KR20200009979A - 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. A compound represented by chemical formula 1 can be used as a material of an organic material layer of an organic light emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.

Description

Novel compound and organic light emitting device comprising the same

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

In general, 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. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

n and m are each independently an integer of 1 to 3,

p is an integer from 1 to 4,

L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene,

Ar ₁ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl,

R ₁ is hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-30 alkyl; Substituted or unsubstituted C _5-60 aryl; Substituted or unsubstituted C _2-30 alkenyl; Substituted or unsubstituted C _2-20 alkynyl; Substituted or unsubstituted C _3-30 cycloalkyl; C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and P; Substituted or unsubstituted C _1-30 alkoxy; Substituted or unsubstituted C _6-30 aryloxy; Substituted or unsubstituted C _1-30 alkylthioxy; Substituted or unsubstituted C _5-30 arylthioxy; Substituted or unsubstituted C _1-30 alkylsilyl; Substituted or unsubstituted C _5-30 arylsilyl; Cyano; Nitro; Hydroxyl or halogen,

Ar ₂ is a monovalent substituent of the compound represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

A is a benzene ring fused with two adjacent rings,

R ₂ and R ₃ are each independently substituted or unsubstituted C _1-30 alkyl; Substituted or unsubstituted C _6-60 aryl; Or R ₂ and R ₃ combine with each other to form a C _6-60 aryl ring,

a and c are each independently an integer of 0 to 4,

b is an integer of 0 to 2,

R ₄ to R ₆ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-30 alkyl; Substituted or unsubstituted C _5-60 aryl; Substituted or unsubstituted C _2-30 alkenyl; Substituted or unsubstituted C _2-20 alkynyl; Substituted or unsubstituted C _3-30 cycloalkyl; C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and P; Substituted or unsubstituted C _1-30 alkoxy; Substituted or unsubstituted C _6-30 aryloxy; Substituted or unsubstituted C _1-30 alkylthioxy; Substituted or unsubstituted C _5-30 arylthioxy; Substituted or unsubstituted C _1-30 alkylsilyl; Substituted or unsubstituted C _5-30 arylsilyl; Cyano; Nitro; Hydroxyl or halogen.

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 comprises a compound represented by Chemical Formula 1. do.

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.
3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 9, a light emitting layer 7, an electron control layer 10, an electron transport layer 8. , An example of an organic light emitting device comprising an electron injection layer 11 and a cathode 4 is shown.

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

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

, 또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

, or

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, S, and P atoms, or two or more substituents connected to the substituents exemplified above. it means. 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, P, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but 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, 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, isoxazolyl group, thiadia There may be a sleepy group, a phenothiazinyl group, a 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.

In Formula 2, preferably, Formula 2 may be the following Formulas 2-1 to 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Chemical Formulas 2-1 to 2-3,

The description of R ₂ to R ₆ and a to c is as defined above.

In Formula 1, R ₁ may be a substituted or unsubstituted C _1-5 alkyl group, preferably methyl, ethyl, propyl, i-propyl, n-butyl, i-butyl or t-butyl, More preferably methyl or t-butyl.

In Formula 2, R ₂ and R ₃ may be methyl, phenyl or R ₂ and R ₃ may be bonded to each other to form fluorene.

Ar ₂ is a monovalent substituent of the compound represented by Formula 2, and specifically, may be a compound having the following structure, but is not limited thereto.

는 화학식 1에 연결되는 결합을 의미하고, R₂ 내지 R₆ 및 a 내지 c에 대한 설명은 앞서 정의한 바와 같다. In the above formula

Means a bond connected to Formula 1, and the description of R ₂ to R ₆ and a to c is as defined above.

In Formula 1, preferably, L ₁ and L ₂ may be each independently a single bond, phenylene or naphthalenediyl.

Also, preferably, n and m may each independently be 1 or 2.

Preferably, Ar ₁ is substituted or unsubstituted C _6-30 aryl; Or C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and P.

In addition, Ar ₁ may be any one selected from the group consisting of:

For example, the compound may be selected from the group consisting of the following compounds:

On the other hand, the compound represented by the formula (1) can be prepared by the same production method as in Scheme 1 below.

Scheme 1

In Scheme 1, L ₁ , L ₂ , R ₂ to R ₆ , a to c and A are as defined above.

Scheme 1 is a Suzuki coupling reaction, in which a compound represented by Chemical Formula 1-a is reacted with a compound represented by Chemical Formula 1-b to prepare a compound represented by Chemical Formula 1-c. The reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The manufacturing method may be more specific in the production 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 may include a compound represented.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1. In this case, the compound represented by Formula 1 may be used as a host material in the light emitting layer, and more specifically, the compound represented by Formula 1 may be used as a host used in the light emitting layer of the blue organic light emitting device.

Efforts have been made to introduce phosphorescence in light emitting devices in the blue region, but progress is still low due to the high singlet and triplet energy needs of the blue host. Therefore, an organic light emitting device using fluorescence is commonly used as a light emitting device in a blue region. In particular, a fluorescent device using an anthracene host has been actively studied. Fluorescent blue hosts are generally synthesized based on high bandgap energy of 3.0 eV or more, and anthracene derivatives have been applied to improve performance by combining various blue dopants and using two or more blue hosts. Specifically, the compound represented by Formula 1 may be used as a fluorescent blue host.

In addition, the light emitting layer may include two or more types of hosts. When the light emitting layer includes two or more types of hosts, one or more of the hosts may be the compound.

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

In addition, the electron transport layer, the electron injection layer, or a layer for the electron transport and the electron injection at the same time may include a compound represented by the formula (1).

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.

3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 9, a light emitting layer 7, an electron control layer 10, an electron transport layer 8. , An example of an organic light emitting device comprising an electron injection layer 11 and a cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in at least one layer of the hole injection layer, hole transport layer, hole control layer, light emitting layer, electron control layer, electron transport layer, electron injection 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, A 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 for receiving holes from the hole injection layer and transporting holes to the light emitting layer. A hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring them 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 transporting and combining holes and electrons from the hole transport layer and the electron transport 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 the 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 that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of 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 an electrode, has a capability of transporting 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.

Preparation 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 Preparation of Compounds A1 to A10

Compounds A1 to A10 of Table 1 below were prepared using the reaction of any one of Steps 1-1 to 1-4.

As a reactant, 1eq of SM1 (boronic acid derivative) and 1.05eq of SM2 (halogen substituted compound) were added to tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (30 vol. Ratio to THF), followed by tetrakistriphenyl-force. Pinopalladium (2 mol%) was added thereto, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. Compounds A1 to A10 were prepared by vacuum distillation after removal of the solvent.

Step 1-1 to Step 1-4 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ A1

73% 398.22 A2

80% 249.23 A3

72% 398.22 A4

75% 398.22 A5

84% 249.23 A6

82% 398.22 A7

91% 249.23 A8

84% 340.19 A9

89% 340.19 A10

70% 419.08

Production Example  2-1: Preparation of Compounds B1 to B4

Compounds B1 to B4 of Table 2 were prepared by using the Step 2-1 or Step 2-2 reaction.

SM1 (1eq), SM2 (1.2eq) and potassium carbonate (4eq) were added to DMF (excess) and the mixture was stirred at reflux. After the reaction was completed, the mixture was cooled to room temperature and filtered. After extraction with water and chloroform at room temperature, the white solid was purified by column purification with ethyl acetate and hexane to prepare compounds B1 to B4.

Step 2-1 to Step 2-2 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ B1 A2

35% 398.22 B2 A5

34% 398.22 B3 A7

36% 398.22 B4

33% 366.18

Production Example  2-2: Preparation of Compounds X1 to X3

Compounds X1 to X3 of Table 3 below were prepared using the Step 2-3 reaction.

SM1 (1eq), SM2 (1.2eq) and potassium carbonate (4eq) were added to DMF (excess) and the mixture was stirred at reflux. After the reaction was completed, the mixture was cooled to room temperature and filtered. After extraction with water and chloroform at room temperature, the white solid was purified by column purification with ethyl acetate and hexane to prepare compounds X1 to X3.

Step 2-3 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ X1

78% 389.99 X2

81% 389.99 X3

75% 389.99

Production Example  2-3: Preparation of Compound Y1 to Y3

Compounds Y1 to Y3 of Table 4 were prepared using the Step 2-4 reaction.

As a reactant, 1eq of SM1 (halogen-substituted compound) and 1.05eq of SM2 (boronic acid derivative) were added to dioxane, followed by adding 2M aqueous potassium carbonate solution (30 vol. Ratio to dioxane), followed by tetrakistriphenyl-force. Pinopalladium (2 mol%) was added thereto, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. Compounds Y1 to Y3 were prepared by vacuum distillation after removal of the solvent.

Step 2-4 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ Y1 X1

71% 398.22 Y2 X2

75% 398.22 Y3 X3

74% 398.22

Production Example  3: Preparation of Compounds C1 to C14

Compounds C1 to C14 of Table 5 below were prepared using the reaction of any one of Steps 3-1 to 3-3.

SM1 (1eq) synthesized in Preparation Example 1 was added under a nitrogen atmosphere, and anhydrous tetrahydrofuran (excess) was added thereto to dissolve, followed by cooling and stirring at -10 ° C. Methylmagnesium bromide or phenylmagnesium bromide (2.5eq) was slowly added thereto for 30 minutes. The reaction solution was heated to room temperature and stirred for 12 hours under a nitrogen atmosphere. After cooling the reaction solution to 0 ° C., an aqueous solution of ammonium chloride (3eq) in distilled water was slowly added thereto. The reaction solution was extracted with distilled water and diethyl ether, the organic layer solution was dried over magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the solid was vacuum dried to prepare compounds C1 to C14.

Step 3-1 to Step 3-3 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ C1 A1 CH ₃ MgBr

83% 398.27 C2 B1 CH ₃ MgBr

85% 398.27 C3 A3 CH ₃ MgBr

84% 398.27 C4 A4 CH ₃ MgBr

83% 398.27 C5 B2 CH ₃ MgBr

85% 398.27 C6 A6 PhMgBr

80% 522.41 C7 B1 PhMgBr

88% 522.41 C8 B3 PhMgBr

84% 522.41 C9 A4 PhMgBr

85% 522.41 C10 Y1 CH ₃ MgBr

82% 398.27 C11 Y1 PhMgBr

83% 522.41 C12 Y2 CH ₃ MgBr

81% 398.27 C13 Y3 CH ₃ MgBr

80% 398.27 C14 Y3 PhMgBr

78% 522.41

Production Example  4: Preparation of Compounds D1 to D14

Compounds D1 to D14 of Table 6 were prepared using the reaction of any one of Steps 4-1 to 4-3.

One of C1 to C14 synthesized in Preparation Example 3 (1eq) was dissolved by adding dichloromethane (excess) under a nitrogen atmosphere, and then cooled and stirred at 0 ° C. Boron trifluoride diethyl etherate (1eq) was slowly added thereto for 10 minutes and the temperature was raised to room temperature, followed by stirring for 12 hours. After the reaction was completed, sodium bicarbonate aqueous solution was slowly added at 0 ° C. and stirred for 30 minutes. The reaction solution was extracted with dichloromethane and distilled water, and the products were then column purified with hexane and dichloromethane to prepare compounds D1 to D14. .

Step 4-1 to Step 4-3 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ D1 C1 BF ₃ , Et ₂ O, CH ₂ Cl ₂

83% 380.25 D2 C2 BF ₃ , Et ₂ O, CH ₂ Cl ₂

84% 380.25 D3 C3 BF ₃ , Et ₂ O, CH ₂ Cl ₂

85% 380.25 D4 C4 BF ₃ , Et ₂ O, CH ₂ Cl ₂

38% 380.25 D5 C5 BF ₃ , Et ₂ O, CH ₂ Cl ₂

35% 380.25 D6 C6 BF ₃ , Et ₂ O, CH ₂ Cl ₂

82% 504.40 D7 C7 BF ₃ , Et ₂ O, CH ₂ Cl ₂

83% 504.40 D8 C8 BF ₃ , Et ₂ O, CH ₂ Cl ₂

34% 504.40 D9 C9 BF ₃ , Et ₂ O, CH ₂ Cl ₂

25% 504.40 D10 C10 BF ₃ , Et ₂ O, CH ₂ Cl ₂

79% 380.25 D11 C11 BF ₃ , Et ₂ O, CH ₂ Cl ₂

81% 504.40 D12 C12 BF ₃ , Et ₂ O, CH ₂ Cl ₂

82% 380.25 D13 C13 BF ₃ , Et ₂ O, CH ₂ Cl ₂

23% 380.25 D14 C14 BF ₃ , Et ₂ O, CH ₂ Cl ₂

24% 504.40

Production Example  5: Preparation of Compounds E1 to E5

Compounds E1 to E5 of Table 7 were prepared using the reaction of any one of Steps 5-1 to 5-3.

As a reaction, one of B4, A8, A9 and A10 (1eq) was dissolved in THF (excess), the temperature was lowered to -78 ° C, and then 2.5M n-BuLi (1.5eq) was added dropwise and SM2 (1.05eq) after 30 minutes. After adding to the RT and stirred for 1 hour. 1N HCl (excess) was added and stirred for 30 minutes, and the layers were separated, the solvent was removed, the residue was purified by ethyl acetate, and the obtained solid was added to acetic acid (excess). Then, 1 ml of sulfuric acid was added dropwise and refluxed. The mixture was cooled to room temperature, neutralized with water, and the filtered solid was recrystallized from tetrahydrofuran and ethyl acetate to prepare compounds E1 to E5.

Step 5-1 to Step 5-3 Intermediate SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ E1 B4

80% 502.38 E2 A8

79% 502.38 E3 A9

28% 502.38 E4 A10

29% 502.38 E5 A9

38% 502.38

Example  1 to 19: Preparation of Compound 1 to 19

Compounds 1 to 19 of Table 8 were prepared by using any one of Step 6-1 to Step 6-6.

2M potassium carbonate aqueous solution (THF) was added to tetrahydrofuran after adding (1eq) and SM2 (1.03eq) of D1 to D14 synthesized in Preparation Example 4 and E1 to E5 synthesized in Preparation Example 5 as reactants. To 30 vol. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. Compound 1 to compound 19 of Table 6 were prepared by recrystallization with tetrahydrofuran and ethyl acetate after removing the solvent.

Step 6-1 to Step 6-6 compound SM1 SM2 Pruduct yield (%) MS [M + H] ⁺ Compound 1 D1

78% 629.77 Compound 2 D2

74% 643.75 Compound 3 D3

80% 679.83 Compound 4 D4

75% 659.82 Compound 5 D5

73% 629.77 Compound 6 D6

72% 753.91 Compound 7 D7

75% 758.94 Compound 8 D8

69% 793.98 Compound 9 D9

72% 793.96 Compound 10 E1

70% 753.91 Compound 11 E2

77% 675.8 Compound 12 E3

73% 781.94 Compound 13 E4

72% 765.88 Compound 14 E5

70% 725.86 Compound 15 D10

73% 643.75 Compound 16 D11

70% 777.94 Compound 17 D12

72% 553.67 Compound 18 D13

75% 629.77 Compound 19 D14

73% 726.88

Experimental Example  1: organic light emitting device manufacturing

The substrate on which 70/1000/70 mm deposited ITO / Ag / ITO was deposited as a positive electrode was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was put in distilled water 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.

H-1 was thermally vacuum deposited to a thickness of 50 kPa on the anode thus prepared to form a hole injection layer, and HT1, which is a material for transporting holes, was vacuum deposited to 1150 kPa to form a hole transport layer. Next, a hole control layer was formed using HT2 (150 kPa), and then the host compound 1 and the dopant BD1 (2 wt%) synthesized in Example 1 were vacuum deposited to a thickness of 360 kPa to form a light emitting layer. Thereafter, ET1 was deposited at 50 kPa to form an electron control layer, and compound ET2 and Liq were mixed at 7: 3 to form an electron transport layer having a thickness of 250 kPa. 50 μm thick magnesium and lithium fluoride (LiF) were sequentially deposited using an electron injection layer <EIL>, and 200 μm of magnesium and silver (1: 4) were used as a cathode, and 600 μm of CP1 was deposited to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec.

HI-1, HT1, HT2, BD1, ET1, ET2, Liq and CP1 compounds are as follows.

Experimental Example 2 to 20: Fabrication of the organic light emitting device

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound shown in Table 9 as a host and a dopant.

BD2 compounds are as follows.

Comparative Examples 1 to 6: organic light emitting device manufacturing

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound shown in Table 9 as a host and a dopant.

The BH1 to BH4 compounds are as follows, respectively.

The current was applied to the organic light emitting diodes manufactured in the Experimental and Comparative Examples to measure the driving voltage, efficiency, color coordinates, and lifetime, and the results are shown in Table 9 below. At this time, the lifetime is defined as the time taken for the luminance to decrease to 95% when the initial luminance is set to 100%.

Experimental Example
20 mA / ㎠ Host Dopant Voltage (V)
(@ 20mA / cm ² ) Cd / A
(@ 20mA / cm ² ) Color coordinates
(x, y) life span
(T95, h)
(@ 20mA / cm ² ) Experimental Example 1 Compound 1 BD1 3.51 6.71 (0.135, 0.138) 49.0 Experimental Example 2 Compound 2 BD1 3.45 6.63 (0.134, 0.137) 50.2 Experimental Example 3 Compound 3 BD1 3.41 6.58 (0.135, 0.138) 55.2 Experimental Example 4 Compound 5 BD1 3.34 6.82 (0.134, 0.138) 51.2 Experimental Example 5 Compound 6 BD1 3.42 6.72 (0.136, 0.139) 48.9 Experimental Example 6 Compound 8 BD1 3.31 6.52 (0.135, 0.138) 48.5 Experimental Example 7 Compound 10 BD1 3.50 6.69 (0.133, 0.139) 49.1 Experimental Example 8 Compound 11 BD1 3.56 6.78 (0.135, 0.138) 50.2 Experimental Example 9 Compound 12 BD1 3.48 6.58 (0.134, 0.138) 50.1 Experimental Example 10 Compound 13 BD1 3.50 6.67 (0.136, 0.139) 55.0 Experimental Example 11 Compound 14 BD1 3.51 6.77 (0.136, 0.139) 53.5 Experimental Example 12 Compound 1 BD2 3.51 7.01 (0.135, 0.122) 40.2 Experimental Example 13 Compound 7 BD2 3.53 7.13 (0.134, 0.121) 43.2 Experimental Example 14 Compound 9 BD2 3.55 7.08 (0.136, 0.123) 41.5 Experimental Example 15 Compound 12 BD2 3.55 7.12 (0.136, 0.120) 42.5 Experimental Example 16 Compound 15 BD1 3.32 6.82 (0.136, 0.139) 51.5 Experimental Example 17 Compound 17 BD1 3.38 6.78 (0.135, 0.138) 58.1 Experimental Example 18 Compound 16 BD1 3.41 6.72 (0.133, 0.139) 53.4 Experimental Example 19 Compound 19 BD2 3.51 7.11 (0.136, 0.123) 43.5 Experimental Example 20 Compound 18 BD2 3.54 7.13 (0.136, 0.120) 42.8 Comparative Example 1 BH1 BD1 4.01 5.12 (0.136, 0.139) 38.0 Comparative Example 2 BH1 BD2 4.12 6.50 (0.135, 0.122) 20.2 Comparative Example 3 BH2 BD1 3.90 5.23 (0.136, 0.139) 35.2 Comparative Example 4 BH3 BD1 3.88 5.31 (0.136, 0.139) 35.2 Comparative Example 5 BH4 BD1 3.87 5.38 (0.136, 0.139) 40.2 Comparative Example 6 BH3 BD2 3.83 6.48 (0.135, 0.122) 23.8

The organic electroluminescent device combined with the compound derivative of Formula 1 according to the present invention can control the role of smooth hole injection into the light emitting layer by using the compounds of Examples 1 to 19 as a host of the blue organic electroluminescent device, and chemical structure Through the balance of holes and electrons of the organic light emitting device according to the present invention, the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

Experimental Example 21 Manufacture of Organic Light-Emitting Device

The substrate on which 70/1000/70 mm deposited ITO / Ag / ITO was deposited as a positive electrode was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was put in distilled water 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.

H-1 was thermally vacuum deposited to a thickness of 50 kPa on the anode thus prepared to form a hole injection layer, and HT1, which is a material for transporting holes, was vacuum deposited to 1150 kPa to form a hole transport layer. Next, a hole-controlling layer was formed using HT2 (150 kPa), and then Compound 1 and BH1 synthesized in Example 1 were co-deposited at a weight ratio of 50:50 and simultaneously dopant BD1 (2% by weight). A light emitting layer was formed to a thickness of 360 kPa. Thereafter, ET1 was deposited at 50 kPa to form an electron control layer, and compound ET2 and Liq were mixed at 7: 3 to form an electron transport layer having a thickness of 250 kPa. 50 μm thick magnesium and lithium fluoride (LiF) were sequentially deposited using an electron injection layer <EIL>, and 200 μm of magnesium and silver (1: 4) were used as a cathode, and 600 μm of CP1 was deposited to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec.

Experimental Examples 22 to 40: Fabrication of an organic light emitting device

An organic light emitting diode was manufactured according to the same method as Experimental Example 21 except for using the compound shown in Table 10 as a host and a dopant.

Comparative Examples 7 to 11: Preparation of an organic light emitting device

An organic light emitting diode was manufactured according to the same method as Experimental Example 21 except for using the compound shown in Table 10 as a host and a dopant.

The current was applied to the organic light emitting diodes manufactured in the Experimental and Comparative Examples, and the driving voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 10 below. At this time, the lifetime is defined as the time taken for the luminance to decrease to 95% when the initial luminance is set to 100%.

Experimental Example
20 mA / ㎠ Host (weight ratio) Dopant Voltage (V)
(@ 20mA / cm ² ) Cd / A
(@ 20mA / cm ² ) Color coordinates
(x, y) life span
(T95, h)
(@ 20mA / cm ² ) Experimental Example 21 Compound 1: BH1 (5: 5) BD1 3.51 6.55 (0.135, 0.138) 49.0 Experimental Example 22 Compound 10: BH1 (5: 5) BD1 3.45 6.68 (0.134, 0.137) 50.2 Experimental Example 23 Compound 13: BH3 (7: 3) BD1 3.41 6.88 (0.135, 0.138) 55.2 Experimental Example 24 Compound 3: BH2 (5: 5) BD1 3.34 6.52 (0.134, 0.138) 51.2 Experimental Example 25 Compound 12: BH4 (5: 5) BD1 3.42 6.33 (0.136, 0.139) 48.9 Experimental Example 26 Compound 14: BH2 (3: 7) BD1 3.31 6.45 (0.135, 0.138) 48.5 Experimental Example 27 Compound 8: Compound 13 (5: 5) BD1 3.50 6.69 (0.133, 0.139) 49.1 Experimental Example 28 Compound 11: Compound 14 (5: 5) BD1 3.56 6.78 (0.135, 0.138) 50.2 Experimental Example 29 Compound 2: Compound 7 (5: 5) BD1 3.48 6.58 (0.134, 0.138) 50.1 Experimental Example 30 Compound 4: Compound 9 (3: 7) BD1 3.50 6.67 (0.136, 0.139) 55.0 Experimental Example 31 Compound 2: Compound 12 (7: 3) BD1 3.51 6.77 (0.136, 0.139) 53.5 Experimental Example 32 Compound 1: Compound 11 (5: 5) BD2 3.54 7.05 (0.136, 0.123) 43.2 Experimental Example 33 Compound 2: Compound 10 (5: 5) BD2 3.61 7.02 (0.136, 0.120) 44.5 Experimental Example 34 Compound 3: Compound 13 (5: 5) BD2 3.48 7.11 (0.133, 0.121) 40.8 Experimental Example 35 Compound 8: Compound 14 (5: 5) BD2 3.55 7.12 (0.134, 0.122) 42.5 Experimental Example 36 Compound 17: BH4 (5: 5) BD1 3.47 6.89 (0.134, 0.138) 55.8 Experimental Example 37 Compound 19: BH1 (3: 7) BD2 3.56 7.23 (0.134, 0.122) 43.5 Experimental Example 38 Compound 8: Compound 18 (5: 5) BD1 3.41 6.90 (0.134, 0.138) 52.8 Experimental Example 39 Compound 11: Compound 16 (5: 5) BD1 3.38 6.78 (0.134, 0.138) 53.1 Experimental Example 40 Compound 15: Compound 17 (5: 5) BD2 3.53 7.28 (0.134, 0.122) 41.8 Comparative Example 7 BH1: BH2 (5: 5) BD1 3.98 5.32 (0.135, 0.138) 50.2 Comparative Example 8 BH1: BH2 (7: 3) BD1 3.82 5.54 (0.134, 0.138) 52.8 Comparative Example 9 BH1: BH2 (3: 7) BD1 4.01 5.48 (0.136, 0.139) 51.5 Comparative Example 10 BH1: BH2 (5: 5) BD2 4.02 6.70 (0.133, 0.121) 38.2 Comparative Example 11 BH1: BH2 (7: 3) BD2 3.99 6.56 (0.136, 0.123) 35.1

The organic electroluminescent device combined with the compound derivative of Formula 1 according to the present invention controls the role of smooth hole injection into the light emitting layer by using the compounds of Examples 1 to 19 as one or more of the mixed host of the blue organic electroluminescent device. Through the balance of holes and electrons in the organic light emitting device according to the chemical structure, the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

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
9: hole control layer 10: electron control layer
11: electron injection layer

Claims (13)

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

In Chemical Formula 1,
n and m are each independently an integer of 1 to 3,
p is an integer from 1 to 4,
L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene,
Ar ₁ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl,
R ₁ is hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-30 alkyl; Substituted or unsubstituted C _5-60 aryl; Substituted or unsubstituted C _2-30 alkenyl; Substituted or unsubstituted C _2-20 alkynyl; Substituted or unsubstituted C _3-30 cycloalkyl; C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and P; Substituted or unsubstituted C _1-30 alkoxy; Substituted or unsubstituted C _6-30 aryloxy; Substituted or unsubstituted C _1-30 alkylthioxy; Substituted or unsubstituted C _5-30 arylthioxy; Substituted or unsubstituted C _1-30 alkylsilyl; Substituted or unsubstituted C _5-30 arylsilyl; Cyano; Nitro; Hydroxyl or halogen,
Ar ₂ is a monovalent substituent of the compound represented by the following formula (2),
[Formula 2]

In Chemical Formula 2,
A is a benzene ring fused with two adjacent rings,
R ₂ and R ₃ are each independently substituted or unsubstituted C _1-30 alkyl; Substituted or unsubstituted C _6-60 aryl; Or R ₂ and R ₃ combine with each other to form a C _6-60 aryl ring,
a and c are each independently an integer of 0 to 4,
b is an integer of 0 to 2,
R ₄ to R ₆ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-30 alkyl; Substituted or unsubstituted C _5-60 aryl; Substituted or unsubstituted C _2-30 alkenyl; Substituted or unsubstituted C _2-20 alkynyl; Substituted or unsubstituted C _3-30 cycloalkyl; C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and P; Substituted or unsubstituted C _1-30 alkoxy; Substituted or unsubstituted C _6-30 aryloxy; Substituted or unsubstituted C _1-30 alkylthioxy; Substituted or unsubstituted C _5-30 arylthioxy; Substituted or unsubstituted C _1-30 alkylsilyl; Substituted or unsubstituted C _5-30 arylsilyl; Cyano; Nitro; Hydroxyl or halogen.
The method of claim 1,
Formula 2 is a compound of Formula 2-1 to 2-3,
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Chemical Formulas 2-1 to 2-3,
The description of R ₂ to R ₆ and a to c is as defined in claim 1.
The method of claim 1,
R ₁ is a substituted or unsubstituted C _1-5 alkyl group.
The method of claim 1,
R ₂ and R ₃ are methyl, phenyl or R ₂ and R ₃ combine with each other to form fluorene.
The method of claim 1,
L ₁ and L ₂ are each independently a single bond, phenylene or naphthalenediyl.
The method of claim 1,
n and m are each independently 1 or 2;
The method of claim 1,
Ar ₁ is substituted or unsubstituted C _6-30 aryl; Or C 2 _-60 heteroaryl comprising one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, S and P.
The method of claim 1,
Ar ₁ is any one selected from the group consisting of:

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 9. That is, an organic light emitting device.
The method of claim 10,
The organic material layer containing the compound is a light emitting layer, an organic light emitting device.
The method of claim 10,
The compound is included as a host, the organic light emitting device.
The method of claim 11,
The light emitting layer includes two or more kinds of hosts, and at least one of the hosts is the compound.

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