KR102044429B1 - Novel hetero-cyclic 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.

Description

New heterocyclic compound and organic light emitting device using the same {NOVEL HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Formula 1, one of R ₁ to R ₃ is a functional group represented by the following formula (2), the other is hydrogen,

[Formula 2]

-L-Ar ₁

In Formula 2, L is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of O, N, Si and S,

Ar ₁ is any one of the following Formulas 3 to 8,

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 3 to 8,

X ₁ to X ₁₅ are each independently N, or CH,

Y ₁ to Y ₈ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms each independently selected from the group consisting of N, O, and S.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound represented by Chemical Formula 1. .

The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
3 shows the 3D structure of the compound of Formula 1-9.
Figure 4 shows a 3D structure of Comparative Example 1-5 chemical formula ET-1-E compound.

Hereinafter, the present invention will be described in more detail to aid in understanding the present invention.

, 또는

는 다른 치환기에 연결되는 결합을 의미하고, 직접 결합은 L 로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. In this specification,

, or

Means a bond connected to another substituent, and a direct bond means a case where no separate atom is present in a portion represented by L.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O and S atoms, or two or more substituents of the above-described substituents connected or substituted. . For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the 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 this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 40 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C60. Specifically methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, iso Pentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, trifluor Romethoxy and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

And so on. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxdiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Phenanthroline, thiazolyl, isooxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, aziridyl, azaindolyl, isoindolyl, and inda Sleepy, purine, pteridine, beta-carbolyl, naphthyridyl (na phthyridine), ter-pyridyl group, phenazinyl group, imidazopyridyl group, pyropyridyl group, azepin group, pyrazolyl group and dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, except that the arylene is a divalent group, the description of the aryl group described above may be applied. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group described above. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group refers to a divalent group having two bonding positions in the heteroaryl group described above. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

On the other hand, the present invention provides a compound represented by the formula (1).

In Chemical Formula 1, S means a sulfur atom.

In Formula 1, one of R ₁ to R ₃ is a functional group represented by Formula 2, and the other may be hydrogen.

That is, the compound may be represented by the following Chemical Formula 1-1, Chemical Formula 1-2, or Chemical Formula 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1, 1-2, and 1-3,

L and Ar ₁ are the same as defined in Formula 1 above.

As such, as the functional group represented by Formula 2 is bonded to one of R ₁ to R ₃ of Formula 1, the compound of Formula 1 intervenes in the conjugation of a lone pair in a condensed ring of sulfur atoms, By providing abundant electrons of sulfur atoms in the condensed ring, the electron and hole mobility resulting from the heterocyclic group can be enhanced. Therefore, the organic light emitting device using the same may have high efficiency, low driving voltage, high brightness, long life, and the like.

On the other hand, when the functional group represented by Formula 2 is bonded to one of the substituents of the fluorene ring instead of one of R ₁ to R ₃ of Formula 1, the compound of Formula 1 is a sulfur atom that provides electrons. Since there is no role, the problem of shortening the lifetime may occur by inhibiting electron and hole mobility of the heterocyclic group.

More specifically, the dipole moment value of the compound in which the functional group represented by Chemical Formula 2 is bonded to one of R ₁ to R ₃ of Chemical Formula 1 is selected from the group in which the functional group represented by Chemical Formula 2 is selected from the fluorene ring. About 10 times more than the dipole moment value of the compound bound to one of the substituents, it can confirm the conjugation effect by the sulfur atom described above.

On the other hand, in Formula 2, L is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of O, N, Si and S, more specific examples, L is a direct bond, or Phenylene, or biphenylene, or naphthylene, or thiophenylene, or furanylene, or pyridinylene.

Examples of the phenylene may be any one selected from the group consisting of:

Examples of the biphenylene may be any one selected from the group consisting of:

Examples of the naphthylene may be any one selected from the group consisting of:

Examples of the thiophenylene may be any one selected from the group consisting of:

Examples of the furanylene may be any one selected from the group consisting of:

Examples of the pyridinylene may be any one selected from the group consisting of the following.

More specifically, L may be any one selected from the group consisting of direct bonds or the following functional groups.

In addition, in Chemical Formula 2, Ar ₁ may be any one of the following Chemical Formulas 3 to 8,

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 3 to 8,

X ₁ to X ₁₅ are each independently N, or CH,

Y ₁ to Y ₈ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms each independently selected from the group consisting of N, O, and S.

More specifically, in Chemical Formulas 3 to 8, X ₁ to X ₁₅ are the same as or different from each other, and each independently N, or CH, N is a nitrogen atom, in CH C is a carbon atom, H is bonded to a carbon atom It may be a hydrogen atom.

In addition, in Chemical Formulas 3 to 8, Y ₁ to Y ₈ are the same as or different from each other, and each independently hydrogen, phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenylnaphthyl, pyridinyl , Pyridinylphenyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuranylphenyl, dibenzothiophenylphenyl or any one selected from the group consisting of:

More specifically, in Formula 2, Ar ₁ may be any one selected from the group consisting of the following functional groups.

In addition, the compound may be any one selected from the group consisting of the following compounds:

.

.

On the other hand, HOMO energy level of the compound represented by Formula 1 may be 6.1 eV or more. According to an exemplary embodiment of the present specification, the HOMO energy level of the compound represented by Formula 1 is 6.0 eV or more, or 6.0 eV to 7.0 eV, or 6.0 eV to 6.5 eV, or 6.0 eV to 6.4 eV, or 6.02 eV to 6.32 eV.

When having a deep HOMO energy level, such as the compound represented by the formula (1) according to one embodiment of the present specification can effectively block holes from the light emitting layer, it can provide a high luminous efficiency, improve the stability of the device long life The device can be provided.

In the present specification, the energy level means the magnitude of energy. Therefore, even when the energy level is displayed in the negative (-) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, the HOMO energy level means the distance from the vacuum level to the highest occupied molecular orbital, and the LUMO energy level means the distance from the vacuum level to the lowest unoccupied Molecular Orbital. .

According to an exemplary embodiment of the present specification, the HOMO level may be measured using an atmospheric photoelectron spectroscopy apparatus (manufactured by RIKEN KEIKI Co., Ltd .: AC3). Specifically, the HOMO level may be measured by irradiating UV of 10 nW to the measurement sample deposited at a thickness of 100 nm at an interval of 0.05 eV, and measuring the amount of electrons accordingly.

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

[Scheme 1]

In Scheme 1, L and Ar ₁ are the same as defined in Formula 1 above.

The compound represented by Formula 1 may be prepared by appropriately replacing the starting material in accordance with the structure of the compound to be prepared with reference to Scheme 1.

On the other hand, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound represented by Chemical Formula 1. .

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

The organic material layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting holes and transporting holes may be represented by Chemical Formula 1 above. It may include a compound represented.

In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.

In addition, the electron transport layer, the electron injection layer, or may include a layer for simultaneously transporting electrons and electron injection, the electron transport layer, the electron injection layer, or a layer for the simultaneous transport and electron injection is represented by the formula (1) It may include a compound.

In addition, the organic material layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.

In addition to the organic layer, the organic light emitting device may include an electron blocking layer (EBL) positioned between the hole transport layer and the light emitting layer and / or a hole blocking layer disposed between the light emitting layer and the electron transport layer. layer: HBL) may be further included. In such a structure, the compound represented by Formula 1 may be included in one or more layers of the electron blocking layer and the hole blocking layer. The electron blocking layer and the hole blocking layer may each be an organic material layer adjacent to the emission layer.

In this case, the compound represented by Chemical Formula 1 may be included in the emission layer, the electron transport layer, or the hole blocking layer.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, 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. It may have a structure to. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.

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

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, the second electrode is an anode.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SNO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic 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 materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

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

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material as described above. The host material may further include a condensed aromatic ring derivative or a hetero ring-containing compound in addition to the compound represented by Formula 1 above. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and styrylamine compounds may be substituted or unsubstituted. At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

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

The electron injection layer is a layer for injecting electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, and the hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

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

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

Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

<Production example>

Preparation Example 1 Synthesis of Chemical Formula E1

                                               Formula E1

Compound 4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-thioxanthene] -2'-yl) -1,3,2-dioxaborolane (10.0 g , 21.1 mmol) and 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.2 g, 21.1 mmol) After dissolving completely in (100 ml), potassium carbonate (8.7 g, 63.2 mmol) was dissolved in 50 ml of water, added, and tetrakistriphenyl-phosphinopalladium (731 mg, 0.63 mmol) was added thereto, followed by heating and stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the white carbonate was filtered by removing the potassium carbonate solution. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate each to prepare the compound of Formula E1 (12.3 g, yield 89%).

MS [M + H] ⁺ = 656

Preparation Example 2 Synthesis of Chemical Formula E2

                                             [Formula E2]

Except that each starting material was the same as the reaction scheme, a compound represented by the formula E2 was prepared in the same manner as in Preparation Example 1.

MS [M + H] ⁺ = 656

Preparation Example 3 Synthesis of Chemical Formula E3

                                               [Formula E3]

A compound represented by Chemical Formula E3 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 655

Preparation Example 4 Synthesis of Chemical Formula E4

                                               [Formula E4]

Except that each starting material was the same as the reaction scheme, a compound represented by the formula E4 was prepared in the same manner as in Preparation Example 1.

MS [M + H] ⁺ = 629

Preparation Example 5 Synthesis of Chemical Formula E5

                                                   [Formula E5]

A compound represented by Chemical Formula E5 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 746

Preparation Example 6 Synthesis of Chemical Formula E6

                                                [Formula E6]

A compound represented by Chemical Formula E6 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 656

Preparation Example 7 Synthesis of Chemical Formula E7

                                                 Formula E7

A compound represented by Chemical Formula E7 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 603

Preparation Example 8 Synthesis of Chemical Formula E8

                                               Formula E8

A compound represented by Chemical Formula E8 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 732

Preparation Example 9 Synthesis of Chemical Formula E9

                                                   [Formula E9]

A compound represented by Chemical Formula E9 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 527

Preparation Example 10 Synthesis of Chemical Formula E10

                                                 Formula E10

A compound represented by Chemical Formula E10 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 745

Preparation Example 11 Synthesis of Chemical Formula E11

                                                 Formula E11

Except that each starting material was the same as the reaction scheme, a compound represented by the formula E11 was prepared in the same manner as in Preparation Example 1.

MS [M + H] ⁺ = 806

Preparation Example 12 Synthesis of Chemical Formula E12

                                                   [Formula E12]

A compound represented by Chemical Formula E12 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 657

Preparation Example 13 Synthesis of Chemical Formula E13

                                                [Formula E13]

A compound represented by Chemical Formula E13 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 744

Preparation Example 14 Synthesis of Chemical Formula E14

                                               Formula E14

A compound represented by Chemical Formula E14 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 762

Preparation Example 15 Synthesis of Chemical Formula E15

                                                   Formula E15

A compound represented by Chemical Formula E15 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 681

Preparation Example 16 Synthesis of Chemical Formula E16

                                                 Formula E16

A compound represented by Chemical Formula E16 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 553

Preparation Example 17 Synthesis of Chemical Formula E17

                                                   Formula E17

A compound represented by Chemical Formula E17 was prepared in the same manner as in Preparation Example 1, except that each starting material was used as in the scheme.

MS [M + H] ⁺ = 553

Preparation Example 18 Synthesis of Chemical Formula E18

                                                   Formula E18

Except that each starting material was the same as the reaction scheme, a compound represented by the formula E18 was prepared in the same manner as in Preparation Example 1.

MS [M + H] ⁺ = 579

<Example 1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The following compound [HI-A] was vacuum-deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer. Hexanitrile hexaazatriphenylene (HAT) of the following formula was deposited on the hole injection layer in vacuo at 50 kPa and the following compound [HT-A] (600 kPa) in order to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 Pa to form a light emitting layer.

The compound of [Formula E1] and the compound [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron transport layer having a thickness of 350 Pa. Lithium fluoride (LiF) and aluminum 1,000 nm thick were sequentially deposited on the electron transport layer to form an electron injection layer and a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride at the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at a deposition rate of 2 Å / sec. ^-7 to 5 × 10 ^- to maintain the ⁸ torr, it was produced in the organic light emitting device.

<Examples 1-2 to 1-18>

An organic light-emitting device of Examples 1-2 to 1-18 using the same method as Example 1-1, except for changing the compound of Formula E1 as shown in Table 1 below when forming an electron transport layer. Were produced respectively.

<Comparative Example 1-1>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-A instead of the compound of Formula E1 in Example 1-1.

[ET-1-A]

<Comparative Example 1-2>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-B instead of the compound of Formula E1 in Example 1-1.

[ET-1-B]

<Comparative Example 1-3>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-C instead of the compound of Formula E1 in Example 1-1.

[ET-1-C]

<Comparative Example 1-4>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-D instead of the compound of Formula E1 in Example 1-1.

[ET-1-D]

<Comparative Example 1-5>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-E instead of the compound of Formula E1 in Example 1-1.

[ET-1-E]

<Comparative Example 1-6>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-F instead of the compound of Formula E1 in Example 1-1.

[ET-1-F]

<Comparative Example 1-7>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-G instead of the compound of Formula E1 in Example 1-1.

[ET-1-G]

<Comparative Example 1-8>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1-H was used instead of the compound of Formula E1 in Example 1-1.

[ET-1-H]

<Comparative Example 1-9>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1-I was used instead of the compound of Formula E1 in Example 1-1.

[ET-1-I]

<Comparative Example 1-10>

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-J instead of the compound of Formula E1 in Example 1-1.

[ET-1-J]

Experimental Example 1

The driving voltage and the luminous efficiency of the organic light emitting diodes manufactured by the method of Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-10 were measured at a current density of 10 mA / Cm ² , and 20 mA. The time (T ₉₀ ) of 90% of the initial luminance at the current density of / Cm ² was measured. The results are shown in Table 1 below.

Electron transport layer compound Voltage
(V @ 10mA / cm ² ) efficiency
(cd / A @ 10mA / cm ² ) Color coordinates
(x, y) Life (h)
T ₉₀ at 20mA / Cm ² Example 1-1 E1 4.29 5.65 (0.142, 0.097) 165 Example 1-2 E2 4.37 5.67 (0.142, 0.096) 161 Example 1-3 E3 4.40 5.70 (0.142, 0.096) 150 Example 1-4 E4 4.41 5.05 (0.142, 0.096) 210 Example 1-5 E5 4.35 5.40 (0.142, 0.096) 159 Example 1-6 E6 4.39 5.71 (0.142, 0.097) 155 Example 1-7 E7 4.27 5.12 (0.142, 0.096) 145 Example 1-8 E8 4.25 5.53 (0.142, 0.099) 144 Example 1-9 E9 4.39 5.07 (0.142, 0.096) 140 Example 1-10 E10 4.33 5.41 (0.142, 0.098) 177 Example 1-11 E11 4.32 5.46 (0.142, 0.096) 155 Example 1-12 E12 4.22 5.38 (0.142, 0.097) 147 Example 1-13 E13 4.30 5.57 (0.142, 0.096) 148 Example 1-14 E14 4.48 5.50 (0.142, 0.097) 180 Example 1-15 E15 4.32 5.48 (0.142, 0.097) 200 Example 1-16 E16 4.41 5.00 (0.142, 0.097) 130 Example 1-17 E17 4.39 5.17 (0.142, 0.097) 137 Example 1-18 E18 4.38 5.19 (0.142, 0.096) 131 Comparative Example 1-1 ET-1-A 4.66 4.10 (0.142, 0.096) 70 Comparative Example 1-2 ET-1-B 4.89 3.91 (0.142, 0.102) 80 Comparative Example 1-3 ET-1-C 4.90 3.99 (0.142, 0.096) 88 Comparative Example 1-4 ET-1-D 4.67 4.09 (0.142, 0.096) 65 Comparative Example 1-5 ET-1-E 5.11 3.55 (0.142, 0.096) 70 Comparative Example 1-6 ET-1-F 5.11 3.66 (0.142, 0.096) 81 Comparative Example 1-7 ET-1-G 5.38 3.20 (0.142, 0.096) 57 Comparative Example 1-8 ET-1-H 5.40 3.30 (0.142, 0.096) 50 Comparative Example 1-9 ET-1-I 5.55 3.00 (0.142, 0.096) 49 Comparative Example 1-10 ET-1-J 5.48 3.23 (0.142, 0.096) 68

With reference to the bar shown in Table 1, when comparing Examples 1-1 to 1-18 and Comparative Examples 1-2, 1-3, 1-5, 1-7, 1-9, Spiro as shown in Formula 1 Compounds in which only one heteroaryl group is substituted in the fluorene thioxanthene skeleton have superior characteristics in terms of driving voltage, efficiency, and lifetime in the organic light emitting device as compared with compounds having two or more substituent substituents.

Example 1-9 according to an exemplary embodiment of the present specification According to FIG. 3 showing the 3D structure of the compound of Formula E9, it may be confirmed that the molecules of the compounds have a horizontal structure, and Comparative Example 1-5 Formula ET According to FIG. 4, which shows the 3D structure of the -1-E compound, the A-axis and the B-axis are substantially perpendicular to each other, indicating that the molecules deviate greatly from the horizontal structure.

Accordingly, it can be seen that the heterocyclic compound according to one embodiment of the present specification has a more horizontal structure according to the orientation difference on the 3D structure of the molecule.

Accordingly, compounds having only one heteroaryl group in the spiro fluorene thioxanthene skeleton as shown in Formula 1 of Examples 1-1 to 1-18 have a stronger horizontal structural tendency than molecules having at least two substituents. Due to the increased electron mobility, the driving voltage is low in the organic light emitting device, it has high efficiency and long life.

In addition, when comparing Examples 1-1 to 1-18 and Comparative Examples 1-4 and 1-6, the structure of Formula 1 containing spiro fluorene thioxanthene is organic light-emitting than the structure containing a spiro fluorene group It can be seen that the device exhibits excellent characteristics.

Experimental Example 2

Compound synthesized in the Preparation Example (Chemical Formulas E1 to E18), and Compounds Used in Comparative Example 1-2 (Compound ET-1-B), Compounds Used in Comparative Example 1-8 ([Formula ET-1-H]), the HOMO energy and LUMO energy values of the compound ([Formula ET-1-J]) used in Comparative Example 1-10 were measured, and are shown in Table 2 below.

Specifically, the HOMO level is a compound synthesized in the preparation example, and the compound used in the comparative example is deposited to a thickness of 100nm using an atmospheric photoelectron spectroscopy (RIKEN KEIKI Co., Ltd .: AC3) The measured sample was irradiated with UV of 10 nW at 0.05 eV intervals, and the amount of electrons was measured to measure the HOMO level, and the LUMO level was calculated as a wavelength value measured through photoluminescence (PL).

compound HOMO (eV) LUMO (eV) Preparation Example 1 (E1) 6.21 2.71 Preparation Example 2 (E2) 6.17 2.93 Preparation Example 3 (E3) 6.19 2.68 Preparation Example 4 (E4) 6.07 2.67 Preparation Example 5 (E5) 6.11 3.02 Preparation Example 6 (E6) 6.24 2.88 Preparation Example 7 (E7) 6.02 3.15 Preparation Example 8 (E8) 6.23 2.93 Preparation Example 9 (E9) 6.02 3.20 Preparation Example 10 (E10) 6.03 3.07 Preparation Example 11 (E11) 6.22 3.22 Preparation Example 12 (E12) 6.23 3.14 Preparation Example 13 (E13) 6.06 2.86 Preparation Example 14 (E14) 6.18 2.88 Preparation Example 15 (E15) 6.32 2.99 Preparation Example 16 (E16) 6.17 2.77 Preparation Example 17 (E18) 6.27 3.02 Comparative Example 1-2 (ET-1-B) 5.92 2.76 Comparative Example 1-8 (ET-1-H) 5.90 2.89 Comparative Example 1-10 (ET-1-J) 5.70 2.87

As shown in Table 2, in the case of the E1 to E18 compounds used in Examples 1-1 to 1-18, respectively, the HOMO energy is measured as 6.02eV to 6.32eV, so as the energy level deepens the electron mobility It was confirmed that the high characteristics can exhibit excellent characteristics in terms of driving voltage, efficiency and lifetime when used in the organic light emitting device. On the other hand, in the case of the compounds used in Comparative Examples 1-2, 1-8, 1-10, it was confirmed that the HOMO energy was measured to be lower than the Example from 5.70 eV to 5.92 eV.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron transport layer
A: direction of one axis B: direction of another axis

Claims (9)

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

In Chemical Formula 1,
One of R ₁ to R ₃ is a functional group represented by the formula (2), the other is hydrogen,
[Formula 2]
-L-Ar ₁
In Chemical Formula 2,
L is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of O, N, Si and S,
Ar ₁ is any one of the following Formulas 3 to 8,
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 3 to 8,
X ₁ to X ₉ and X ₁₂ to X ₁₅ are each independently N, or CH,
X ₁₀ and X ₁₁ are N,
Y ₁ to Y ₈ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _2-60 heteroaryl containing one or more heteroatoms each independently selected from the group consisting of N, O, and S.
The method of claim 1,
Formula 1 is represented by the following formula 1-1, formula 1-2 or formula 1-3,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1, 1-2, and 1-3,
L and Ar ₁ are as defined in claim ₁ above.
The method of claim 1,
In Formulas 3 to 8, Y ₁ to Y ₈ are the same as or different from each other, and each independently hydrogen, phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenylnaphthyl, pyridinyl, pyri Divinylphenyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuranylphenyl, dibenzothiophenylphenyl or any one selected from the group consisting of
compound:

. The method of claim 1,
Wherein Ar ₁ is any one selected from the group consisting of the following functional groups:

.
The method of claim 1,
Wherein L is any one selected from the group consisting of a direct bond or a functional group:

.
The method of claim 1,
The compound is any one selected from the group consisting of the following compounds:

.
delete A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 7. That is, an organic light emitting device.
The method of claim 8,
The organic material layer containing the compound is an electron injection layer; Electron transport layer; Or an organic light emitting element, which is a layer for simultaneously performing electron injection and electron transport.

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