KR20200026080A - 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, wherein the compound is represented by chemical formula 1. The compound can 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 using the same.

In general, organic light emitting phenomenon refers to a phenomenon of converting 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, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.

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

There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2013-073537

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

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

A compound represented by formula (1):

[Formula 1]

In Chemical Formula 1,

Y is a direct bond; O or S,

이고, 단, 이들 중 하나 이상이 나프탈렌 고리 또는

이고,A ₁ and A ₂ are each independently a benzene ring; Naphthalene ring; or

Provided that at least one of these is a naphthalene ring or

ego,

Each X is independently CR ₁ R ₂ ; SiR ₃ R ₄ ; NR ₅ ; O; S; Or SO ₂ ,

R ₁ to R ₅ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl, or substituted or unsubstituted C _6-60 aryl;

L ₁ and L ₂ are each independently a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of N, O and S,

B ₁ and B ₂ are each independently * -NR ₆ R ₇ ,

R ₆ and R ₇ are each independently substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 haloalkoxy; Tri (C _1-60 alkyl) silyl; Substituted or unsubstituted C _6-60 aryl; Tri (C _6-60 aryl) silyl; Substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or combine with an adjacent group to form a substituted or unsubstituted condensed ring,

R ' ₁ and R' ₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 haloalkoxy; Tri (C _1-60 alkyl) silyl; Or substituted or unsubstituted C _6-60 aryl,

m and n are each independently an integer of 0-3.

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

The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compound represented by Chemical 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 element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows an example of an organic light emitting element 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.

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

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

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O, and S atoms, or two or more substituents connected to the substituents exemplified above. . For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a straight chain, branched chain or cyclic alkyl group 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, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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

In the present specification, the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group and the like.

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

In the present specification, the alkyl group may be linear or branched chain, 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 include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

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

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

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the 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, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

And so on. However, the present invention 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 a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, except that the arylene is a divalent group, the description of the aryl group described above may be applied. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic group 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, the compound represented by Chemical Formula 1 is any one of the compounds represented by the following Chemical Formulas 1-1 to 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the above formula,

A ₁ , A ₂ , B ₁ , B ₂ , L ₁ , L ₂ , R ' ₁ , R' ₂ , m and n are as previously defined.

Preferably, in Chemical Formula 1,

A ₁ is a benzene ring, A ₂ is a naphthalene ring;

A ₁ is a naphthalene ring, A ₂ is a benzene ring;

이거나; A ₁ is a benzene ring, A ₂ is

Or;

, A₂는 벤젠 고리이거나; A ₁ is

, A ₂ is a benzene ring;

이거나; A ₁ is a naphthalene ring, A ₂ is

Or;

, A₂는 나프탈렌 고리이거나; A ₁ is

, A ₂ is a naphthalene ring;

A ₁ is a naphthalene ring, A ₂ is a naphthalene ring; or

이고, A₂은

이고, 여기서, X는 앞서 정의한 바와 같다.A ₁ is

And A ₂ is

Where X is as defined above.

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

In the above formula,

X ₁ and X ₂ are each independently CR ₁ R ₂ ; SiR ₃ R ₄ ; NR ₅ ; O; S; Or SO ₂ ,

Y, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , B ₁ , B ₂ , R _{1 ′} , R _{2 ′} , m and n are as defined above.

Preferably, X is each independently CR ₁ R ₂ , O, or S, wherein R ₁ and R ₂ are each independently methyl or ethyl.

Preferably, L ₁ and L ₂ are each independently a direct bond or phenylene.

Preferably, R ₆ and R ₇ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, cyclohexenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, Combine with benzonaphthofuranyl, benzonaphthothiophenyl, benzodimethylfluorenyl, or adjacent substituents to form a substituted or unsubstituted condensed ring,

They are each independently deuterium, * -CD ₃ , C _1-4 alkyl, *-(C _1-4 alkyl) phenyl, C _3-10 cycloalkyl, phenyl, halogen, cyano, * -SiR ₁₁ R ₁₂ R Substituted or unsubstituted with ₁₃ ;

R ₁₁ , R ₁₂ and R ₁₃ are each independently methyl, ethyl, tertbutyl or phenyl.

Here, R ₆ and R ₇ is a structure formed by including a nitrogen atom when combined with an adjacent substituent to form a substituted or unsubstituted condensed ring.

Preferably, B ₁ and B ₂ are each independently any one selected from the group consisting of:

.

.

.

.

Preferably, R ' ₁ and R' ₂ are each independently hydrogen or deuterium.

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

.

.

The compound represented by Formula 1 according to the present invention includes a core structure of fluorene substituted with adamantane (ADAMANTANE), so that the bulk structure and rigidity of the core structure, excellent sublimation and stability of the chemical structure, luminous efficiency is improved It rises and is excellent in thermal stability. In particular, by including an amine substituent of a specific structure, it is possible to improve the efficiency and life of the OLED device by controlling the electrical properties and the light emission characteristics at the same time, and the existing simple spiro structure of compounds (for example, dimethyl fluorene) Compared with the adopted organic light emitting element, it can have high efficiency, low drive voltage, high brightness, long life, and the like.

The compound represented by Chemical Formula 1 may be prepared by a manufacturing method according to the multi-step reaction of Scheme 1 below. The manufacturing method may be more specific in the production examples to be described later.

Scheme 1

In the formula, the remaining variables except X 'are as defined above, and each X' is independently halogen, preferably chloro or bromo, more preferably bromo.

In Scheme 1, the reactants, catalysts, solvents, and the like used may be changed to suit the desired product.

The STEP 2 reaction 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 changed as known in the art.

On the other hand, the synthesis of the asymmetric compound of the amine substituent (* -L ₁ -B ₁ / *-L ₂ -B ₂ ) in the final product proceeds to two Suzuki coupling reactions for intermediate compounds of different structures in STEP 2, respectively Can be. The preparation method of the compound may be more specified in the preparation examples to be described later.

In another aspect, the present invention provides an organic light emitting device comprising a compound represented by the formula (1). In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do.

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

The organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole may be represented by Formula 1 above. It includes the compound represented.

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

In addition, the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).

In addition, the electron transport layer, the electron injection layer, or a layer for simultaneously injecting and transporting electrons includes a compound represented by the formula (1). In particular, the compound represented by 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 Chemical Formula 1 is used in an organic material layer capable of simultaneously injecting and transporting electrons, an n-type dopant used in the art may be mixed and used.

In addition, the organic layer may include a light emitting layer and an electron transport layer, the electron transport layer may include a compound represented by the formula (1).

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

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

2 shows an example of an organic light emitting element 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. In such a structure, the compound represented by Formula 1 may be included in one or more layers 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, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (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, the second electrode is an anode.

As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. 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), indium zinc oxide (IZO); Combinations of oxides with metals 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, and the like, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, 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 layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

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

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

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 hetero ring-containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the above-described arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer for receiving electrons from the electron injection layer and transporting electrons to the light emitting layer. As an electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer for injecting electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-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) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. It is not limited to this.

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

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

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

Preparation Example 1 Synthesis of Compound 1

(1) Preparation Example 1-1: Synthesis of Intermediate Compound C

Compound A (30 g, 90.0 mmol) was added to tetrahydrofuran (900 mL). 2.5M nBuLi (36 mL) was added at 0 ° C, and the mixture was stirred for 5 hours under nitrogen conditions. After raising the temperature to room temperature, Compound B (13.5 g, 90.0 mmol) was added and stirred for 12 hours. After the reaction, 3M NH ₄ Cl (300 mL) was added, and the organic layer was extracted and recrystallized with ethanol to prepare Compound C (32.0 g, yield 88%, MS: [M + H] + = 405).

(2) Preparation Example 1-2: Synthesis of Intermediate Compound D

Compound C (32 g, 79.10 mmol) and CH ₃ SO ₂ OH (64 mL) were added thereto, followed by stirring for 5 hours. After cooling to room temperature, the reaction mixture was poured into water, and the resulting solid was filtered and the resulting solid was recrystallized from chloroform and ethanol to prepare Compound D (23.3 g, yield 76%, MS: [M + H] + = 387). .

(3) Preparation Example 1-3: Synthesis of Intermediate Compound E

Compound D (23.3 g, 60.3 mmol) was added to chloroform (400 mL). Br ₂ (19.3 g) was slowly added dropwise and stirred for 5 hours. After completion of the reaction, the solid produced by filtration was recrystallized with tetrahydrofuran and ethanol to prepare Compound E (17.4 g, yield 53%, MS: [M + H] + = 545).

(4) Preparation Example 1-4: Synthesis of Compound 1

Compound E (17.4 g, 32.0 mmol) and Compound F (20.2 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give Compound 1 (16.2 g, yield 50%, MS: [M + H] + = 1014).

Preparation Example 2 Synthesis of Compound 2

(1) Preparation Example 2-1: Synthesis of Intermediate Compound H

Compound G (30 g, 106 mmol) was added to tetrahydrofuran (900 mL). 2.5M nBuLi (42.4 mL) was added at 0 ° C, and the mixture was stirred for 5 hours under nitrogen conditions. After raising the temperature to room temperature, Compound B (15.9 g, 106 mmol) was added and stirred for 12 hours. After the reaction, 3M NH ₄ Cl (300 mL) was added, and the organic layer was extracted and recrystallized with ethanol to prepare Compound H (31.9 g, yield 85%, MS: [M + H] + = 355).

(2) Preparation Example 2-2: Synthesis of Intermediate Compound I

Compound H (31.9 g, 90.1 mmol) and CH ₃ SO ₂ OH (73 mL) were added, followed by stirring for 5 hours. After cooling to room temperature, the reaction mixture was poured into water, and the resulting solid was filtered and the resulting solid was recrystallized from chloroform and ethanol to obtain Compound I (21.2 g, yield 70%, MS: [M + H] + = 337). .

(3) Preparation Example 2-3: Synthesis of Intermediate Compound J

Into the compound I (21.2 g, 63.1 mmol) chloroform (400 mL). Br ₂ (20.2 g) was slowly added dropwise and stirred for 5 hours. After the reaction was completed, the solid produced by filtration was recrystallized with tetrahydrofuran and ethanol to prepare the compound J (15.0 g, yield 48%, MS: [M + H] + = 495).

(3) Preparation Example 2-4: Synthesis of Compound 2

Compound J (15.0 g, 30.3 mmol) and Compound K (15.7 g, 60.6 mmol) were added to xylene (400 mL). NatBuO (17.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with ethyl acetate three times to obtain Compound 2 (10.1 g, yield 39%, MS: [M + H] + = 852).

Preparation Example 3 Synthesis of Compound 3

Compound 3-1 (20.0 g, 32.0 mmol) and Compound 3-2 (17.63 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to obtain compound 3 (23.02 g, yield 71%, MS: [M + H] + = 1014).

Preparation Example 4 Synthesis of Compound 4

Compound 4-1 (20.0 g, 32.0 mmol) and Compound 4-2 (16.22 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to obtain compound 4 (20.16 g, yield 65%, MS: [M + H] + = 970).

Preparation Example 5 Synthesis of Compound 5

Compound 5-1 (21.0 g, 32.0 mmol) and Compound 5-2 (19.80 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 5 (28.86 g, yield 81%, MS: [M + H] + = 1114).

Preparation Example 6 Synthesis of Compound 6

Compound 6-1 (17.1 g, 32.0 mmol) and Compound 6-2 (19.16 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 6 (23.93 g, yield 77%, MS: [M + H] + = 972).

Preparation Example 7 Synthesis of Compound 7

Compound 7-1 (20.5 g, 32.0 mmol) and Compound 7-2 (15.70 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 7 (24.19 g, yield 78%, MS: [M + H] + = 970).

Preparation Example 8 Synthesis of Compound 8

Compound 8-1 (19.2 g, 32.0 mmol) and Compound 8-2 (18.01 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 8 (22.11 g, yield 69%, MS: [M + H] + = 765).

Preparation Example 9 Synthesis of Compound 9

Compound 9-1 (17.4 g, 32.0 mmol) and Compound 9-2 (19.04 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 9 (20.65 g, yield 66%, MS: [M + H] + = 978).

Preparation Example 10 Synthesis of Compound 10

Compound 10-1 (19.5 g, 32.0 mmol) and Compound 10-2 (26.99 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with ethyl acetate three times to obtain compound 10 (33.49 g, yield 81%, MS: [M + H] + = 1292).

Preparation Example 11 Synthesis of Compound 11

Compound 11-1 (19.5 g, 32.0 mmol) and Compound 11-2 (13.01 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with ethyl acetate three times to prepare compound 11 (19.16 g, yield 70%, MS: [M + H] + = 856).

Preparation Example 12 Synthesis of Compound 12

Compound 12-1 (20.5 g, 32.0 mmol) and Compound 12-2 (10.83 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 12 (19.87 g, yield 76%, MS: [M + H] + = 818).

Preparation Example 13 Synthesis of Compound 13

Compound 13-1 (20.5 g, 32.0 mmol) and Compound 13-2 (14.42 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 13 (19.92 g, yield 67%, MS: [M + H] + = 930).

Preparation 14 Synthesis of Compound 14

Compound 14-1 (16.3 g, 32.0 mmol) and Compound 14-2 (13.3 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 14 (14.9 g, yield 61%, MS: [M + H] + = 765).

Preparation Example 15 Synthesis of Compound 15

Compound 15-1 (18.4 g, 32.0 mmol) and Compound 15-2 (10.8 g, 64.0 mmol) were added to xylene (400 mL). NatBuO (18.5 g) and BTP (0.2 g) were added, followed by stirring and reflux for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with three ethyl acetate to give compound 15 (18.8 g, yield 78%, MS: [M + H] + = 754).

Example 1 Fabrication of Organic Light Emitting Diode

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Fischer Co. was used for the detergent, and Millipore Co. Secondary filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

The following HAT was thermally vacuum deposited to a thickness of 50 kPa on the thus prepared ITO transparent electrode to form a hole injection layer. The following HT-A 1000 Pa was vacuum-deposited on the hole transport layer, and the following HT-B 100 Pa was deposited. As a light emitting layer, 4 wt% of Compound 3 of Preparation Example 3 was doped with H-A as a host and vacuum deposited to a thickness of 200 μs. Next, 300 μs of ET-A and Liq below were deposited at a 1: 1 ratio, and magnesium (Mg) doped with 10 wt% of 150 μm thick silver (Ag) and aluminum 1000 μm thick were sequentially deposited thereon. The cathode was formed to manufacture an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, LiF was maintained at a deposition rate of 0.2 Å / sec, and aluminum was 3 Å / sec to 7 Å / sec.

Examples 2 to 39 and Comparative Examples 1 to 12: Preparation of an organic light emitting device

In the preparation of the organic light emitting device of Example 1, using the compound of Table 1 to Table 3 instead of Compound 3 of Preparation Example 3 as a light emitting layer dopant, instead of HA as a light emitting layer host Except for the organic light emitting device was manufactured in the same manner as in Example 1.

Experimental Example

The driving voltage and the luminous efficiency of the organic light emitting diodes of Examples 1 to 39 and Comparative Examples 1 to 12 were measured at a current density of 10 mA / cm ² , and 95% of the initial luminance was obtained at a current density of 20 mA / cm ² . The time to become (LT95) was measured. The results are shown in Tables 1 to 3 below.

division Host Dopant @ 10 mA / cm ² LT95 Voltage (V) Efficiency (cd / A) color Life (hr) Example 1 H-A Compound 3 4.21 6.28 blue 100 Example 2 H-A Compound 4 4.22 5.84 blue 110 Example 3 H-A Compound 5 4.25 6.81 blue 120 Example 4 H-A Compound 6 4.26 6.50 blue 120 Example 5 H-A Compound 7 4.31 6.70 blue 115 Example 6 H-A Compound 8 4.19 6.68 blue 120 Example 7 H-A Compound 9 4.21 6.98 blue 130 Example 8 H-A Compound 10 4.18 6.28 blue 125 Example 9 H-A Compound 11 4.23 6.29 blue 110 Example 10 H-A Compound 12 4.10 6.27 blue 115 Example 11 H-A Compound 13 4.00 6.78 blue 110 Example 12 H-A Compound 14 4.10 6.28 blue 120 Example 13 H-A Compound 15 4.20 6.10 blue 140 Comparative Example 1 H-A D-1 4.39 5.31 blue 75 Comparative Example 2 H-A D-2 4.42 3.50 blue 50 Comparative Example 3 H-A D-3 4.40 4.88 blue 85 Comparative Example 4 H-A D-4 4.54 5.12 blue 55

Host Dopant @ 10 mA / cm ² LT95 Voltage (V) Efficiency (cd / A) color Life (hr) Example 14 H-B Compound 3 4.32 7.12 blue 120 Example 15 H-B Compound 4 4.31 6.77 blue 120 Example 16 H-B Compound 5 4.40 6.98 blue 130 Example 17 H-B Compound 6 4.46 6.45 blue 125 Example 18 H-B Compound 7 4.41 6.44 blue 115 Example 19 H-B Compound 8 4.29 6.97 blue 120 Example 20 H-B Compound 9 4.30 6.28 blue 130 Example 21 H-B Compound 10 4.30 6.57 blue 125 Example 22 H-B Compound 11 4.25 6.48 blue 115 Example 23 H-B Compound 12 4.25 6.53 blue 125 Example 24 H-B Compound 13 4.27 6.08 blue 125 Example 25 H-B Compound 14 4.29 6.65 blue 115 Example 26 H-B Compound 15 4.28 6.10 blue 140 Comparative Example 5 H-B D-1 4.56 5.12 blue 80 Comparative Example 6 H-B D-2 4.54 4.50 blue 60 Comparative Example 7 H-B D-3 4.55 5.32 blue 95 Comparative Example 8 H-B D-4 4.60 4.80 blue 70

division Host Dopant @ 10 mA / cm ² LT95 Voltage (V) Efficiency (cd / A) color Life (hr) Example 27 H-C Compound 3 4.00 7.10 blue 120 Example 28 H-C Compound 4 4.10 6.64 blue 110 Example 29 H-C Compound 5 4.11 6.91 blue 120 Example 30 H-C Compound 6 4.01 6.28 blue 130 Example 31 H-C Compound 7 4.05 6.31 blue 115 Example 32 H-C Compound 8 4.09 6.22 blue 120 Example 33 H-C Compound 9 4.11 6.90 blue 125 Example 34 H-C Compound 10 4.12 6.24 blue 125 Example 35 H-C Compound 11 4.07 6.24 blue 110 Example 36 H-C Compound 12 4.01 6.22 blue 130 Example 37 H-C Compound 13 4.07 6.61 blue 120 Example 38 H-C Compound 14 4.05 6.25 blue 100 Example 39 H-C Compound 15 4.10 6.22 blue 120 Comparative Example 9 H-C D-1 4.32 5.10 blue 70 Comparative Example 10 H-C D-2 4.33 4.50 blue 50 Comparative Example 11 H-C D-5 4.40 4.78 blue 75 Comparative Example 12 H-C D-6 4.44 4.01 blue 55

From Tables 1 to 3, it can be confirmed that Examples 1 to 36 of the present application have a lower driving voltage of the device than Comparative Examples 1 to 12, and are excellent in efficiency and lifespan characteristics.

Specifically, Comparative Examples 1, 3 to 5, 7 to 9, 11, and 12 each have pyrene, naphthobenzofuran, fluorene, dibenzofluorene, or dinaphthofuran bonded between two amine groups. Compound D-1, Compound D-3, Compound D-4, Compound D-5, or Compound D-6 is used as a dopant for the light emitting layer, but these structures do not include adamantane, and thus are more effective than devices using the present compound. It can be seen that the performance is significantly reduced.

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 (11)

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

In Chemical Formula 1,
Y is a direct bond; O or S,
A ₁ and A ₂ are each independently a benzene ring; Naphthalene ring; or

Provided that at least one of these is a naphthalene ring or

ego,
Each X is independently CR ₁ R ₂ ; SiR ₃ R ₄ ; NR ₅ ; O; S; Or SO ₂ ,
R ₁ to R ₅ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl or substituted or unsubstituted C _6-60 aryl;
L ₁ and L ₂ are each independently a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of N, O and S,
B ₁ and B ₂ are each independently * -NR ₆ R ₇ ,
R ₆ and R ₇ are each independently substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 haloalkoxy; Tri (C _1-60 alkyl) silyl; Substituted or unsubstituted C _6-60 aryl; Tri (C _6-60 aryl) silyl; Substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or combine with an adjacent group to form a substituted or unsubstituted condensed ring,
R ' ₁ and R' ₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 haloalkoxy; Tri (C _1-60 alkyl) silyl; Or substituted or unsubstituted C _6-60 aryl,
m and n are each independently an integer from 0 to 3.
The method of claim 1,
The compound represented by Formula 1 is any one of the compounds represented by Formulas 1-1 to 1-3 below:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the above formula,
A ₁ , A ₂ , B ₁ , B ₂ , L ₁ , L ₂ , R ' ₁ , R' ₂ , m and n are as defined in claim 1.
The method of claim 1,
A ₁ is a benzene ring, A ₂ is a naphthalene ring;
A ₁ is a naphthalene ring, A ₂ is a benzene ring;
A ₁ is a benzene ring, A ₂ is

Or;
A ₁ is

, A ₂ is a benzene ring;
A ₁ is a naphthalene ring, A ₂ is

Or;
A ₁ is

, A ₂ is a naphthalene ring;
A ₁ is a naphthalene ring, A ₂ is a naphthalene ring; or
A ₁ is

And A ₂ is

Phosphorus, compound:
In the above formula,
X is as defined in claim 1.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

In the above formula,
X ₁ and X ₂ are each independently CR ₁ R ₂ ; SiR ₃ R ₄ ; NR ₅ ; O; S; Or SO ₂ ,
Y, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , B ₁ , B ₂ , R _{1 ′} , R _{2 ′} , m and n are as defined in claim 1.
The method of claim 1,
Each X is independently CR ₁ R ₂ , O, or S,
R ₁ and R ₂ are each independently methyl or ethyl.
The method of claim 1,
L ₁ and L ₂ are each independently a direct bond or phenylene.
The method of claim 1,
R ₆ and R ₇ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, cyclohexenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, benzonaphthofuranyl , Benzonaphthothiophenyl, benzodimethylfluorenyl, or adjacent substituents to form a substituted or unsubstituted condensed ring,
They are each independently deuterium, * -CD ₃ , C _1-4 alkyl, *-(C _1-4 alkyl) phenyl, C _3-10 cycloalkyl, phenyl, halogen, cyano, * -SiR ₁₁ R ₁₂ R Substituted or unsubstituted with ₁₃ ;
R ₁₁ , R ₁₂ , R ₁₃ are each independently methyl, ethyl, tertbutyl or phenyl.
The method of claim 1,
B ₁ and B ₂ are each independently any one selected from the group consisting of:

.
The method of claim 1,
R ' ₁ and R' ₂ are each independently hydrogen or deuterium.
The method of claim 1,
Compound represented by Formula 1 is any one selected from the group consisting of:

.
A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 10. That is, an organic light emitting device.

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