KR20200035905A - 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 compound represented by chemical formula 1 can be used as a material for an organic material layer of the organic light emitting device, and can improve efficiency, lower driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

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 emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The 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 have been 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layered structure composed of different materials, for example, 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. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

A is substituted or unsubstituted C _10-60 aryl,

X ₁ , X ₂ and X ₃ are each independently CH or N, provided that at least two of X _1, X ₂ and X ₃ are N,

Y is O or S,

L is a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene comprising one or more of N, O and S,

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl comprising one or more of N, O and S.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. do.

The compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and / or life 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, hole suppression and transport, light emission, electron transport, or electron injection material.

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

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

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

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a linkage to another substituent.

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

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

In the present specification, the oxygen of the ester group may be substituted 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 this specification, the number of carbon atoms of the imide group is not particularly limited, but 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 is specifically 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 straight chain or branched chain, and carbon number 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 are 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 is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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, steelbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is 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 one embodiment, the carbon number of the aryl group is 10 to 60. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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 combine with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl 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, isooxazolyl group, tiadiia A sleepy group, a phenothiazinyl group and a dibenzofuranyl group, and the like, but are not limited thereto.

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

Preferably, A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl-dimethylfluorenyl, spirobifluor Neil, phenyl-triphenylenyl, naphthyl-phenyl, phenanthrenyl-phenyl, dimethylfluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents:

More preferably, A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl-dimethylfluorenyl, spirobiflu Orenyl, naphthyl-phenyl, phenanthrenyl-phenyl, dimethylfluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents:

Most preferably, A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H- Fluorenyl, 9,9-dimethyl-2-phenyl-9H-fluorenyl, 9,9'-spirobifluorenyl, naphthyl-phenyl, phenanthrenyl-phenyl, 9,9-dimethyl-9H- Fluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents:

Preferably, X _1, X ₂ and X ₃ may all be N.

Preferably, L is a single bond; Substituted or unsubstituted C _6-20 arylene; Or a substituted or unsubstituted C _6-20 heteroarylene comprising one or more of N, O and S,

More preferably, L may be a single bond, phenylene, biphenylylene, or terphenylylene,

Most preferably, L may be a single bond or phenylene.

Preferably, at least one of Ar ₁ and Ar ₂ may be substituted or unsubstituted C _6-60 aryl,

More preferably, at least one of Ar ₁ and Ar ₂ may be substituted or unsubstituted C _6-20 aryl.

Preferably, Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-20 aryl; Or C _6-20 heteroaryl including one or more of substituted or unsubstituted N, O, and S,

More preferably, Ar ₁ and Ar ₂ may each independently be phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or carbazoleyl substituted with phenyl,

Most preferably, Ar ₁ and Ar ₂ may each independently be phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenyl-9H-carbazolyl have.

Preferably, the formula 1 may be represented by any one of the following formulas 1-1 to 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formula 1-1 to Formula 1-4, A, X ₁ , X ₂ , X ₃ , Y, L, Ar ₁ and Ar ₂ are as defined in Formula 1 above.

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

The compound represented by Chemical Formula 1 may be prepared, for example, by the same method as in Scheme 1 below, and other compounds may be similarly prepared.

[Scheme 1]

In Reaction Scheme 1, A, X ₁ , X ₂ , X ₃ , Y, L, Ar ₁ and Ar ₂ are as defined in Chemical Formula 1, X is halogen, and preferably X is chloro or bromo.

Reaction Scheme 1 is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified 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 comprising the compound represented by the formula (1). In one example, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. 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 multi-layer 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 as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1. In particular, the compound according to the present invention can be used as a host for a light emitting layer.

Further, the organic material layer may include the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection may include the It may include a compound represented by the formula (1).

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

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

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

2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9) And an example of an organic light-emitting device comprising the cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, the hole blocking 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 layer of the organic material layer 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, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound represented by Chemical 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

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

In one 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.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode 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); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably 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 is a multilayer structure material such as LiF / Al or LiO ₂ / Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and which has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer by receiving holes, and is a material that can transport holes to the light emitting layer by receiving holes from the anode or the hole injection layer as a hole transport material and has a high mobility for holes. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

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

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Preferably, the compound represented by Formula 1 may be included as a host material.

Examples of the dopant material 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 arylamino groups such as pyrene, anthracene, chrysene, periplanten, and the substituted or unsubstituted styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

The hole blocking layer is a layer interposed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and passing into the electron transport layer, and is also referred to as a hole blocking layer or a hole blocking layer. A material having a large ionization energy is preferable for the hole suppressing layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. 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 those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a 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 forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

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

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

The preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

[Production example]

Preparation Example 1 Preparation of Compound 1

1) Preparation of intermediate A1

In a nitrogen atmosphere, 2,7-dichlorobenzothiazole (10.0 g, 49.0 mmol) and [1,1'-biphenyl] -3-ylboronic acid (16.6 g, 51.5 mmol) were added to 100 ml of dioxane and stirred and refluxed. Did. Thereafter, cesium carbonate (31.9 g, 98.0 mmol) was dissolved in 50 ml of water, stirred sufficiently, and bis (tri- t -butylphosphine) palladium (0) (0.25 g, 0.49 mmol) was added. After the reaction for 5 hours, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried using magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using a mixed solution of chloroform and ethyl acetate. The resulting solid was filtered and dried to prepare intermediate A1 (11.3 g, yield 72%).

MS: [M + H] + = 322

2) Preparation of intermediate A2

Intermediate A1 (11.3 g, 27.3 mmol), bis (pinacolato) diboron (7.6 g, 30.1 mmol) and potassium acetate (8.05 g, 82.0 mmol) were mixed in a nitrogen atmosphere, added to 150 ml of dioxane and stirred. Heated. In reflux, bis (dibenzylidineacetone) palladium (0.47 g, 0.82 mmol) and tricyclohexylphosphine (0.46 g, 1.6 mmol) were added and heated and stirred for 6 hours. After the reaction was completed, the temperature was reduced to room temperature and filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the mixture was recrystallized with ethyl acetate to prepare intermediate A2 (8.7 g, yield 77%).

MS: [M + H] + = 414

3) Preparation of compound 1

Intermediate A2 (8.7 g, 21.0 mmol) and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5 in a 250 mL round bottom flask in a nitrogen atmosphere. -Triazine (7.23 g, 21.0 mmol) was dissolved in 100 mL of tetrahydrofuran, and then 1.5 M aqueous potassium carbonate solution (65 mL) was added, bis (tri- t -butylphosphine) palladium (0) (0.11 g, 0.2 mmol) and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was separated and removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using tetrahydrofuran and ethyl acetate, and dried to prepare Compound 1 (7.1 g, yield 57%).

MS: [M + H] ⁺ = 595

Preparation Example 2: Preparation of compound 2

1) Preparation of intermediate A3

The intermediate was prepared in the same manner as the method for preparing intermediate A1, except that (9,9-dimethyl-9H-fluoren-2-yl) boronic acid was used instead of [1,1'-biphenyl] -3-ylboronic acid. A3 (12.6 g, yield 71%) was prepared.

MS: [M + H] ⁺ = 362

2) Preparation of intermediate A4

The intermediate A4 (11.7 g, yield 74%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate A3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 454

3) Preparation of compound 2

Intermediates A4 and 2- (4-bromophenyl) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 2 (10.5 g, yield 64%) was prepared by the same method as the method of preparing compound 1, except that -4,6-diphenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 635

Preparation Example 3: Preparation of compound 3

1) Preparation of Intermediate A5

The intermediate A5 (13.0 g, yield 77%) was prepared in the same manner as the method for preparing intermediate A1, except that phenanthrene-3-ylboronic acid was used instead of [1,1'-biphenyl] -3-ylboronic acid. Did.

MS: [M + H] ⁺ = 346

2) Preparation of Intermediate A6

The intermediate A6 (13.6 g, yield 83%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate A5 was used instead of intermediate A1.

MS: [M + H] ⁺ = 438

3) Preparation of compound 3

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates A6 and 9- (4-chloro-6- Compound 3 (12.7 g, yield 65%) was prepared by the same method as the method of preparing compound 1, except that phenyl-1,3,5-triazin-2-yl) -9H-carbazole was used.

MS: [M + H] ⁺ = 632

Preparation Example 4 Preparation of Compound 4

1) Preparation of intermediate B1

2,7-dichlorobenzothiazole and 2,7-dichlorobenzoxazole and [1,1 ': 4', 1 ''-terphenyl] instead of [1,1'-biphenyl] -3-ylboronic acid The intermediate B1 (13.1 g, yield 65%) was prepared in the same manner as the method for preparing intermediate A1, except that 3-ylboronic acid was used.

MS: [M + H] ⁺ = 275

2) Preparation of intermediate B2

The intermediate B2 (10.6 g, yield 65%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate B1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 382

3) Preparation of compound 4

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates B2 and 2-chloro-4- (dibenzo The compound 4 (9.9 g, yield 66%) was prepared by the same method as the method of preparing compound 1, except that furan-4-yl) -6-phenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 669

Preparation Example 5: Preparation of compound 5

1) Preparation of intermediate B3

Method of preparing intermediate A1 except that 2,7-dichlorobenzoxazole and naphthalene-1ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid. In the same manner, the intermediate B3 (11.6 g, yield 78%) was prepared.

MS: [M + H] ⁺ = 280

2) Preparation of intermediate B4

The intermediate B4 (9.7 g, yield 77%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate B3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 372

3) Preparation of compound 5

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates B4 and 2- (4-chlorophenyl)- Compound 5 (10.0 g, yield 59%) in the same manner as in the method of preparing compound 1, except that 4- (dibenzofuran-3-yl) -6-phenyl-1,3,5-triazine was used. Was prepared.

MS: [M + H] ⁺ = 643

Preparation Example 6: Preparation of compound 6

1) Preparation of intermediate C1

Using 2,6-dichlorobenzothiazole and [1,1'-biphenyl] -4-ylboronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid The intermediate C1 (10.9 g, yield 69%) was prepared in the same manner as the method for preparing intermediate A1.

MS: [M + H] ⁺ = 322

2) Preparation of intermediate C2

The intermediate C2 (10.5 g, yield 75%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate C1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 414

3) Preparation of compound 6

Intermediates C2 and (4-chloro-6-phenyl-) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine 1,3,5-triazine-2 days) Compound 6 (10.7 g, yield 62%) was prepared by the same method as the method of preparing compound 1, except that 9-phenyl-9H-carbazole was used. .

MS: [M + H] ⁺ = 684

Preparation Example 7: Preparation of compound 7

1) Preparation of intermediate C3

2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid instead of 2,6-dichlorobenzothiazole and [1,1 ': 4', 1 ''-terphenyl]- The intermediate C3 (13.6 g, yield 70%) was prepared in the same manner as the method for preparing intermediate A1 except that 4-ylboronic acid was used.

MS: [M + H] ⁺ = 398

2) Preparation of intermediate C4

The intermediate C4 (12.7 g, yield 76%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate C2 was used instead of intermediate A1.

MS: [M + H] ⁺ = 490

3) Preparation of compound 7

Intermediates C4 and 2-chloro-4 (dibenzofuran) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine -1 day) Compound 7 (12.9 g, yield 73%) was prepared by the same method as the method of preparing compound 1, except that 6-phenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 685

Preparation Example 8: Preparation of compound 8

1) Preparation of intermediate C5

Method for preparing intermediate A1 except that 2,6-dichlorobenzothiazole and phenanthrene-3ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid In the same manner as the intermediate C5 (12.4 g, yield 73%) was prepared.

MS: [M + H] ⁺ = 346

2) Preparation of Intermediate C6

The intermediate C6 (11.5 g, yield 73%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate C5 was used instead of intermediate A1.

MS: [M + H] ⁺ = 438

3) Preparation of compound 8

Intermediates C2 and 9- (4- (4-chloro) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Phenyl) -6-phenyl-1,3,5-triazin-2-yl) -9H-carbazole except for using Compound 8 (13.0 g, yield 70%). ).

MS: [M + H] ⁺ = 708

Preparation Example 9: Preparation of compound 9

1) Preparation of intermediate D1

2,7-dichlorobenzothiazole and 2,6-dichlorobenzoxazole instead of [1,1'-biphenyl] -3-ylboronic acid (4- (9,9-dimethyl-9H-fluorene-2- 1) The intermediate D1 (12.9 g, yield 58%) was prepared in the same manner as in the method for preparing intermediate A1, except that phenyl) boronic acid was used.

MS: [M + H] ⁺ = 422

2) Preparation of intermediate D2

The intermediate D2 (9.9 g, yield 63%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate D1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 514

3) Preparation of compound 9

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates D2 and 2-chloro-4- (dibenzo Compound 9 (9.2 g, yield 67%) was prepared by the same method as the method of preparing compound 1, except that furan-3-yl) -6-phenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 709

Preparation Example 10 Preparation of Compound 10

1) Preparation of intermediate D3

2,6-dichlorobenzoxazole and (3- (triphenylen-2-yl) phenyl) boronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid The intermediate D3 (15.0 g, yield 62%) was prepared in the same manner as the method for preparing intermediate A1, except that it was used.

MS: [M + H] ⁺ = 456

2) Preparation of intermediate D4

The intermediate D4 (11.8 g, yield 65%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate D3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 548

3) Preparation of compound 10

Intermediates D2 and 2-chloro-4,6-phenyl instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine The compound 10 (10.0 g, yield 71%) was prepared by the same method as the method of preparing compound 1, except that -1,3,5-triazine was used.

MS: [M + H] ⁺ = 653

Preparation Example 11 Preparation of Compound 11

1) Preparation of intermediate E1

The intermediate E1 (12.0 g, yield 76%) was prepared in the same manner as in the method for preparing intermediate A1, except that 2,5-dichlorobenzothiazole was used instead of 2,7-dichlorobenzothiazole.

MS: [M + H] ⁺ = 322

2) Preparation of intermediate E2

The intermediate E2 (9.8 g, yield 63%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate E1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 414

3) Preparation of compound 11

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates E2 and 2-([1,1'- Biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine, except that Compound 1 was prepared in the same manner as in Compound 1 (9.5 g, yield 67%) ).

MS: [M + H] ⁺ = 595

Preparation Example 12 Preparation of Compound 12

1) Preparation of intermediate E3

Preparation of intermediate A1 except that 2,5-dichlorobenzothiazole and phenanthrene-9-ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid The intermediate E3 (11.7 g, yield 69%) was prepared in the same manner as the method.

MS: [M + H] ⁺ = 346

2) Preparation of intermediate E4

The intermediate E4 (11.0 g, yield 74%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate E3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 438

3) Preparation of compound 12

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates E4 and 2-chloro-4- (dibenzo Compound 12 (10.6 g, yield 67%) was prepared by the same method as the method of preparing compound 1, except that furan-4-yl) -6-phenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 633

Preparation 13: Preparation of compound 13

1) Preparation of Intermediate E5

2,7-dichlorobenzothiazole and 2,5-dichlorobenzothiazole (9,9-diphenyl-9H-fluoren-2-yl) instead of [1,1'-biphenyl] -3-ylboronic acid The intermediate E5 (14.7 g, yield 59%) was prepared in the same manner as in the method for preparing intermediate A1, except that boronic acid was used.

MS: [M + H] ⁺ = 486

2) Preparation of intermediate E6

The intermediate E6 (11.9 g, yield 71%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate E5 was used instead of intermediate A1.

MS: [M + H] ⁺ = 578

3) Preparation of compound 13

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates E6 and 4- (4-chloro-6- Compound 13 (11.2 g, yield 64%) in the same manner as in the method for preparing compound 1, except that phenyl-1,3,5-triazin-2-yl) -9-phenyl-9H-carbazole was used. Was prepared.

MS: [M + H] ⁺ = 848

Preparation 14: Preparation of compound 14

1) Preparation of intermediate F1

Using 2,5-dichlorobenzoxazole and [1,1'-biphenyl] -4-ylboronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid The intermediate F1 (10.4 g, yield 62%) was prepared in the same manner as the method for preparing intermediate A1.

MS: [M + H] ⁺ = 306

2) Preparation of intermediate F2

The intermediate F2 (8.9 g, yield 68%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate F1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 398

3) Preparation of compound 14

Intermediates F2 and 9- (4- (3-chloro) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Phenyl) -6-phenyl-1,3,5-triazin-2-yl) -9H-carbazole, except that Compound 1 was prepared in the same manner as in Compound 1 (9.5 g, yield 64%) ).

MS: [M + H] ⁺ = 668

Preparation 15: Preparation of compound 15

1) Preparation of intermediate F3

2,7-dichlorobenzothiazole and 2,5-dichlorobenzoxazole instead of [1,1'-biphenyl] -3-ylboronic acid [1,1 ': 3', 1 ''-terphenyl]- The intermediate F3 (12.3 g, yield 61%) was prepared in the same manner as the method for preparing intermediate A1 except that 5'-ylboronic acid was used.

MS: [M + H] ⁺ = 382

2) Preparation of intermediate F4

The intermediate F4 (10.8 g, 71%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate F3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 474

3) Preparation of compound 15

Intermediates F2 and 2-chloro-4- (dibenzo) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine The compound 15 (10.6 g, yield 68%) was prepared by the same method as the method of preparing compound 1, except that thiophen-4-yl) -6-phenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 685

Preparation Example 16 Preparation of Compound 16

1) Preparation of intermediate G1

Method for preparing intermediate A1 except that 2,7-dichlorobenzothiazole and 2,4-dichlorothiazole and naphthalene-1-ylboronic acid were used instead of [1,1'-biphenyl] -3-ylboronic acid. In the same manner, the intermediate G1 (8.9 g, yield 62%) was prepared.

MS: [M + H] ⁺ = 296

2) Preparation of intermediate G2

The intermediate G2 (8.1 g, yield 70%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate G1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 388

3) Preparation of compound 16

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates G2 and 2-chloro-4- (dibenzo Compound 16 (8.6 g, yield 71%) was prepared by the same method as the method of preparing compound 1, except that furan-2-yl) -6-phenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 583

Preparation Example 17 Preparation of Compound 17

1) Preparation of intermediate G3

2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid instead of 2,4-dichlorothiazole and [1,1 ': 4', 1 ''-terphenyl] -3 -The intermediate G3 (12.6 g, yield 65%) was prepared in the same manner as the method for preparing intermediate A1, except that ilboronic acid was used.

MS: [M + H] ⁺ = 398

2) Preparation of intermediate G4

The intermediate G4 (10.9 g, yield 70%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate G3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 490

3) Preparation of compound 17

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates G4 and 2- (3-chlorophenyl)- Compound 17 (12.1 g, yield 70%) in the same manner as in the method of preparing compound 1, except that 4- (dibenzothiophen-4-yl) -6-phenyl-1,3,5-triazine was used. ).

MS: [M + H] ⁺ = 777

Preparation Example 18 Preparation of Compound 18

1) Preparation of Intermediate G5

2,7-dichlorobenzothiazole and 2,4-dichlorothiazole and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid instead of [1,1'-biphenyl] -3-ylboronic acid The intermediate G5 (10.8 g, yield 61%) was prepared in the same manner as in the method for preparing intermediate A1 except for using.

MS: [M + H] ⁺ = 362

2) Preparation of intermediate G6

The intermediate G4 (8.6 g, 63%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate G3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 454

3) Preparation of compound 18

Intermediates G2 and 2-chloro-4,6-phenyl instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine The compound 18 (7.2 g, yield 68%) was prepared by the same method as the method of preparing compound 1, except that -1,3,5-triazine was used.

MS: [M + H] ⁺ = 559

Preparation 19: Preparation of compound 19

1) Preparation of intermediate H1

2,7-dichlorobenzothiazole and [1,1'-biphenyl] -3-ylboronic acid instead of 2,4-dichlorooxazole and [1,1 ': 3', 1 ''-terphenyl] -5 '-Intermediate H1 (12.8 g, yield 63%) was prepared in the same manner as the method for preparing intermediate A1, except that ilboronic acid was used.

MS: [M + H] ⁺ = 382

2) Preparation of intermediate H2

The intermediate H2 (11.2 g, yield 70%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate H1 was used instead of intermediate A1.

MS: [M + H] ⁺ = 474

3) Preparation of compound 19

Intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of intermediates H2 and 2- (4-chlorophenyl)- The compound 19 (12.6 g, yield 69%) in the same manner as in the method of preparing compound 1, except that 4- (dibenzofuran-3-yl) -6-phenyl-1,3,5-triazine was used. Was prepared.

MS: [M + H] ⁺ = 745

Preparation Example 20: Preparation of compound 20

1) Preparation of intermediate H3

The intermediate A1 was prepared except that 2,7-dichlorobenzothiazole and [2,4-dichlorooxazole and triphenylene-2-ylboronic acid were used instead of [1,1'-biphenyl] -3-ylboronic acid. The intermediate H3 (14.0 g, yield 69%) was prepared in the same manner as the method.

MS: [M + H] ⁺ = 380

2) Preparation of intermediate H4

The intermediate H4 (13.1 g, yield 75%) was prepared in the same manner as the method for preparing intermediate A2, except that intermediate H3 was used instead of intermediate A1.

MS: [M + H] ⁺ = 472

3) Preparation of compound 20

Intermediates H2 and 2- (3-bromophenyl) instead of intermediates A2 and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 20 (12.7 g, yield 70%) was prepared by the same method as the method of preparing compound 1, except that -4,6-diphenyl-1,3,5-triazine was used.

MS: [M + H] ⁺ = 653

[Example]

Example 1

The glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 2 minutes with distilled water twice. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

The following compound HI-A was thermally vacuum-deposited to a thickness of 100 증착 on the prepared ITO transparent electrode to form a hole injection layer. Subsequently, only the compound HT-A was thermally vacuum-deposited to a thickness of 800 ,, and the compound HT-B was subsequently vacuum-deposited to a thickness of 500 Å to form a hole transport layer. Subsequently, Compound 1 and the following Compound H1 prepared above were vacuum-deposited on the light emitting layer at a weight ratio of 50:50 and 6 wt% of the compound GD of the two host weights at a thickness of 350 MPa. Subsequently, the following compound ET-A was vacuum-deposited to a thickness of 50 MPa as a hole blocking layer. Subsequently, the following compounds ET-B and Liq as an electron transport and injection layer were thermally vacuum-deposited to a thickness of 250 Pa at a ratio of 1: 1, and then LiF was vacuum-deposited to a thickness of 30 Pa. Aluminum was deposited on the electron injection layer to a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light emitting device.

Examples 2 to 16

Each of the organic light emitting devices of Examples 2 to 16 was manufactured using the same method as in Example 1, except that the host material was changed as shown in Table 1 below.

Comparative Examples 1 to 3

Each of the organic light emitting devices of Comparative Examples 1 to 3 was manufactured using the same method as in Example 1, except that the host material was changed as shown in Table 1 below. Compounds C1 to C3 of Table 1 below are as follows.

[Experimental Example]

By applying a current to the organic light-emitting device prepared in Examples 1 to 16 and Comparative Examples 1 to 3, voltage, efficiency, and lifetime (T95) were measured and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm ² , and T95 means the time until the initial luminance decreased to 95% at the current density of 50 mA / cm ² .

Host material @ 10mA / cm ² @ 50mA / cm ² Voltage (V) Efficiency (cd / A) Life (T95, hr) Example 1 Compound 1 4.2 63.5 90 Example 2 Compound 2 4.1 62.4 88 Example 3 Compound 3 4.3 63.0 105 Example 4 Compound 4 4.2 62.9 95 Example 5 Compound 6 4.2 62.6 93 Example 6 Compound 7 4.3 62.8 85 Example 7 Compound 9 4.1 64.0 80 Example 8 Compound 10 4.2 63.7 82 Example 9 Compound 11 4.2 63.9 91 Example 10 Compound 13 4.2 63.0 80 Example 11 Compound 14 4.2 62.8 81 Example 12 Compound 15 4.2 63.4 80 Example 13 Compound 17 4.1 63.6 86 Example 14 Compound 18 4.2 63.0 90 Example 15 Compound 19 4.2 62.5 92 Example 16 Compound 20 4.2 62.6 85 Comparative Example 1 Compound C1 4.2 55 55 Comparative Example 2 Compound C2 4.9 50.6 25 Comparative Example 3 Compound C3 5.4 20.4 20

As shown in Table 1, it can be seen that, in the case of the organic light emitting device manufactured by using the compound according to the present invention as a host of the light emitting layer, it shows superior performance in terms of efficiency and lifespan compared to the organic light emitting device of the comparative example.

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

Claims (8)

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

In Chemical Formula 1,
A is substituted or unsubstituted C _10-60 aryl,
X ₁ , X ₂ and X ₃ are each independently CH or N, provided that at least two of X _1, X ₂ and X ₃ are N,
Y is O or S,
L is a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene comprising one or more of N, O and S,
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl comprising one or more of N, O and S.
According to claim 1,
A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl-dimethylfluorenyl, spirobifluorenyl, phenyl- Triphenylenyl, naphthyl-phenyl, phenanthrenyl-phenyl, dimethylfluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents,
compound:

.
According to claim 1,
X _1, X ₂ and X ₃ are all N,
compound.
According to claim 1,
L is a single bond, phenylene, biphenylylene, or terphenylylene,
compound.
According to claim 1,
At least one of Ar ₁ and Ar ₂ is substituted or unsubstituted C _6-60 aryl,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or carbazolyl substituted with phenyl,
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
compound:

. A first electrode; A second electrode provided to face the first electrode; And at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 7. To do,
Organic light emitting device.

Images