KR20190103790A - Organic light emitting device - Google Patents

Abstract

According to the present specification, provided is an organic light emitting device comprising a first electrode, a second electrode provided to face the first electrode, and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode. The first organic material layer includes a compound represented by chemical formula 1; and the second organic material layer includes a compound represented by chemical formula 2 or chemical formula 3. Therefore, the organic light emitting device of the present invention can have low driving voltage, high luminous efficiency, or long lifespan.

Description

Organic light emitting element {ORGANIC LIGHT EMITTING DEVICE}

The present application relates to an organic light emitting device.

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. 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.

Conventionally, aromatic diamine derivatives and aromatic condensed ring diamine derivatives have been known as hole transport materials used in organic EL devices. However, in this case, since the applied voltage is mostly high, problems such as deterioration of device life and large power consumption have arisen. As a solution of the above problem, a method of doping an electron-accepting compound such as Lewis acid or using a hole injection layer of an organic EL device has been proposed. However, the above method has shown that there is a limitation in the injection and transport of holes, and thus the effect of low voltage, high efficiency, and long life can be achieved by the material combination between the hole transport layer or the hole control layer, or the material of the hole transport layer and the multilayer hole control layer. I tried to draw. In general, the hole transport layer aromatics were substituted tertiary amines, and the device characteristics found in the combination group of the materials have shown various results. Therefore, there is a continuous demand for the development of new materials for improving device characteristics due to hole transport and carrier control.

Korean Unexamined Patent Publication No. 10-2017-0036641

The present application is to provide an organic light emitting device.

The present application is the first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode.

The first organic material layer includes a compound represented by Formula 1,

The second organic material layer is an organic light emitting device comprising a compound represented by the following formula (2) or (3):

 [Formula 1]

In Chemical Formula 1,

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

Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 to R4 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

b to d are each independently an integer of 0 to 4,

a is an integer of 0 to 3,

when a to d are each independently 2 or more, the substituents in parentheses are the same as or different from each other,

[Formula 2]

In Chemical Formula 2,

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

Ar3 and Ar4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L2, Ar3 and Ar4 may combine with each other adjacent groups to form a ring,

R5 to R8 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

f to h are each independently an integer of 0 to 4,

e is an integer from 0 to 3,

when e to h are each independently 2 or more, the substituents in parentheses are the same as or different from each other,

[Formula 3]

In Chemical Formula 3,

L3 to L5 are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar5 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R9 to R12 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

i, j and l are each independently an integer of 0 to 4,

k is an integer from 0 to 3,

When i to l are each independently 2 or more, the substituents in parentheses are the same as or different from each other.

The organic light emitting device using the compound according to the exemplary embodiment of the present application is capable of low driving voltage, high luminous efficiency or long life.

In addition, the compound according to the exemplary embodiment of the present application may be used as a hole transport material or a hole control material.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows a substrate 1, an anode 2, a first hole control layer 5, a second hole control layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked An example of the organic light emitting element is shown.

Hereinafter, this specification is demonstrated in detail.

The present application is the first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, wherein the first organic material layer includes a compound represented by Formula 1 below, and the second organic material layer is represented by Formula 2 or It provides an organic light emitting device comprising a compound represented by the formula (3).

According to an exemplary embodiment of the present application, the compound represented by Formula 1 has the advantage of controlling the triplet energy by having the core structure as described above, and when used as a compound of the host, respectively, long life and high efficiency Can exhibit characteristics.

Examples of substituents herein 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; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. 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 and can be interpreted as a substituent to which two phenyl groups are linked.

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

In this specification, although carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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. Specific examples 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-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 60 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. Do not.

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-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, 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. 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, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

Etc., but is not limited thereto.

In the present specification, the heterocyclic 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. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. 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, benzimidazole 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 heterocyclic 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. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. 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, benzimidazole 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 one embodiment of the present application, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-1 to 1-4,

The definitions of L1, Ar1, Ar2, R1 to R4 and a to d are the same as those of Chemical Formula 1.

In one embodiment of the present application, Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Chemical Formulas 2-1 to 2-4,

The definitions of L 2, Ar 3, Ar 4, R 5 to R 8, and e to h are the same as in Chemical Formula 2.

In one embodiment of the present application, Chemical Formula 3 is represented by any one of the following Chemical Formulas 3-1 to 3-4.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Chemical Formulas 3-1 to 3-4,

Definitions of L3 to L5, Ar5, R9 to R12 and i to l are the same as in Chemical Formula 3.

In one embodiment of the present application, the L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present application, the L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present application, the L1 is a direct bond; Or a phenylene group, a biphenylene group, a terphenylene group, a 1-naphthylenyl group, or a 2-naphthylenyl group.

In one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Silyl groups substituted with an aryl group having 6 to 30 carbon atoms; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Fluorene group; Phenanthrene group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group.

In one embodiment of the present application, R1 to R4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present application, R1 to R4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present application, R1 to R4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present application, R1 to R4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present application, R1 to R4 are each independently hydrogen; Or deuterium.

In one embodiment of the present application, L2 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present application, L2 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present application, L2 is a direct bond; Or a phenylene group, a biphenylene group, a terphenylene group, a 1-naphthylenyl group, or a 2-naphthylenyl group.

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

In one embodiment of the present application, Ar3 and Ar4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present application, Ar3 and Ar4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present application, Ar3 and Ar4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present application, R5 to R8 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present application, R5 to R8 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present application, R5 to R8 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present application, R5 to R8 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present application, R5 to R8 are each independently hydrogen; Or deuterium.

In one embodiment of the present application, the L3 to L5 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present application, the L3 to L5 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present application, the L3 to L5 is a direct bond; It is a phenylene group or a biphenylene group.

In one embodiment of the present application, Ar5 is each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present application, Ar5 is each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present application, Ar5 is each independently hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Fluorene group; Phenanthrene group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group.

In an exemplary embodiment of the present application, R9 to R12 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In an exemplary embodiment of the present application, R9 to R12 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In an exemplary embodiment of the present application, R9 to R12 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present application, R9 to R12 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present application, R9 to R12 are each independently hydrogen; Or deuterium.

In addition, in an exemplary embodiment of the present application, Chemical Formula 1 is selected from the following structural formulas.

In addition, in an exemplary embodiment of the present application, Chemical Formula 2 is selected from the following structural formulas.

In addition, in an exemplary embodiment of the present application, Chemical Formula 3 is selected from the following structural formulas.

In the present application, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

In the present application, when a part "includes" a certain component, it means that it may further include other components, without excluding other components unless specifically stated otherwise.

The first and second organic material layers of the organic light emitting device of the present application may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the first organic material layer of the present application may be composed of 1 to 3 layers. In addition, the organic light emitting device of the present application may have a structure including a hole injection layer, a light emitting layer, an electron transport layer and the like as an organic material layer. However, the structure of the organic light emitting diode is not limited thereto, and may include more or fewer organic layers.

In one embodiment of the present application, the organic light emitting device is a hole injection layer, a hole transport layer. It further comprises one or two or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

In one embodiment of the present application, the organic light emitting device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more first and second organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein the two or more first and second organic material layers are represented by Chemical Formula 1, respectively. The compound represented and the compound represented by the said Formula (2) or 3 are included.

According to an exemplary embodiment of the present application, the first organic material layer includes a first hole control layer, the second organic material layer includes a second hole control layer, and the first hole control layer is represented by Formula 1 It includes a compound, the second hole control layer may include a compound represented by the formula (2) or (3).

In an exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group, or a benzocarbazole group in addition to the organic material layer including the compound.

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

1 illustrates a structure of a general organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.

2 shows a substrate 1, an anode 2, a first hole control layer 5, a second hole control layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked The structure of the organic light emitting device is illustrated. In this structure, the compound represented by Chemical Formula 1 may be included in the first hole control layer 5, and the compound represented by Chemical Formula 2 or 3 may be included in the second hole control layer 6.

The organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the first or second organic material layer includes a compound of the present application, that is, the compound.

When the organic light emitting device includes a plurality of first or second organic material layers, the organic material layers may be formed of the same material or different materials.

 The organic light emitting device of the present application is a material and method known in the art, except that at least one layer of the first or second organic material layer includes the compound, that is, the compound represented by any one of Formulas 1 to 3 above. Can be prepared.

For example, the organic light emitting device of the present application may be manufactured by sequentially stacking first electrodes, first and second organic material layers, and second electrodes on a substrate. In this case, 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. And 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 compounds of Formulas 1 to 3 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 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 (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the first or second organic material layer. Specific examples of the positive electrode material that can be used in the present invention 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); ZnO: Al or SNO 2: Combination of metals and oxides such as 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. 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 an electrode. The hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material. 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 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 electron transporting layer is a layer for receiving electrons from the electron injection layer and transporting electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; 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 to transport electrons to the electron injection material, has an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, The compound which prevents the movement of the produced excitons to the hole injection 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 like and 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 hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

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

Fabrication of an organic light emitting device including the compound represented by Chemical Formulas 1 to 3 will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Production Example  1 (Formula 1 of  synthesis)

● Synthesis of A1 ~ A7

Synthesis of A1

1-bromo-2-iodobenzene (20 g, 70.6 mmol) and 4-chlorophenylboronic acid (11.3 g, 74.2 mmol) were added to tetrahydrofuran (300 ml), followed by 2M aqueous potassium carbonate solution (150 ml). Tetrakistriphenyl-phosphinopalladium (1.63 g, 2 mol%) was added thereto, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed to separate the layers. Removal of the solvent and vacuum distillation afforded A1 (17 g, yield 90%).

MS [M + H] ⁺ = 268.55

Synthesis of A2

Except for using 4-chlorophenylboronic acid instead of 4-chlorophenylboronic acid in the synthesis of A1 was synthesized in the same manner to prepare A2.

MS [M + H] ⁺ = 268.55

Synthesis of A3

Except for using 4-chlorophenyl boronic acid instead of 4-chlorophenyl boronic acid in the synthesis of A1 was synthesized in the same manner to prepare A3.

MS [M + H] ⁺ = 268.55

Synthesis of A4

A4 was prepared by the same method as in the synthesis of A1 except that (4'-chloro- [1,1'-biphenyl] -4-yl) boronic acid was used instead of 4-chlorophenylboronic acid. .

MS [M + H] ⁺ = 344.65

Synthesis of A5

A5 was prepared by the same method as in the synthesis of A1, except that (3'-chloro- [1,1'-biphenyl] -3-yl) boronic acid was used instead of 4-chlorophenylboronic acid. .

MS [M + H] ⁺ = 344.65

Synthesis of A6

A6 was prepared by the same method as in the synthesis of A1, except that (2'-chloro- [1,1'-biphenyl] -3-yl) boronic acid was used instead of 4-chlorophenylboronic acid. .

MS [M + H] ⁺ = 344.65

Synthesis of A7

A7 was prepared by the same method as in the synthesis of A1, except that (3'-chloro- [1,1'-biphenyl] -2-yl) boronic acid was used instead of 4-chlorophenylboronic acid. .

MS [M + H] ⁺ = 344.65

● Synthesis of B1 ~ B7

Synthesis of B1

After dissolving A1 (20 g, 74.7 mmol) in THF (250 ml), the temperature was lowered to -78 degrees, and then 2.5M n-BuLi (41.8 ml) was added dropwise and 10,10-dimethylanthracene-9 (10H) -one after 30 minutes. (16.64 g, 74.9 mmol) was added thereto, and the residue was stirred for 1 hour. 1N HCl (300ml) was added thereto, stirred for 30 minutes, the layers were separated, the solvent was removed, the residue was purified by ethyl acetate, and the obtained solid was added to acetic acid (250ml), and 1ml of sulfuric acid was added dropwise and refluxed. The mixture was cooled to room temperature, neutralized with water, and the filtered solid was recrystallized from tetrahydrofuran and ethyl acetate to prepare B1 (24.94 g, 85%).

MS [M + H] ⁺ = 393.93

Synthesis of B2

Except for using A2 in place of A1 in the synthesis of B1 synthesized in the same manner to prepare B2.

MS [M + H] ⁺ = 393.93

Synthesis of B3

Except that A3 was used instead of A1 in the synthesis of B1, B3 was synthesized in the same manner.

MS [M + H] ⁺ = 393.93

Synthesis of B4

Except for using A4 instead of A1 in the synthesis of B1 was synthesized in the same manner to prepare B4.

MS [M + H] ⁺ = 470.02

Synthesis of B5

Except for using A5 instead of A1 in the synthesis of B1 was synthesized in the same manner to prepare B5.

MS [M + H] ⁺ = 470.02

Synthesis of B6

Except for using A6 in place of A1 in the synthesis of B1 synthesized in the same manner to prepare B6.

MS [M + H] ⁺ = 470.02

Synthesis of B7

Except for using A7 in place of A1 in the synthesis of B1 synthesized in the same manner to prepare B7.

MS [M + H] ⁺ = 470.02

● the synthesis of compounds 1-1 to 1-11

Compound 1- 1 of  synthesis

B1 (20 g, 50.8 mmol), N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine (18.95 g, 52.4 mmol), sodium -t-Butoxide (6.83 g, 71.1 mol) was added to xylene, heated and stirred, and refluxed, followed by [bis (tri-t-butylphosphine)] palladium (518 mg. 2 mmol%). After the temperature was lowered to room temperature and the reaction was terminated, Compound 1-1 (30.27 g, 83%) was prepared by recrystallization using tetrahydrofuran and ethyl acetate.

MS [M + H] ⁺ = 718.96

Compound 1- 2 of  synthesis

N- (9,9-dimethyl- in place of N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine in the synthesis of Compound 1-1. Compound 1-2 was prepared in the same manner except 9H-fluoren-2-yl) dibenzo [b, d] thiophen-4-amine was used.

MS [M + H] ⁺ = 749.00

Compound 1- 3 of  synthesis

In the synthesis of Compound 1-1, B2 instead of B1 and N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N-phenyl- Compound 1-3 was prepared in the same manner except for using [1,1 '; 3', 1 "-terphenyl] -5'-amine.

MS [M + H] ⁺ = 678.89

Compound 1- 4 of  synthesis

In the synthesis of Compound 1-1, B2 instead of B1 and N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N-phenylnaphthalene Compound 1-4 was prepared by synthesis in the same manner except for using -1-amine.

MS [M + H] ⁺ = 576.76

Compound 1- 5 of  synthesis

In the synthesis of Compound 1-1, B3 instead of B1, N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N, 9, Compound 1-5 was prepared by synthesis in the same manner except 9-triphenyl-9H-fluoren-2-amine was used.

MS [M + H] ⁺ = 767.00

Compound 1- 6 of  synthesis

B3 instead of B1 in the synthesis of Compound 1-1, N, 9- instead of N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine Compound 1-6 was prepared by synthesis in the same manner except that diphenyl-9H-carbazol-2-amine was used.

MS [M + H] ⁺ = 691.89

Compound 1- 7 of  synthesis

In the synthesis of Compound 1-1, B4 instead of B1 and N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N-phenylnaphthalene Compound 1-7 was prepared by synthesis in the same manner except for using 2-amine.

MS [M + H] ⁺ = 652.85

Compound 1- 8 of  synthesis

In the synthesis of Compound 1-1, B4 instead of B1, N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N-([ Compound 1-8 was prepared in the same manner except for using 1,1'-diphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine.

MS [M + H] ⁺ = 795.05

Compound 1- 9 of  synthesis

Compound 1-9 was prepared by the same method as in the synthesis of Compound 1-1, except that B5 was used instead of B1.

MS [M + H] ⁺ = 795.05

Compound 1- 10 of  synthesis

In the synthesis of Compound 1-1, B6 instead of B1, N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N- (4 Compound 1-10 was prepared in the same manner except for using -naphthalen-1-yl) phenyl) = [1.1'-biphenyl] -4-amine.

MS [M + H] ⁺ = 805.05

Compound 1- Of 11  synthesis

In the synthesis of Compound 1-1, B7 instead of B1, N-([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N-phenyldi Compound 1-11 was prepared by synthesis in the same manner except that benzo [b, d] thiophen-4-amine was used.

MS [M + H] ⁺ = 708.94

Production Example  2 (Formula 2 to Formula 3 of  synthesis)

● the synthesis of compounds 2-1 to 2-6

Compound 2- 1 of  synthesis

In the synthesis of Compound 1-1, 2-bromo-9,9'-spirobi [fluorene] was substituted for B1, and N-([1,1'-biphenyl] -2-yl) -9,9- Except for using N- (4-dibenzo [b, d] thiophen-4-yl) phenyl)-[1,1'-biphenyl] -4-amine in place of dimethyl-9H-fluoren-2-amine Compound 2-1 was prepared by synthesis in the same manner.

MS [M + H] ⁺ = 742.95

Compound 2- 2 of  synthesis

In the synthesis of the compound 2-1, 4-bromo-9,9'-spirobia [fluorene] instead of 2-bromo-9,9'-spirobia [fluorene], N- (4-dibenzo N-([1,1'-biphenyl] -4-yl) -9,9 instead of [b, d] thiophen-4-yl) phenyl)-[1,1'-biphenyl] -4-amine Compound 2-2 was prepared by synthesis in the same manner except that dimethyl-9H-fluoren-2-amine was used.

MS [M + H] ⁺ = 676.88

Compound 2- 3 of  synthesis

In the synthesis of the compound 2-1, 4-bromo-9,9'-spirobia [fluorene] instead of 2-bromo-9,9'-spirobia [fluorene], N- (4-dibenzo N-([1,1 '; 4', 1 "-terphenyl] -4- instead of [b, d] thiophen-4-yl) phenyl)-[1,1'-biphenyl] -4-amine Compound 2-3 was prepared in the same manner as in one) except that one) -9,9-dimethyl-9H-fluoren-2-amine was used.

MS [M + H] ⁺ = 752.97

Compound 2- 4 of  synthesis

In the synthesis of the compound 2-1, 9- (4-bromophenyl) -9H-carbazole instead of 2-bromo-9,9'-spirobi [fluorene], N- (4-dibenzo [b , d] thiophen-4-yl) phenyl)-[1,1'-biphenyl] -4-amine instead of N- (4- (dibenzo [b, d] furan-4-yl) phenyl)-[ Compound 2-4 was prepared by synthesis in the same manner except that 1,1'-biphenyl] -3-amine was used.

MS [M + H] ⁺ = 653.80

Compound 2- 5 of  synthesis

In the synthesis of the compound 2-1, 9- (3-bromophenyl) -9H-carbazole instead of 2-bromo-9,9'-spirobiby [fluorene], N- (4-dibenzo [b , d] thiophen-4-yl) phenyl)-[1,1'-biphenyl] -4-amine instead of N- (4- (dibenzo [b, d] furan-4-yl) phenyl)-[ Compound 2-5 was prepared in the same manner except for using 1,1'-biphenyl] -4-amine.

MS [M + H] ⁺ = 653.80

Compound 2- 6 of  synthesis

9- (4'-chloro- [1,1'-biphenyl] -4-yl) -9H- in place of 2-bromo-9,9'-spirobi [fluorene] in the synthesis of Compound 2-1 Carbazole is replaced by 4- (dibenzo [b, d] instead of N- (4-dibenzo [b, d] thiophen-4-yl) phenyl)-[1,1'-biphenyl] -4-amine Compound 2-6 was prepared in the same manner except using furan-4-yl) phenyl) -N-phenylaniline.

MS [M + H] ⁺ = 653.80

< Example  1> OLED  Manufacture

The substrate on which ITO / Ag / ITO was deposited 70/1000 / 70O was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was put in distilled water and washed ultrasonically. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

HIL1 was thermally vacuum deposited to a thickness of 50 kPa on the prepared anode to form a hole injection layer, and HTM1, a material for transporting holes, was vacuum deposited to 1150 kPa to form a hole transport layer. Next, the first hole control layer was formed using Compound 1-1 (950 kPa) synthesized in Preparation Example 1, and the second hole control layer was formed by depositing Compound 2-1 (150 kPa) synthesized in Preparation Example 2. It was. Then, the host RH1 and the dopant RD1 (2% by weight) were vacuum deposited to a thickness of 360 kPa to form a light emitting layer. Thereafter, ETM1 was deposited at 50 kV to form an electron control layer, and compound ETM2 and Liq were mixed at 7: 3 to form an electron transport layer having a thickness of 250 kPa>. 50 μm thick magnesium and lithium fluoride (LiF) were sequentially deposited using an electron injection layer <EIL>, 200 μg of magnesium and silver (1: 4) were used as a cathode, and 600 μL of CPL1 was deposited to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec.

The organic light emitting device manufactured by using the compound synthesized in Preparation Examples 1 and 2 as Examples 1 to 41 and Comparative Examples 1 to 12 as the first hole control layer, the second hole control layer, and a host material In Table 1-1 to Table 1-3, the experimental results are shown in Table 2-1 and Table 2-2.

Table 1-1

TABLE 1-2

Table 1-3

Table 2-1

Table 2-2

<Example 42>

HTM1 was thermally vacuum deposited to a thickness of 500 kPa on the anode prepared as in Example 1 to form a hole injection layer, but the compound HIL2 was doped at a doping concentration of 5%. After the hole transport layer was formed, Compound 1-1 (950 Pa) synthesized in Preparation Example 1 was sequentially formed as the first hole control layer, and Compound 2-2 (150 Pa) synthesized in Preparation Example 2 was deposited to deposit the second hole. A control layer was formed. Then, the host RH1 and the dopant RD1 (2 wt%) were vacuum deposited to a thickness of 360 kPa to form a light emitting layer. Thereafter, ETM1 was deposited by 50 kV into the electron control layer and formed as an electron transport layer with compound ETM2 and Liq 7: 3 (250 kPa). 50 μm thick magnesium and lithium fluoride (LiF) were sequentially formed into an electron injection layer, and 200 μg of magnesium and silver (1: 4) were formed as a cathode, and 600 μg of CPL1 was deposited to complete the device.

Examples of the organic light emitting device manufactured by using the compounds synthesized in Preparation Examples 1 and 2 as Examples 42 to 82 and Comparative Examples 13 to 24 as the first hole control layer, the second hole control layer, and a host material In 3-1 to Table 3-3, the experimental result is shown to Table 4-1 and Table 4-2.

Table 3-1

Table 3-2

Table 3-3

Table 4-1

Table 4-2

The organic electroluminescent device combined with the compound derivative of the formula according to the present invention can control the role of smooth hole injection into the light emitting layer by using the hole control layer of the compound as the compound of the chemical structure of Preparation Examples 1, 2, chemical structure Through the balance of holes and electrons of the organic light emitting device according to the present invention, the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and stability.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: first hole control layer
6: second hole control layer
7: electron transport layer

Claims (10)

A first electrode; A second electrode provided to face the first electrode; And a first organic material layer and a second organic material layer provided between the first electrode and the second electrode.
The first organic material layer includes a compound represented by Formula 1,
The second organic material layer is an organic light emitting device comprising a compound represented by the following formula (2) or (3):
[Formula 1]

In Chemical Formula 1,
L 1 is a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R1 to R4 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
b to d are each independently an integer of 0 to 4,
a is an integer of 0 to 3,
when a to d are each independently 2 or more, the substituents in parentheses are the same as or different from each other,
[Formula 2]

In Chemical Formula 2,
L 2 is a direct bond; Or a substituted or unsubstituted arylene group,
Ar3 and Ar4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L2, Ar3 and Ar4 may combine with each other adjacent groups to form a ring,
R5 to R8 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
f to h are each independently an integer of 0 to 4,
e is an integer from 0 to 3,
when e to h are each independently 2 or more, the substituents in parentheses are the same as or different from each other,
[Formula 3]

In Chemical Formula 3,
L3 to L5 are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar5 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R9 to R12 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted haloalkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
i, j and l are each independently an integer of 0 to 4,
k is an integer from 0 to 3,
When i to l are each independently 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
Formula 1 is represented by any one of the following Formula 1-1 to Formula 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-1 to 1-4,
The definitions of L1, Ar1, Ar2, R1 to R4 and a to d are the same as those of Chemical Formula 1. The method according to claim 1,
Formula 2 is an organic light-emitting device represented by any one of the following formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Chemical Formulas 2-1 to 2-4,
The definitions of L 2, Ar 3, Ar 4, R 5 to R 8, and e to h are the same as in Chemical Formula 2. The method according to claim 1,
Formula 3 is an organic light emitting device represented by any one of the following Formula 3-1 to Formula 3-4:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Chemical Formulas 3-1 to 3-4,
Definitions of L3 to L5, Ar5, R9 to R12 and i to l are the same as in Chemical Formula 3. The method according to claim 1,
Formula 1 is selected from the following structural formula organic light emitting device:

. The method according to claim 1,
Formula 2 is an organic light emitting device is selected from the following structural formula:

. The method according to claim 1,
Formula 3 is an organic light emitting device is selected from the following structural formula:

. The method according to claim 1,
The first organic material layer is composed of one to three layers of the organic light emitting device. The method according to claim 1,
The first organic material layer includes a first hole control layer,
The second organic material layer includes a second hole control layer,
The first hole control layer includes a compound represented by Formula 1,
The second hole control layer is an organic light emitting device comprising a compound represented by the formula (2) or (3). The method according to claim 9,
The first or second organic material layer has a multilayer structure,
The first organic material layer includes a first hole control layer,
The second organic material layer includes a second hole control layer,
The first hole control layer includes a compound represented by Formula 1,
The second hole control layer is an organic light emitting device comprising a compound represented by the formula (2) or (3).

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