WO2020263000A1 - Novel compound and organic light emitting device using same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device using the same

Cross-reference with related application(s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0078375 filed June 28, 2019 and Korean Patent Application No. 10-2020-0077220 filed June 24, 2020. All contents disclosed in the literature are included as part of this specification.

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy 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.

The 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, etc. 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. It glows when it falls back to the ground.

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

[Prior technical literature]

[Patent Document] (Patent Document 1) Korean Patent Publication No. 10-2000-0051826

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

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

[Formula 1]

In Formula 1,

Each X is independently N or CH, provided that at least two of X are N,

L is a trivalent or higher C _6-10 aromatic ring,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,

Ar ₃ is substituted or unsubstituted C _6-60 aryl,

R is all hydrogen, or two adjacent R are combined to form a benzene ring,

n is an integer of 1≤n≤10.

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 a compound represented by Formula 1 do.

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.

FIG. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 I did it.

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

The present invention provides a compound represented by Chemical Formula 1.

In this specification,

or

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; 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 a substituted or unsubstituted 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 linked with two or more substituents 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 it 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 an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. 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, and a phenyl boron group, 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 a linear or branched chain, 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 is preferably 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,

Etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbons 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, acridyl group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl 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, isoxazolyl group, thiiadia There may be a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, 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 the 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 above-described heterocyclic group may be applied, except that two substituents are bonded to each other.

compound

The present invention provides a compound represented by Chemical Formula 1.

The compound represented by Formula 1 is based on a structure in which 5H-benzo[b]carbazole or a derivative thereof; is bonded with a pyrimidine or triazine-based substituent.

Specifically, the pyrimidine or triazine-based substituent group, via the linking group (L) substituted with at least one aryl (Ar ₃ ), the 5H-benzo[b]carbazole (5H-benzo[b]carbazole ) Or its derivative N.

Such a structure is 5H-benzo[b]carbazole or a derivative thereof, a pyrimidine or triazine-based substituent, and a linking group substituted with at least one aryl (Ar ₃ ) (L ) A structure lacking any one of; Alternatively, it may have heat resistance, high melting point, etc., in contrast to a structure in which any one is replaced with another substituent.

Therefore, when the compound represented by Formula 1 is used as an organic material layer of an organic light-emitting device, particularly as a material for a light-emitting layer, low voltage, high efficiency, color reproducibility, life characteristics, etc. can be improved by synergistic effects of the substituents.

Hereinafter, the formula 1 and the compound represented by the formula will be described in detail as follows.

In Formula 1, it may be represented by the following Formulas 1-1, 1-2, 1-3, or 1-4 according to R:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, X, L, Ar ₁ , Ar _2, Ar ₃ , and n are as defined above.

Each X is independently N or CH, provided that at least two of X are N.

For example, all of X may be N.

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-30 aryl; Or it may be a substituted or unsubstituted C _2-30 heteroaryl including any one or more selected from the group consisting of N, O and S.

Specifically, Ar ₁ and Ar ₂ are each independently, phenyl, biphenylyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H- It may be carbazolyl. Here, Ar ₁ and Ar ₂ may each independently be unsubstituted or substituted with one or more deuterium.

For example, Ar ₁ and Ar ₂ are each independently unsubstituted phenyl, biphenylyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl- Is 9H-carbazolyl; It may be phenyl or biphenylyl substituted with 5 deuterium.

Here, at least one of Ar ₁ and Ar ₂ may be unsubstituted phenyl, but is not limited thereto.

L is a trivalent or higher C _6-10 aromatic ring, and the oxidation number may be determined according to the number of substituents (n) of L.

Specifically, n may be an integer of 1≦n≦4, and thus L may have a 3 to hexavalent oxidation number.

For example, L may be trivalent to hexavalent benzene or naphthalene. The bonding position of Ar ₃ to the L is not particularly limited.

Ar ₃ may be substituted or unsubstituted C _6-30 aryl.

Specifically, Ar ₃ may be phenyl, biphenylyl, or naphthyl, and Ar ₃ may be unsubstituted or substituted with one or more deuterium.

For example, Ar ₃ is unsubstituted phenyl, biphenylyl, or naphthyl; It may be phenyl substituted with 5 deuterium. When n is an integer of 2≤n≤4, Ar ₃ may be the same or different.

Representative examples of the compound represented by Formula 1 are as follows:

.

The compound represented by Formula 1 may be prepared using the following Scheme 1.

[Scheme 1]

(In the above reaction formula, the definition of the substituent is as described above.)

However, the manufacturing method is an example, and may be more specific in the manufacturing example to be described later.

Organic light emitting element

In addition, the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1. 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 an emission layer, and the emission layer includes the compound represented by Chemical Formula 1. In particular, the compound according to the present invention can be used as a dopant for a light emitting layer.

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

In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously transports electrons and injects electrons includes the compound represented by Formula 1 above.

In addition, the organic material layer may include a light emitting 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 an organic light emitting device having a structure (normal type) 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.

FIG. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 I did it. 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 light emitting layer, and the electron transport 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 an 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 a light emitting layer or a light emitting material. 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 light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples of 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-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, and periflanthene 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 an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

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 receiving electrons from the cathode and transferring them to the emission layer 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 on 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 has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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.

Hereinafter, the action and effect of the invention will be described in more detail through specific examples of the invention. However, this is presented as an example of the invention, and the scope of the invention is not limited to any meaning.

Synthesis Example 1

In a nitrogen atmosphere, sub 1 (10 g, 23.8 mmol), formula a (5.7 g, 26.2 mmol), and sodium tert-butoxide (4.6 g, 47.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10 g of compound 1. (Yield 70%, MS: [M+H]+= 601)

Synthesis Example 2

In a nitrogen atmosphere, sub 2 (10 g, 21.3 mmol), formula a (5.1 g, 23.4 mmol), sodium tert-butoxide (4.1 g, 42.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound 2. (Yield 62%, MS: [M+H]+= 651)

Synthesis Example 3

In a nitrogen atmosphere, sub 3 (10 g, 19.2 mmol), formula a (4.6 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 3. (Yield 56%, MS: [M+H]+= 701)

Synthesis Example 4

In a nitrogen atmosphere, sub 4 (10 g, 21.3 mmol), formula a (5.1 g, 23.4 mmol), sodium tert-butoxide (4.1 g, 42.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 4. (Yield 70%, MS: [M+H]+= 651)

Synthesis Example 5

In a nitrogen atmosphere, sub 5 (10 g, 19.2 mmol), formula a (4.6 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of compound 5. (Yield 51%, MS: [M+H]+= 701)

Synthesis Example 6

In a nitrogen atmosphere, sub 6 (10 g, 19.6 mmol), formula a (4.7 g, 21.6 mmol), sodium tert-butoxide (3.8 g, 39.2 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.4 g of compound 6. (Yield 55%, MS: [M+H]+= 691)

Synthesis Example 7

In a nitrogen atmosphere, sub 7 (10 g, 19 mmol), formula a (4.5 g, 20.9 mmol), sodium tert-butoxide (3.7 g, 38 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 7. (Yield 59%, MS: [M+H]+= 707)

Synthesis Example 8

In a nitrogen atmosphere, sub 8 (10 g, 17.4 mmol), formula a (4.1 g, 19.1 mmol), sodium tert-butoxide (3.3 g, 34.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.1 g of compound 8. (Yield 69%, MS: [M+H]+= 757)

Synthesis Example 9

In a nitrogen atmosphere, sub 9 (10 g, 17.1 mmol), formula a (4.1 g, 18.8 mmol), sodium tert-butoxide (3.3 g, 34.2 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 9. (Yield 60%, MS: [M+H]+= 766)

Synthesis Example 10

In a nitrogen atmosphere, sub 10 (10 g, 15.7 mmol), formula a (3.8 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.2 g of compound 10. (Yield 56%, MS: [M+H]+= 816)

Synthesis Example 11

In a nitrogen atmosphere, sub 11 (10 g, 18.3 mmol), formula a (4.4 g, 20.1 mmol), sodium tert-butoxide (3.5 g, 36.6 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 11. (Yield 58%, MS: [M+H]+= 727)

Synthesis Example 12

In a nitrogen atmosphere, sub 12 (10 g, 17.5 mmol), formula a (4.2 g, 19.3 mmol), sodium tert-butoxide (3.4 g, 35.1 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of compound 12. (Yield 68%, MS: [M+H]+= 751)

Synthesis Example 13

In a nitrogen atmosphere, sub 13 (10 g, 17.5 mmol), formula a (4.2 g, 19.3 mmol), sodium tert-butoxide (3.4 g, 35.1 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of compound 13. (Yield 61%, MS: [M+H]+= 751)

Synthesis Example 14

In a nitrogen atmosphere, sub 14 (10 g, 16.4 mmol), formula a (3.9 g, 18 mmol), sodium tert-butoxide (3.2 g, 32.8 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of compound 14. (Yield 53%, MS: [M+H]+= 791)

Synthesis Example 15

In a nitrogen atmosphere, sub 15 (10 g, 18.3 mmol), formula a (4.4 g, 20.1 mmol), sodium tert-butoxide (3.5 g, 36.6 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.5 g of compound 15. (Yield 64%, MS: [M+H]+= 727)

Synthesis Example 16

In a nitrogen atmosphere, sub 16 (10 g, 18.3 mmol), formula a (4.4 g, 20.1 mmol), sodium tert-butoxide (3.5 g, 36.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.3 g of compound 16. (Yield 55%, MS: [M+H]+= 727)

Synthesis Example 17

In a nitrogen atmosphere, sub 17 (10 g, 15.7 mmol), formula a (3.8 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.4 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of compound 17. (Yield 52%, MS: [M+H]+= 817)

Synthesis Example 18

In a nitrogen atmosphere, sub 18 (10 g, 15.1 mmol), formula a (3.6 g, 16.6 mmol), sodium tert-butoxide (2.9 g, 30.2 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound 18. (Yield 66%, MS: [M+H]+= 842)

Synthesis Example 19

In a nitrogen atmosphere, sub 19 (10 g, 23.3 mmol), formula a (5.6 g, 25.6 mmol), sodium tert-butoxide (4.5 g, 46.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 19. (Yield 53%, MS: [M+H]+= 611)

Synthesis Example 20

In a nitrogen atmosphere, sub 20 (10 g, 21.1 mmol), formula a (5 g, 23.2 mmol), sodium tert-butoxide (4 g, 42.1 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.2 g of compound 20. (Yield 52%, MS: [M+H]+= 656)

Synthesis Example 21

In a nitrogen atmosphere, sub 21 (10 g, 23.8 mmol), formula d (7 g, 26.2 mmol), sodium tert-butoxide (4.6 g, 47.6 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of compound 21. (Yield 65%, MS: [M+H]+= 651)

Synthesis Example 22

In a nitrogen atmosphere, sub 22 (10 g, 19.2 mmol), formula d (5.7 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 22. (Yield 65%, MS: [M+H]+= 751)

Synthesis Example 23

In a nitrogen atmosphere, sub 23 (10 g, 19.2 mmol), formula d (5.7 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 23. (Yield 65%, MS: [M+H]+= 751)

Synthesis Example 24

In a nitrogen atmosphere, sub 24 (10 g, 19.2 mmol), formula d (5.7 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.2 g of compound 24. (Yield 50%, MS: [M+H]+= 751)

Synthesis Example 25

In a nitrogen atmosphere, sub 25 (10 g, 17.9 mmol), formula d (5.3 g, 19.6 mmol), sodium tert-butoxide (3.4 g, 35.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 25. (Yield 56%, MS: [M+H]+= 791)

Synthesis Example 26

In a nitrogen atmosphere, sub 26 (10 g, 16.6 mmol), formula d (4.9 g, 18.3 mmol), sodium tert-butoxide (3.2 g, 33.2 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 26. (Yield 67%, MS: [M+H]+= 833)

Synthesis Example 27

In a nitrogen atmosphere, sub 27 (10 g, 14.1 mmol), formula d (4.1 g, 15.5 mmol), sodium tert-butoxide (2.7 g, 28.1 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of compound 27. (Yield 54%, MS: [M+H]+= 942)

Synthesis Example 28

In a nitrogen atmosphere, sub 28 (10 g, 15.7 mmol), formula d (4.6 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.8 g of compound 28. (Yield 50%, MS: [M+H]+= 866)

Synthesis Example 29

In a nitrogen atmosphere, sub 29 (10 g, 19.2 mmol), formula d (5.7 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 29. (Yield 60%, MS: [M+H]+= 751)

Synthesis Example 30

In a nitrogen atmosphere, sub 30 (10 g, 16.8 mmol), formula d (4.9 g, 18.5 mmol), sodium tert-butoxide (3.2 g, 33.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.3 g of compound 30. (Yield 53%, MS: [M+H]+= 827)

Synthesis Example 31

In a nitrogen atmosphere, sub 31 (10 g, 15.7 mmol), formula d (4.6 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.4 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 31. (Yield 69%, MS: [M+H]+= 867)

Synthesis Example 32

In a nitrogen atmosphere, sub 32 (10 g, 21.1 mmol), formula d (6.2 g, 23.2 mmol), sodium tert-butoxide (4 g, 42.1 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 32. (Yield 59%, MS: [M+H]+= 703)

Synthesis Example 33

In a nitrogen atmosphere, sub 33 (10 g, 21.3 mmol), formula c (6.3 g, 23.4 mmol), sodium tert-butoxide (4.1 g, 42.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of compound 33. (Yield 60%, MS: [M+H]+= 701)

Synthesis Example 34

In a nitrogen atmosphere, sub 34 (10 g, 21.3 mmol), formula c (6.3 g, 23.4 mmol), sodium tert-butoxide (4.1 g, 42.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9 g of compound 34. (Yield 60%, MS: [M+H]+= 701)

Synthesis Example 35

In a nitrogen atmosphere, sub 35 (10 g, 21.3 mmol), formula c (6.3 g, 23.4 mmol), sodium tert-butoxide (4.1 g, 42.6 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound 35. (Yield 58%, MS: [M+H]+= 701)

Synthesis Example 36

In a nitrogen atmosphere, sub 36 (10 g, 17.5 mmol), formula c (5.2 g, 19.3 mmol), sodium tert-butoxide (3.4 g, 35.1 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 36. (Yield 66%, MS: [M+H]+= 801)

Synthesis Example 37

In a nitrogen atmosphere, sub 37 (10 g, 17.9 mmol), formula c (5.3 g, 19.6 mmol), sodium tert-butoxide (3.4 g, 35.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of compound 37. (Yield 58%, MS: [M+H]+= 791)

Synthesis Example 38

In a nitrogen atmosphere, sub 38 (10 g, 16.6 mmol), formula c (4.9 g, 18.3 mmol), sodium tert-butoxide (3.2 g, 33.2 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 38. (Yield 54%, MS: [M+H]+= 833)

Synthesis Example 39

In a nitrogen atmosphere, sub 39 (10 g, 15.7 mmol), formula c (4.6 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 39. (Yield 55%, MS: [M+H]+= 866)

Synthesis Example 40

In a nitrogen atmosphere, sub 40 (10 g, 16.8 mmol), formula c (4.9 g, 18.5 mmol), sodium tert-butoxide (3.2 g, 33.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound 40. (Yield 62%, MS: [M+H]+= 827)

Synthesis Example 41

In a nitrogen atmosphere, sub 41 (10 g, 20.2 mmol), formula c (5.9 g, 22.2 mmol), sodium tert-butoxide (3.9 g, 40.3 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.1 g of compound 41. (Yield 55%, MS: [M+H]+= 727)

Synthesis Example 42

In a nitrogen atmosphere, sub 42 (10 g, 15.7 mmol), formula c (4.6 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.4 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 42. (Yield 69%, MS: [M+H]+= 867)

Synthesis Example 43

In a nitrogen atmosphere, sub 43 (10 g, 23.3 mmol), formula c (6.8 g, 25.6 mmol), sodium tert-butoxide (4.5 g, 46.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound 43. (Yield 56%, MS: [M+H]+= 661)

Synthesis Example 44

In a nitrogen atmosphere, sub 44 (10 g, 17.5 mmol), formula c (5.1 g, 19.2 mmol), sodium tert-butoxide (3.4 g, 35 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 44. (Yield 66%, MS: [M+H]+= 803)

Synthesis Example 45

In a nitrogen atmosphere, sub 45 (10 g, 21.3 mmol), formula b (6.3 g, 23.4 mmol), sodium tert-butoxide (4.1 g, 42.6 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.5 g of compound 45. (Yield 57%, MS: [M+H]+= 701)

Synthesis Example 46

In a nitrogen atmosphere, sub 46 (10 g, 18.3 mmol), formula b (5.4 g, 20.1 mmol), sodium tert-butoxide (3.5 g, 36.6 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.3 g of compound 46. (Yield 51%, MS: [M+H]+= 777)

Synthesis Example 47

In a nitrogen atmosphere, sub 47 (10 g, 19.2 mmol), formula b (5.7 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2 g of compound 47. (Yield 57%, MS: [M+H]+= 751)

Synthesis Example 48

In a nitrogen atmosphere, sub 48 (10 g, 19.2 mmol), formula b (5.7 g, 21.2 mmol), sodium tert-butoxide (3.7 g, 38.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.6 g of compound 48. (Yield 53%, MS: [M+H]+= 751)

Synthesis Example 49

In a nitrogen atmosphere, sub 49 (10 g, 17.4 mmol), formula b (5.1 g, 19.1 mmol), sodium tert-butoxide (3.3 g, 34.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.1 g of compound 49. (Yield 65%, MS: [M+H]+= 807)

Synthesis Example 50

In a nitrogen atmosphere, sub 50 (10 g, 17.4 mmol), formula b (5.1 g, 19.1 mmol), sodium tert-butoxide (3.3 g, 34.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound 50. (Yield 60%, MS: [M+H]+= 807)

Synthesis Example 51

In a nitrogen atmosphere, sub 51 (10 g, 15.7 mmol), formula b (4.6 g, 17.3 mmol), sodium tert-butoxide (3 g, 31.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 51. (Yield 57%, MS: [M+H]+= 866)

Synthesis Example 52

In a nitrogen atmosphere, sub 52 (10 g, 17.5 mmol), formula b (5.2 g, 19.3 mmol), sodium tert-butoxide (3.4 g, 35.1 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.5 g of compound 52. (Yield 68%, MS: [M+H]+= 801)

Synthesis Example 53

In a nitrogen atmosphere, sub 53 (10 g, 15.5 mmol), formula b (4.6 g, 17 mmol), sodium tert-butoxide (3 g, 31 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.6 g of compound 53. (Yield 56%, MS: [M+H]+= 877)

Synthesis Example 54

In a nitrogen atmosphere, sub 54 (10 g, 17.1 mmol), formula b (5 g, 18.8 mmol), sodium tert-butoxide (3.3 g, 34.1 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 54. (Yield 57%, MS: [M+H]+= 817)

Synthesis Example 55

In a nitrogen atmosphere, sub 55 (10 g, 15.3 mmol), formula b (4.5 g, 16.9 mmol), sodium tert-butoxide (2.9 g, 30.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.4 g of compound 55. (Yield 55%, MS: [M+H]+= 883)

Synthesis Example 56

In a nitrogen atmosphere, sub 56 (10 g, 15.1 mmol), formula b (4.4 g, 16.6 mmol), sodium tert-butoxide (2.9 g, 30.2 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of compound 56. (Yield 53%, MS: [M+H]+= 892)

Comparative Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. 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 cleaning 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.

The HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 Å, but the compound A-1 was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Subsequently, an electron blocking layer was formed by vacuum vapor deposition of the following EB-1 compound having a thickness of 150 Å on the hole transport layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 vapor deposition film to form a red light emitting layer having a thickness of 400 Å. A hole blocking layer was formed by vacuum vapor deposition of the following HB-1 compound having a thickness of 30 Å on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) at a thickness of 12 Å and aluminum at a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2X10 ^-7 ~ Maintaining 5X10 ^-6 torr, an organic light emitting device was produced.

Examples 1 to 56

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

Comparative Examples 1 to 9

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

When a current was applied to the organic light-emitting devices prepared in Examples 1 to 56 and Comparative Examples 1 to 9, voltage, efficiency, and lifetime were measured (based on 6000 nit), and the results are shown in Table 1 below. . Life T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division	matter	Driving voltage (V)	Efficiency (cd/A)	Life T95(hr)	Luminous color
Comparative Example 1	RH-1	4.32	37.6	187	Red
Comparative Example 2	A	4.55	33.3	125	Red
Comparative Example 3	B	3.95	36.1	121	Red
Comparative Example 4	C	4.63	32.4	90	Red
Comparative Example 5	D	4.44	29.8	88	Red
Comparative Example 6	E	5.00	31.0	91	Red
Comparative Example 7	F	4.13	38.2	130	Red
Comparative Example 8	G	4.99	32.0	111	Red
Comparative Example 9	H	4.63	29.4	107	Red
Example 1	Compound 1	2.5	48.3	331	Red
Example 2	Compound 2	2.7	45.5	333	Red
Example 3	Compound 3	2.95	47.1	280	Red
Example 4	Compound 4	3.01	49.1	300	Red
Example 5	Compound 5	3.32	46.5	288	Red
Example 6	Compound 6	3.41	44.4	318	Red
Example 7	Compound 7	3.43	43.5	279	Red
Example 8	Compound 8	3.34	45.1	289	Red
Example 9	Compound 9	3.28	43.7	311	Red
Example 10	Compound 10	3.38	47.3	315	Red
Example 11	Compound 11	3.35	49.3	302	Red
Example 12	Compound 12	3.46	48.1	340	Red
Example 13	Compound 13	3.45	49.1	324	Red
Example 14	Compound 14	3.29	47.3	318	Red
Example 15	Compound 15	3.75	44.6	324	Red
Example 16	Compound 16	3.56	47.9	329	Red
Example 17	Compound 17	3.61	43.1	308	Red
Example 18	Compound 18	3.58	42.2	298	Red
Example 19	Compound 19	2.99	50.6	350	Red
Example 20	Compound 20	3.00	48.8	348	Red
Example 21	Compound 21	3.26	47.6	303	Red
Example 22	Compound 22	3.55	48.1	307	Red
Example 23	Compound 23	3.52	49.2	318	Red
Example 24	Compound 24	3.40	48.5	333	Red
Example 25	Compound 25	3.43	45.3	326	Red
Example 26	Compound 26	3.68	42.7	301	Red
Example 27	Compound 27	3.53	44.4	336	Red
Example 28	Compound 28	3.67	49.0	311	Red
Example 29	Compound 29	3.33	48.0	363	Red
Example 30	Compound 30	3.63	45.8	350	Red
Example 31	Compound 31	3.59	48.8	321	Red
Example 32	Compound 32	3.00	49.6	348	Red
Example 33	Compound 33	3.25	48.9	338	Red
Example 34	Compound 34	3.23	49.1	336	Red
Example 35	Compound 35	3.21	49.3	321	Red
Example 36	Compound 36	3.43	47.6	318	Red
Example 37	Compound 37	3.38	45.5	301	Red
Example 38	Compound 38	3.54	47.0	288	Red
Example 39	Compound 39	3.35	47.2	295	Red
Example 40	Compound 40	3.42	46.6	311	Red
Example 41	Compound 41	3.44	47.0	310	Red
Example 42	Compound 42	3.58	47.9	320	Red
Example 43	Compound 43	3.03	49.1	344	Red
Example 44	Compound 44	3.55	43.6	300	Red
Example 45	Compound 45	3.33	49.5	330	Red
Example 46	Compound 46	3.41	48.6	309	Red
Example 47	Compound 47	3.28	49.7	327	Red
Example 48	Compound 48	3.33	48.4	331	Red
Example 49	Compound 49	3.61	47.1	312	Red
Example 50	Compound 50	3.58	46.2	319	Red
Example 51	Compound 51	3.48	47.7	335	Red
Example 52	Compound 52	3.34	49.5	310	Red
Example 53	Compound 53	3.37	46.8	296	Red
Example 54	Compound 54	3.41	47.6	289	Red
Example 55	Compound 55	3.53	45.1	287	Red
Example 56	Compound 56	3.39	47.8	313	Red

From Table 1, the compound represented by Formula 1 is 5H-benzo[b]carbazole or a derivative thereof, a pyrimidine or triazine-based substituent, and at least one aryl ( Ar ₃ ) A structure lacking any one of the linking groups (L) substituted with; Alternatively, it can be seen that, in contrast to a structure in which any one has been replaced with another substituent, it is used as a material of the light emitting layer of an organic light emitting device, thereby improving low voltage, high efficiency, color reproducibility, and life characteristics.

[Explanation of code]

1: substrate 2: anode

3: light emitting layer 4: cathode

5: hole injection layer 6: hole transport layer

7: light emitting layer 8: electron transport layer

Claims (12)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Formula 1,

   Each X is independently N or CH, provided that at least two of X are N,

   L is a trivalent or higher C _6-10 aromatic ring,

   Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,

   Ar ₃ is substituted or unsubstituted C _6-60 aryl,

   R is all hydrogen, or two adjacent R are combined to form a benzene ring,

   n is an integer of 1≤n≤10.
2. The method of claim 1,

   Formula 1 is represented by the following Formula 1-1, 1-2, 1-3, or 1-4,

   compound:

   [Formula 1-1]

   

   [Formula 1-2]

   

   [Formula 1-3]

   

   [Formula 1-4]

   

   In Formulas 1-1 to 1-4,

   X, L, Ar ₁ , Ar _2, Ar ₃ , and n are as defined in claim 1.
3. The method of claim 1,

   X is all N,

   compound.
4. The method of claim 1,

   L is trivalent to hexavalent phenyl or naphthyl,

   compound.
5. The method of claim 1,

   n is an integer of 1≤n≤4,

   compound.
6. The method of claim 1,

   Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl ,

   The Ar ₁ and Ar ₂ are each independently, unsubstituted or substituted with one or more deuterium,

   compound.
7. The method of claim 1,

   Ar ₁ and Ar ₂ are each independently unsubstituted phenyl, biphenylyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H- Is carbazolyl; Phenyl or biphenylyl substituted with 5 deuterium

   compound.
8. The method of claim 6,

   At least one of Ar ₁ and Ar ₂ is phenyl,

   compound.
9. The method of claim 1,

   Ar ₃ is phenyl, biphenylyl, or naphthyl,

   Ar ₃ is unsubstituted or substituted with one or more deuterium,

   compound.
10. The method of claim 1,

    Ar ₃ is unsubstituted phenyl, biphenylyl, or naphthyl; Which is phenyl substituted with 5 deuterium,

    compound.
11. The method of claim 1,

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

    compound:

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

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12. A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 11 That is, an organic light-emitting device.

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