KR20220048180A - 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 comprising the same. The compound is represented by chemical formula 1. According to the present invention, efficiency and life properties of the organic light emitting device can be improved.

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 including the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted 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, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An 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. The organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, it may be made of an electron injection layer, etc. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

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

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 the following formula (1).

[Formula 1]

In Formula 1,

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

L ₃ is a direct bond; Or a substituted or unsubstituted C _6-60 arylene,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;

A is each independently substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

R ₁ are each independently hydrogen; heavy hydrogen; halogen; nitrile; silyl; substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

R ₂ are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C _6-60 aryl,

p is an integer from 1 to 4,

a is an integer of 0 to 3, provided that a+p is 1 to 4,

b is an integer from 0 to 4.

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 layer of the organic material layer includes the compound represented by Formula 1 above. do.

The compound represented by Chemical Formula 1 described above may be used as a material for an organic layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device. In particular, the compound represented by the above formula (1) may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.

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

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

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" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more, or substituted or unsubstituted, two or more of the above-exemplified substituents are linked. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but 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, in the ester group, oxygen of the ester group may be substituted with a linear, 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 the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 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 specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a 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, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a 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, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. 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 are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. 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 an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. 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 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 carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a 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 be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

etc. can be However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl 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 and a jolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the 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 above-described alkyl group. In the present specification, the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied, except that arylene is a divalent group. In the present specification, the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

(compound)

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

Preferably, Chemical Formula 1 may be represented by any one selected from the group consisting of Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

L ₁ , L ₂ , L ₃ , Ar ₁ , Ar ₂ , A, R ₁ , R ₂ , p, a, b are as defined in claim 1.

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

Preferably, it is L ₃ direct bond, or phenylene.

Preferably, Ar ₁ and Ar ₂ are each independently phenyl, phenyl substituted with tert-butyl, phenyl substituted with adamantyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenylcarbazolyl.

Preferably, each A is independently phenyl, phenyl substituted with tert-butyl, phenyl substituted with carbazol-9-yl, biphenylyl, naphthyl, dibenzofuranyl, or dibenzotheophenyl.

Preferably, R ₁ is hydrogen or phenyl.

Preferably, R ₂ is hydrogen or phenyl.

Preferably, p is 1 or 2.

Preferably, a and b are each 0 or 1.

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

In addition, the present invention provides a method for preparing a compound represented by Formula 1 as shown in Scheme 1 below.

[Scheme 1]

In Scheme 1, L ₁ to L ₃ , Ar ₁ , Ar ₂ , A, R ₁ , R ₂ , a, b, p are as defined above, X is halogen, preferably bromo, or chloro am.

The reaction, as an amine substitution reaction, is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art. The manufacturing method may be more specific 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 Formula 1 above. In one example, the present invention provides 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 layer of the organic material layer includes the compound represented by Formula 1 above. 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, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 It may include the indicated compound.

The organic material layer may include an electron blocking layer, and an electron blocking layer between the anode and the light emitting layer. Preferably, the electron blocking layer is included in contact with the anode side of the light emitting layer. The electron suppression layer serves to improve the efficiency of the organic light emitting device by suppressing electrons injected from the cathode from being transferred to the anode without recombination in the light emitting layer. The electron blocking layer may include a compound represented by Formula 1 above.

In addition, the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.

In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Formula 1 above.

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 further comprises a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode in addition to the light emitting layer as an organic layer can have a structure that However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.

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

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a hole transport layer 3 , a light emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 . In such a structure, the compound represented by Formula 1 may be included in the hole transport layer.

2 is a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light emitting layer (4), a hole blocking layer (9), an electron injection and transport layer ( 5) and an example of an organic light-emitting device including a cathode 6 are shown. In such a structure, the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron suppression layer.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, 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 diode 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 PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode And, after forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this 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 Formula 1 may be formed into 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode 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.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides 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 anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and 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 the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. A material capable of transporting holes from the anode or hole injection layer to the light emitting layer as a hole transport material. A material with high hole mobility. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron suppression layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, adjusts hole mobility, prevents excessive movement of electrons, and increases the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device It means a layer that plays a role in improving The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Formula 1 or an arylamine-based organic material may be used, but is not limited thereto.

The light emitting material is a material capable of emitting light in the visible ray 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 for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to control electron mobility and prevent excessive movement of holes to increase the hole-electron coupling probability, thereby improving the efficiency of the organic light emitting device layer that plays a role. The hole blocking layer includes a hole blocking material. Examples of the hole blocking material include an electron withdrawing group such as an azine derivative including triazine, a triazole derivative, an oxadiazole derivative, a phenanthroline derivative, and a phosphine oxide derivative. compounds may be used, but the present invention is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. Do. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, 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-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs both the role of the electron injection layer and the electron transport layer, and the materials serving the respective layers may be used alone or in combination, but limited thereto. doesn't happen

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

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

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

[Example]

Example 1: Synthesis of compound 1

Step 1) Synthesis of compound 1-A

After dissolving 2,2'-dibromo-1,1'-biphenyl (50.00 g, 160.25 mmol) in tetrahydrofuran (THF) (300 ml), the temperature was lowered to -78°C. 1.6 M n-butyllithium (100 ml) was slowly added to the solution and stirred for 10 minutes. (4-chlorophenyl)(phenyl)methanone (34.72 g, 160.25 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) in the solution, and then slowly added. After completion of the reaction, 1 N hydrochloric acid (400 ml) was added to separate the layers. After removal of the solvent, acetic acid (800 ml) was added, refluxed, stirred, and sulfuric acid (cat.) was added dropwise. After completion of the reaction and filtration, the layers were separated with chloroform and an aqueous solution of sodium hydrogen carbonate (NaHCO 3 ). After removal of the solvent, it was recrystallized from ethyl acetate to obtain compound 1-A (52.0 g, 75.16 % yield).

Step 2) Synthesis of compound 1-B

Tetrahydrofuran (THF) (240 ml) was added to Compound 1-A (50.00 g, 115.81 mmol) and phenylboronic acid (14.83 g, 121.60 mmol) obtained in Step 1 of Synthesis Example 1, followed by heating and stirring. . To the solution was added potassium carbonate (48.02 g, 347.43 mmol) aqueous solution (120 ml), followed by heating and stirring for 5 minutes. [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.68 g, 0.93 mmol) was slowly added dropwise to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with chloroform and water. After removal of the solvent, it was recrystallized from ethyl acetate to obtain compound 1-B (38.0 g, 76.49 % yield).

Step 3) Synthesis of compound 1

Compound 1-B (20.00 g, 46.62 mmol), 4-(phenanthren-9-yl) -N -phenylaniline (16.43 g, 47.56 mmol) obtained in step 2 of Synthesis Example 1, and sodium tert-butoxide (6.27 g, 65.27 mmol) was added with xylene (200 ml), followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.12 g, 0.23 mmol) dissolved in xylene (20ml) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, it was recrystallized from ethyl acetate to obtain Compound 1 (27.0 g, 78.48 % yield).

MS: [M+H] ⁺ = 738

Example 2: Synthesis of compound 2

Using compound 1-B (20.0 g, 46.62 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.29 g, 47.56 mmol) obtained in step 2 of Example 1 above Compound 2 (26.0 g, 78.12 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 714

Example 3: Synthesis of compound 3

Compound 1-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 1 and N -([1,1'-biphenyl]-4-yl) -9,9 -dimethyl-9H-flu Compound 3 (27.5 g, 78.23 % yield) was obtained in the same manner as in step 3 of Example 1 using oren-2-amine (17.19 g, 47.56 mmol).

MS: [M+H] ⁺ = 754

Example 4: Synthesis of compound 4

Compound 1-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 1 and N -([1,1'-biphenyl]-4-yl)dibenzo[ b , d ]furan-4- Compound 4 (27.0 g, 79.56 % yield) was obtained in the same manner as in step 3 of Example 1 using an amine (15.95 g, 47.56 mmol).

MS: [M+H] ⁺ = 728

Example 5: Synthesis of compound 5

Compound 1-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 1 and N- (4-(naphthalen-1-yl)phenyl)naphthalen-1-amine (16.43 g, 47.56 mmol) were used. to obtain the compound 5 (27.0 g, 78.48 % yield) in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 738

Example 6: Synthesis of compound 6

Using Compound 1-B (20.0 g, 46.62 mmol) obtained in Step 2 of Example 1 and bis(4-(naphthalen-1-yl)phenyl)-amine (19.65 g, 47.56 mmol) Compound 6 (30.2 g, 79.58 % yield) was obtained in the same manner as in Step 3 of 1.

MS: [M+H] ⁺ = 814

Example 7. Synthesis of compound 7

Compound 1-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 1 and bis(9,9-dimethyl-9H-fluoren-2-yl)amine (19.10 g, 47.56 mmol) were used. to obtain the compound 7 (28.5 g, 76.99 % yield) in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 794

Example 8: Synthesis of compound 8

Step 1) Synthesis of compound 8-A

Example 1 using Compound 1-A (50.00 g, 115.81 mmol) and [1,1'-biphenyl]-4-ylboronic acid (24.08 g, 121.60 mmol) obtained in Step 1 of Example 1 Compound 8-A (45.0 g, 76.93 % yield) was obtained in the same manner as in step 2.

Step 2) Synthesis of compound 8

Using compound 8-A (20.0 g, 39.60 mmol) obtained in step 1 of Example 8 and di([1,1'-biphenyl]-4-yl)amine (12.98 g, 40.39 mmol) Compound 8 (25.0 g, 79.91 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 790

Example 9: Synthesis of compound 9

Compound 8-A (20.0 g, 39.60 mmol) obtained in step 1 of Example 8 and N -([1,1'-biphenyl]-4-yl) -9,9 -dimethyl-9H-flu Compound 9 (25.8 g, 78.49 % yield) was obtained in the same manner as in step 3 of Example 1 using oren-2-amine (14.60 g, 40.39 mmol).

MS: [M+H] ⁺ = 830

Example 10: Synthesis of compound 10

Step 1) Synthesis of compound 10-A

In the same manner as in Step 2 of Example 1, using Compound 1-A (50.00 g, 115.81 mmol) and naphthalen-1-ylboronic acid (20.91 g, 121.60 mmol) obtained in Step 1 of Example 1 above Compound 10-A (44.0 g, 79.31 % yield) was obtained.

Step 2) Synthesis of compound 10

Using the compound 10-A (20.0 g, 41.75 mmol) obtained in step 1 of Example 10 and di([1,1'-biphenyl]-4-yl)amine (13.69 g, 42.59 mmol) The compound 10 (25.5 g, 79.95 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 764

Example 11: Synthesis of compound 11

Step 1) Synthesis of compound 11-A

In the same manner as in Step 2 of Example 1, using Compound 1-A (50.00 g, 115.81 mmol) and naphthalen-2-ylboronic acid (20.91 g, 121.60 mmol) obtained in Step 1 of Example 1 above Compound 11-A (43.0 g, 77.51 % yield) was obtained.

Step 2) Synthesis of compound 11

Using compound 11-A (20.0 g, 41.75 mmol) obtained in step 1 of Example 11 and di([1,1'-biphenyl]-4-yl)amine (13.69 g, 42.59 mmol) Compound 11 (26.0 g, 81.51 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 764

Example 12: Synthesis of compound 12

Step 1) Synthesis of compound 12-A

Compound 1-A (50.00 g, 115.81 mmol) obtained in Step 1 of Example 1 and dibenzo[ b , d ]furan-4-ylboronic acid (25.78 g, 121.60 mmol) of Example 1 Compound 12-A (47.0 g, 78.19 % yield) was obtained in the same manner as in step 2.

Step 2) Synthesis of compound 12

Using the compound 12-A (20.0 g, 38.52 mmol) obtained in step 1 of Example 12 and di([1,1'-biphenyl]-4-yl)amine (12.63 g, 39.30 mmol) Compound 12 (24.5 g, 79.11 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 804

Example 13: Synthesis of compound 13

Compound 12-A (20.0 g, 38.52 mmol) obtained in step 1 of Example 12 and N -([1,1'-biphenyl]-4-yl) -9,9 -dimethyl-9H-flu Compound 13 (25.0 g, 76.89 % yield) was obtained in the same manner as in step 3 of Example 1 using oren-2-amine (14.21 g, 39.30 mmol).

MS: [M+H] ⁺ = 844

Example 14. Synthesis of compound 14

Step 1) Synthesis of compound 14-A

2,2'-dibromo-1,1'-biphenyl (50.00 g, 160.25 mmol) and (3-chlorophenyl) (phenyl) methanone (34.72 g, 160.25 mmol) of Example 1 Compound 14-A (55.0 g, 79.49 % yield) was obtained in the same manner as in step 1.

Step 2) Synthesis of compound 14-B

Compound 14-A (50.00 g, 115.81 mmol) and phenylboronic acid (14.83 g, 121.60 mmol) obtained in Step 1 of Example 14 were used in the same manner as in Step 2 of Example 1 above. B (39.0 g, 78.51 % yield) was obtained.

Step 3) Synthesis of compound 14

Using the compound 14-B (20.00 g, 46.62 mmol) and 4-(phenanthren-9-yl) -N -phenylaniline (16.43 g, 47.56 mmol) obtained in step 2 of Example 14 above Compound 14 (28.0 g, 81.39 % yield) was obtained in the same manner as in Step 3 of 1.

MS: [M+H] ⁺ = 738

Example 15: Synthesis of compound 15

Using compound 14-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 14 and di([1,1'-biphenyl]-4-yl)amine (15.29 g, 47.56 mmol) Compound 15 (26.5 g, 79.62 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 714

Example 16: Synthesis of compound 16

Compound 14-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 14 and N -([1,1'-biphenyl]-4-yl) -9,9 -dimethyl-9H-flu Compound 16 (27.0 g, 76.81 % yield) was obtained in the same manner as in Step 3 of Example 1 using oren-2-amine (17.19 g, 47.56 mmol).

MS: [M+H] ⁺ = 754

Example 17: Synthesis of compound 17

Compound 14-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 14 and N -([1,1'-biphenyl]-4-yl)dibenzo[ b , d ]furan-4- Compound 17 (26.8 g, 78.97 % yield) was obtained in the same manner as in step 3 of Example 1 using an amine (15.95 g, 47.56 mmol).

MS: [M+H] ⁺ = 728

Example 18. Synthesis of compound 18

Compound 14-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 14 and N- (4-(naphthalen-1-yl)phenyl)naphthalen-1-amine (16.43 g, 47.56 mmol) were used. to obtain the compound 18 (27.5 g, 79.93 % yield) in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 738

Example 19: Synthesis of compound 19

Using the compound 14-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 14 and bis(4-(naphthalen-1-yl)phenyl)-amine (19.65 g, 47.56 mmol) Compound 19 (31.0 g, 81.69 % yield) was obtained in the same manner as in Step 3 of 1.

MS: [M+H] ⁺ = 814

Example 20: Synthesis of compound 20

Compound 14-B (20.0 g, 46.62 mmol) obtained in step 2 of Example 14 and bis(9,9-dimethyl-9H-fluoren-2-yl)amine (19.10 g, 47.56 mmol) were used. to obtain the compound 20 (29.0 g, 78.34 % yield) in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 794

Example 21. Synthesis of compound 21

Step 1) Synthesis of compound 21-A

Example 1 using compound 14-A (50.00 g, 115.81 mmol) and [1,1'-biphenyl]-4-ylboronic acid (24.08 g, 121.60 mmol) obtained in step 1 of Example 14 above Compound 21-A (46.0 g, 78.64 % yield) was obtained in the same manner as in step 2.

Step 2) Synthesis of compound 21

Using the compound 21-A (20.0 g, 39.60 mmol) obtained in step 1 of Example 21 and di([1,1'-biphenyl]-4-yl)amine (12.98 g, 40.39 mmol) Compound 21 (25.0 g, 79.91 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 790

Example 22: Synthesis of compound 22

Compound 21-A (20.0 g, 39.60 mmol) obtained in step 1 of Example 21 and N -([1,1'-biphenyl]-4-yl) -9,9 -dimethyl-9H-flu Compound 22 (26.0 g, 79.10 % yield) was obtained in the same manner as in step 3 of Example 1 using oren-2-amine (14.60 g, 40.39 mmol).

MS: [M+H] ⁺ = 830

Example 23: Synthesis of compound 23

Step 1) Synthesis of compound 23-A

Using the compound 14-A (50.00 g, 115.81 mmol) and naphthalen-1-ylboronic acid (20.91 g, 121.60 mmol) obtained in step 1 of Example 14, in the same manner as in step 2 of Example 1, Compound 23-A (42.5 g, 76.61 % yield) was obtained.

Step 2) Synthesis of compound 23

Using the compound 23-A (20.0 g, 41.75 mmol) obtained in step 1 of Example 23 and di([1,1'-biphenyl]-4-yl)amine (13.69 g, 42.59 mmol) Compound 23 (26.0 g, 81.51 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 764

Example 24: Synthesis of compound 24

Step 1) Synthesis of compound 24-A

In the same manner as in Step 2 of Example 1, using Compound 14-A (50.00 g, 115.81 mmol) and naphthalen-2-ylboronic acid (20.91 g, 121.60 mmol) obtained in Step 1 of Example 14 above Compound 24-A (44.0 g, 79.31 % yield) was obtained.

Step 2) Synthesis of compound 24

Using compound 24-A (20.0 g, 41.75 mmol) and di([1,1'-biphenyl]-4-yl)amine (13.69 g, 42.59 mmol) obtained in step 1 of Example 24 above Compound 24 (25.0 g, 78.38 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 764

Example 25: Synthesis of compound 25

Step 1) Synthesis of compound 25-A

Compound 14-A (50.00 g, 115.81 mmol) obtained in step 1 of Example 14 and dibenzo[ b , d ]furan-4-ylboronic acid (25.78 g, 121.60 mmol) of Example 1 Compound 25-A (48.0 g, 79.85 % yield) was obtained in the same manner as in step 2.

Step 2) Synthesis of compound 25

Using the compound 25-A (20.0 g, 38.52 mmol) obtained in step 1 of Example 25 and di([1,1'-biphenyl]-4-yl)amine (12.63 g, 39.30 mmol) Compound 25 (25.0 g, 80.72 % yield) was obtained in the same manner as in step 3 of Example 1.

MS: [M+H] ⁺ = 804

Example 26: Synthesis of compound 26

Compound 25-A (20.0 g, 38.52 mmol) obtained in step 1 of Example 25 and N -([1,1'-biphenyl]-4-yl) -9,9 -dimethyl-9H-flu Compound 26 (26.0 g, 79.97 % yield) was obtained in the same manner as in step 3 of Example 1 using oren-2-amine (14.21 g, 39.30 mmol).

MS: [M+H] ⁺ = 844

Example 27: Synthesis of compound 27

Compound 1-B (20.00 g, 46.62 mmol) and (4-(diphenylamino)phenyl)boronic acid (14.16 g, 48.96 mmol) obtained in step 2 of Example 1 above 1-4-dioxane (100) ml) was added, followed by heating and stirring. To the solution was added potassium carbonate (19.33 g, 139.86 mmol) aqueous solution (50 ml), followed by heating and stirring for 5 minutes. Bis(tri-tert-butylphosphine)palladium (0.07 g, 0.14 mmol) was slowly added dropwise to the solution, followed by heating and stirring for 5 hours. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, it was recrystallized from ethyl acetate to obtain compound 27 (22.0 g, 73.99 % yield).

MS: [M+H] ⁺ = 638

Example 28: Compound 28 synthesis of

Compound 1-B (20.00 g, 46.62 mmol) obtained in step 2 of Example 1 and (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (21.61 g, 48.96 mmol) was used to obtain Compound 28 (28.5 g, 77.38 % yield) in the same manner as in Example 27.

MS: [M+H] ⁺ = 790

Example 29: Compound 29 synthesis of

Compound 14-B (20.00 g, 46.62 mmol) obtained in step 2 of Example 14 and (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (21.61 g, 48.96 mmol) was used to obtain Compound 29 (29.0 g, 78.74 % yield) in the same manner as in Example 27.

MS: [M+H] ⁺ = 790

Example 30: Synthesis of compound 30

Compound 14-B (20.00 g, 46.62 mmol) obtained in step 2 of Example 14 and (4-([1,1'-biphenyl]-4-yl( 9,9 -dimethyl-9H-flu) Compound 30 (30.0 g, 77.52 % yield) was obtained in the same manner as in Example 27 using oren-2-yl)amino)phenyl)boronic acid (23.57 g, 48.96 mmol).

MS: [M+H] ⁺ = 830

Example 31: Synthesis of compound 31

Step 1) Synthesis of compound 31-A

2,2'-dibromo-1,1'-biphenyl (50.00 g, 160.25 mmol) and (2-chlorophenyl) (phenyl) methanone (34.72 g, 160.25 mmol) of Example 1 Compound 31-A (52.0 g, 75.16 % yield) was obtained in the same manner as in step 1.

Step 2) Synthesis of compound 31-B

Compound 31-A (50.00 g, 115.81 mmol) and phenylboronic acid (14.83 g, 121.60 mmol) obtained in Step 1 of Example 31 were used in the same manner as in Step 2 of Example 1 above. B (38.0 g, 76.49 % yield) was obtained.

Step 3) Synthesis of compound 31

Compound 31-B (20.00 g, 46.62 mmol) obtained in step 2 of Example 31 and (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (21.61 g, 48.96 mmol) was used to obtain compound 31 (28.0 g, 76.02 % yield) in the same manner as in Example 27.

MS: [M+H] ⁺ = 790

Example 32: Compound 32 synthesis of

Compound 31-B (20.00 g, 46.62 mmol) obtained in step 2 of Example 31 and (4-(bis(9,9-dimethyl-9H- fluoren -2-yl)amino)phenyl)boronic acid Compound 32 (31.0 g, 76.42 % yield) was obtained in the same manner as in Example 27 using (25.53 g, 48.96 mmol).

MS: [M+H] ⁺ = 870

[Experimental example]

Experimental Example 1-1

A glass substrate coated with ITO (Indium Tin Oxide) to a thickness of 1,400 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of a compound represented by the following formula HAT on the prepared ITO transparent electrode to a thickness of 100 Å. After vacuum deposition of the compound represented by the following formula HT1 as a hole transport layer to a thickness of 1150 Å, the compound 1 prepared in Example 1 was thermally vacuum deposited to a thickness of 150 Å as an electron suppression layer. Then, as a light emitting layer, the compound represented by the following formula BH and the compound represented by the following formula BD were vacuum-deposited to a thickness of 200 Å in a weight ratio of 25:1. Then, as a hole blocking layer, a compound represented by the following Chemical Formula HB1 was vacuum-deposited to a thickness of 50 Å. Then, as a layer that simultaneously transports electrons and injects electrons, a compound represented by the following formula ET1 and a compound represented by the following LiQ were thermally vacuum deposited to a thickness of 310 Å in a weight ratio of 1:1. An organic light-emitting device was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron transport and electron injection layers to form a cathode.

Experimental Examples 1-2 to 1-26

Organic light emitting devices of Experimental Examples 1-2 to 1-26 were prepared in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.

Comparative Experimental Examples 1-1 to 1-4

Organic light emitting devices of Comparative Experimental Examples 1-1 to 1-4 were prepared in the same manner as in Experimental Example 1-1 except that the following compounds EB1, EB2, EB3, and EB4 were used instead of Compound 1.

When a current of 10 mA/cm ² was applied to the organic light emitting diodes prepared in Experimental Examples 1-1 to 1-26 and Comparative Experimental Examples 1-1 to 1-4, voltage, efficiency, color coordinates, and lifetime were measured and the The results are shown in Table 1 below. On the other hand, T95 means the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.

electron suppression layer Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) color coordinates (x, y) T95
(hr@10mA/cm ² ) Experimental Example 1-1 compound 1 3.69 6.08 0.140, 0.043 210 Experimental Example 1-2 compound 2 3.63 6.10 0.140, 0.043 220 Experimental Example 1-3 compound 3 3.60 5.95 0.141, 0.044 195 Experimental Example 1-4 compound 4 3.68 6.01 0.140, 0.044 215 Experimental Example 1-5 compound 5 3.69 6.03 0.141, 0.043 215 Experimental Example 1-6 compound 6 3.63 6.08 0.141, 0.043 215 Experimental Example 1-7 compound 8 3.70 6.01 0.140, 0.043 210 Experimental Example 1-8 compound 9 3.61 5.94 0.141, 0.044 195 Experimental Example 1-9 compound 10 3.69 6.00 0.140, 0.044 210 Experimental Example 1-10 compound 11 3.68 6.00 0.140, 0.044 205 Experimental Example 1-11 compound 12 3.69 6.05 0.140, 0.043 210 Experimental Example 1-12 compound 13 3.64 5.94 0.141, 0.044 190 Experimental Example 1-13 compound 14 3.68 6.09 0.140, 0.043 210 Experimental Example 1-14 compound 15 3.61 6.13 0.140, 0.043 225 Experimental Example 1-15 compound 16 3.60 5.91 0.141, 0.044 205 Experimental Example 1-16 compound 17 3.68 6.01 0.141, 0.044 205 Experimental Example 1-17 compound 18 3.67 6.02 0.140, 0.044 210 Experimental Example 1-18 compound 19 3.63 6.05 0.140, 0.044 215 Experimental Example 1-19 compound 21 3.69 6.00 0.141, 0.043 215 Experimental Example 1-20 compound 23 3.70 6.03 0.141, 0.043 210 Experimental Example 1-21 compound 24 3.68 6.00 0.140, 0.043 200 Experimental Example 1-22 compound 25 3.64 6.09 0.140, 0.044 215 Experimental Example 1-23 compound 27 3.69 6.03 0.141, 0.043 205 Experimental Example 1-24 compound 28 3.63 5.95 0.140, 0.044 205 Experimental Example 1-25 compound 29 3.63 6.07 0.140, 0.043 210 Experimental Example 1-26 compound 31 3.64 5.96 0.140, 0.044 195 Comparative Experimental Example 1-1 EB1 3.93 5.11 0.144, 0.048 150 Comparative Experimental Example 1-2 EB2 3.98 5.16 0.145, 0.048 115 Comparative Experimental Example 1-3 EB3 3.90 4.95 0.144, 0.048 105 Comparative Experimental Example 1-4 EB4 4.12 4.86 0.145, 0.049 70

As shown in Table 1, the compound of the present invention has excellent electron suppression ability, and it was confirmed that the organic light emitting device using the same as the electron suppression layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.

Experimental Examples 2-1 to 2-19 and Comparative Experimental Examples 2-1 to 2-4

Experiment in the same manner as in Experimental Example 1-1, except that the compound represented by Formula EB1 was used instead of Compound 1, and the compound shown in Table 2 was used instead of the compound represented by Formula HT1 as the hole transport layer. Organic light emitting devices of Examples 2-1 to 2-19 and Comparative Experimental Examples 2-1 to 2-4 were prepared.

When a current of 10 mA/cm ² was applied to the organic light emitting diodes prepared in Experimental Examples and Comparative Experimental Examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in Table 2 below. Meanwhile, T95 denotes a time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

hole transport layer Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) color coordinates (x, y) T95
(hr@10mA/cm ² ) Experimental Example 2-1 compound 2 3.67 6.05 0.141, 0.044 200 Experimental Example 2-2 compound 3 3.58 6.08 0.141, 0.043 205 Experimental Example 2-3 compound 4 3.70 6.00 0.141, 0.044 195 Experimental Example 2-4 compound 7 3.57 6.10 0.140, 0.043 215 Experimental Example 2-5 compound 8 3.64 5.96 0.140, 0.044 195 Experimental Example 2-6 compound 9 3.59 6.05 0.140, 0.044 205 Experimental Example 2-7 compound 13 3.60 6.06 0.140, 0.044 200 Experimental Example 2-8 compound 15 3.67 6.00 0.140, 0.044 200 Experimental Example 2-9 compound 16 3.59 6.05 0.140, 0.043 210 Experimental Example 2-10 compound 17 3.68 5.99 0.141, 0.044 205 Experimental Example 2-11 compound 20 3.55 6.12 0.140, 0.043 220 Experimental Example 2-12 compound 21 3.69 6.02 0.141, 0.044 190 Experimental Example 2-13 compound 22 3.59 6.08 0.140, 0.044 205 Experimental Example 2-14 compound 26 3.59 6.04 0.141, 0.043 210 Experimental Example 2-15 compound 28 3.67 6.00 0.141, 0.043 200 Experimental Example 2-16 compound 29 3.59 6.01 0.141, 0.044 195 Experimental Example 2-17 compound 30 3.60 6.05 0.141, 0.043 205 Experimental Example 2-18 compound 31 3.67 6.00 0.141, 0.044 200 Experimental Example 2-19 compound 32 3.66 5.98 0.140, 0.044 200 Comparative Experimental Example 1-1 HT1 3.93 5.11 0.144, 0.048 150 Comparative Experimental Example 2-1 HT2 3.89 5.05 0.145, 0.048 160 Comparative Experimental Example 2-2 HT3 4.05 4.85 0.145, 0.049 125 Comparative Experimental Example 2-3 HT4 3.98 4.96 0.144, 0.048 130 Comparative Experimental Example 2-4 HT5 4.10 4.75 0.144, 0.049 80

As shown in Table 2, the compound of the present invention has excellent hole transport ability, and it was confirmed that the organic light emitting device using the same as the hole transport layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

1: Substrate 2: Anode
3: hole transport layer 4: light emitting layer
5: Electron injection and transport layer 6: Cathode
7: hole injection layer 8: electron suppression layer
9: hole blocking layer

Claims (13)

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

In Formula 1,
L ₁ and L ₂ are each independently a direct bond; substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,
L ₃ is a direct bond; Or a substituted or unsubstituted C _6-60 arylene,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl; or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
A is each independently substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
R ₁ are each independently hydrogen; heavy hydrogen; halogen; nitrile; silyl; substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
R ₂ are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C _6-60 aryl,
p is an integer from 1 to 4,
a is an integer of 0 to 3, provided that a+p is 1 to 4,
b is an integer from 0 to 4.
According to claim 1,
Formula 1 is represented by any one selected from the group consisting of the following Formulas 1-1 to 1-3,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-5,
L ₁ , L ₂ , L ₃ , Ar ₁ , Ar ₂ , A, R ₁ , R ₂ , p, a, b are as defined in claim 1.
According to claim 1,
L ₁ and L ₂ are each independently a direct bond, phenylene, or biphenylylene;
compound.
According to claim 1,
L ₃ is a direct bond, or phenylene,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, phenyl substituted with tert-butyl, phenyl substituted with adamantyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl , diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenylcarbazolyl;
compound.
According to claim 1,
A is each independently phenyl, phenyl substituted with tert-butyl, phenyl substituted with carbazol-9-yl, biphenylyl, naphthyl, dibenzofuranyl, or dibenzotheophenyl;
compound.
According to claim 1,
R ₁ is hydrogen or phenyl;
compound.
According to claim 1,
R ₂ is hydrogen or phenyl
compound.
According to claim 1,
p is 1 or 2;
compound.
According to claim 1,
a and b are each 0 or 1;
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following compounds,
compound:

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 organic material layer includes the compound according to any one of claims 1 to 11 which is an organic light emitting device.
13. The method of claim 12,
The organic layer is an electron suppression layer, or a hole transport layer,
organic light emitting device.

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