WO2019168320A1

WO2019168320A1 - Compound and organic light emitting diode comprising same

Info

Publication number: WO2019168320A1
Application number: PCT/KR2019/002316
Authority: WO
Inventors: 차용범; 정민우; 홍성길; 서상덕; 이재구
Original assignee: 주식회사 엘지화학
Priority date: 2018-02-28
Filing date: 2019-02-26
Publication date: 2019-09-06
Also published as: KR102255556B1; CN111201214A; CN111201214B; KR20190103773A

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light emitting diode comprising same.

Description

Compound and organic light emitting device comprising same

The present invention relates to a compound represented by Formula 1 and an organic light emitting device including the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0024609 filed with the Korea Intellectual Property Office on February 28, 2018, the entire contents of which are incorporated herein.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer has a multi-layered structure composed of different materials in order to increase efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected at the anode, electrons are injected into the organic material layer at the cathode, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.

There is a continuing need for the development of new materials for such organic light emitting devices.

The present specification provides a compound and an organic light emitting device including the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted fluorene ring,

R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

One of A and B is -L1-Ar1, the other is -L2-NAr2Ar3,

L 1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L2 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C24 aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer of 0-6, and when a is 2 or more, R <3> is same or different from each other.

In addition, an exemplary embodiment of the present specification is an organic light emitting device including a cathode, an anode, and a light emitting layer provided between the cathode and the anode, wherein the compound is included in the organic material layer provided between the anode and the light emitting layer. Provided is an organic light emitting device.

In some embodiments, the organic light emitting device including the compound of the present invention may be improved in efficiency.

In some embodiments, the organic light emitting device including the compound of the present invention may have a low driving voltage.

In some embodiments, the organic light emitting device including the compound of the present invention may have improved lifetime characteristics.

FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 11, a light emitting layer 6, and a cathode 10.

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

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

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

Examples of the substituents are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Nitrile group; Nitro group; Hydroxyl group; An alkyl group; Aralkyl group; An alkoxy group; Alkenyl groups; Aryloxy group; Aryl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of a heteroaryl group, or two or more substituents of the substituents selected from the group means substituted or unsubstituted. Examples of the group to which three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, a heteroaryl group substituted with an aryl group substituted with a heteroaryl group, and the like.

In one embodiment of the present specification, the term "substituted or unsubstituted" is deuterium; An alkyl group; Aralkyl group; And it is substituted or unsubstituted with one or more groups selected from the group consisting of aryl groups, or substituted or unsubstituted with a group to which two or more groups from the substituents selected from the group connected.

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

In the present specification, the alkoxy group means a group in which an alkyl group is bonded to an oxygen atom, and the carbon number is not particularly limited, but is preferably 1 to 20. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like.

In the present specification, the aryloxy group means a group in which an aryl group is bonded to an oxygen atom, and carbon number is not particularly limited, but is preferably 6 to 40. According to an exemplary embodiment, the aryloxy group has 6 to 30 carbon atoms. Specific examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, 3-biphenyloxy group, 1- Naphthyloxy group, 2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryl jade There is a period.

In the present specification, the alkyl group means a straight or branched hydrocarbon group, and the carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, octyl, n-octyl , tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl , 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cyclic alkyl group in the alkyl group is referred to as a cycloalkyl group. Although carbon number of a cycloalkyl group is not specifically limited, It is preferable that it is 3-60. According to an exemplary 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 is not limited thereto.

In the present specification, the alkenyl group represents a straight-chain or pulverized unsaturated hydrocarbon group including a carbon-carbon double bond, and the carbon number is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to an exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples include, but are not limited to, ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl.

In the present specification, the aralkenyl group means an alkenyl group substituted with an aryl group.

In the present specification, an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated. Although carbon number is not specifically limited, It is preferable that it is C6-C60, It may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 40 carbon atoms. 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. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a terphenyl group, but are not limited thereto. As said polycyclic aryl group, a naphthyl group, anthracenyl group, a phenanthrenyl group, a perrylenyl group, a fluoranthenyl group, a triphenylenyl group, a penalenyl group, a pyrenyl group, a tetrasenyl group, a chrysenyl group, a pentaxenyl group , Fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

As the substituted fluorenyl group

,

,

,

.

And

Etc., but is not limited thereto.

In the present specification, the heteroaryl group is an aromatic ring group containing at least one of N, O, and S as a hetero atom, and carbon number is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group are thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, tria Genyl group, triazolyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, Pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl , Benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthrolinyl group (phenanthrolinyl), thiazolyl Group, isooxazolyl group, oxadiazolyl group, Oh thiadiazolyl group, but include benzothiazolyl group, a page group, and a phenothiazine noksa possess thiazinyl group, but are not limited thereto.

The aryl group described above may be applied to the aryl group in the aralkyl group and the aryloxy group.

In the present specification, the arylene group means a divalent aryl group, and the description about the aryl group described above may be applied to the arylene group.

An exemplary embodiment of the present invention provides a compound represented by Chemical Formula 1.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, or combine with each other to form a substituted or unsubstituted fluorene ring.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or combine with each other to form a substituted or unsubstituted fluorene ring.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-A to 1-C.

[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

In Chemical Formulas 1-A to 1-C,

The definitions of R 3, A, B and a are the same as defined in the formula (1).

In one embodiment of the present specification, R3 is hydrogen or deuterium.

In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2.

[Formula 2]

In Chemical Formula 2,

Definitions of R1 to R3, L1, L2, Ar1 to Ar3 and a are as defined in the formula (1).

In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

In one embodiment of the present specification, -L1-Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, -L1-Ar1 is an aryl group unsubstituted or substituted with an aryl group; Or a heteroaryl group.

In one embodiment of the present specification, -L1-Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In one embodiment of the present specification, -L1-Ar1 is a phenyl group; Biphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In one embodiment of the present specification, -L1-Ar1 is a phenyl group; Biphenyl group; Naphthyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or 9,9-dimethylfluorenyl group.

In one embodiment of the present specification, L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L1 is a direct bond; Or an arylene group having 6 to 12 carbon atoms unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, L1 is a direct bond; Or a phenylene group.

In one embodiment of the present specification, L1 is a direct bond; Or p-phenylene group.

In one embodiment of the present specification, Ar1 is an aryl group which is unsubstituted or substituted with an aryl group; Or a heteroaryl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted methyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Naphthyl group; Dibenzofuranyl group; Dibenzothiophenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Or a 9,9'-spirobifluorenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group; [1,1'-biphenyl] -4-yl group; 2-naphthyl group; Dibenzofuranyl group; Or 9,9-dimethylfluorenyl group.

In one embodiment of the present specification, L2 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L2 is a direct bond; Or an arylene group having 6 to 12 carbon atoms unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, L2 is a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L2 is a direct bond.

In one embodiment of the present specification, L2 is a phenylene group.

In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 6 to 24 carbon atoms.

In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently an aryl group having 6 to 18 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group.

In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Or a 9,9'-spirobifluorenyl group.

In one embodiment of the present specification, a is 0.

In the present specification, the meaning that a is 0 means that none of R 3 is substituted in the central fluorene structure.

In one embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by Formula 3 is any one selected from the following compounds.

According to an exemplary embodiment of the present specification, the compound of Formula 1 may be prepared according to the following formula (1). The method for preparing the compound of Formula 1 is not limited to the following Formula 1, and may be prepared by a production method known in the art. In one embodiment, some steps of the manufacturing method of Formula 1 may be performed by another method.

[Formula 1]

In Formula 1, A and B are as defined in formula (1).

In addition, the present specification provides an organic light emitting device including the compound represented by Formula 1.

In an exemplary embodiment of the present specification, an organic light emitting device including a cathode, an anode, and a light emitting layer provided between the cathode and the anode, wherein the compound of Formula 1 is disposed on the organic material layer provided between the anode and the light emitting layer. It provides an organic light emitting device to be included.

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

In one embodiment of the present specification, the compound of Formula 1 is included in at least one layer of a hole injection layer, a hole transport layer and a hole transport and injection at the same time provided between the anode and the light emitting layer.

In one embodiment of the present specification, the compound of Formula 1 is included in an electron blocking layer provided between the anode and the light emitting layer.

In one embodiment of the present specification, the organic light emitting diode includes at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer between the cathode and the light emitting layer.

In one embodiment of the present specification, the organic light emitting device further includes a layer for simultaneously injecting and transporting electrons between the cathode and the light emitting layer.

In one embodiment of the present specification, the organic light emitting diode further includes a hole blocking layer between the cathode and the light emitting layer.

In one embodiment of the present specification, the compound of Formula 1 is included in an electron blocking layer provided between the anode and the light emitting layer, and further includes a hole transport layer between the electron blocking layer and the anode.

In one embodiment of the present specification, the compound of Formula 1 is included in an electron blocking layer provided between the anode and the light emitting layer, and further includes a hole injection layer between the electron blocking layer and the anode.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a normal structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having 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 diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.

FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 11, a light emitting layer 6, and a cathode 10. In one embodiment, the organic layer 11 includes a hole transport layer, a hole injection layer, at least one layer of a hole transport and injection at the same time, and an electron blocking layer, the hole transport layer, hole injection layer, hole transport and At least one of the layer to be injected at the same time and the electron blocking layer includes the compound described above. In one embodiment, the compound described above is included in the electron blocking layer.

2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8. , An example of an organic light emitting element comprising an electron injection layer 9 and a cathode 10 is shown. In one embodiment, the compound described above is included in the electron blocking layer. In one embodiment, the compound described above is included in the hole injection layer. In one embodiment, the compound described above is included in the hole transport layer.

The organic light emitting device of the present specification 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 of the present specification, that is, the compound of Formula 1.

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 of the present specification may be manufactured by sequentially stacking a cathode, an organic material layer and an anode on a substrate, or sequentially stacking an anode, an organic material layer and a cathode on a substrate. At this time, by using a physical vapor deposition (PVD, physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or alloys thereof on the substrate It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode 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 of Formula 1 may be formed of 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 such a 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. However, the manufacturing method is not limited thereto.

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

The cathode material is generally a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode materials 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 an electrode. The hole injection material has a capability of transporting holes to a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect to a light emitting layer or a light emitting material, and is produced in a light emitting layer. The compound which prevents the movement of an exciton to an electron injection layer or an electron injection material, and is excellent in thin film formation ability is preferable. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode 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 substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. In one embodiment, the hole injection layer is provided between the anode and the hole transport layer.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As the hole transporting material, a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together. In one embodiment, the hole transport layer is provided between the hole injection layer and the light emitting layer. In one embodiment, the hole transport layer is provided between the hole injection layer and the electron blocking layer.

The electron blocking layer is a layer for preventing excess electrons passing through the light emitting layer from moving toward the hole transport layer. The electron blocking material is preferably a material having a lower Unoccupied Molecular Orbital (LUMO) level than the hole transport layer, and may be selected as an appropriate material in consideration of the energy level of the surrounding layer. In one embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto. In one embodiment, the electron blocking layer comprises a compound represented by the above formula (1).

The emission layer is a layer that emits light while being converted into photons by combining holes and electrons. 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 of the luminescent material include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material.

The host material of the light emitting layer may be a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but is not limited thereto.

The dopant material of the light emitting layer includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamine group, and the styrylamine compound may be substituted or unsubstituted. A compound in which at least one arylvinyl group is substituted in the substituted arylamine may be used, and the styrylamine compound may have a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamine group. May be 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 hole blocking layer serves to prevent holes from flowing into the cathode through the light emitting layer in the driving process of the organic light emitting diode. As the hole blocking material, it is preferable to use a material having a very high Occupied Molecular Orbital (HOMO) level. Specifically, the hole blocking material includes TPBi, BCP, CBP, PBD, PTCBI, BPhen, and the like, but is not limited thereto. In one embodiment, the hole blocking layer is 2- (3 '-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl] -3-yl) -4 , 6-diphenyl-1,3,5-triazine.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples of the electron transporting material 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 lithium, cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection material has the ability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, Moreover, the compound excellent in the thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidenemethane, 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 specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.

Hereinafter, the manufacturing method and characteristics of the compound of the present invention and the organic light emitting device including the same for the detailed understanding of the present invention.

<화합물 A의 제조예><Preparation Example of Compound A>

<화합물 B의 제조예><Preparation Example of Compound B>

<화합물 C의 제조예><Preparation Example of Compound C>

<화합물 D의 제조예><Preparation Example of Compound D>

<제조예 1><Manufacture example 1>

250 ml of xylene is placed in a 500 ml round bottom flask in a nitrogen atmosphere, compound A (7.50 g, 17.52 mmol), di ([1,1'-biphenyl] -4-yl) amine (6.47 g, 20.15 mmol) and sodium t-butoxide (2.19 g, 22.78 mmol) was added, bis (tri-t-butylphosphine) palladium (0.09 g, 0.18 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. After cooling to room temperature to remove the base by filtering, xylene was concentrated under reduced pressure completely, and recrystallized from 260 ml of ethyl acetate to give the compound 1 (7.62 g, 61% yield). (MS [M + H] ⁺ = 714)

<제조예 2><Manufacture example 2>

Add 250 ml of xylene to a 500 ml round bottom flask in nitrogen atmosphere and place Compound A (7.5 g, 17.52 mmol), N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-flu Orene-2-amine (7.27 g, 20.15 mmol) and sodium t-butoxide (2.19 g, 22.78 mmol) are added, bis (tri-t-butylphosphine) palladium (0.09 g, 0.18 mmol) is added. Heat stirring for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, xylene was completely concentrated under reduced pressure and recrystallized from 220 ml of ethyl acetate to obtain Compound 2 (6.17 g, 47% yield). (MS [M + H] ⁺ = 754)

<제조예 3><Manufacture example 3>

Compound A (7.5 g, 15.79 mmol) and (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) in a 500 ml round bottom flask under nitrogen atmosphere ) Amino) phenyl) boronic acid (8.35, 17.37mmol) was dissolved completely in 220ml of tetrahydrofuran, then 2M aqueous potassium carbonate solution (110ml) was added, and tetrakis- (triphenylphosphine) palladium (0.55g, 0.47mmol) ) Was added and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 3 (10.37 g, yield 79%).

MS [M + H] ⁺ = 830

<제조예 4><Manufacture example 4>

Compound A (7.5 g, 17.52 mmol) and (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid (8.5 g, 19.28 mmol) in a 500 ml round bottom flask under nitrogen atmosphere ) Was completely dissolved in 220 ml of tetrahydrofuran, 2 M aqueous potassium carbonate solution (110 ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (0.76 g, 0.66 mmol) was added thereto, followed by stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 ml of tetrahydrofuran to prepare compound 4 (11.29 g, yield 82%). (MS [M + H] ⁺ = 790)

<제조예 5>Production Example 5

250 ml of xylene was added to a 500 ml round bottom flask in a nitrogen atmosphere. Compound B (7.5 g, 15.76 mmol), N-phenyl- [1,1'-biphenyl] -4-amine (4.44 g, 18.12 mmol) and sodium t -Butoxide (1.97g, 20.48mmol) was added, bis (tri-t-butylphosphine) palladium (0.08g, 0.16mmol) was added thereto, and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, xylene was completely concentrated under reduced pressure and recrystallized from 260 ml of ethyl acetate to obtain Compound 5 (5.56 g, yield 51%). (MS [M + H] ⁺ = 686)

<제조예 6><Manufacture example 6>

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound B (7.5 g, 17.52 mmol) and (4- (diphenylamino) phenyl) boronic acid (5.49 g, 19.28 mmol) were completely dissolved in 220 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution. (110ml) was added, tetrakis- (triphenylphosphine) palladium (0.61g, 0.53mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain compound 6 (4.82 g, yield 40%). (MS [M + H] ⁺ = 686)

<제조예 7><Manufacture example 7>

Compound C (11.5 g, 17.11 mmol) and dibenzo [b, d] furan-4-ylboronic acid (3.99 g, 18.82 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere, followed by 2M carbonate. Aqueous potassium solution (120 ml) was added, tetrakis- (triphenylphosphine) palladium (0.59 g, 0.51 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of ethyl acetate to obtain compound 7 (8.05 g, yield 59%). (MS [M + H] ⁺ = 804)

<제조예 8><Manufacture example 8>

Dissolve Compound C (11.5 g, 17.11 mmol) and dibenzo [b, d] thiophen-2-ylboronic acid (4.29 g, 18.82 mmol) in 220 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere. Aqueous potassium carbonate solution (110ml) was added, tetrakis- (triphenylphosphine) palladium (0.59g, 0.51mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 ml of ethyl acetate to obtain compound 8 (7.29 g, yield 52%). (MS [M + H] ⁺ = 820)

<제조예 9><Manufacture example 9>

Dissolve Compound C (11.5 g, 17.11 mmol) and [1,1'-biphenyl] -4-ylboronic acid (3.73 g, 18.82 mmol) in 220 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere. Aqueous potassium carbonate solution (110ml) was added, tetrakis- (triphenylphosphine) palladium (0.59g, 0.51mmol) was added thereto, and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain compound 9 (9.89 g, yield 70%). (MS [M + H] ⁺ = 790)

<제조예 10>Production Example 10

Compound C (11.5 g, 17.11 mmol) and naphthalene-2-ylboronic acid (3.24 g, 18.82 mmol) were completely dissolved in 260 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, and then 2 M aqueous potassium carbonate solution (130 ml) was added. Tetrakis- (triphenylphosphine) palladium (0.59g, 0.51mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to obtain compound 10 (8.35 g, yield 64%). (MS [M + H] ⁺ = 764)

<제조예 11>Production Example 11

Dissolve Compound D (11.5 g, 19.39 mmol) and [1,1'-biphenyl] 4-ylboronic acid (4.22 g, 21.33 mmol) in 300 ml of tetrahydrofuran in a 500 ml round-bottom flask in nitrogen atmosphere Potassium aqueous solution (150ml) was added, tetrakis- (triphenylphosphine) palladium (0.67g, 0.58mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 ml of tetrahydrofuran to prepare compound 11 (9.64 g, yield 70%). (MS [M + H] ⁺ = 712)

<실시예 1-1><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. In this case, Fischer Co. product was used as the detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as the 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 compound of the following compound HI1 and the following compound HI2 was thermally vacuum-deposited on the thus prepared ITO transparent electrode (anode) at a molar ratio of 98: 2 to form a hole injection layer (thickness 100 kPa). A compound represented by Chemical Formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer (thickness 1150 Pa). Subsequently, Compound 1 of Preparation Example 1 was vacuum deposited on the hole transport layer to form an electron blocking layer (thickness of 50 GPa). Subsequently, the compound represented by the following formula BH and the compound represented by the following formula BD were vacuum deposited on the electron blocking layer at a weight ratio of 50: 1 to form a light emitting layer (thickness of 200 kPa). A compound represented by the following Chemical Formula HB1 was vacuum deposited on the emission layer to form a hole blocking layer (thickness of 50 kPa). Subsequently, the compound represented by the following formula ET1 and the compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form an electron injection and transport layer (thickness: 30 GPa). 12 주입 of lithium fluoride (LiF) and 1,000 Å of aluminum were deposited on the electron injection and transport layer sequentially to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4Å / sec or more and 0.7Å / sec, and the lithium fluoride of the cathode was 0.3Å / sec, and the aluminum was maintained at the deposition rate of 2Å / sec. The organic light emitting device was manufactured by maintaining 2 × 10 ⁻⁷ torr or more and 5 × 10 ⁻⁶ torr or less.

<실시예 1-2 내지 실시예 1-11><Example 1-2 to Example 1-11>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of the compound 1 of Preparation Example 1.

<비교예 1-1 내지 1-6><Comparative Examples 1-1 to 1-6>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of the compound 1 of Preparation Example 1. The compounds of EB1, EB2, EB3, EB4, EB5 and EB6 used in Table 1 below are as follows.

<실험예 1>Experimental Example 1

When the current was applied to the organic light emitting diodes manufactured in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).

	화합물(전자차단층)Compound (electron blocking layer)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	색좌표(x,y)Color coordinates (x, y)	T95(hr)T95 (hr)
실시예 1-1Example 1-1	1One	4.114.11	6.316.31	(0.140, 0.045)(0.140, 0.045)	290290
실시예 1-2Example 1-2	22	4.134.13	6.336.33	(0.141, 0.045)(0.141, 0.045)	280280
실시예 1-3Example 1-3	33	4.154.15	6.376.37	(0.140, 0.046)(0.140, 0.046)	285285
실시예 1-4Example 1-4	44	4.174.17	6.386.38	(0.141, 0.047)(0.141, 0.047)	275275
실시예 1-5Example 1-5	55	4.164.16	6.396.39	(0.141, 0.046)(0.141, 0.046)	280280
실시예 1-6Example 1-6	66	4.284.28	6.316.31	(0.141, 0.047)(0.141, 0.047)	285285
실시예 1-7Example 1-7	77	4.094.09	6.466.46	(0.141, 0.046)(0.141, 0.046)	260260
실시예 1-8Example 1-8	88	4.074.07	6.556.55	(0.140, 0.047)(0.140, 0.047)	255255
실시예 1-9Example 1-9	99	4.064.06	6.456.45	(0.142, 0.047)(0.142, 0.047)	265265
실시예 1-10Example 1-10	1010	4.034.03	6.456.45	(0.143, 0.048)(0.143, 0.048)	260260
실시예 1-11Example 1-11	1111	4.084.08	6.536.53	(0.142, 0.045)(0.142, 0.045)	250250
비교예 1-1Comparative Example 1-1	EB1EB1	4.734.73	5.795.79	(0.142, 0.047)(0.142, 0.047)	160160
비교예 1-2Comparative Example 1-2	EB2EB2	5.065.06	5.505.50	(0.143, 0.043)(0.143, 0.043)	220220
비교예 1-3Comparative Example 1-3	EB3EB3	4.564.56	5.915.91	(0.143, 0.042)(0.143, 0.042)	135135
비교예 1-4Comparative Example 1-4	EB4EB4	5.315.31	5.265.26	(0.145, 0.044)(0.145, 0.044)	210210
비교예 1-5Comparative Example 1-5	EB5EB5	4.464.46	6.026.02	(0.142, 0.047)(0.142, 0.047)	180180
비교예 1-6Comparative Example 1-6	EB6EB6	4.494.49	6.036.03	(0.143, 0.043)(0.143, 0.043)	175175

As shown in Table 1, the organic light emitting device using the compound of the present invention as an electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.

In Examples 1-1 to 1-6, when the amine group was substituted at the carbon position 2 of the fluorene-based core and the aryl group or the heteroaryl group connected at the carbon position 4 was used as the electron blocking layer, the device was low voltage and high efficiency. And long life.

In Examples 1-7 to 1-11, when the amine group was substituted at the carbon position of the fluorene core and the aryl group or the heteroaryl group connected to the carbon position was used as the electron blocking layer, the device was low voltage and high efficiency. And long life.

Comparing Examples 1-2 and 1-3 with Examples, the device (Comparative Example 1-2) using a material having an amine group bonded to the carbon position 2 of the fluorene core (Comparative Example 1-2) has a strong service life. It can be seen that the device (Comparative Examples 1-3) using a material having an amine group bonded to the carbon position 4 of the fluorene core has advantages in efficiency.

If the substituent is further connected to the 2 or 4 carbon position of the fluorene and the amine group is substituted only at the 2 or 4 carbon position of the fluorene-based core, the molecular structure is distorted. As a result, the stability of the device is increased, thereby increasing the life of the device and increasing the efficiency of the device.

All of the compounds used as the electron blocking layer in Examples 1-1 to 1-6 and Comparative Examples 1-2 have an amine group substituted at the carbon position 2 of fluorene. However, the device of Examples 1-1 to 1-6 using a compound having an aryl group or a heteroaryl group at position 4 of fluorene, Comparative Example 1 using a compound having no substituent at position 4 of fluorene Compared with the device of -2, the driving voltage is low and the efficiency is high, and the life is much improved.

The compounds used as the electron blocking layer in Examples 1-7 to 1-11 and Comparative Examples 1-3 all have an amine group substituted at the carbon position 4 of fluorene. However, the device of Examples 1-7 to 1-11 using a compound having an aryl group or a heteroaryl group at position 2 of fluorene is Comparative Example 1- using a compound having no substituent at position 2 of fluorene. Compared with the device of 3, the driving voltage is lower and the life is long, and the efficiency is much improved.

Compound EB4 does not have a twisted structure like the compounds of the present invention. Accordingly, the device using the material in which the amine group is bonded to the carbon position 2 of the fluorene core and the substituent is connected to the carbon position 7 (Comparative Example 1-4) is a material having an amine group bonded to the carbon position 2 of the fluorene core The results showed that the voltage and efficiency characteristics were reduced compared to the devices used (Comparative Examples 1-2).

Examples 1-5, 6, and 11 wherein R1 and R2 are bonded to form a fluorene ring as an electron blocking layer A comparison using the structure where R1 and R2 are bonded to form a benzofluorene ring as an electron blocking layer Compared with Examples 1-5 and 1-6, the lifespan was significantly improved. When R1 and R2 combine to form a benzofluorene ring, the core of the compound becomes bulky, affecting the flow of electrons, causing a voltage increase and a decrease in efficiency, and a lifetime also decreases.

As shown in Table 1, the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.

Although the preferred embodiment of the present invention (electron blocking layer) has been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention. It belongs to the scope of the invention.

1: substrate

2: anode

3: hole injection layer

4: hole transport layer

5: electron blocking layer

6: light emitting layer

7: hole blocking layer

8: electron transport layer

9: electron injection layer

10: cathode

11: organic layer

Claims

Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted fluorene ring,

R3 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

One of A and B is -L1-Ar1, the other is -L2-NAr2Ar3,

L 1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L2 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer of 0-6, and when a is 2 or more, R <3> is same or different from each other.
The compound of claim 1, wherein Formula 1 is represented by Formula 2 below:

[Formula 2]

In Chemical Formula 2,

Definitions of R1 to R3, L1, L2, Ar1 to Ar3 and a are as defined in the formula (1).
The compound of claim 1, wherein Formula 1 is represented by Formula 3:

[Formula 3]

In Chemical Formula 3,

Definitions of R1 to R3, L1, L2, Ar1 to Ar3 and a are as defined in the formula (1).
The method according to claim 1, wherein -L1-Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
The method according to claim 1, Ar2 and Ar3 are the same as or different from each other, each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
The compound of claim 2, wherein the compound of Formula 2 is any one selected from the following compounds:

.
The compound of claim 3, wherein the compound of Formula 3 is any one selected from the following compounds:

.
An organic light emitting device comprising a cathode, an anode, and a light emitting layer provided between the cathode and the anode, wherein the compound according to any one of claims 1 to 7 is included in the organic material layer provided between the anode and the light emitting layer Phosphorescent organic light-emitting device.
The organic light-emitting device as claimed in claim 8, wherein the compound is included in at least one of a hole injection layer, a hole transport layer, and a layer for simultaneously transporting and injecting holes provided between the anode and the light emitting layer.
The organic light emitting device of claim 8, wherein the compound is included in an electron blocking layer provided between the anode and the light emitting layer.