KR20210096954A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light-emitting device using the same. The present invention can be used as a material for hole injection, hole transport, hole injection and transport, luminescence, electron transport, or electron injection.

Description

Novel compound and organic light emitting device using the same

The present invention relates to a novel compound and an organic light emitting device comprising 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 formed of a multi-layered 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, an electron injection layer, and the like. 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,

R ₁ is C _6-60 aryl,

any one of the hydrogens of R ₁ is substituted with _{C 3-20 alkyl;} the rest are each independently hydrogen or deuterium,

R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; nitrile; silyl; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _6-60 aryl; substituted or unsubstituted C _2-60 alkenyl; _{It is C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _6-60 aryl; substituted or unsubstituted C _2-60 alkenyl; _{C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted adamantyl,

L, L ₁ , and L ₂ are each independently, a direct bond; substituted or unsubstituted C _1-60 alkylene; substituted or unsubstituted C _6-60 arylene; substituted or unsubstituted C _1-60 alkoxyylene; substituted or unsubstituted C _2-60 alkenylene; _{Or substituted or unsubstituted C 2-60} heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,

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

The compound represented by Chemical Formula 1 described above may be used as a material for the organic material layer of the 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 Formula 1 described above 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.

(Definition of Terms)

및

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

and

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; 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 heteroaryl containing one or more, or substituted or unsubstituted with two or more substituents of the above-exemplified substituents connected . 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 or 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, the 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 this specification; Examples of halogen groups are 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 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 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 having aromaticity. 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 phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and the like, but is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing 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 heteroaryl 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, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl 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, thiadiazolyl group group, phenothiazinyl group, and dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the above-described aryl group. 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, as for heteroaryl among heteroarylamines, the description regarding heteroaryl described above 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 heteroaryl described above 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 heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.

(compound)

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

The compound represented by Formula 1 has a structure in which an amine-based substituent is bonded to the 2-position of the dimethylfluorene core, and an aryl (R ₁ ) is bonded to the 7-position.

In particular, in the aryl (R ₁ ) bonded to the 7th position of the core, any one of the hydrogens is alkyl-substituted; The rest are each independently hydrogen or deuterium.

The organic light emitting device comprising a compound of the formula (1) as a component of the organic layer, with a binding site of an amine-based substituent and aryl (R ₁₎ for said core, to which the aryl group (R ₁₎ alkyl substituted As a synergistic effect by the

Hereinafter, Chemical Formula 1 and the compound represented by the Chemical Formula 1 will be described in detail as follows.

R ₁ may be C _3-20 aryl, specifically phenyl or biphenyl. In this case, any one of the hydrogens of _{R 1 is substituted with C 3-20} alkyl, specifically C _3-10 alkyl, more specifically C _3-5 alkyl; The rest may each independently be hydrogen or deuterium.

For example, R ₁ may be a substituent represented by the following Chemical Formula 2:

[Formula 2]

In Formula 2,

any one of X _{1 is C 3-20} branched chain alkyl, specifically C _3-10 branched chain alkyl, more specifically C _3-5 branched chain alkyl; the rest are each independently hydrogen or deuterium,

The dotted line indicates the bonding position.

In Formula 1, L, L ₁ , and L ₂ are each independently a direct bond; substituted or unsubstituted C _6-30 alkylene; substituted or unsubstituted C _6-30 arylene; substituted or unsubstituted C _6-30 alkoxyylene; substituted or unsubstituted C _6-30 alkenylene; Or it may be _{a C 2-30} heteroarylene including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

Specifically, L, L ₁ , and L ₂ are each independently a direct bond; phenylene; biphenylene; naphthylene; terphenylene; quaterphenylene; carbazolylene; fluorenylene; dibenzofuranylene; dibenzothiophenylene. In this case, the L, L ₁ , and L ₂ are each independently, unsubstituted, one or more deuterium; substituted or unsubstituted C _1-18 alkyl; substituted or unsubstituted C _6-18 aryl; Or it may be one substituted with _{C 2-18} heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

For example, L, L ₁ , and L ₂ are each independently a direct bond; Or it may be any one selected from the group consisting of the following formulas:

In each of the above formulas,

R ₁₀ is the same or different and is hydrogen; heavy hydrogen; substituted or unsubstituted C _1-18 alkyl; substituted or unsubstituted C _6-18 aryl; _{or C 2-18} heteroaryl containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S,

The dotted line indicates the bonding position.

m may be an integer of 0 to 3, n may be an integer of 0 to 3, and specifically, both m and n may be 0.

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _1-30 alkyl; substituted or unsubstituted C _6-30 aryl; substituted or unsubstituted C _1-30 alkenyl; _{C 2-30} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or it may be a substituted or unsubstituted adamantyl.

Specifically, Ar ₁ and Ar ₂ are each independently, phenyl; biphenyl; naphthyl; terphenyl; quarterphenyl; anthracenyl; fluoranthenyl; fluorenyl; carbazolyl; dibenzofuranyl; dibenzothiophenyl; or adamantyl. In this case, Ar ₁ and Ar ₂ are each independently, unsubstituted, one or more deuterium; substituted or unsubstituted C _1-18 alkyl; substituted or unsubstituted C _6-18 aryl; _{C 2-18} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or it may be substituted with adamantyl.

For example, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of the following formulas:

In each of the above formulas,

R ₁₂ is the same or different and is hydrogen; heavy hydrogen; substituted or unsubstituted C _1-18 alkyl;

The dotted line indicates the bonding position.

For example, the compound represented by Formula 1 may be any one selected from the group consisting of the following compounds:

.

.

Meanwhile, the compound represented by Formula 1 may be prepared by, for example, a preparation method as shown in Scheme 1 below. This may be used when preparing a compound in which L ₁ and L ₂ are the same and Ar1 and Ar2 have the same structure.

[Scheme 1]

The compound represented by Formula 1 may be prepared by a series of preparation methods according to the following Reaction Schemes 2-1 and 2-2. This may be used when preparing a compound in which L ₁ and L ₂ are different and Ar ₁ and Ar _{2 have different structures.}

[Scheme 2-1]

[Scheme 2-2]

However, the above reaction schemes are examples, and the method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.

(organic light emitting element)

Meanwhile, the present invention provides an organic light emitting device including 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 of the organic material layers includes 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 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, 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 injects and transports holes at the same time, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 The compounds shown are included.

In addition, the organic material layer may include a light emitting layer, the light emitting layer includes 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, in addition to the light emitting layer as an organic material layer, 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. 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.

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

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a 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 comprising 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 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 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 material 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, spraying, 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 preferable to facilitate hole injection 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 with respect to 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, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. material is suitable. As the hole transport material, the compound represented by Formula 1 may be used, or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used, but the present invention is not limited thereto. .

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 probability of hole-electron coupling by increasing the efficiency of the organic light emitting device 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 may be used, 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 receiving 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 light emitting layer may include a host material and a dopant material as described above. The host material may further include 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 type 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, and periflanthene having an arylamino group, and the styrylamine compound is a substituted or unsubstituted derivative. 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, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by controlling electron mobility and preventing excessive movement of holes to increase the hole-electron coupling probability layer that plays a role. The hole-blocking layer includes a hole-blocking material, and examples of the hole-blocking material include: azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but the present invention is not limited thereto.

The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from the electrode and transporting the received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer. As the electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Examples of specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto. or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metal complex compounds , or may be used together with a nitrogen-containing 5-membered ring derivative, and the like, but is 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. The present invention is not limited thereto.

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

The 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 for illustrating the present invention, and the scope of the present invention is not limited thereto.

<Synthesis example>

Synthesis Example 1: Synthesis of Compound 1

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol), bromobenzene (14.14 g, 90.04 mmol) and sodium tert- Toluene (200 ml) was added to butoxide (11.82 g, 122.98 mmol), followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.18 g, 0.35 mmol) dissolved in toluene (20 ml) 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 with ethyl acetate to obtain Compound 1 (16.0 g, 73.79 % yield). (MS[M+H]+ = 494)

Synthesis Example 2: Synthesis of compound 2

Step 1) Synthesis of compound 2-A

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (50.0 g, 146.41 mmol), bromobenzene (22.99 g, 146.41 mmol) and sodium tert- Toluene (400 ml) was added to butoxide (19.70 g, 204.97 mmol), followed by heating and stirring for 10 minutes. 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.54 g, 0.73 mmol) dissolved in toluene (30 ml) 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 chloroform and water. After removal of the solvent, it was recrystallized with ethyl acetate to obtain the compound 2-A (45.0 g, 73.60 % yield).

Step 2) Synthesis of compound 2

Compound 2-A (20.0 g, 47.89 mmol), 4-bromo-1,1'-biphenyl (11.39 g, 48.85 mmol) obtained in step 1 of Synthesis Example 2, and sodium tert-butoxide (6.44 g) , 67.05 mmol) was added to toluene (200 ml), followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.12 g, 0.24 mmol) dissolved in toluene (20 ml) 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 2 (21.0 g, 76.96 % yield). (MS[M+H]+ = 570)

Synthesis Example 3: Synthesis of compound 3

Compound 2-A (20.0 g, 47.89 mmol) obtained in step 1 of Synthesis Example 2 and 4-bromo-1,1':4',1''-terphenyl (15.11 g, 48.85 mmol) were used. to obtain the compound 3 (24.5 g, 79.21 % yield) in the same manner as in step 2 of Synthesis Example 2. (MS[M+H]+ = 646)

Synthesis Example 4: Synthesis of compound 4

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 4-bromo-1,1'-biphenyl (10.44 g, 90.04 mmol) was used to obtain Compound 4 (23.0 g, 81.09 % yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 646)

Synthesis Example 5: Synthesis of compound 5

Step 1) Synthesis of compound 5-A

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (50.0 g, 146.41 mmol) and 4-bromo-1,1'-biphenyl (34.13 g, 146.41 mmol) was used to obtain Compound 5-A (57.0 g, 78.86 % yield) in the same manner as in Step 1 of Synthesis Example 2.

Step 2) Synthesis of compound 5

The step of Synthesis Example 2 using compound 5-A (20.0 g, 40.51 mmol) and 2-bromo-1,1'-biphenyl (9.63 g, 41.32 mmol) obtained in Step 1 of Synthesis Example 5 Compound 5 (19.5 g, 74.53 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 646)

Synthesis Example 6: Synthesis of compound 6

The compound 5-A (20.0 g, 40.51 mmol) and 2-bromo-9,9-dimethyl -9 H obtained in the above Synthesis Example 51-a using the fluorene (11.29 g, 41.32 mmol) synthesized Compound 6 (21.5 g, 77.37 % yield) was obtained in the same manner as in Step 2 of Example 2. (MS[M+H]+ = 686)

Synthesis Example 7: Synthesis of compound 7

The use of fluorene (16.42 g, 41.32 mmol) - The compound 5-A (20.0 g, 40.51 mmol) and 2-bromo-9,9-diphenyl--9 H obtained in the above Synthesis Example 51 Compound 7 (26.0 g, 79.23 % yield) was obtained in the same manner as in Step 2 of Synthesis Example 2. (MS[M+H]+ = 810)

Synthesis Example 8: Synthesis of compound 8

Using compound 5-A (20.0 g, 40.51 mmol) and 4-(4-bromophenyl)dibenzo[ b,d ]furan (13.35 g, 41.32 mmol) obtained in step 1 of Synthesis Example 5 above The compound 8 (24.0 g, 80.50 % yield) was obtained in the same manner as in step 2 of Synthesis Example 2. (MS[M+H]+ = 736)

Synthesis Example 9: Synthesis of compound 9

The step of Synthesis Example 2 using Compound 5-A (20.0 g, 40.51 mmol) and 1-(4-bromophenyl)adamantene (12.03 g, 41.32 mmol) obtained in Step 1 of Synthesis Example 5 Compound 9 (22.0 g, 77.14 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 704)

Synthesis Example 10: Synthesis of compound 10

Using compound 5-A (20.0 g, 40.51 mmol) and 1-bromo-3-( tert -butyl)benzene (8.81 g, 41.32 mmol) obtained in step 1 of Synthesis Example 5, Compound 10 (19.0 g, 74.94 % yield) was obtained in the same manner as in step 2. (MS[M+H]+ = 626)

Synthesis Example 11: Synthesis of compound 11

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 1-bromo-4- (tert-butyl) benzene ( 19.19 g, 90.04 mmol) was used to obtain Compound 11 (20.0 g, 75.16 % yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 606)

Synthesis Example 12: Synthesis of compound 12

Step 1) Synthesis of compound 12-A

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (50.0 g, 146.41 mmol) and 1-bromo-4- (tert-butyl) benzene ( 31.20 g, 146.41 mmol) was used to obtain Compound 12-A (54.0 g, 77.86 % yield) in the same manner as in Step 1 of Synthesis Example 2.

Step 2) Synthesis of compound 12

The step of Synthesis Example 2 using Compound 12-A (20.0 g, 42.20 mmol) and 4-bromo-1,1'-biphenyl (10.03 g, 43.05 mmol) obtained in Step 1 of Synthesis Example 12 Compound 12 (20.8 g, 78.75 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 626)

Synthesis Example 13: Synthesis of compound 13

Compound 12-A (20.0 g, 42.20 mmol) obtained in step 1 of Synthesis Example 12 and 4-bromo-4'-( tert -butyl)-1,1'-biphenyl (12.45 g, 43.05 mmol) was used to obtain the compound 13 (22.5 g, 78.18 % yield) in the same manner as in step 2 of Synthesis Example 2. (MS[M+H]+ = 682)

Synthesis Example 14: Synthesis of compound 14

The compound 12-A (20.0 g, 42.20 mmol) and 2-bromo-9,9-dimethyl -9 H obtained in the above Synthesis Example 12 1 - the use of fluorene (11.76 g, 43.05 mmol) synthesized Compound 14 (21.5 g, 76.50 % yield) was obtained in the same manner as in Step 2 of Example 2. (MS[M+H]+ = 666)

Synthesis Example 15: Synthesis of compound 15

The use of fluorene (17.01 g, 43.05 mmol) - The compound 12-A (20.0 g, 42.20 mmol) and 2-bromo-9,9-diphenyl--9 H obtained in the above Synthesis Example 12 1 Compound 15 (26.0 g, 77.98 % yield) was obtained in the same manner as in Step 2 of Synthesis Example 2. (MS[M+H]+ = 790)

Synthesis Example 16: Synthesis of compound 16

7- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 4-bromo-4 '- (tert-butyl) Compound 16 (26.0 g, 78.09 % yield) was obtained in the same manner as in Synthesis Example 1 using 1,1'-biphenyl (26.02 g, 90.04 mmol). (MS[M+H]+ = 758)

Synthesis Example 17: Synthesis of compound 17

7- (3- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 4-bromo-1,1'-biphenyl (10.44 g, 90.04 mmol) was used to obtain Compound 17 (22.0 g, 77.55 % yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 646)

Synthesis Example 18. Synthesis of compound 18

7- (3- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 1-bromo-4- (tert-butyl) benzene ( 19.19 g, 90.04 mmol) was used to obtain Compound 18 (20.5 g, 77.03 % yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 606)

Synthesis Example 19: Synthesis of compound 19

Step 1) Synthesis of compound 19-A

7- (3- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (50.0 g, 146.41 mmol) and 1-bromo-4- (tert-butyl) benzene ( 31.20 g, 146.41 mmol) was used to obtain Compound 19-A (55.0 g, 79.30 % yield) in the same manner as in Step 1 of Synthesis Example 2.

Step 2) Synthesis of compound 19

The step of Synthesis Example 2 using Compound 19-A (20.0 g, 42.20 mmol) and 4-bromo-1,1'-biphenyl (10.03 g, 43.05 mmol) obtained in Step 1 of Synthesis Example 19 Compound 19 (20.5 g, 77.61 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 626)

Synthesis Example 20: Synthesis of compound 20

The compound 19-A (20.0 g, 42.20 mmol) and 2-bromo-9,9-dimethyl -9 H obtained in the above Synthesis Example 19 1 - the use of fluorene (11.76 g, 43.05 mmol) synthesized Compound 20 (21.3 g, 75.79 % yield) was obtained in the same manner as in Step 2 of Example 2. (MS[M+H]+ = 666)

Synthesis Example 21: Synthesis of compound 21

7- (2- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 4-bromo-1,1'-biphenyl (10.44 g, 90.04 mmol) was used to obtain Compound 21 (21.5 g, 75.79 % yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 646)

Synthesis Example 22: Synthesis of compound 22

7- (2- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 1-bromo-4- (tert-butyl) benzene ( 19.19 g, 90.04 mmol) was used to obtain Compound 22 (20.0 g, 75.16 % yield) in the same manner as in Synthesis Example 1. (MS[M+H]+ = 606)

Synthesis Example 23: Synthesis of compound 23

7- (4 '- (tert-butyl) - [1,1'-biphenyl] -4-yl) -9 H 9,9-dimethyl-fluorene-2-amine (15.0 g, 35.92 mmol) and Compound 23 (20.5 g, 79.05 % yield) was obtained in the same manner as in Synthesis Example 1 using 4-bromo-1,1'-biphenyl (17.17 g, 73.64 mmol). (MS[M+H]+ = 722)

Synthesis Example 24: Synthesis of compound 24

7- (4 '- (tert-butyl) - [1,1'-biphenyl] -4-yl) -9 H 9,9-dimethyl-fluorene-2-amine (15.0 g, 35.92 mmol) and Compound 24 (19.0 g, 77.56 % yield) was obtained in the same manner as in Synthesis Example 1 using 1-bromo-4-( tert-butyl)benzene (15.69 g, 73.64 mmol). (MS[M+H]+ = 682)

Synthesis Example 25: Synthesis of compound 25

Step 1) Synthesis of compound 25-A

7- (4 '- (tert-butyl) - [1,1'-biphenyl] -4-yl) -9 H 9,9-dimethyl-fluorene-2-amine (50.0 g, 119.73 mmol) and Compound 25-A (50.0 g, 75.96 % yield) was obtained in the same manner as in Step 1 of Synthesis Example 2 using 1-bromo-4-( tert-butyl)benzene (25.52 g, 119.73 mmol). .

Step 2) Synthesis of compound 25

The step of Synthesis Example 2 using the compound 25-A (20.0 g, 36.38 mmol) and 4-bromo-1,1'-biphenyl (8.65 g, 37.10 mmol) obtained in Step 1 of Synthesis Example 25 Compound 25 (20.0 g, 78.31 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 702)

Synthesis Example 26: Synthesis of compound 26

The compound 25-A (20.0 g, 36.38 mmol) and 2-bromo-9,9-dimethyl -9 H obtained in the above Synthesis Example 25 1 - the use of fluorene (10.13 g, 37.10 mmol) synthesized Compound 26 (21.0 g, 77.79 % yield) was obtained in the same manner as in Step 2 of Example 2. (MS[M+H]+ = 742)

<Experimental Examples and Comparative Experimental Examples>

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 ITO for 30 minutes, ultrasonic cleaning 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, dried, and then 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, the compound represented by the following formula BH and the compound represented by the following formula BD as a light emitting layer 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 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 1-22 and Comparative Experimental Examples 1-1 to 1-6

Experimental Examples 1-2 to 1-22 and Comparative Experimental Example 1-1 in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1-1. to 1-6 organic light emitting devices were manufactured. ^{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 1 below. Meanwhile, T95 denotes a time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

electron suppression layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental Example 1-1 compound 1 3.62 6.15 0.142, 0.043 275 Experimental Example 1-2 compound 2 3.60 6.18 0.140, 0.043 270 Experimental Example 1-3 compound 3 3.60 6.15 0.141, 0.044 270 Experimental Example 1-4 compound 4 3.55 6.20 0.141, 0.044 270 Experimental Example 1-5 compound 5 3.55 6.18 0.141, 0.044 285 Experimental Example 1-6 compound 7 3.65 6.12 0.140, 0.043 275 Experimental Example 1-7 compound 8 3.62 6.11 0.141, 0.043 270 Experimental Example 1-8 compound 9 3.65 6.10 0.141, 0.044 275 Experimental Example 1-9 compound 10 3.65 6.10 0.141, 0.043 265 Experimental Example 1-10 compound 11 3.56 6.16 0.140, 0.043 280 Experimental Example 1-11 compound 12 3.58 6.16 0.139, 0.044 275 Experimental Example 1-12 compound 13 3.53 6.19 0.142, 0.043 280 Experimental Example 1-13 compound 15 3.63 6.10 0.141, 0.044 275 Experimental Example 1-14 compound 16 3.61 6.13 0.141, 0.044 270 Experimental Example 1-15 compound 17 3.65 6.15 0.142, 0.044 270 Experimental Example 1-16 compound 18 3.65 6.12 0.141, 0.043 265 Experimental Example 1-17 compound 19 3.66 6.15 0.141, 0.044 270 Experimental Example 1-18 compound 21 3.60 6.10 0.141, 0.043 270 Experimental Example 1-19 compound 22 3.62 6.14 0.141, 0.044 265 Experimental Example 1-20 compound 23 3.58 6.17 0.141, 0.043 275 Experimental Example 1-21 compound 24 3.56 6.15 0.141, 0.043 280 Experimental Example 1-22 compound 25 3.60 6.12 0.141, 0.044 270 Comparative Experimental Example 1-1 EB1 4.07 5.48 0.144, 0.048 200 Comparative Experimental Example 1-2 EB2 4.20 5.10 0.145, 0.048 160 Comparative Experimental Example 1-3 EB3 4.00 5.01 0.145, 0.048 180 Comparative Experimental Example 1-4 EB4 4.12 5.10 0.145, 0.048 165 Comparative Experimental Example 1-5 EB5 4.02 5.08 0.146, 0.048 180 Comparative Experimental Example 1-6 EB6 4.50 4.50 0.145, 0.048 100

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 exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

In particular, the compound of the present invention is the same as in Chemical Formula 1, except when the 7th position of the core is unsubstituted (EB1, EB2) as well as unsubstituted aryl (EB3); alkyl (EB4); aryl substituted aryl (EB5); In contrast to the case in which an aryl-substituted alkylaryl (EB6) or the like is bonded to the 7th position of the core, it is applied as an electron suppression layer of an organic light emitting device to exhibit remarkable effects in terms of driving voltage, efficiency, and lifespan.

Experimental Examples 2-1 to 2-22 and Comparative Experimental Examples 1-1, 2-1 to 2-5

In Experimental Example 1-1, the compound represented by Formula EB1 was used instead of Compound 1 as the electron blocking layer, and the compound shown in Table 2 was used instead of the compound represented by Formula HT1 as the hole transport layer, except for using, Organic light emitting devices of Experimental Examples 2-1 to 2-22 and Comparative Experimental Examples 2-1 to 2-5 were manufactured in the same manner as in Experimental Example 1-1. ^{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) life span
(T95, hr) Experimental Example 2-1 compound 1 3.65 6.12 0.141, 0.043 275 Experimental Example 2-2 compound 2 3.66 6.13 0.140, 0.044 265 Experimental Example 2-3 compound 3 3.65 6.12 0.142, 0.044 265 Experimental Example 2-4 compound 4 3.68 6.10 0.141, 0.043 260 Experimental Example 2-5 compound 6 3.58 6.21 0.140, 0.043 280 Experimental Example 2-6 compound 7 3.60 6.15 0.141, 0.043 275 Experimental Example 2-7 compound 9 3.65 6.12 0.141, 0.043 260 Experimental Example 2-8 compound 10 3.62 6.10 0.142, 0.044 265 Experimental Example 2-9 compound 11 3.61 6.15 0.141, 0.044 275 Experimental Example 2-10 compound 12 3.60 6.18 0.140, 0.044 270 Experimental Example 2-11 compound 13 3.62 6.15 0.141, 0.044 270 Experimental Example 2-12 compound 14 3.59 6.20 0.140, 0.044 280 Experimental Example 2-13 compound 15 3.62 6.18 0.141, 0.043 270 Experimental Example 2-14 chemical 16 3.65 6.10 0.140, 0.044 265 Experimental Example 2-15 compound 18 3.62 6.15 0.140, 0.043 280 Experimental Example 2-16 compound 19 3.63 6.10 0.141, 0.043 265 Experimental Example 2-17 compound 20 3.60 6.18 0.141, 0.043 275 Experimental Example 2-18 compound 22 3.63 6.10 0.141, 0.043 260 Experimental Example 2-19 compound 23 3.60 6.14 0.141, 0.043 265 Experimental Example 2-20 compound 24 3.64 6.15 0.141, 0.044 270 Experimental Example 2-21 compound 25 3.64 6.13 0.140, 0.044 270 Experimental Example 2-22 compound 26 3.58 6.18 0.140, 0.043 280 Comparative Experimental Example 1-1 HT1 4.07 5.48 0.144, 0.048 200 Comparative Experimental Example 2-1 HT2 3.90 5.33 0.144, 0.048 220 Comparative Experimental Example 2-2 HT3 4.15 5.45 0.145, 0.048 185 Comparative Experimental Example 2-3 HT4 3.99 5.12 0.145, 0.048 150 Comparative Experimental Example 2-4 HT5 4.21 5.03 0.145, 0.048 115 Comparative Experimental Example 2-5 HT6 4.17 5.21 0.144, 0.048 135

As shown in Table 2, 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 a hole transport layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.

In particular, the compound of the present invention, the compound of the present invention, the core itself is a compound (HT1) completely different from Formula 1, the rest is the same as Formula 1, but the 7th position of the core is unsubstituted compound (HT2 to 4) and the like, of course, alkyl (HT5); In contrast to the case where an aryl-substituted aryl (HT6) or the like is bonded to the 7th position of the core, it is applied as a hole transport layer of an organic light emitting device to exhibit 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 (10)

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

In Formula 1,
R ₁ is C _6-60 aryl,
any one of the hydrogens of R ₁ is substituted with _{C 6-20 alkyl;} the rest are each independently hydrogen or deuterium,
R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; nitrile; silyl; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _6-60 aryl; substituted or unsubstituted C _2-60 alkenyl; _{It is C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _6-60 aryl; substituted or unsubstituted C _2-60 alkenyl; _{C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted adamantyl,
L, L ₁ , and L ₂ are each independently, a direct bond; substituted or unsubstituted C _1-60 alkylene; substituted or unsubstituted C _6-60 arylene; substituted or unsubstituted C _1-60 alkoxyylene; substituted or unsubstituted C _2-60 alkenylene; _{Or substituted or unsubstituted C 2-60} heteroarylene containing any one or more heteroatoms selected from the group consisting of N, O and S,
m and n are each independently an integer of 0 to 3.
According to claim 1,
R ₁ is phenyl or biphenyl,
any one of the hydrogens of R ₁ is substituted with _{C 3-20 alkyl;} The rest are each independently hydrogen or deuterium,
compound.
According to claim 1,
R ₁ is a substituent represented by the following formula (2),
compound:
[Formula 2]

In Formula 2,
any one of X _{1 is C 3-20} branched chain alkyl; the rest are each independently hydrogen or deuterium,
The dotted line indicates the bonding position.
According to claim 1,
L, L ₁ , and L ₂ are each independently, a direct bond; phenylene; biphenylene; naphthylene; terphenylene; quaterphenylene; carbazolylene; fluorenylene; dibenzofuranylene; dibenzothiophenylene,
The L, L ₁ , and L ₂ are each independently, unsubstituted, one or more deuterium; substituted or unsubstituted C _1-18 alkyl; substituted or unsubstituted C _6-18 aryl; _{Or substituted with C 2-18} heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
compound.
According to claim 1,
L, L ₁ , and L ₂ are each independently, a direct bond; Or any one selected from the group consisting of the following formulas,
compound:

In each of the above formulas,
R ₁₀ is the same or different and is hydrogen; heavy hydrogen; substituted or unsubstituted C _1-18 alkyl; substituted or unsubstituted C _6-18 aryl; _{or C 2-18} heteroaryl containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S,
The dotted line indicates the bonding position.
According to claim 1,
m and n are both 0,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently, phenyl; biphenyl; naphthyl; terphenyl; quarterphenyl; anthracenyl; fluoranthenyl; fluorenyl; carbazolyl; dibenzofuranyl; dibenzothiophenyl; or adamantyl;
The Ar ₁ and Ar ₂ are each independently, unsubstituted, one or more deuterium; substituted or unsubstituted C _1-18 alkyl; substituted or unsubstituted C _6-18 aryl; _{C 2-18} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or substituted with adamantyl,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of the following formulas,
compound:

In each of the above formulas,
R ₁₂ is the same or different and is hydrogen; heavy hydrogen; substituted or unsubstituted C _1-18 alkyl;
The dotted line indicates the bonding position.
According to claim 1,
The compound 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 of the organic material layers contains the compound according to any one of claims 1 to 9 which is an organic light emitting device.

Images