KR102095001B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel hetero-cyclic compound and organic light emitting device comprising the same}

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

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

[Formula 1]

In Chemical Formula 1,

X is O, or S,

At least two of R ₁ to R ₄ are the same -L-Ar, the rest are hydrogen,

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

Ar is substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing one or more of O, N, Si and S,

However, Ar is not pyridinyl.

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 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 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.

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

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

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

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 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, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups and dibenzofuranyl groups, 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 the description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this 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, two of R ₁ to R ₄ are the same -L-Ar, and the rest are hydrogen. That is, the compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-6.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

Preferably, L is a single bond, or any one selected from the group consisting of:

More preferably, L is 1,3-phenylene, 1,4-phenylene, or biphenyl-4,4'-diyl.

Preferably, Ar is any one selected from the group consisting of:

In the above,

X ₁ , X ₂ and X ₃ are each independently CH, or N,

X ₄ and X ₅ are each independently S, O, or NH,

X ₆ and X ₇ are each independently CH, or N,

At least one of X ₈ to X ₁₀ is N, the other is CH,

R ₁ to R ₇ are each independently hydrogen, C _6-60 aryl, or C _2-60 heteroaryl comprising one or more of O, N, Si and S.

이 연결되거나, 또는 R₁ 내지 R₄가 치환될 수 있다. In the above, when X ₁ to X ₇ is NH or CH, instead of H of NH or CH

This may be linked, or R ₁ to R ₄ may be substituted.

Preferably, R ₁ to R ₇ are each independently hydrogen, phenyl, biphenylyl, naphthyl, or pyridinyl.

More preferably, Ar is any one selected from the group consisting of:

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

The compound represented by Chemical Formula 1 may be prepared by the following Reaction Scheme 1. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme 1]

In Reaction Scheme 1,

X, R ₁ , R ₂ , R ₃ , R ₄ , L and Ar are as defined above,

At least two of R ' ₁ to R' ₄ are 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl (4,4,5,5-tetramethyl-1,3,2 -dioxaborolanyl) and the rest is hydrogen, X 'is halogen, or

At least two of R ' ₁ to R' ₄ are halogen and the rest are hydrogen, and X 'is 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl (4,4,5) , 5-tetramethyl-1,3,2-dioxaborolanyl).

It is preferable to react the reaction in the presence of potassium carbonate. In addition, the reaction is preferably reacted under a tetrakistriphenyl-phosphino palladium catalyst. In addition, the reaction is preferably performed for 1 hour to 10 hours, and after completion of the reaction, washing and / or drying may be additionally performed as necessary.

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 hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 It includes the compound displayed.

Further, the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

Further, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.

In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron injection and electron transport includes the compound represented by Chemical Formula 1. In particular, the compound represented by Chemical Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability. In addition, when the compound represented by Formula 1 is used in an organic material layer capable of electron injection and electron transport at the same time, an n-type dopant used in the art may be mixed and used.

In addition, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport 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.

Figure 2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done. 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, 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 material is a layer for injecting holes from an electrode, and the hole injection material has the ability to transport holes, 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 a light emitting layer A compound that prevents migration of the excited excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferred. 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.

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. Preferably, a compound represented by the following Chemical Formula 2 may be used as the dopant material.

[Formula 2]

In Chemical Formula 2,

R ₈ to R ₁₅ are each independently hydrogen, halogen, substituted or unsubstituted C _1-20 alkyl, substituted or unsubstituted C _3-10 cycloalkyl, substituted or unsubstituted C _3-30 alkylsilyl, substituted Or unsubstituted C _8-30 arylsilyl, substituted or unsubstituted C _1-20 alkoxy, substituted or unsubstituted C _6-20 aralkyl, or substituted or unsubstituted C _6-10 aryl,

Ar ₁ to Ar ₄ are each independently substituted or unsubstituted C _6-30 aryl, provided that at least one of Ar ₁ to Ar ₄ is each independently C _1-20 alkyl, cyano, halogen, nitro, or car It is substituted with carbonyl.

Preferably, among R ₈ to R ₁₅ , R ₉ and R ₁₃ are each independently substituted or unsubstituted C _1-20 alkyl, and the rest are hydrogen. More preferably, among R ₈ to R ₁₅ , R ₉ and R ₁₃ are isopropyl, and the rest are hydrogen.

Preferably, Ar ₁ to Ar ₄ are phenyl substituted with C _1-20 alkyl or cyano. More preferably, Ar ₁ and Ar ₃ are phenyl substituted with C _1-20 alkyl, and Ar ₂ and Ar ₄ are phenyl substituted with cyano.

Representative examples of the compound represented by Formula 2 are as follows:

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons This is suitable. 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 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 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 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.

Example  1 (E1)

The compound represented by Formula A (10.0 g, 23.8 mmol) and the compound represented by Formula B (12.7 g, 47.6 mmol) were completely dissolved in THF (100 mL), followed by potassium carbonate (9.9 g, 71.4 mmol). It was dissolved in 50 mL of water and added. After adding tetrakistriphenyl-phosphino palladium (825 mg, 0.71 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed to filter the white solid. The filtered white solid was washed twice each with THF and ethyl acetate to prepare a compound represented by Formula E1 (13.4 g, yield 89%).

MS [M + H] ⁺ = 631

Example  2 (E2)

A compound represented by Chemical Formula E2 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 783

Example  3 (E3)

A compound represented by Chemical Formula E3 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 783

Example  4 (E4)

A compound represented by Chemical Formula E4 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 721

Example  5 (E5)

A compound represented by Chemical Formula E5 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 781

Example  6 (E6)

A compound represented by Chemical Formula E6 was prepared in the same manner as in Example 1, except that each starting material was the same as the above reaction formula.

MS [M + H] ⁺ = 799

Example  7 (E7)

A compound represented by Chemical Formula E7 was prepared in the same manner as in Example 1, except that each starting material was the same as the above reaction formula.

MS [M + H] ⁺ = 729

Example  8 (E8)

A compound represented by Chemical Formula E8 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 783

Example  9 (E9)

A compound represented by Chemical Formula E9 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 781

Example  10 (E10)

A compound represented by Chemical Formula E10 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 539

Example  11 (E11)

A compound represented by Chemical Formula E11 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 693

Example  12 (E12)

A compound represented by Chemical Formula E12 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 693

Example  13 (E13)

A compound represented by Chemical Formula E13 was prepared in the same manner as in Example 1, except that each starting material was as in the above reaction formula.

MS [M + H] ⁺ = 625

Experimental example  One

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. 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, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, the following HI-A compound was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. The following HAT compound 50 Å and the following HT-A compound 600 상 에 were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, a BH compound and a BD compound having a thickness of 200 mm 2 were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 to form a light emitting layer.

On the light-emitting layer, the compound (E1) of Example 1 and the following LiQ compound were vacuum-deposited in a 1: 1 weight ratio to form an electron injection and transport layer with a thickness of 350 MPa. On the electron injection and transport layer, lithium fluoride (LiF) having a thickness of 10 와 and aluminum having a thickness of 1000 순차적 were sequentially deposited to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å / sec and aluminum at 2 2 / sec, and the vacuum degree during deposition was 1 × 10. ^An organic light emitting device was manufactured by maintaining ^-7 to 5 x 10 ^-5 torr.

Experimental example  2 to 13

An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds (E2 to E13) of Examples 2 to 13 were used instead of the compound (E1) of Example 1.

compare Experimental example  1 to 12

An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the following compounds (ET-A to ET-L) were used instead of the compound (E1) of Example 1.

The driving voltage and the luminous efficiency of the organic light-emitting device manufactured in the above Experimental Example and Comparative Experimental Example were measured at a current density of 10 mA / cm ² , and the time to be 90% compared to the initial luminance at a current density of 20 mA / cm ² ( T90). The results are shown in Tables 1 and 2 below.

Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10 mA / cm ² ) Color coordinate
(x, y) Life (h)
(T90 at 20 mA / cm ² ) Experimental Example 1 (E1) 4.45 5.11 (0.142, 0.096) 200 Experimental Example 2 (E2) 4.13 5.54 (0.142, 0.096) 150 Experimental Example 3 (E3) 4.11 5.50 (0.142, 0.096) 161 Experimental Example 4 (E4) 4.27 5.21 (0.142, 0.096) 187 Experimental Example 5 (E5) 4.07 5.60 (0.142, 0.096) 137 Experimental Example 6 (E6) 4.14 5.52 (0.142, 0.097) 153 Experimental Example 7 (E7) 4.35 5.20 (0.142, 0.096) 199 Experimental Example 8 (E8) 4.20 5.48 (0.142, 0.099) 135 Experimental Example 9 (E9) 4.33 5.49 (0.142, 0.096) 178 Experimental Example 10 (E10) 4.41 5.10 (0.142, 0.099) 220 Experimental Example 11 (E11) 4.15 5.38 (0.142, 0.096) 166 Experimental Example 12 (E12) 4.20 5.34 (0.142, 0.097) 148 Experimental Example 13 (E13) 4.24 5.36 (0.142, 0.096) 147

Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10 mA / cm ² ) Color coordinate
(x, y) Life (h)
(T90 at 20 mA / cm ² ) Comparative Experimental Example 1 (ET-A) 4.98 3.90 (0.142, 0.098) 97 Comparative Experimental Example 2 (ET-B) 4.76 4.02 (0.142, 0.102) 73 Comparative Experimental Example 3 (ET-C) 4.70 4.11 (0.142, 0.096) 75 Comparative Experimental Example 4 (ET-D) 4.69 4.10 (0.142, 0.096) 65 Comparative Experimental Example 5 (ET-E) 5.22 3.40 (0.142, 0.096) 22 Comparative Experimental Example 6 (ET-F) 4.75 4.00 (0.142, 0.096) 69 Comparative Experimental Example 7 (ET-G) 5.01 3.60 (0.142, 0.096) 92 Comparative Experimental Example 8 (ET-H) 5.11 3.53 (0.142, 0.096) 88 Comparative Experimental Example 9 (ET-I) 4.88 3.44 (0.142, 0.096) 61 Comparative Experimental Example 10 (ET-J) 4.81 3.47 (0.142, 0.096) 59 Comparative Experimental Example 11 (ET-K) 5.04 3.55 (0.142, 0.096) 95 Comparative Experimental Example 12 (ET-L) 5.10 3.50 (0.142, 0.096) 82

As shown in Table 1, it was confirmed that the compound represented by Chemical Formula 1 according to the present invention can be used in an organic material layer capable of simultaneously electron injection and electron transport of the organic light emitting device.

In addition, when comparing the experimental examples of Table 1 and Comparative Experimental Examples 1, 2, 3 and 6 of Table 2, the same two substituents are substituted for dibenzofuran or dibenzothiophene as in Formula 1 according to the present invention. It was confirmed that the compound was remarkably superior in terms of driving voltage, efficiency, and lifespan of the organic light emitting device compared to the compound in which different substituents were substituted.

In addition, when comparing Experimental Example 5 of Table 1 with Comparative Experimental Example 5 of Table 2, it was confirmed that the characteristics of the organic light emitting device were improved compared to the case of having a substituent having poor electron transport ability, such as pyridine.

In addition, when comparing the experimental examples of Table 1 and Comparative Experimental Examples 4, 7 to 12 of Table 2, the same substituents on one phenyl group in the dibenzofuran and dibenzothiophene skeletons as shown in Chemical Formula 1 according to the present invention It was confirmed that the substituted compound was significantly superior in terms of driving voltage, efficiency, and lifespan of the organic light emitting device compared to the compound in which the same substituent was substituted with different phenyl groups.

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

Claims (10)

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

In Chemical Formula 1,
X is O, or S,
At least two of R ₁ to R ₄ are the same -L-Ar, the rest are hydrogen,
L is a single bond, substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more of O, N, Si and S,
Ar is any one selected from the group consisting of:

In the above,
X ₁ , X ₂ and X ₃ are each independently CH, or N,
X ₄ and X ₅ are each independently S, O, or NH,
X ₆ and X ₇ are each independently CH, or N,
At least one of X ₈ to X ₁₀ is N, the other is CH,
R ₁ to R ₇ are each independently hydrogen, C _6-60 aryl, or C _2-60 heteroaryl including one or more of O, N, Si and S,
However, Ar is not unsubstituted pyridinyl.
According to claim 1,
Two of R ₁ to R ₄ are the same -L-Ar, and the rest are hydrogen,
compound.
According to claim 1,
L is a single bond, or any one selected from the group consisting of:

compound.
According to claim 1,
L is 1,3-phenylene, 1,4-phenylene, or biphenyl-4,4'-diyl,
compound.
delete According to claim 1,
Ar is any one selected from the group consisting of,
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 one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is any one of claims 1 to 4, 6, and 7 An organic light emitting device comprising the compound according to one item.
The method of claim 8,
The organic layer containing the compound is an electron injection layer; Electron transport layer; Or characterized in that it is a layer that performs electron injection and electron transport at the same time,
Organic light emitting device.
The method of claim 8,
The organic light emitting device comprises a light emitting layer, the light emitting layer is characterized in that it comprises a compound represented by the following formula (2) as a dopant,
Organic light emitting device:
[Formula 2]

In Chemical Formula 2,
R ₈ to R ₁₅ are each independently hydrogen, halogen, substituted or unsubstituted C _1-20 alkyl, substituted or unsubstituted C _3-10 cycloalkyl, substituted or unsubstituted C _3-30 alkylsilyl, substituted Or an unsubstituted C _8-30 arylsilyl group, a substituted or unsubstituted C _1-20 alkoxy, a substituted or unsubstituted C _6-20 aralkyl, or a substituted or unsubstituted C _6-10 aryl,
Ar ₁ to Ar ₄ are each independently substituted or unsubstituted C _6-30 aryl, provided that at least one of Ar ₁ to Ar ₄ is each independently C _1-20 alkyl, cyano, halogen, nitro, or car It is substituted with carbonyl.

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