KR20210120526A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

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 made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and 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]

R _{1 is C 6-60} aryl substituted with one or more C _{3-20 alkyl,}

R ₂ and R ₃ are each independently hydrogen, deuterium, halogen, nitrile, silyl, 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 at least one heteroatom 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, substituted or unsubstituted N , O and S including any one or more heteroatoms selected from the group consisting of C _2-60 heteroaryl, or 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 alkoxy Silene, substituted or unsubstituted C _{2-60 alkenylene, or C 2-60} heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

a is an integer from 0 to 2, b is an integer from 0 to 4,

p, q, and r are each independently an integer from 0 to 4.

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 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.

(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, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkyl group Thioxy group, arylthioxy group, alkylsulfoxy group, arylsulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine substituted or unsubstituted with one or more substituents selected from the group consisting of a group, a heteroarylamine group, an arylamine group, an arylphosphine group, or a heteroaryl group containing at least one of N, O and S atoms; It means a substituted or unsubstituted one in which two or more substituents among the above-exemplified substituents are 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 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 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 examples 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, 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 dimethylfluorene as a core, an alkylaryl is bonded to carbon 3 of the core, an amine-based substituent is bonded to carbon 2 of the core, and both sides of the amine-based substituent based on the structure in which there is an aryl or heteroaryl, respectively.

Here, the bonding position of each substituent to the core corresponds to a position capable of controlling the energy barrier with the organic material layer by controlling the HOMO and LUMO energy levels of the compound without degrading the functions of each other.

In particular, a structure in which an amine-based substituent is bonded to carbon 2 of the core, and an alkylaryl is bonded to carbon 3 of the core; When an unsubstituted aryl is bonded to carbon 3 of the core, it may contribute to heat resistance, high melting point, and the like, in preparation for a case in which hydrogen is bonded to carbon 3 of the core.

Therefore, when the compound represented by Formula 1 is used as a material for an organic layer of an organic light emitting device, low voltage, high efficiency, color reproducibility, lifespan characteristics, etc. can be improved by the synergistic effect of the substituents, and hole injection and hole transport , hole injection and transport, light emission, electron transport, electron suppression, or electron injection can express remarkably excellent ability.

The effect of the compound represented by Formula 1 is supported by the experimental examples to be described later. In particular, when the compound represented by Formula 1 is applied as a material for a hole transport layer or an electron suppression layer of an organic light emitting device, a compound having the same core as that of Formula 1 but having a different substituent (especially a compound containing no alkylaryl- example For example, when an unsubstituted aryl is bonded to carbon 3 of the core, when a hydrogen is bonded to carbon 3 of the core), in preparation for a compound having the same substituent as in Formula 1 but having a different core, etc., Low voltage, high efficiency, color reproducibility, and lifespan characteristics are remarkably improved.

Here, the organic light emitting device may include a hole transport layer having a multilayer structure, and the compound represented by Chemical Formula 1 may be applied to some or all layers of the hole transport layer having a multilayer structure.

However, such a description is an example, and may be embodied by the following description.

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

In Formula 1, R ₁ may be _{C 6-30} aryl substituted with one or more C _{3-20 alkyl.}

Specifically, R ₁ may be phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, or fluorenyl.

Here, R ₁ may be substituted with one or more C _{3-20 alkyl.}

More specifically, R ₁ may be a substituent represented by the following Chemical Formula 2:

[Formula 2]

In Formula 2,

At least one of X _{1 is C 3-20} branched chain alkyl, the rest are hydrogen,

A dotted line indicates a bonding position with _{L 1 of Formula 1 above.}

For example, R ₁ can be phenyl substituted with 1 or 2 C _{3-5 branched chain alkyl.}

Ar ₁ and Ar ₂ are each independently, 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 _{2- 30 alkenyl, C 2-30} heteroaryl containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, or adamantyl.

Specifically, Ar ₁ and Ar ₂ are each independently, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, sp lobbyfluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or adamantyl.

Here, Ar ₁ and Ar ₂ are each independently, unsubstituted; At least one heteroatom selected from the group consisting of one or more deuterium, substituted or unsubstituted C _1-30 alkyl, substituted or unsubstituted C _6-30 aryl, or substituted or unsubstituted N, O and S; It may be substituted with C _{2-30 heteroaryl containing.}

More specifically, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, dimethyl fluore nyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or adamantyl.

Here, Ar ₁ and Ar ₂ are each independently, unsubstituted; 1 to 5 C _3-20 branched chain alkyl, 1 to 5 C _3-10 branched chain alkyl, or 1 to 5 C _3-5 branched chain alkyl.

For example, Ar ₁ and Ar ₂ may each independently be substituted with 1 or 2 C _3-5 branched chain alkyl.

L, L ₁ , and L ₂ are each independently a direct bond, substituted or unsubstituted C _1-30 alkylene, substituted or unsubstituted C _6-30 arylene, substituted or unsubstituted C _1-30 alkoxy It may be silane, substituted or unsubstituted C _{2-30 alkenylene, or 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, or dibenzothiophenylene.

Here, the L, L ₁ , and L ₂ are each independently, unsubstituted; At least one heteroatom selected from the group consisting of one or more deuterium, substituted or unsubstituted C _1-30 alkyl, substituted or unsubstituted C _6-30 aryl, or substituted or unsubstituted N, O and S; It may be substituted with C _{2-30 heteroaryl containing.}

More specifically, L, L ₁ , and L ₂ may each independently be a direct bond, phenylene, or biphenylene.

Here, the L, L ₁ , and L ₂ are each independently, unsubstituted; 1 to 5 C _3-20 branched chain alkyl, 1 to 5 C _3-10 branched chain alkyl, or 1 to 5 C _3-5 branched chain alkyl.

For example, L, L ₁ , and L ₂ may each independently be substituted with one or two C _3-5 branched chain alkyl.

Both R ₂ and R ₃ may be hydrogen.

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 Chemical Formula 1 may be prepared by, for example, the following Reaction Schemes 1-1 and 1-2.

[Scheme 1-1]

[Scheme 1-2]

(In each of the above schemes, the definition of the substituent is as described above.)

However, the manufacturing method 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. As an example, the present invention provides an organic light emitting device including a first electrode, a second electrode provided to face the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, At least one layer of the organic material layer includes the compound represented by Formula 1, and provides an organic light emitting device.

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 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 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 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.

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 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, zinc oxide, indium oxide, indium tin oxide (ITO), metal oxide such as indium zinc oxide (IZO), ZnO: Al or SnO ₂ : combinations of oxides with metals such as Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole and polyaniline The same conductive polymer, etc., but is 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, LiF/Al or LiO ₂ /Al multi-layered materials, and the like, but are 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 them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them 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 compound, dimerized styryl compound, BAlq, 10-hydroxybenzoquinoline-metal compound, benzoxazole, benzthiazole and benz There are imidazole-based compounds, 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 for example, an electron withdrawing group such as an azine derivative including triazine, a triazole derivative, an oxadiazole derivative, a phenanthroline derivative, or a phosphine oxide derivative is introduced. compounds 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. Specific examples of the electron injection and transport material include _{, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq 3} , an organic radical compound, a hydroxyflavone-metal complex, and a triazine derivative. 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, etc., 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

Step 1) Synthesis of compound 1-A

3- (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 1-A (47.5 g, 77.69 % yield).

Step 2) Synthesis of compound 1

Compound 1-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 1, 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, recrystallization was performed with ethyl acetate to obtain Compound 1 (21.0 g, 76.96 % yield). (MS[M+H]+ = 570)

Synthesis Example 2: Synthesis of compound 2

Compound 1-A (20.0 g, 47.89 mmol) obtained in step 1 of Synthesis Example 1 and 4-bromo-1,1':4',1''-terphenyl (15.10 g, 48.85 mmol) were used. to obtain Compound 2 (23.5 g, 75.97 % yield) in the same manner as in Step 2 of Synthesis Example 1. (MS[M+H]+ = 646)

Synthesis Example 3: Synthesis of compound 3

Using compound 1-A (20.0 g, 47.89 mmol) and 9-(4-chlorophenyl)phenanthrene (14.11 g, 48.85 mmol) obtained in step 1 of Synthesis Example 1, step 2 of Synthesis Example 1 and Compound 3 (24.5 g, 76.37 % yield) was obtained in the same manner. (MS[M+H]+ = 670)

Synthesis Example 4: Synthesis of compound 4

Using the compound 1-A (20.0 g, 47.89 mmol) and 1-bromo-4-( tert -butyl)benzene (10.41 g, 48.85 mmol) obtained in step 1 of Synthesis Example 1, Compound 4 (20.0 g, 75.96 % yield) was obtained in the same manner as in step 2. (MS[M+H]+ = 550)

Synthesis Example 5: Synthesis of compound 5

Step 1) Synthesis of compound 5-A

3- (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 (42.0 g, 79.20 % yield) in the same manner as in Step 1 of Synthesis Example 1.

Step 2) Synthesis of compound 5

The step of Synthesis Example 1 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 (20.0 g, 76.44 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 646)

Synthesis Example 6: Synthesis of compound 6

Compound 5-A (20.0 g, 40.51 mmol) obtained in step 1 of Synthesis Example 5 and 4-bromo-1,1':4',1''-terphenyl (12.78 g, 41.32 mmol) were used. to obtain the compound 6 (23.0 g, 78.64 % yield) in the same manner as in step 2 of Synthesis Example 1. (MS[M+H]+ = 722)

Synthesis Example 7: Synthesis of compound 7

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 7 (21.0 g, 75.57 % yield) was obtained in the same manner as in Step 2 of Example 1. (MS[M+H]+ = 686)

Synthesis Example 8: Synthesis of compound 8

Using compound 5-A (20.0 g, 40.51 mmol) and 1-bromo-4-( tert -butyl)benzene (8.81 g, 41.32 mmol) obtained in step 1 of Synthesis Example 5, Compound 8 (19.8 g, 78.09 % yield) was obtained in the same manner as in step 2. (MS[M+H]+ = 626)

Synthesis Example 9: Synthesis of compound 9

Compound 5-A (20.0 g, 40.51 mmol) obtained in step 1 of Synthesis Example 5 and 4-bromo-4'-( tert -butyl)-1,1'-biphenyl (11.95 g, 41.32 mmol) was used to obtain the compound 9 (22.0 g, 77.36 % yield) in the same manner as in step 2 of Synthesis Example 1. (MS[M+H]+ = 702)

Synthesis Example 10: Synthesis of compound 10

The above synthesis using compound 5-A (20.0 g, 40.51 mmol) obtained in step 1 of Synthesis Example 5 and 4-(4-chlorophenyl)dibenzo[ b,d ]furan (11.52 g, 41.32 mmol) Compound 10 (23.5 g, 78.82 % yield) was obtained in the same manner as in Step 2 of Example 1. (MS[M+H]+ = 736)

Synthesis Example 11: Synthesis of compound 11

The step of Synthesis Example 1 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 11 (22.5 g, 78.89 % yield) was obtained in the same manner as in 2 above. (MS[M+H]+ = 704)

Synthesis Example 12: Synthesis of compound 12

Step 1) Synthesis of compound 12-A

3- (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 (53.0 g, 76.42 % yield) in the same manner as in Step 1 of Synthesis Example 1.

Step 2) Synthesis of compound 12

Compound 12-A (20.0 g, 42.22 mmol) obtained in step 1 of Synthesis Example 12 and 4-bromo-1,1':4',1''-terphenyl (13.32 g, 43.07 mmol) were used. to obtain the compound 12 (23.5 g, 79.29 % yield) in the same manner as in step 2 of Synthesis Example 1. (MS[M+H]+ = 702)

Synthesis Example 13: Synthesis of compound 13

The compound 12-A (20.0 g, 42.22 mmol) and 2-bromo-9,9-dimethyl -9 H obtained in the above Synthesis Example 12 1 - the use of fluorene (11.77 g, 43.07 mmol) synthesized Compound 13 (22.0 g, 78.24 % yield) was obtained in the same manner as in Step 2 of Example 1. (MS[M+H]+ = 666)

Synthesis Example 14: Synthesis of compound 14

Compound 12-A (20.0 g, 42.22 mmol) obtained in step 1 of Synthesis Example 12 and 4-bromo-4'-( tert -butyl)-1,1'-biphenyl (12.46 g, 43.07 mmol) Compound 14 (22.5 g, 78.14 % yield) was obtained in the same manner as in Step 2 of Synthesis Example 1 using (MS[M+H]+ = 682)

Synthesis Example 15: Synthesis of compound 15

3- (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 from ethyl acetate to obtain the compound 15 (16.0 g, 73.79 % yield). (MS[M+H]+ = 494)

Synthesis Example 16: Synthesis of compound 16

3- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 4-bromo-1,1'-biphenyl (20.99 g, 90.04 mmol) was used to obtain compound 16 (22.0 g, 77.55 % yield) in the same manner as in Synthesis Example 15. (MS[M+H]+ = 646)

Synthesis Example 17: Synthesis of compound 17

3- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 2-bromo-9,9-dimethyl -9 H - Compound 17 (24.0 g, 75.27 % yield) was obtained in the same manner as in Synthesis Example 15 using fluorene (24.60 g, 90.04 mmol). (MS[M+H]+ = 726)

Synthesis Example 18: Synthesis of compound 18

3- (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 18 (20.5 g, 77.03 % yield) in the same manner as in Synthesis Example 15. (MS[M+H]+ = 606)

Synthesis Example 19. Synthesis of compound 19

3- (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 19 (25.5 g, 76.59 % yield) was obtained in the same manner as in Synthesis Example 15 using 1,1'-biphenyl (26.04 g, 90.04 mmol). (MS[M+H]+ = 758)

Synthesis Example 20: Synthesis of compound 20

3- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 1-bromo-3- (tert-butyl) benzene ( 19.19 g, 90.04 mmol) was used to obtain Compound 20 (20.0 g, 75.16 % yield) in the same manner as in Synthesis Example 15. (MS[M+H]+ = 606)

Synthesis Example 21: Synthesis of compound 21

3- (4- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 1- (4-bromophenyl) adamantane ten (26.22 g, 90.04 mmol) was used to obtain Compound 21 (25.5 g, 76.18 % yield) in the same manner as in Synthesis Example 15. (MS[M+H]+ = 762)

Synthesis Example 22: Synthesis of compound 22

3- (4 '- (tert-butyl) - [1,1'-biphenyl] -4-yl) -9 H 9,9-dimethyl-fluorene-2-amine (15.0 g, 35.92 mmol) and Compound 22 (15.5 g, 75.73 % yield) was obtained in the same manner as in Synthesis Example 15 using bromobenzene (11.56 g, 73.64 mmol). (MS[M+H]+ = 570)

Synthesis Example 23: Synthesis of compound 23

3- (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 (20.0 g, 77.12 % yield) was obtained in the same manner as in Synthesis Example 15 using 4-bromo-1,1'-biphenyl (17.17 g, 73.64 mmol). (MS[M+H]+ = 722)

Synthesis Example 24: Synthesis of compound 24

3- (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 15 using 1-bromo-4-( tert-butyl)benzene (15.69 g, 73.64 mmol). (MS[M+H]+ = 682)

Synthesis Example 25: Synthesis of compound 25

3- (3- (tert-butyl) phenyl) 9,9-dimethyl -9 H-fluorene-2-amine (15.0 g, 43.92 mmol) and 4-bromo-1,1'-biphenyl (20.99 g, 90.04 mmol) was used to obtain Compound 25 (22.0 g, 77.55 % yield) in the same manner as in Synthesis Example 15. (MS[M+H]+ = 646)

Synthesis Example 26: Synthesis of compound 26

3- (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 ( 21.11 g, 99.04 mmol) was used to obtain compound 26 (20.0 g, 75. 16 % yield) in the same manner as in Synthesis Example 15. (MS[M+H]+ = 606)

<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 Formula A1 as a first hole transport layer to a thickness of 1150 Å, the compound represented by Formula B1 as a second hole transport layer was thermally vacuum-deposited to a thickness of 450 Å. Subsequently, 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, a compound represented by the following formulas H1 and H2 (H1:H2=1:1) and a compound represented by the following formula DP were vacuum-deposited to a thickness of 350 Å in a weight ratio of 85:15. Then, as a hole blocking layer, a compound represented by the following Chemical Formula HB was vacuum-deposited to a thickness of 50 Å. Subsequently, a compound represented by the following formula ET and a compound represented by the following LiQ as a layer for simultaneously performing electron transport and electron injection 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 1-21 and Comparative Experimental Examples 1-1 to 1-3

Experimental Examples 1-2 to 1-21 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 1-3 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 nit) 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 3.52 6.18 0.140, 0.043 285 Experimental Example 1-2 compound 2 3.51 6.20 0.140, 0.044 290 Experimental Example 1-3 compound 3 3.52 6.17 0.140, 0.044 275 Experimental Example 1-4 compound 4 3.54 6.16 0.140, 0.043 280 Experimental Example 1-5 compound 5 3.51 6.22 0.140, 0.043 290 Experimental Example 1-6 compound 6 3.49 6.19 0.141, 0.044 290 Experimental Example 1-7 compound 8 3.56 6.14 0.140, 0.043 280 Experimental Example 1-8 compound 9 3.53 6.12 0.141, 0.044 285 Experimental Example 1-9 compound 10 3.56 6.15 0.140, 0.043 270 Experimental Example 1-10 compound 11 3.52 6.15 0.140, 0.043 275 Experimental Example 1-11 compound 12 3.51 6.20 0.140, 0.044 285 Experimental Example 1-12 compound 15 3.51 6.17 0.140, 0.043 280 Experimental Example 1-13 compound 16 3.48 6.22 0.140, 0.043 295 Experimental Example 1-14 compound 18 3.50 6.19 0.140, 0.043 290 Experimental Example 1-15 compound 20 3.54 6.17 0.140, 0.044 280 Experimental Example 1-16 compound 21 3.59 6.20 0.141, 0.044 280 Experimental Example 1-17 compound 22 3.54 6.15 0.141, 0.044 275 Experimental Example 1-18 compound 23 3.51 6.20 0.140, 0.043 290 Experimental Example 1-19 compound 24 3.54 6.14 0.141, 0.043 275 Experimental Example 1-20 compound 25 3.53 6.19 0.141, 0.044 290 Experimental Example 1-21 compound 26 3.56 6.15 0.140, 0.043 275 Comparative Experimental Example 1-1 EB1 4.08 5.25 0.145, 0.049 190 Comparative Experimental Example 1-2 EB2 4.44 4.89 0.145, 0.049 140 Comparative Experimental Example 1-3 EB3 4.20 5.01 0.144, 0.049 175

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.

Experimental Examples 2-1 to 2-18 Comparative Experimental Examples 1-1, 2-1 to 2-3

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 A1 as the first hole transport layer, except for using was prepared in the same manner as in Experimental Example 1-1, Experimental Examples 2-1 to 2-18 Comparative Experimental Examples 2-1 to 2-3 organic light emitting devices. ^{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 nit) to 95%.

first 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 3.53 6.13 0.140, 0.044 275 Experimental Example 2-2 compound 2 3.49 6.14 0.141, 0.044 290 Experimental Example 2-3 compound 4 3.51 6.12 0.140, 0.043 280 Experimental Example 2-4 compound 6 3.49 6.15 0.140, 0.043 275 Experimental Example 2-5 compound 7 3.44 6.14 0.140, 0.043 290 Experimental Example 2-6 compound 8 3.54 6.12 0.140, 0.044 285 Experimental Example 2-7 compound 9 3.50 6.17 0.140, 0.043 285 Experimental Example 2-8 compound 12 3.54 6.14 0.140, 0.043 270 Experimental Example 2-9 compound 13 3.45 6.13 0.141, 0.043 280 Experimental Example 2-10 compound 14 3.55 6.12 0.141, 0.044 270 Experimental Example 2-11 chemical 16 3.44 6.18 0.140, 0.043 295 Experimental Example 2-12 compound 17 3.42 6.15 0.140, 0.044 285 Experimental Example 2-13 compound 18 3.49 6.16 0.140, 0.043 290 Experimental Example 2-14 compound 19 3.54 6.12 0.141, 0.043 275 Experimental Example 2-15 compound 21 3.54 6.12 0.141, 0.044 270 Experimental Example 2-16 compound 23 3.48 6.15 0.140, 0.043 290 Experimental Example 2-17 compound 24 3.56 6.12 0.140, 0.044 280 Experimental Example 2-18 compound 26 3.49 6.18 0.140, 0.043 290 Comparative Experimental Example 1-1 A1 4.08 5.25 0.145, 0.049 190 Comparative Experimental Example 2-1 A2 3.88 5.12 0.145, 0.049 185 Comparative Experimental Example 2-2 A3 4.22 5.30 0.144, 0.049 145 Comparative Experimental Example 2-3 A4 4.44 4.48 0.145, 0.049 85

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 first hole transport layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.

Experimental Examples 3-1 to 3-22 and Comparative Experimental Examples 1-1, 3-1 to 3-5

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 3 was used instead of the compound represented by Formula B1 as the second hole transport layer. to fabricated the organic light emitting devices of Experimental Examples 3-1 to 3-22 and Comparative Experimental Examples 3-1 to 3-5 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 nit) to 95%.

second hole transport layer Voltage (V @ 10mA/cm ² ) Efficiency (cd/A @ 10mA/cm ² ) color coordinates (x, y) life span
(T95, hr) Experimental Example 3-1 compound 1 3.52 6.16 0.140, 0.044 280 Experimental Example 3-2 compound 2 3.48 6.18 0.140, 0.043 290 Experimental Example 3-3 compound 4 3.52 6.17 0.140, 0.043 280 Experimental Example 3-4 compound 6 3.49 6.18 0.141, 0.043 295 Experimental Example 3-5 compound 7 3.46 6.16 0.140, 0.043 290 Experimental Example 3-6 compound 8 3.53 6.15 0.140, 0.043 280 Experimental Example 3-7 compound 9 3.49 6.18 0.141, 0.044 285 Experimental Example 3-8 compound 12 3.52 6.13 0.140, 0.043 285 Experimental Example 3-9 compound 13 3.46 6.18 0.140, 0.043 290 Experimental Example 3-10 compound 14 3.54 6.14 0.141, 0.043 280 Experimental Example 3-11 compound 15 3.49 6.18 0.140, 0.043 275 Experimental Example 3-12 compound 16 3.46 6.22 0.140, 0.043 300 Experimental Example 3-13 compound 17 3.43 6.18 0.140, 0.043 290 Experimental Example 3-14 chemical 18 3.50 6.16 0.140, 0.044 295 Experimental Example 3-15 compound 19 3.56 6.15 0.140, 0.043 285 Experimental Example 3-16 compound 20 3.58 6.13 0.141, 0.044 285 Experimental Example 3-17 compound 21 3.55 6.16 0.140, 0.043 275 Experimental Example 3-18 compound 22 3.49 6.20 0.140, 0.043 290 Experimental Example 3-19 compound 23 3.48 6.19 0.140, 0.043 290 Experimental Example 3-20 compound 24 3.55 6.13 0.141, 0.043 275 Experimental Example 3-21 compound 25 3.50 6.19 0.140, 0.044 290 Experimental Example 3-22 compound 26 3.54 6.14 0.141, 0.043 285 Comparative Experimental Example 1-1 B1 4.08 5.25 0.145, 0.049 190 Comparative Experimental Example 3-1 B2 3.85 5.45 0.144, 0.049 215 Comparative Experimental Example 3-2 B3 4.31 5.49 0.145, 0.049 155 Comparative Experimental Example 3-3 B4 4.00 4.89 0.144, 0.049 140 Comparative Experimental Example 3-4 B5 4.10 5.00 0.145, 0.049 115 Comparative Experimental Example 3-5 B6 4.40 5.29 0.145, 0.049 75

As shown in Table 3, 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 second hole transport layer exhibited remarkable effects in terms of driving voltage, efficiency, and lifespan.

Synthesis

From the above experimental examples, when the compound represented by Chemical Formula 1 is applied as a material of a hole transport layer or an electron suppression layer of an organic light emitting device, a compound having the same core as that of Chemical Formula 1 but having a different substituent (especially, not including alkylaryl) compound-for example, when an unsubstituted aryl is bonded to carbon 3 of the core, when a hydrogen is bonded to carbon 3 of the core, etc.), having the same substituent as in Formula 1, but having a different core Compared to the compound, it can be seen that the low voltage, high efficiency, color reproducibility, and lifespan characteristics are remarkably improved.

Here, the organic light emitting device may include a hole transport layer having a multilayer structure, and the compound represented by Chemical Formula 1 may be applied to some or all layers of the hole transport layer having a multilayer structure.

The effect of the compound represented by Formula 1 is due to its structural characteristics.

Specifically, the compound represented by Formula 1 has dimethyl fluorene as a core, an alkylaryl is bonded to carbon 3 of the core, an amine-based substituent is bonded to carbon 2 of the core, and the amine-based compound is It is based on structures in which aryl or heteroaryl is present on either side of the substituent, respectively.

Here, the bonding position of each substituent to the core corresponds to a position capable of controlling the energy barrier with the organic material layer by controlling the HOMO and LUMO energy levels of the compound without degrading the functions of each other.

In particular, a structure in which an amine-based substituent is bonded to carbon 2 of the core, and an alkylaryl is bonded to carbon 3 of the core; When an unsubstituted aryl is bonded to carbon 3 of the core, it may contribute to heat resistance, high melting point, and the like, in preparation for a case in which hydrogen is bonded to carbon 3 of the core.

Therefore, when the compound represented by Formula 1 is used as a material for the organic layer of the organic light emitting device, low voltage, high efficiency, color reproducibility, lifespan characteristics, etc. can be improved by the synergistic effect of the substituents, and electron suppression and hole transport In addition to the ability, it is possible to express remarkably excellent ability in all aspects of hole injection, hole transport, hole injection and transport, light emission, electron transport, electron suppression, or electron injection.

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 substituted with one or more C _{3-20 alkyl,}
R ₂ and R ₃ are each independently hydrogen, deuterium, halogen, nitrile, silyl, 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 at least one heteroatom 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, substituted or unsubstituted N , O and S including any one or more heteroatoms selected from the group consisting of C _2-60 heteroaryl, or 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 alkoxy Silene, substituted or unsubstituted C _{2-60 alkenylene, or C 2-60} heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
a is an integer from 0 to 2, b is an integer from 0 to 4,
p, q, and r are each independently an integer from 0 to 4.
According to claim 1,
R ₁ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, or fluorenyl,
_Wherein R ₁ is substituted with one or more C 3-20 alkyl,
compound.
According to claim 1,
R ₁ is a substituent represented by the following formula (2),
compound:
[Formula 2]

In Formula 2,
At least one of X _{1 is C 3-20} branched chain alkyl, the rest are hydrogen,
A dotted line indicates a bonding position with _{L 1 of Formula 1 above.}
According to claim 1,
Ar ₁ and Ar ₂ are each independently, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorene nyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or adamantyl;
wherein Ar ₁ and Ar ₂ are each independently, unsubstituted; At least one heteroatom selected from the group consisting of one or more deuterium, substituted or unsubstituted C _1-30 alkyl, substituted or unsubstituted C _6-30 aryl, or substituted or unsubstituted N, O and S; which is substituted with _{C 2-30 heteroaryl comprising,}
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently, phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, dimethylfluorenyl, diphenyl fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or adamantyl;
wherein Ar ₁ and Ar ₂ are each independently, unsubstituted; substituted with one or more C _3-20 branched chain alkyl,
compound.
According to claim 1,
L, L ₁ , and L ₂ are each independently a direct bond, phenylene, biphenylene, naphthylene, terphenylene, quaterphenylene, carbazolylene, fluorenylene, dibenzofuranylene, or dibenzo thiophenylene,
The L, L ₁ , and L ₂ are each independently, unsubstituted; At least one heteroatom selected from the group consisting of one or more deuterium, substituted or unsubstituted C _1-30 alkyl, substituted or unsubstituted C _6-30 aryl, or substituted or unsubstituted N, O and S; which is substituted with _{C 2-30 heteroaryl comprising,}
compound.
According to claim 1,
L, L ₁ , and L ₂ are each independently a direct bond, phenylene, or biphenylene,
The L, L ₁ , and L ₂ are each independently, unsubstituted; which is substituted with 1 to 5 C _3-20 branched chain alkyl,
compound.
According to claim 1,
R ₂ and R ₃ are both hydrogen;
compound.
According to claim 1,
The compound is any one selected from the group consisting of the following compounds:

.
An organic light emitting device comprising a first electrode, a second electrode provided to face the first electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises: The organic light-emitting device comprising the compound according to any one of claims 1 to 9.

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