KR20210011351A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 can be used as a material for an organic layer of the organic light emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.

Description

A novel compound and an organic light-emitting device using the same {NOVEL COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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, 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. 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.

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,

R ₁ to R ₄ are each independently hydrogen or deuterium, or two adjacent two of R ₁ to R ₄ are bonded to each other to form a C _6-60 aromatic ring unsubstituted or substituted with deuterium,

R ₅ to R ₇ are each independently hydrogen or deuterium,

a is an integer from 1 to 6,

b is an integer of 1 to 3,

c is an integer from 1 to 4,

Any one of Z ₁ and Z ₂ is substituted with the following Formula 2, and the other is hydrogen or deuterium,

[Formula 2]

In Chemical Formula 2,

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

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 heteroatoms selected from the group consisting of N, O and S.

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 Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, electron suppression, 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 suppression layer (7), a light emitting layer (3), a hole blocking layer (8), an electron injection and transport layer ( 9) and an example of an organic light-emitting device comprising a cathode 4 is shown.

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

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

및

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

And

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano 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 heteroaryl 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 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, 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 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, cyclohexylmethyl, 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 monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.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, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, 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 ( phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited thereto.

In the present specification, the aromatic ring refers to a condensed monocyclic or condensed polycyclic ring including only carbon as a ring-forming atom and having aromaticity in the entire molecule. The number of carbon atoms in the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. In addition, the aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a pyrene ring, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl 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 above-described description of heteroaryl 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 above-described heteroaryl 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 heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.

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

The compound represented by Formula 1 has a structure in which a triazinyl-based substituent and a benzocarbazolyl-based substituent are connected by a benzonaphthofuranylene linker. An organic light-emitting device employing such a compound has a high efficiency and long lifespan compared to an organic light-emitting device employing a compound that does not have a triazinyl-based substituent and a benzocarbazolyl-based substituent at the same time and a compound having a structure in which these two substituents are connected by different linkers Characteristics.

Preferably, the compound represented by Formula 1 may be one selected from the group consisting of compounds represented by the following Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

X, Ar ₁ , Ar ₂ , R ₁ to R ₇ , a, b and c are as defined in Chemical Formula 1.

Preferably, R ₁ to R ₄ are each independently hydrogen or deuterium; Or two adjacent ones of R ₁ to R ₄ may be bonded to each other to form a benzene ring unsubstituted or substituted with deuterium.

More preferably, R ₁ to R ₄ are all hydrogen, or all deuterium; Alternatively, two adjacent ones of R ₁ to R ₄ may be bonded to each other to form a benzene ring unsubstituted or substituted with deuterium, and the remainder may be hydrogen or deuterium.

At this time, the fact that two adjacent ones of R ₁ to R ₄ are bonded to each other to form a benzene ring means that R ₁ and R ₂ are bonded to each other to form a benzene ring; R ₂ and R ₃ are bonded to each other to form a benzene ring; Or it means that R ₃ and R ₄ are bonded to each other to form a benzene ring.

Specifically, the compound may be one selected from the group consisting of compounds represented by any one of the following Formulas 3-1 to 3-4.

[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4,

R ₁ to R ₄ and R are each independently hydrogen or deuterium,

d is an integer from 1 to 4,

Z ₁ , Z ₂ , R ₅ to R ₇ , a, b and c are as defined in Chemical Formula 1.

Preferably, X may be all N.

Preferably, Ar ₁ and Ar ₂ may each independently be C _6-20 aryl unsubstituted or substituted with deuterium.

More preferably, Ar ₁ and Ar ₂ are each independently It may be any one selected from the group consisting of the following.

Preferably, R ₅ to R ₇ may be hydrogen.

For example, the compound may be any one selected from the group consisting of the following compounds.

On the other hand, the compound represented by Formula 1 may be prepared by a manufacturing method such as the following Scheme 1 as an example. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme 1]

In Reaction Scheme 1, the definitions other than Q are as defined above, and Q is halogen, more preferably bromo or chloro. The reaction is a Suzuki coupling reaction or the like, and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

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 host of a light emitting layer.

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

In addition, the electron transport layer, the electron injection layer, the hole blocking layer, or the layer that simultaneously transports electrons and injects electrons includes the 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.

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

Specifically, the organic material layer may include an emission layer, and the emission layer may include a host material.

In this case, the host material may include the compound represented by Chemical Formula 1.

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 multi-layered 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, etc., 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.

For example, the dopant may be any one selected from compounds represented by the following Dp-1 to Dp-38.

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 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, perylene tetracarboxylic 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 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.

Preparation of the compound represented by Formula 1 and an 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.

Preparation Example 1: Preparation of compound a

1) Preparation of compound a-1

Naphthalen-2-amine (300.0 g, 1.0 eq), 1-bromo-2-iodobenzene, 592.7 g, 1.0 eq), sodium tert-butoxide (NaOtBu, 302.0 g, 1.5 eq), palladium acetate (Pd(OAc) ₂ , 4.70 g, 0.01 eq), Xantphos (12.12 g, 0.01 eq), 1,4-dioxane (1,4-dioxane , 5 L) and refluxed, followed by stirring. When the reaction was completed after 3 hours, the pressure was reduced to remove the solvent. After that, it was completely dissolved in ethylene acetate, washed with water, and reduced pressure to remove about 70% of the solvent. In the reflux state, hexene was added, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound a-1. (443.5 g, yield 71%, MS: [M+H] ⁺ =299)

2) Preparation of compound a

Compound a-1 (443.5 g, 1.0 eq) bis (tri-tert-butylphosphine) palladium (0) (Pd (t-Bu ₃ P) ₂ , 8.56 g, 0.01 eq) and potassium carbonate (K ₂ CO ₃ , 463.2 g, 2.00 eq) were added to diethylacetamide (Dimethylacetamide, 4 L), followed by reflux and stirred. After 3 hours, the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to drop crystals, cooled, and filtered. This was purified by column chromatography to obtain compound a (5H-benzo[b]carbazole). (174.8 g, yield 48%, MS: [M+H] ⁺ =218)

Preparation Example 2: Preparation of compound b

The following intermediate in the same manner as in Preparation Example 1, except that 1-bromo-2-iodonaphthalene was used instead of 1-bromo-2-iodobenzene b(7H-dibenzo[b,g]carbazole) was obtained.

Preparation Example 3: Preparation of compound c

In the same manner as in Preparation Example 1, except that 2,3-dibromonaphthalene was used instead of 1-bromo-2-iodobenzene, the following intermediate c(6H- dibenzo[b,h]carbazole) was obtained.

Preparation Example 4: Preparation of compound d

The following intermediate in the same manner as in Preparation Example 1, except that 2-bromo-1-iodonaphthalene was used instead of 1-bromo-2-iodobenzene d(13H-dibenzo[a,h]carbazole) was prepared.

Preparation Example 5: Preparation of Intermediate 1-a

1) Synthesis of Intermediate 1-1

Add naphtho[2,1-b]benzofuran-2-ylboronic acid (30.0 g, 114.5 mmol) and N-chlorosuccinimide (15.29 g, 46.2 mmol) in dimethylformamide (300 ml) at room temperature Stirred at. After the reaction for 3 hours, the reactant was poured into water to drop crystals and filtered. This was again dissolved in 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 purified by silica gel column chromatography to prepare Intermediate 1-1. (28.17 g, yield 83%, MS: [M+H] ⁺ = 297)

2) Synthesis of Intermediate 1-a

In a nitrogen atmosphere, intermediate 1-1 (31.2 g, 105.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (28.2 g, 105.2 mmol) were added to THF (624 ml) and stirred. Then, potassium carbonate (58.2 g, 420.9 mmol) was dissolved in water and added, stirred sufficiently, and when refluxed, bis (tri-tert-butylphosphine) palladium (0) (0.5 g, 1.1 mmol) was added. After the reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 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 purified by silica gel column chromatography to prepare Intermediate 1-a. (34.1 g, yield 67%, MS: [M+H] ⁺ = 485)

Example 1: Preparation of compound 1

In a nitrogen atmosphere, intermediate 1-a (20 g, 41.3 mmol), compound a (9 g, 41.3 mmol), sodium tert-butoxide (7.9 g, 82.7 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 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 compound 1. (9.6 g, yield 35%, MS: [M+H] ⁺ = 666)

Example 2: Preparation of compound 2

In a nitrogen atmosphere, intermediate 2-a (20 g, 31.4 mmol), compound a (6.8 g, 31.4 mmol), sodium tert-butoxide (6 g, 62.9 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 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 compound 2. (9.8 g, yield 38%, MS: [M+H] ⁺ = 818)

Example 3: Preparation of compound 3

In a nitrogen atmosphere, intermediate 3-a (20 g, 32.8 mmol), compound a (7.1 g, 32.8 mmol), sodium tert-butoxide (6.3 g, 65.6 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 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 compound 3. (13.5 g, yield 52%, MS: [M+H] ⁺ = 792)

Example 4: Preparation of compound 4

In a nitrogen atmosphere, intermediate 4-a (20 g, 30.8 mmol), compound a (6.7 g, 30.8 mmol), sodium tert-butoxide (5.9 g, 61.5 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 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 compound 4. (14.3 g, yield 56%, MS: [M+H] ⁺ = 832)

Example 5: Preparation of compound 5

In a nitrogen atmosphere, intermediate 5-a (20 g, 34.9 mmol), compound a (7.6 g, 34.9 mmol), sodium tert-butoxide (6.7 g, 69.8 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 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 compound 5. (15.8 g, yield 60%, MS: [M+H] ⁺ = 755)

Example 6: Preparation of compound 6

In a nitrogen atmosphere, intermediate 6-a (20 g, 34.2 mmol), compound a (7.4 g, 34.2 mmol), sodium tert-butoxide (6.6 g, 68.5 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 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 compound 6. (15.5 g, yield 59%, MS: [M+H] ⁺ = 766)

Example 7: Preparation of compound 7

In a nitrogen atmosphere, intermediate 7-a (20 g, 34.8 mmol), compound a (7.6 g, 34.8 mmol), sodium tert-butoxide (6.7 g, 69.7 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 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 compound 7. (13.9 g, yield 53%, MS: [M+H] ⁺ = 756)

Example 8: Preparation of compound 8

In a nitrogen atmosphere, intermediate 8-a (20 g, 32.8 mmol), compound a (7.1 g, 32.8 mmol), sodium tert-butoxide (6.3 g, 65.6 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 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 compound 8. (10.4 g, yield 40%, MS: [M+H] ⁺ = 792)

Example 9: Preparation of compound 9

In a nitrogen atmosphere, intermediate 9-a (20 g, 30 mmol), compound a (6.5 g, 30 mmol), sodium tert-butoxide (5.8 g, 60 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, 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 compound 9. (10.4 g, yield 41%, MS: [M+H] ⁺ = 848)

Example 10: Preparation of compound 10

In a nitrogen atmosphere, intermediate 10-a (20 g, 28.6 mmol), compound a (6.2 g, 28.6 mmol), sodium tert-butoxide (5.5 g, 57.2 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 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 compound 10. (10.8 g, yield 43%, MS: [M+H] ⁺ = 881)

Example 11: Preparation of compound 11

In a nitrogen atmosphere, intermediate 11-a (20 g, 41.3 mmol), compound c (11 g, 41.3 mmol), sodium tert-butoxide (7.9 g, 82.7 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 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 compound 11. (13.6 g, yield 46%, MS: [M+H] ⁺ = 716)

Example 12: Preparation of compound 12

In a nitrogen atmosphere, intermediate 12-a (20 g, 34.2 mmol), compound b (9.2 g, 34.2 mmol), sodium tert-butoxide (6.6 g, 68.5 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After 2 hours, the reaction was completed, 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 compound 12. (10.3 g, yield 37%, MS: [M+H] ⁺ = 816)

Example 13: Preparation of compound 13

In a nitrogen atmosphere, intermediate 13-a (20 g, 32 mmol), compound c (8.6 g, 32 mmol), sodium tert-butoxide (6.2 g, 64.1 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 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 compound 13. (15.1 g, yield 55%, MS: [M+H] ⁺ = 856)

Example 14: Preparation of compound 14

In a nitrogen atmosphere, intermediate 14-a (20 g, 33.9 mmol), compound c (9.1 g, 33.9 mmol), sodium tert-butoxide (6.5 g, 67.8 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After 4 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 compound 14. (15.6 g, yield 56%, MS: [M+H] ⁺ = 822)

Example 15: Preparation of compound 15

In a nitrogen atmosphere, intermediate 15-a (20 g, 30.8 mmol), compound d (8.2 g, 30.8 mmol), sodium tert-butoxide (5.9 g, 61.6 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 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 compound 15. (12.5 g, yield 46%, MS: [M+H] ⁺ = 881)

Example 16: Preparation of compound 16

In a nitrogen atmosphere, intermediate 16-a (20 g, 32.8 mmol), compound b (8.8 g, 32.8 mmol), sodium tert-butoxide (6.3 g, 65.6 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 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 compound 16. (10.8 g, yield 39%, MS: [M+H] ⁺ = 842)

Example 17: Preparation of compound 17

In a nitrogen atmosphere, intermediate 17-a (20 g, 31.4 mmol), compound b (8.4 g, 31.4 mmol), sodium tert-butoxide (6 g, 62.9 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 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 compound 17. (14.2 g, yield 52%, MS: [M+H] ⁺ = 868)

Example 18: Preparation of compound 18

In a nitrogen atmosphere, intermediate 18-a (20 g, 34.2 mmol), compound c (9.2 g, 34.2 mmol), sodium tert-butoxide (6.6 g, 68.5 mmol) was added to xylene (400 ml) and stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After 4 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 compound 18. (15.6 g, yield 56%, MS: [M+H] ⁺ = 816)

Example 19: Preparation of compound 19

In a nitrogen atmosphere, intermediate 19-a (20 g, 30.8 mmol), compound d (8.2 g, 30.8 mmol), sodium tert-butoxide (5.9 g, 61.5 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 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 compound 19. (13.5 g, yield 50%, MS: [M+H] ⁺ = 881)

Example 20: Preparation of compound 20

In a nitrogen atmosphere, intermediate 20-a (20 g, 30.8 mmol), compound d (8.2 g, 30.8 mmol), sodium tert-butoxide (5.9 g, 61.6 mmol) was added to xylene (400 ml), stirred and refluxed. . After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 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 compound 20. (9.2 g, yield 34%, MS: [M+H] ⁺ = 881)

Experimental Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing 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, the following EB-1 compound having a thickness of 150 Å was vacuum deposited on the hole transport layer to form an electron suppressing layer. Subsequently, on the electron suppression layer, the compound 1 prepared in Example 1 and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 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.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, the deposition rate of aluminum was maintained 2Å / sec, the degree of vacuum upon deposition 2ⅹ10 ^-7 ~ An organic light-emitting device was fabricated by maintaining 5x10 ^-6 torr.

Experimental example 2 to 20 and Comparative Experimental Example 1 to 9

In the organic light-emitting device of Experimental Example 1, an organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1.

The voltage, efficiency and lifetime were measured at 10 mA/cm ² current density in the organic light emitting devices prepared in Experimental Examples 1 to 20 and Comparative Experimental Examples 1 to 9, and the results are shown in Table 1 below. At this time, the lifetime T ₉₅ means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division Host Driving voltage (V) Efficiency (cd/A) Life T ₉₅ (hr) Luminous color Experimental Example 1 Compound 1 3.57 23.5 171 Red Experimental Example 2 Compound 2 3.58 24.7 175 Red Experimental Example 3 Compound 3 3.54 24.8 167 Red Experimental Example 4 Compound 4 3.56 25.1 160 Red Experimental Example 5 Compound 5 3.61 24.5 171 Red Experimental Example 6 Compound 6 3.62 25.3 165 Red Experimental Example 7 Compound 7 3.75 25.9 168 Red Experimental Example 8 Compound 8 3.73 24.5 171 Red Experimental Example 9 Compound 9 3.70 25.3 163 Red Experimental Example 10 Compound 10 3.72 25.7 169 Red Experimental Example 11 Compound 11 3.74 26.8 177 Red Experimental Example 12 Compound 12 3.69 25.3 189 Red Experimental Example 13 Compound 13 3.74 26.9 183 Red Experimental Example 14 Compound 14 3.71 27.1 191 Red Experimental Example 15 Compound 15 3.68 28.0 203 Red Experimental Example 16 Compound 16 3.52 28.2 205 Red Experimental Example 17 Compound 17 3.58 28.6 210 Red Experimental Example 18 Compound 18 3.53 27.5 203 Red Experimental Example 19 Compound 19 3.61 28.1 218 Red Experimental Example 20 Compound 20 3.51 27.5 204 Red Comparative Experimental Example 1 RH-1 4.02 21.1 124 Red Comparative Experiment 2 C-1 4.31 16.1 31 Red Comparative Experiment 3 C-2 4.42 15.9 13 Red Comparative Experimental Example 4 C-3 4.38 14.7 15 Red Comparative Experimental Example 5 C-4 4.35 14.2 19 Red Comparative Experiment 6 C-5 4.21 16.2 81 Red Comparative Experimental Example 7 C-6 4.27 16.8 94 Red Comparative Experimental Example 8 C-7 3.99 22.0 128 Red Comparative Experimental Example 9 C-8 3.95 22.5 141 Red

According to Table 1, it was confirmed that the driving voltage was significantly lowered in the experimental example compared to the comparative experimental example, and the efficiency was also increased significantly, and accordingly, the experimental example transferred energy from the host to the red dopant compared to the comparative experimental example. It is predictable that this will work. In addition, it was confirmed that the experimental example significantly improved the lifespan characteristics by more than two times while maintaining high efficiency compared to the comparative experimental example, and accordingly, it was predicted that the experimental example had higher stability against electrons and holes compared to the comparative experimental example. I can. Accordingly, it was confirmed that when the compound of the present invention was used as a host of the emission layer, the driving voltage, luminous efficiency, and lifetime characteristics of the organic light emitting device could be improved.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: hole blocking layer
9: electron injection and transport layer

Claims (10)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
R ₁ to R ₄ are each independently hydrogen or deuterium, or two adjacent two of R ₁ to R ₄ are bonded to each other to form a C _6-60 aromatic ring unsubstituted or substituted with deuterium,
R ₅ to R ₇ are each independently hydrogen or deuterium,
a is an integer from 1 to 6,
b is an integer of 1 to 3,
c is an integer from 1 to 4,
Any one of Z ₁ and Z ₂ is substituted with the following formula (2), and the other is hydrogen or deuterium,
[Formula 2]

In Chemical Formula 2,
Each X is independently N or CH, provided that at least two of X are N,
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 heteroatoms selected from the group consisting of N, O and S.
The method of claim 1,
The compound is any one selected from the group consisting of compounds represented by the following Formula 1-1 or 1-2,
compound:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
X, Ar ₁ , Ar ₂ , R ₁ to R ₇ , a, b and c are as defined in claim 1.
The method of claim 1,
X is all N,
compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently Any one selected from the group consisting of,
compound:

The method of claim 1,
R ₅ to R ₇ are hydrogen,
compound.
The method of claim 1,
The compound is any one selected from the group consisting of compounds represented by the following formulas 3-1 to 3-4,
compound:
[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4,
R ₁ to R ₄ and R are each independently hydrogen or deuterium,
d is an integer from 1 to 4,
Z ₁ , Z ₂ , R ₅ to R ₇ , a, b and c are as defined in claim 1.
The method of claim 1,
The compound is any one selected from the group consisting of the following compounds,
compound:

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 contains the compound according to any one of claims 1 to 7 That is, an organic light emitting device.
The method of claim 8,
The organic material layer may include an emission layer, and the emission layer includes a host material.
The method of claim 9,
The host material includes a compound represented by Formula 1 above.

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