 mmol) and (4-chloro-3,5-difluorophenyl) boronic acid (35.9 g, 187.2 mmol) were tetrahydrated in a nitrogen atmosphere. It was put into 1000ml of hydrofuran and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561.7 mmol) was dissolved in 78 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (6.5 g, 5.6 mmol) was added. After 2 hours of reaction, the mixture was allowed to cool to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 1419 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 1-1 (40.5 g, yield: 57%, MS: [M+H] ⁺ = 380.1).

2) Preparation of compound sub 1-2

In a nitrogen atmosphere, sub 1-1 (30 g, 79.1 mmol) and 9H-Carbazole (13.2 g, 79.1 mmol) were added to 600 ml of dimethylformamide and stirred and refluxed. Thereafter, sodium tertiary-butoxide (50.4 g, 237.4 mmol) was added, stirred sufficiently, allowed to react for 4 hours, allowed to cool to room temperature, and filtered the organic layer to remove salts, and the filtered organic layer was distilled. This was again added to 533 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale yellow solid compound sub 1-2 (26.6 g, yield: 50%, MS: [M+H] ⁺ = 674.2).

Synthesis Example 1-2: Preparation of compound sub 2-3

1) Preparation of compound sub 2-1

In a nitrogen atmosphere, 2-bromo-5-chloro-1,3-difluorobenzene (50 g, 221.3 mmol) and phenyl boronic acid (27 g, 221.3 mmol) were added to 1000 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (91.8 g, 664 mmol) was dissolved in 92 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (7.7 g, 6.6 mmol) was added. After reaction for 3 hours, the mixture was allowed to cool to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 992 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 1-2 (26.8 g, yield: 54%, MS: [M+H] ⁺ = 225).

2) Preparation of compound sub 2-2

In a nitrogen atmosphere, sub 1-21 (30 g, 133.9 mmol) and 9H-Carbazole (22.4 g, 133.9 mmol) were added to 600 ml of dimethylformamide and stirred and refluxed. Thereafter, sodium tertiary-butoxide (85.3 g, 401.7 mmol) was added, stirred sufficiently, allowed to react for 7 hours, cooled to room temperature, and filtered to remove salts of the organic layer, and the filtered organic layer was distilled. This was again added to 694 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale yellow solid compound sub 2-2 (45.1 g, yield: 65%, MS: [M+H] ⁺ = 519.2).

3) Preparation of compound sub 2-3

In a nitrogen atmosphere, sub 2-2 (30 g, 57.9 mmol) and bis (pinacolato) diboron (16.2 g, 63.7 mmol) were added to 600 ml of Diox and stirred and refluxed. Thereafter, potassium acetate (16.7 g, 173.7 mmol) was added, stirred sufficiently, and then palladium dibenzylidene acetone palladium (1 g, 1.7 mmol) and tricyclohexylphosphine (1 g, 3.5 mmol) were added. After reaction for 4 hours, after cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 353 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a gray solid compound sub 2-3 (29g, yield: 82%, MS: [M+H] ⁺ = 611.3).

Synthesis Example 1-3: Preparation of compound sub 3-2

1) Preparation of compound sub 3-1

In a nitrogen atmosphere, sub 2-1 (50 g, 223.2 mmol) and bis (pinacolato) diboron (62.4 g, 245.5 mmol) were added to 1000 ml of Diox and stirred and refluxed. After that, potassium acetate (64.4 g, 669.6 mmol) was added and sufficiently stirred, and then palladium dibenzylidene acetone palladium (3.9 g, 6.7 mmol) and tricyclohexylphosphine (3.8 g, 13.4 mmol) were added. After reaction for 4 hours, after cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 706 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a gray solid compound sub 3-1 (54.3 g, yield: 77%, MS: [M+H] ⁺ = 317.1).

2) Preparation of compound sub 3-2

In a nitrogen atmosphere, sub 3-1 (30 g, 94.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (25.3 g, 94.9 mmol) were added to 600 ml of tetrahydrofuran and stirred and refluxed. . Thereafter, potassium carbonate (39.3 g, 284.7 mmol) was dissolved in 39 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (3.3 g, 2.8 mmol) was added. After reaction for 3 hours, the mixture was allowed to cool to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 799 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound sub 3-2 (26g, yield: 65%, MS: [M+H] ⁺ = 422.1).

Synthesis Example 2-1: Preparation of Compound 1

In a nitrogen atmosphere, sub 1-2 (15 g, 22.3 mmol) and phenylboronic acid (2.7 g, 22.3 mmol) were added to 300 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (9.2 g, 66.8 mmol) was dissolved in 9 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.8 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 797 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 1 (10 g, yield: 63%, MS: [M+H] ⁺ = 716.3).

Synthesis Example 2-2: Preparation of Compound 2

In a nitrogen atmosphere, sub 1-2 (15 g, 22.3 mmol) and [1,1'-biphenyl]-4-ylboronic acid (4.4 g, 22.3 mmol) were added to 300 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (9.2 g, 66.8 mmol) was dissolved in 9 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.8 g, 0.7 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was added to 882 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 2 (9.7 g, yield: 55%, MS: [M+H] ⁺ = 792.3).

Synthesis Example 2-3: Preparation of Compound 3

In a nitrogen atmosphere, sub 1-2 (15 g, 22.3 mmol) and [1,1'-biphenyl]-3-ylboronic acid (4.4 g, 22.3 mmol) were added to 300 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (9.2 g, 66.8 mmol) was dissolved in 9 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.8 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 882 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 3 (11.1 g, yield: 63%, MS: [M+H] ⁺ = 792.3).

Synthesis Example 2-4: Preparation of compound 4

In a nitrogen atmosphere, sub 1-2 (15 g, 22.3 mmol) and (phenyl-d5) boronic acid (2.8 g, 22.3 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (9.2 g, 66.8 mmol) was dissolved in 9 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.8 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 802 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Compound 4 (11.1g, yield: 69%, MS: [M+H] ⁺ = 721.3).

Synthesis Example 2-5: Preparation of Compound 5

In a nitrogen atmosphere, sub 1-2 (15 g, 22.3 mmol) and naphthalen-2-ylboronic acid (3.8 g, 22.3 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (9.2 g, 66.8 mmol) was dissolved in 9 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.8 g, 0.7 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was added to 853 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound Compound 5 (10.4g, yield: 61%, MS: [M+H] ⁺ = 766.3).

Synthesis Example 2-6: Preparation of Compound 6

In a nitrogen atmosphere, sub 1-2 (15 g, 22.3 mmol) and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (5.3 g, 22.3 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. . Thereafter, potassium carbonate (9.2 g, 66.8 mmol) was dissolved in 9 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.8 g, 0.7 mmol) was added. After reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 926 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 6 (12.4g, yield: 67%, MS: [M+H] ⁺ = 832.3).

Synthesis Example 2-7: Preparation of Compound 7

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 2-chloro-4,6-bis (phenyl-d5)-1,3,5-triazine (6.8 g, 24.6 mmol) were added to 300 ml of tetrahydrofuran. Put it and stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 891 mL of chloroform to dissolve it, and the organic layer was separated after washing twice with water, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 7 (13.4 g, yield: 75%, MS: [M+H] ⁺ = 726.3).

Synthesis Example 2-8: Preparation of compound 8

In a nitrogen atmosphere, add sub 2-3 (15 g, 24.6 mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (6.7 g, 24.6 mmol) in tetrahydrofuran 300 ml Into the mixture was stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 885 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Compound 8 (11.2g, yield: 63%, MS: [M+H] ⁺ = 721.3).

Synthesis Example 2-9: Preparation of Compound 9

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine(8.4 g) , 24.6mmol) was added to 300ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 972 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound Compound 9 (10.7 g, yield: 55%, MS: [M+H] ⁺ = 792.3).

Synthesis Example 2-10: Preparation of Compound 10

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine(8.4 g) , 24.6mmol) was added to 300ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 972 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound Compound 10 (11.1g, yield: 57%, MS: [M+H] ⁺ = 792.3).

Synthesis Example 2-11: Preparation of Compound 11

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (8.8 g, 24.6mmol) was added to 300ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was added to 990 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound Compound 11 (13.9g, yield: 70%, MS: [M+H] ⁺ = 806.3).

Synthesis Example 2-12: Preparation of Compound 12

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (8.8 g, 24.6mmol) was added to 300ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 990 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound Compound 12 (10.5g, yield: 53%, MS: [M+H] ⁺ = 806.3).

Synthesis Example 2-13: Preparation of compound 13

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (9.2 g, 24.6mmol) was added to 300ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was added to 1009 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 13 (10.1 g, yield: 50%, MS: [M+H] ⁺ = 822.3).

Synthesis Example 2-14: Preparation of compound 14

In a nitrogen atmosphere, sub 2-3 (15 g, 24.6 mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (8.8 g, 24.6 mmol) were added. Into 300ml of tetrahydrofuran was stirred and refluxed. Thereafter, potassium carbonate (10.2 g, 73.7 mmol) was dissolved in 10 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 0.7 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 988 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Compound 14 (11.9g, yield: 60%, MS: [M+H] ⁺ = 805.3).

Synthesis Example 2-15: Preparation of compound 15

In a nitrogen atmosphere, sub 3-2 (15 g, 35.6 mmol) and 3-phenyl-9H-carbazole (8.7 g, 35.6 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (14.8 g, 106.9 mmol) was dissolved in 15 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (1.2 g, 1.1 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1545 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 15 (21.3g, yield: 69%, MS: [M+H] ⁺ = 868.3).

Synthesis Example 2- 16: Preparation of Compound 16

In a nitrogen atmosphere, sub 3-2 (15 g, 35.6 mmol) and 4-phenyl-9H-carbazole (8.7 g, 35.6 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (14.8 g, 106.9 mmol) was dissolved in 15 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (1.2 g, 1.1 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1545 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 16 (16.7 g, yield: 54%, MS: [M+H] ⁺ = 868.3).

Synthesis Example 2-17: Preparation of compound 17

In a nitrogen atmosphere, sub 3-2 (15 g, 35.6 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (6.2 g, 35.6 mmol) were added to 300 ml of tetrahydrofuran. It was stirred and refluxed. Thereafter, potassium carbonate (14.8 g, 106.9 mmol) was dissolved in 15 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (1.2 g, 1.1 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was added to 1302 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 17 (18.2g, yield: 70%, MS: [M+H] ⁺ = 732.4).

Synthesis Example 2-18: Preparation of compound 18

In a nitrogen atmosphere, sub 3-2 (15 g, 35.6 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (6.2 g, 35.6 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. . Thereafter, potassium carbonate (14.8 g, 106.9 mmol) was dissolved in 15 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (1.2 g, 1.1 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 1295 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a pale yellow solid compound Compound 18 (17.9 g, yield: 69%, MS: [M+H] ⁺ = 728.4).

[Example]

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,300Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, the following HI-1 compound was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and the following HT-2 compound was vacuum deposited on the HT-1 evaporated film to a thickness of 50 Å to form an electron blocking layer. As a light emitting layer on the HT-2 deposited film, a light emitting layer having a thickness of 400 Å was formed by co-depositing Compound 1 prepared in Preparation Example 1, the following YGH-1 compound, and a phosphorescent dopant YGD-1 at a weight ratio of 44:44:12. On the light emitting layer, the following ET-1 compound was vacuum-deposited to a thickness of 250 Å to form an electron transport layer, and the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98:2 to form an electron injection layer having a thickness of 100 Å. Formed. A cathode was formed by depositing aluminum to a thickness of 1000 Å on the electron injection layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 ~ 5 × 10 ^-8 torr. I did.

Examples 2 to 10

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of the compound 1 of Synthesis Example 2-1 in Example 1.

Comparative Examples 1 to 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of the compound 1 of Synthesis Example 2-1 in Example 1.

The compounds of CE1 to CE3 in Table 1 are as follows.

Experimental example

The voltage and efficiency were measured at a current density of ^{10 mA/cm 2} of the organic light emitting device prepared in the above Examples and Comparative Examples, ^{and the lifetime was measured at a current density of 50 mA/cm 2} and the results are shown in Table 1 below. .

At this time, LT95 means the time to become 95% of the initial luminance.

division	compound	Voltage(V)(@10mA/cm 2 )	Efficiency(Cd/A)(@10mA/cm 2 )	Color coordinate (x,y)	Life (h)(LT 95 at 50mA/cm 2 )
Example 1	Compound 1	4.0	81	0.44, 0.54	230
Example 2	Compound 2	4.1	80	0.45, 0.54	220
Example 3	Compound 3	4.0	81	0.46, 0.54	215
Example 4	Compound 4	4.0	81	0.46, 0.54	250
Example 5	Compound 5	4.0	79	0.46, 0.53	220
Example 6	Compound 6	3.9	81	0.46, 0.54	195
Example 7	Compound 7	4.0	81	0.46, 0.54	260
Example 8	Compound 8	4.0	81	0.46, 0.54	240
Experimental Example 9	Compound 9	4.1	80	0.46, 0.53	240
Example 10	Compound 10	4.0	81	0.46, 0.54	250
Example 11	Compound 11	3.8	80	0.46, 0.54	195
Example 12	Compound 12	3.9	81	0.46, 0.54	210
Example 13	Compound 13	4.1	79	0.46, 0.54	240
Example 14	Compound 14	4.2	80	0.46, 0.54	250
Example 15	Compound 15	4.1	80	0.46, 0.54	210
Example 16	Compound 16	4.2	79	0.46, 0.54	240
Example 17	Compound 17	4.0	81	0.44, 0.54	260
Example 18	Compound 18	4.0	81	0.44, 0.54	255
Comparative Example 1	CE1	4.5	75	0.46, 0.54	85
Comparative Example 2	CE2	4.4	77	0.46, 0.55	15
Comparative Example 3	CE3	4.8	66	0.46, 0.55	120

As shown in Table 1, when the compound of the present invention was used as the light emitting layer material, it was confirmed that the compound of the present invention exhibited excellent properties in terms of efficiency and lifespan compared to the comparative experimental example.

Explanation of the sign

1: substrate 2: anode

3: light-emitting layer 4: cathode

5: hole injection layer 6: hole transport layer

7: electron blocking layer 8: electron transport layer

9: electron injection layer

Claims (8)

1. Compound represented by the following formula 1:

   [Formula 1]

   

   In Formula 1,

   X ₁ to X ₃ are each independently CH; Or N, provided that at least one of _{X 1} to X _{3 is N,}

   Ar is substituted or unsubstituted C _6-60 aryl,

   R ₁ and R ₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

   R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

   Each R ₅ is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 5-60} heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

   n1 and n2 are each independently an integer of 0 to 8,

   n3 is an integer from 0 to 2.
2. The method of claim 1,

   X ₁ to X ₃ are all N,

   compound.
3. The method of claim 1,

   R ₁ and R ₂ are each independently phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Dibenzothiophenyl; Carbazole-9-yl; 9-phenyl-9H-carbazolyl; Or 9H-carbazol-9-yl-N-phenyl,

   These are each independently, unsubstituted or substituted with one or more deuterium,

   compound.
4. The method of claim 1,

   R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Or diphenylfluorenyl,

   The phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; And diphenylfluorenyl is each independently substituted or unsubstituted with one or more deuterium,

   compound.
5. The method of claim 1,

   Each R ₅ is independently hydrogen; heavy hydrogen; Phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Dibenzothiophenyl; Carbazole-9-yl; Or 9-phenyl-9H-carbazolyl,

   The phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Dibenzothiophenyl; Carbazole-9-yl; And 9-phenyl-9H-carbazolyl is each independently substituted or unsubstituted with one or more deuterium,

   compound.
6. The method of claim 1,

   Ar is phenyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Or diphenylfluorenyl; and,

   Each independently, deuterium; C _1-60 alkyl; C _6-60 aryl; And C _6-60 unsubstituted or substituted with one or more substituents selected from the group consisting of aralkyl,

   compound.
7. The method of claim 1,

   The compound represented by Formula 1 is any one selected from the group consisting of,

   compound:

   

   

   

   

   

   

   .
8. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 7 That is, an organic light emitting device.

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