KR20200069247A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device comprising the same}

The present invention relates to a novel compound and an organic light emitting device using 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 a 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, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

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. 10-2013-073537

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

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

[Formula 1]

[Formula 1-1]

In Formula 1, two adjacent carbons of C ₁ to C ₄ are respectively connected to * of the compound represented by Formula 1-1,

Y ₁ , Y ₂ and Y ₃ are each independently CH; Or N, provided that Y ₁ , Two or more of Y ₂ and Y ₃ are N,

X ₁ is NR', X ₂ is S, or X ₁ is S, X ₂ is NR',

Wherein R'is substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

L ₁ and L ₂ are each independently, a direct bond; Or substituted or unsubstituted C _6-60 arylene,

R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

n, m and p are each independently an integer from 0 to 3,

o is an integer from 0 to 2.

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

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or 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.

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.
FIG. 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 Did.

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

(compound)

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a linkage to another substituent.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar 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 this 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-butyl dimethyl 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 a straight chain or a branched chain, 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, styrenyl 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, 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 of the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the above-described alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. 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, the compound represented by Formula 1, the compound represented by Formula 1 may be any one selected from compounds represented by the following Formulas 1-2 to 1-7:

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Chemical Formulas 1-2 to 1-7,

X ₁ , X ₂ , Y ₁ , Y ₂ , Y ₃ , L ₁ , L ₂ , R ₁ , R ₂ , R ₃ , R _4, Ar ₁ , Ar ₂ , n, m, o and p are as defined above.

Preferably, R'is phenyl; Biphenylyl; Naphthyl; Carbazolyl; Dibenzofuranyl; Or dibenzothiophenyl.

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

Preferably, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen; methyl; ethyl; profile; Phenyl; Or biphenylyl.

Preferably, Ar ₁ and Ar ₂ are each independently phenyl; Biphenylyl; Naphthyl; Dibenzofuranyl; Or dibenzothiophenyl.

Preferably, n, m and o may each independently be 0 or 1.

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

.

.

.

.

The compound represented by Chemical Formula 1 according to the present invention has a structure in which a carbazole group serving as an electron donor and a monocyclic nitrogen heterocycle serving as an electron acceptor are substituted at both ends of benzothiocarbazole. Since two substituents are located at both ends of one molecule, it exhibits excellent properties in both hole transport and electron transport. Accordingly, when the compound represented by Formula 1 is applied as a host compound in the light emitting layer of an organic light emitting device, high efficiency, low driving voltage, and long life It can have properties.

The compound represented by Chemical Formula 1 may be prepared through the following Reaction Scheme 1.

[Scheme 1]

In Reaction Scheme 1, definitions for other substituents except X'are as described above, and X'is halogen, preferably Br, Cl or I.

Reaction Scheme 1 is preferably performed in the presence of a palladium catalyst and a base as a Suzuki coupling reaction, and the reactor for the Suzuki coupling reaction can be changed as known in the art.

In the compound represented by Chemical Formula 1, the position of each substituent can be prepared by appropriately changing the structure of the starting material with reference to Reaction Scheme 1. The method for preparing the compound represented by Chemical Formula 1 may be more specifically described in Preparation Examples to be described later.

(Organic light emitting element)

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 an organic light emitting device is provided. 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 fewer 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 contains the compound displayed.

In addition, 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.

Preferably, when the organic material layer including the compound represented by Formula 1 is a light emitting layer, the light emitting layer may further include a compound represented by Formula 2 below:

[Formula 2]

In Chemical Formula 2,

Ar' ₁ and Ar' ₂ are each independently substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

R ₅ and R ₆ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,

a and b are each independently an integer from 0 to 7.

Preferably, Ar' ₁ and Ar' ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or dimethylfluorenyl.

Preferably, R ₅ and R ₆ are each independently hydrogen.

Preferably, the compound represented by Formula 2 is any one selected from the group consisting of:

.

.

Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. 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.

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 Did. 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 can be made of materials and methods known in the art, except that at least one layer of the organic material layer contains 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 can 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 metal or conductive metal oxides or alloys 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); Metal and oxide combinations such as ZnO:Al or SNO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred. It is preferred that the high 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 matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based , Organic 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 from the hole injection layer to the light-emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. 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 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 pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a 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. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.

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

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and injects holes 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-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

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

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

[Synthesis example]

Synthesis Example 1: Synthesis of Intermediate A

Step 1) Synthesis of Intermediate A-1

2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0g, 48.4mmol) and 1-bromo-4- in nitrogen atmosphere Chloro-2-nitrobenzene (12.6 g, 53.2 mmol) was added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (26.7g, 193.4mmol) was dissolved in 80ml of water, stirred sufficiently, and tetrakis(triphenylphosphine)palladium(0) (1.7g, 1.5mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.4 g of Intermediate A-1.

(Yield 63%, MS: [M+H] + = 341)

Step 2) Synthesis of Intermediate A-2

In a nitrogen atmosphere, intermediate A-1 (20.0g, 58.9mmol) and triphenylphosphine (12.2ml, 88.3mmol) were stirred under reflux in 200ml o-dichlorobenzene. After the reaction for 5 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.0 g of Intermediate A-2.

(Yield 44%, MS: [M+H] + = 309)

Step 3) Synthesis of Intermediate A

In a nitrogen atmosphere, intermediate A-2 (20.0 g, 65 mmol) and N-bromosuccinimide (12.1 ml, 68.2 mmol) were placed in 400 ml of N,N-dimethylmethanamide and stirred at room temperature. After the reaction for 5 hours, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.8 g of Intermediate A.

(Yield 75%, MS: [M+H] + = 388)

Synthesis Example 2: Synthesis of Intermediate B and Intermediate C

Step 1) Synthesis of Intermediate B-1

In a nitrogen atmosphere, 3-bromo-7-chlorodibenzo[b,d]thiophene (15.0g, 50.4mmol) and 9H-carbazole (9.3g, 55.4mmol) were added to 300 ml of toluene and stirred and refluxed. After this, sodium tert-butoxide (7.3g, 75.6mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.8g, 1.5mmol) were added. After the reaction for 4 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.1 g of Intermediate B-1.

(Yield 73%, MS: [M+H] + = 385)

Step 2) Synthesis of Intermediate B-2

In a nitrogen atmosphere, compound B-1 (15.0 g, 39.1 mmol) and bis (pinacolato) diboron (10.9 g, 43.0 mmol) were refluxed and stirred in 300 ml of 1,4-dioxane. After this, potassium acetate (5.8g, 58.6mmol) was added and stirred sufficiently, followed by bis(dibenzylideneacetone)palladium(0) (0.7g, 1.2mmol) and tricyclohexylphosphine (0.7g, 2.3mmol). After reacting for 5 hours, cooled to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.5 g of Intermediate B-2.

(Yield 78%, MS: [M+H] + = 476)

Step 3) Synthesis of Intermediate B-3

In a nitrogen atmosphere, intermediate B-2 (15.0 g, 31.6 mmol) and 1-bromo-4-chloro-2-nitrobenzene (8.2 g, 34.7 mmol) were placed in 300 ml of THF and stirred and refluxed. After that, potassium carbonate (17.4g, 126.2mmol) was dissolved in 52ml of water and stirred sufficiently, followed by tetrakis(triphenylphosphine)palladium(0) (1.1g, 0.9mmol). After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6 g of Intermediate B-3.

(Yield 73%, MS: [M+H] + = 506)

Step 3) Synthesis of Intermediates B and C

In a nitrogen atmosphere, intermediate B-3 (20.0g, 39.6mmol) and triphenylphosphine (8.2ml, 59.4mmol) were stirred under reflux in 200ml o-dichlorobenzene. After the reaction for 7 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7.4g and 4.5g of Intermediate B and Intermediate C, respectively.

(Intermediate B yield: 44%, Intermediate C yield: 27%, MS: [M+H] + = 423)

Synthesis Example 3: Synthesis of Intermediate D

In Synthesis Example 2, except for using 3-bromo-7-chlorodibenzo[b,d]thiophene 7-bromo-1-chlorodibenzo[b,d]thiophene, the same method as in Intermediate A Intermediate D was prepared.

(MS[M+H] ⁺ = 474)

Synthesis Example 4: Synthesis of Compound 1

Step 1) Synthesis of Compound 1-1

In a nitrogen atmosphere, intermediate A (15.0 g, 38.8 mmol) and iodobenzene (8.7 g, 42.7 mmol) were added to 300 ml of toluene, stirred and refluxed. After that, sodium tert-butoxide (5.6g, 58.2mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.6g, 1.2mmol) were added. After the reaction for 5 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.0 g of compound 1-1.

(Yield 50%, MS: [M+H] + = 464)

Step 2) Synthesis of Compound 1-2

Compound 1-1 (15.0g, 32.4mmol) and bis(pinacolato)diboron (9.1g, 35.7mmol) were stirred under reflux in 300ml of 1,4-dioxane in a nitrogen atmosphere. After this, potassium acetate (4.8g, 48.6mmol) was added and stirred sufficiently, followed by bis(dibenzylideneacetone)palladium(0) (0.6g, 1.0mmol) and tricyclohexylphosphine (0.5g, 1.9mmol). After reacting for 7 hours, cooled to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g of Compound 1-2.

(Yield 68%, MS: [M+H] + = 511)

Step 3) Synthesis of Compound 1-3

Compound 1-2 (15.0 g, 29.4 mmol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (10.1 g, 32.4 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (16.3g, 117.7mmol) was dissolved in 49ml of water, stirred sufficiently, and tetrakis(triphenylphosphine)palladium(0) (1g, 0.9mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8 g of Compound 1-3.

(Yield 71%, MS: [M+H] + = 616)

Step 4) Synthesis of Compound 1

In a nitrogen atmosphere, Compound 1-3 (15.0 g, 24.4 mmol) and 9H-carbazole (4.5 g, 26.8 mmol) were added to 300 ml of toluene, stirred and refluxed. After that, sodium tert-butoxide (3.5g, 36.6mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.4g, 0.7mmol) were added. After the reaction for 4 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 7.1 g of compound 1 was prepared through a sublimation tablet.

(Yield 39%, MS: [M+H] + = 747)

Synthesis Example 5: Synthesis of Compound 2

Step 1) Synthesis of Compound 2-1

In a nitrogen atmosphere, intermediate B (15.0 g, 31.7 mmol) and iodobenzene (7.1 g, 34.9 mmol) were added to 300 ml of toluene, stirred and refluxed. After that, sodium tert-butoxide (4.6g, 47.6mmol) and bis(tri-tert-butylphosphine)palladium (0 (0.5g, 1.0mmol)) were added in. After 1 hour reaction, the mixture was cooled to room temperature, and the organic layer was used with chloroform and water. After separation, the organic layer was distilled, dissolved in chloroform again, washed twice with water to separate the organic layer, added anhydrous magnesium sulfate, stirred and filtered to distill the filtrate under reduced pressure. Purification to prepare 10.6 g of compound 2-1.

(Yield 61%, MS: [M+H] + = 550)

Step 2) Synthesis of Compound 2-2

In a nitrogen atmosphere, compound 2-1 (15.0 g, 27.3 mmol) and bis (pinacolato) diboron (7.6 g, 30 mmol) were stirred under reflux to 300 ml of 1,4-dioxane. After this, potassium acetate (4.0g, 41mmol) was added and stirred sufficiently, followed by bis(dibenzylideneacetone)palladium(0) (0.5g, 0.8mmol) and tricyclohexylphosphine (0.5g, 1.6mmol). After reacting for 5 hours, cooled to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6 g of Compound 2-2.

(Yield 66%, MS: [M+H] + = 642)

Step 3) Synthesis of Compound 2

Compound 2-2 (15.0g, 23.4mmol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (8.0g, 25.8mmol) were added to 300 ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (12.9g, 93.7mmol) was dissolved in 39ml of water, stirred thoroughly, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After the reaction for 9 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 4.9 g of Compound 2 was prepared through sublimation purification.

(Yield 28%, MS: [M+H] + = 747)

Synthesis Example 6: Synthesis of Compound 3

In Synthesis Example 5, Compound 3 was prepared by the same method as the method for preparing Compound 2, except that Intermediate B was changed to Intermediate C.

(MS[M+H] ⁺ = 747)

Synthesis Example 7: Synthesis of Compound 4

In Synthesis Example 1, intermediate B is intermediate C, 2-bromo-4,6-diphenyl-1,3,5-triazine is 2-([1,1'-biphenyl]-3-yl)-4-bromo Compound 4 was prepared by the same method as the method of preparing compound 2, except that it was changed to -6-phenyl-1,3,5-triazine.

(MS[M+H] ⁺ = 823)

Synthesis Example 8: Synthesis of Compound 5

In Synthesis Example 5, Compound 5 was prepared by the same method as the method for preparing Compound 2, except that Intermediate B was changed to Intermediate D.

(MS[M+H] ⁺ = 747)

Synthesis Example 9: Synthesis of Compound 6

In Synthesis Example 1, Compound 6 was prepared by the same method as the method for preparing Compound 2, except that Intermediate B was changed to Intermediate D and iodobenzene was changed to 2-bromodibenzo[b,d]furan.

(MS[M+H] ⁺ = 837)

[Example]

Example 1

ITO (Indium Tin Oxide) was coated with a thin film coated with a thickness of 1,400 에 in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic 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 then transported 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 ITO transparent electrode thus prepared, the following HT and 5 wt% of PD were thermally vacuum-deposited to a thickness of 100 Å, and then only the HT material was deposited to a thickness of 1150 Å to form a hole transport layer. The following EB as an electron blocking layer was thermally vacuum-deposited to a thickness of 450 MPa. Subsequently, Compound 1 and 15% by weight of GD were used as a dopant and vacuum-deposited to a thickness of 400 MPa. Subsequently, the following ET-A was vacuum-deposited to a thickness of 50 MPa as a hole blocking layer. Subsequently, the following ET-B and Liq were thermally vacuum-deposited to a thickness of 250 MPa at a ratio of 2:1 as an electron transporting and injection layer, and then LiF and magnesium were vacuum-deposited to a thickness of 30 MPa at a ratio of 1:1. Magnesium and silver were deposited on the electron injection layer at a thickness of 160 로 at a ratio of 1:4 to form a cathode to prepare an organic light emitting device.

Examples 2 to 9 and Comparative Examples 1 to 77

An organic light emitting device was manufactured in the same manner as in Example 1, except that the host material was changed as shown in Table 1 below. In this case, when a mixture of two types of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds.

By applying a current to the organic light-emitting device prepared in Examples 1 to 9 and Comparative Examples 1 to 7, voltage, efficiency, and lifetime (T95) were measured and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10mA/cm ² , and T95 means the time until the initial luminance drops to 95% at the current density of 20mA/cm ² .

division Host
matter @ 10mA/cm ² @ 20mA/cm ² Voltage
(V) efficiency
(cd/A) life span
(T95, hr) Example 1 Compound 1 4.63 46.2 111 Example 2 Compound 2 4.61 47.3 113 Example 3 Compound 3 4.62 42.4 108 Example 4 Compound 4 4.69 45.6 121 Example 5 Compound 5 4.64 44.5 117 Example 6 Compound 6 4.65 45.6 122 Example 7 PGH: Compound 1 (60:40) 4.33 56.5 153 Example 8 PGH:Compound 3 (60:40) 4.35 56.1 157 Example 9 PGH:Compound 5 (60:40) 4.34 54.5 160 Comparative Example 1 GH-A 4.89 38.1 70 Comparative Example 2 GH-B 5.71 13.5 42 Comparative Example 3 GH-C 4.98 40.1 80 Comparative Example 4 GH-D 5.97 10.3 50 Comparative Example 5 GH-E 5.17 36.8 76 Comparative Example 6 PGH:GH-A (60:40) 4.65 45.0 91 Comparative Example 7 PGH:GH-C(60:40) 4.66 43.5 93

The compound of Formula 1 has a structure in which benzothiocarbazole is connected between a carbazole serving as an electron donor and a nitrogen-containing heterocycle serving as an electron acceptor. Benzothiocarbazole, like carbazole, has a strong electron donor property, and since carbazole is linked through a nitrogen atom, it has stronger electron donor properties. In addition, as shown in Chemical Formula 1, the meta-position of X ₁ is a direction in which the conjugation is well connected, which is advantageous for transferring electrons to the nitrogen-containing heterocycle serving as an electron acceptor. Therefore, the carbazole is strongly formed in the CT (charge transfer) state compared to GH-D or GH-B, which is connected to carbon, or GH-C, which is connected to the para-position of the sulfur atom.

In addition, the sulfur atom is richer in electrons than the oxygen or carbon atom, so the compound of Formula 1 has stronger CT characteristics than GH-A or GH-E. Therefore, the compound of Formula 1 has excellent CT characteristics by strengthening the electron donating properties in the compound and having a structure that transmits well to the nitrogen-containing ring that serves as an electron acceptor, which is excellent in injection characteristics of charges and energy transfer characteristics to dopants. By contributing to the improvement of and increasing the stability of the material, it exhibits characteristics of low voltage, high efficiency, and long life. In particular, when used in combination with a compound of Formula 2, such as PGH, the effect becomes more remarkable, and exhibits a better effect than when a compound of a different structure is used with a compound of Formula 2.

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 (13)

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

[Formula 1-1]

In Formula 1, two adjacent carbons of C ₁ to C ₄ are respectively connected to * of the compound represented by Formula 1-1,
Y ₁ , Y ₂ and Y ₃ are each independently CH; Or N, provided that Y ₁ , Two or more of Y ₂ and Y ₃ are N,
X ₁ is NR', X ₂ is S, or X ₁ is S, X ₂ is NR',
Wherein R'is substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,
L ₁ and L ₂ are each independently, a direct bond; Or substituted or unsubstituted C _6-60 arylene,
R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,
n, m and p are each independently an integer from 0 to 3,
o is an integer from 0 to 2.
According to claim 1,
The compound represented by Formula 1 is any one selected from compounds represented by Formulas 1-2 to 1-7 below:
[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Chemical Formulas 1-2 to 1-7,
X ₁ , X ₂ , Y ₁ , Y ₂ , Y ₃ , L ₁ , L ₂ , R ₁ , R ₂ , R ₃ , R _4, Ar ₁ , Ar ₂ , n, m, o and p are as defined in claim 1.
According to claim 1,
R'is phenyl; Biphenylyl; Naphthyl; Carbazolyl; Dibenzofuranyl; Or dibenzothiophenyl.
According to claim 1,
L ₁ and L ₂ are each independently, a direct bond; Or phenylene.
According to claim 1,
R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen; methyl; ethyl; profile; Phenyl; Or biphenylyl.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl; Biphenylyl; Naphthyl; Dibenzofuranyl; Or dibenzothiophenyl.
According to claim 1,
n, m, o and p are each independently 0 or 1, a compound.
According to claim 1,
The 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 layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 8. That is, an organic light emitting device.
The method of claim 9,
The organic material layer containing the compound is a light emitting layer, an organic light emitting device.
The method of claim 10,
The light emitting layer further comprises a compound represented by the formula (2), an organic light emitting device:
[Formula 2]

In Chemical Formula 2,
Ar' ₁ and Ar' ₂ are each independently substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing one or more hetero atoms selected from the group consisting of N, O and S,
R ₅ and R ₆ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing one or more hetero atoms selected from the group consisting of N, O and S,
a and b are each independently an integer from 0 to 7.
The method of claim 11,
Ar' ₁ and Ar' ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl, an organic light emitting device.
The method of claim 11,
The compound represented by Chemical Formula 2 is any one selected from the group consisting of:

.

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