KR101807924B1 - Heterocyclic compounds and organic light emitting device using the same - Google Patents

Heterocyclic compounds and organic light emitting device using the same Download PDF

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KR101807924B1
KR101807924B1 KR1020150180975A KR20150180975A KR101807924B1 KR 101807924 B1 KR101807924 B1 KR 101807924B1 KR 1020150180975 A KR1020150180975 A KR 1020150180975A KR 20150180975 A KR20150180975 A KR 20150180975A KR 101807924 B1 KR101807924 B1 KR 101807924B1
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compound
light emitting
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김수연
이호용
권혁준
김민준
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주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/0072—
    • H01L51/5012—
    • H01L51/5056—
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Abstract

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

Description

HETEROCYCLIC COMPOUNDS AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME [0002]

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same. This application claims the benefit of Korean Patent Application No. 10-2014-0183604 filed on December 18, 2014, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The display field, which implements various information on the screen, is developing as a core technology in the age of information communication, in the direction of thinness, light weight, and high performance.

Conventional CRTs (cathode ray tubes) operate under high voltage and are constrained by their size and weight. Therefore, they are rapidly replaced by flat panel displays which can reduce power consumption and make large screens.

The organic light emitting device is a self-emissive display (OLED) which uses a phenomenon in which excitons are recombined with electrons injected through the anode and cathode to the anode of the organic thin film to form excitons and light of a specific wavelength is generated due to the energy of the excitons formed. Device.

Development of new materials for such organic light emitting devices has been continuously required.

Korean Patent Application Publication No. 2014-0055137

It is an object of the present invention to provide a heterocyclic compound and an organic light emitting device including the same.

One embodiment of the present disclosure provides compounds represented by Formula 1:

[Chemical Formula 1]

Figure 112015123932651-pat00001

In Formula 1,

Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R 1 and R 2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; Or a substituted or unsubstituted alkylaryl group,

L 1 and L 2 are the same or different and are a direct bond or a substituted or unsubstituted arylene group,

n, m and p are the same or different from each other and each is an integer of 0 to 4,

q is an integer of 0 to 7,

When n, m, p and q are 2 or more, the substituents in the parentheses are the same or different from each other.

In addition, one embodiment of the present invention is an organic light emitting device comprising an anode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes the compound of Formula 1 And an organic electroluminescent device.

The heterocyclic compound according to the present specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device.

The heterocyclic compound according to some embodiments of the present specification can be used as the material of the light emitting layer of the organic light emitting device. Specifically, the compound can be used as a red host material of an organic light emitting device.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

Hereinafter, the present invention will be described in detail.

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

In the present specification,

Figure 112015123932651-pat00002
Quot; represents a position capable of bonding with an adjacent substituent.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term "substituted or unsubstituted" heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or does not have any substituent (s).

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent. For example, the position to be substituted is not limited as long as it is a position at which the hydrogen atom is substituted, that is, the substituent is a substitutable position, and when two or more are substituted, the two or more substituents may be the same or different.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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 has 3 to 40 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, the fluorenyl group may have a substituent, and substituents may have a structure linked to each other. When the fluorenyl group is substituted,

Figure 112015123932651-pat00003
,
Figure 112015123932651-pat00004
,
Figure 112015123932651-pat00005
And
Figure 112015123932651-pat00006
And the like. However, the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group is a heteroaryl group containing at least one of O, N and S as a heteroatom. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms. Specific examples thereof include a thiophene group, a furan group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, Group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).

(2)

Figure 112015123932651-pat00007

(3)

Figure 112015123932651-pat00008

In the general formulas (2) and ( 3) , the definitions of Ar 1 to Ar 3 , L 1 to L 2 and R 1 to R 2 are as shown in general formula (1).

In the above formulas (2) and (3), the definitions of n and m are as shown in formula (1).

In the above Formulas 2 and 3, the definitions of p and q are as shown in Formula (1).

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each represents a substituted or unsubstituted arylamine group having 6 to 18 carbon atoms; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 6 to 15 carbon atoms.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and are a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or substituted or unsubstituted triphenylamine.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and are 9,9-dimethylfluorenyl; Naphthyl; Dibenzothiophenyl; Phenyl; Biphenyl; Lt; / RTI > or triphenylamine.

According to one embodiment of the present disclosure, Ar 1 is naphthyl; 9,9-dimethylfluorenyl; Phenyl; Dibenzothiophenyl; Biphenyl; Terphenyl; Or triphenylamine.

According to one embodiment of the present disclosure, Ar 2 is selected from the group consisting of naphthyl; 9,9-dimethylfluorenyl; Phenyl; Dibenzothiophenyl; Biphenyl; Terphenyl; Or triphenylamine.

According to one embodiment of the present disclosure, Ar 3 is phenyl; Or biphenyl.

In one embodiment of the present specification, L 1 and L 2 are the same or different from each other, and are each independently a direct bond; And a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L 1 and L 2 are the same or different and are a direct bond or a substituted or unsubstituted phenylene group.

According to one embodiment of the present disclosure, L < 1 > is a phenylene group.

According to one embodiment of the present disclosure, L < 1 >

Figure 112015123932651-pat00009
,
Figure 112015123932651-pat00010
or
Figure 112015123932651-pat00011
to be.

In one embodiment of the present disclosure, L < 1 >

Figure 112015123932651-pat00012
to be.

In one embodiment of the present disclosure, L < 1 >

Figure 112015123932651-pat00013
to be.

According to one embodiment of the present disclosure, L < 2 > is a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L < 2 > is a direct bond.

In one embodiment of the present invention, L < 2 > is a phenylene group.

In one embodiment of the present disclosure, L < 2 >

Figure 112015123932651-pat00014
,
Figure 112015123932651-pat00015
or
Figure 112015123932651-pat00016
to be.

In one embodiment of the present disclosure, L < 2 >

Figure 112015123932651-pat00017
or
Figure 112015123932651-pat00018
to be.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted arylalkyl group.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 1 to 40 carbon atoms.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different from each other and are hydrogen; A substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different from each other and can be hydrogen, phenyl, biphenyl, substituted or unsubstituted 9,9-dimethylfluorenyl.

According to another embodiment of the present invention, R 1 and R 2 are the same as or different from each other and each represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, a n-propyl group, an isopropyl group, a butyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group and a 1-ethyl-butyl group.

According to one embodiment of the present disclosure, R 1 and R 2 are hydrogen.

According to one embodiment of the present invention, n, m and p are the same as or different from each other and each is an integer of 0 to 4, q is an integer of 0 to 7, and when p and q are each 2 or more, They are the same or different.

According to one embodiment of the present disclosure, n, m and p are each an integer from 0 to 3, and q is 0 or 7.

According to one embodiment of the present disclosure, the compound of formula 1 may be selected from the following formulas.

Figure 112015123932651-pat00019

Figure 112015123932651-pat00020

Figure 112015123932651-pat00021

Figure 112015123932651-pat00022

Figure 112015123932651-pat00023

Figure 112015123932651-pat00024

Figure 112015123932651-pat00025

Figure 112015123932651-pat00026

Figure 112015123932651-pat00027

Figure 112015123932651-pat00028

Figure 112015123932651-pat00029

Figure 112015123932651-pat00030

Figure 112015123932651-pat00031

Figure 112015123932651-pat00032

Figure 112015123932651-pat00033

Figure 112015123932651-pat00034

Figure 112015123932651-pat00035

Figure 112015123932651-pat00036

Figure 112015123932651-pat00037

Figure 112015123932651-pat00038

Figure 112015123932651-pat00039

Figure 112015123932651-pat00040

Figure 112015123932651-pat00041

Figure 112015123932651-pat00042

Figure 112015123932651-pat00043

Figure 112015123932651-pat00044

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1.

One embodiment of the present invention relates to an organic light emitting device comprising an anode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes the compound of Formula 1 An organic light emitting device is provided.

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

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound of the above formula (1).

In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1).

In one embodiment of the present invention, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic material layer containing the compound of Formula 1.

In one embodiment of the present invention, the light emitting layer comprises a compound of the general formula (1), and further comprises a luminescent dopant.

In another embodiment, the light emitting layer comprises the compound of Formula 1 and the luminescent dopant, and the weight of the compound of Formula 1 is 65 to 99 parts by weight when the entire luminescent layer is 100.

In another embodiment, the light emitting layer comprises a compound of Formula 1, and the light emitting dopant comprises a phosphorescent dopant.

In another embodiment, the light emitting layer comprises a compound of formula (I) and the phosphorescent dopant comprises an iridium phosphorescent dopant.

In another embodiment, the light emitting layer comprises a compound of formula (1), wherein the iridium phosphorescent dopant is Ir (ppy) 3 .

In one embodiment of the present invention, the organic material layer containing the compound of Formula 1 includes the compound of Formula 1 as a host, and includes another organic compound, metal or metal compound as a dopant.

In one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound of the above formula (1).

In one embodiment of the present invention, the organic material layer further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In such a structure, the compound may be included in the light emitting layer.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).

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

 The organic light emitting device of the present invention can 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 Formula 1, that is, the compound represented by Formula 1.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode thereon.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

The anode is preferably made of a conductive material having a high work function so that injection of holes into the organic material layer can be smoothly performed. Exemplary conductive materials may include metals, metal oxides, or conductive polymers. Specifically, carbon, aluminum, vanadium, chromium, copper, zinc, silver, gold, other metals and alloys thereof; Zinc oxide, indium oxide, tin oxide, indium tin oxide (ITO), indium zinc oxide and other similar metal oxides; ZnO: Al and a mixture of an oxide and a metal such as Sn 2 O: Sb. Also included are poly (3-methylthiophene), poly (3-hexylthiophene) (P3HT), poly [3,4- (ethylene-1,2-dioxy) thiophene (PEDOT) , Polypyrrole, and polyaniline.

As the anode material, a transparent material may be used, or an opaque material may be used. In the case of a structure in which light is emitted in the anode direction, the anode may be formed to be transparent. Here, the transparency means that light emitted from the organic material layer can be transmitted, and the transparency of light is not particularly limited.

For example, when the organic light emitting element according to the present specification is a top emission type and the anode is formed on the substrate before formation of the organic layer and the cathode, an opaque material having excellent light reflectance as well as a transparent material as the anode material may be used. For example, when the organic light emitting device according to the present specification is of a back light emission type and the anode is formed on the substrate before formation of the organic material layer and the cathode, a transparent material is used as the anode material, or a thin film is formed so that the opaque material becomes transparent .

The cathode material is preferably a material having a small work function so that electron injection into the organic material layer is facilitated. For example, a material having a work function of 2 eV to 5 eV may be used as the cathode material, but is not limited thereto. The cathode may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; A multi-layer structure material such as LiF / Al or LiO 2 / Al, and the like.

The cathode may be formed of the same material as the anode. In this case, the cathode may be formed of materials exemplified as the material of the anode in advance. Alternatively, the cathode or anode may comprise a transparent material.

The hole transport layer is a layer that allows the holes transported through the hole injection in the anode or the hole injection layer to move to the light emission layer more smoothly and binds electrons transported from the cathode to the light emission layer, Materials with high hole mobility are suitable. For example, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but the present invention is not limited thereto.

Since hole transport and electron transport occur simultaneously in the light emitting layer, the light emitting layer may have both n-type and p-type characteristics. For convenience sake, it can be defined as an n-type luminescent layer when the electron transport is faster than the hole transport, and a p-type luminescent layer when the hole transport is faster than the electron transport.

The electron transporting layer is a layer for allowing electrons transported through the electron injection in the cathode or the electron injection layer to move to the light emitting layer more smoothly and to bind the holes transported from the anode to the light emitting layer. The material is suitable. For example, an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; 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 is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The dopant material includes an organic compound, a metal, or a metal compound.

Examples of the organic compound as the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, and a fluoranthene compound. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. As the metal or metal compound, a common metal or metal compound can be used. Specifically, metal complexes can be used. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

The electron blocking layer serves to improve the probability of recombination of electrons and holes by blocking electrons while transporting holes, and is a layer having a function of transporting holes and having a remarkably small capacity for transporting electrons Suitable. As the material of the electron blocking layer, the above-mentioned material for the hole transporting layer can be used as needed, and not limited thereto, a known electron blocking layer can be used.

According to an embodiment of the present invention, the organic light emitting display device may further include a substrate provided on a surface of the anode facing the organic layer. The substrate may be a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto and is a substrate commonly used in an organic light emitting device.

In one embodiment of the present disclosure, an anode; A cathode facing the anode; And a light emitting layer provided between the anode and the cathode; Wherein at least one of the two or more organic layers comprises at least one compound selected from the group consisting of a compound represented by Formula 1, . In one embodiment, the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, and a hole blocking layer.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes a compound represented by the above formula (1). Specifically, in one embodiment of the present invention, the compound represented by Formula 1 may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In one embodiment of the present invention, when the compound represented by Formula 1 is contained in each of the two or more electron transporting layers, the materials other than the compound represented by Formula 1 may be the same or different from each other .

According to an embodiment of the present invention, the light scattering layer may be further provided between the substrate and the anode.

According to an embodiment of the present invention, the light scattering layer may include a flat layer. In this case, the light-scattering layer is not limited as long as it can induce light scattering and improve internal light extraction efficiency of the device. The light scattering layer can increase the internal light extraction efficiency by forming a large difference in refractive index between the scattering particles and the flat layer.

According to an embodiment of the present invention, the organic light emitting device may be a flexible organic light emitting device. In this case, the substrate may comprise a flexible material. Specifically, the substrate may be a glass, plastic, or film-like substrate in the form of a thin film that can be bent.

The material of the plastic substrate is not particularly limited, but films such as PET, PEN, PC, PEEK, and PI may generally be included in a single layer or a multilayer form.

According to an embodiment of the present invention, there is provided a lighting device including the organic light emitting device. In the illumination device, the organic light emitting diode may serve as a light emitting unit. In addition, configurations necessary for the illumination device can be applied to those known in the art.

According to an embodiment of the present invention, there is provided a display device including the organic light emitting device. In the display device, the organic light emitting diode may serve as a pixel or a backlight. Besides, the configuration of the display device may be applied to those known in the art.

Hereinafter, the present invention will be described in detail by way of examples to illustrate the present invention. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

Typical synthesis methods

(1) a general preparation method of the formula M1

Figure 112015123932651-pat00045

(2) a general preparation method of formula M2

Figure 112015123932651-pat00046

(3) a general method for producing a compound

Figure 112015123932651-pat00047

Manufacturing example  1: Preparation of the formula M 1-1

(1) Preparation of the compound of formula A-1

Figure 112015123932651-pat00048

35 g (176 mmol) of 2,4-dichloroquinoline, 21.2 g (174 mmol) of phenylboronic acid and 4.06 g (3.52 mmol) of tetrakistriphenylphosphine palladium were added to a 2 L round bottom flask with 1,4- 880 ml, mixed with 200 ml of an aqueous solution of 72 g (528 mmol) of potassium carbonate and refluxed for 24 hours. The impurities were removed using chloroform and water, and anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized from chloroform and ethyl acetate to obtain 35.6 g (84%) of a compound of the formula A-1.

(2) Preparation of the compound of the formula M 1-1

Figure 112015123932651-pat00049

15 g (62.3 mmol) of formula A-1, 19 g (74.8 mmol) of bispinacoloborate, 18 g (187 mmol) of potassium acetate and 1 g of dibenzylideneacetone) dipalladium in a 1 L round- (1.87 mmol) and tricyclohexyl phosphite (1 g, 3.7 mmol) were placed in 1,4-dioxane (200 ml), the temperature of the reactor was raised to 120 ° C, and the mixture was refluxed for 12 hours. The reaction was filtered to terminate the reaction, and anhydrous magnesium sulfate was added to the filtrate to remove moisture. After removing all the solvent, the residue was recrystallized using chloroform and ethanol to obtain 17.1 g (yield: 85%) of the formula M 1-1.

Manufacturing example  2: < 2 of  Produce

Figure 112015123932651-pat00050

(Yield: 78%) was obtained in the same manner as in the preparation of M < 1-1 >, except that biphenylboronic acid was used in place of phenylboronic acid.

Manufacturing example  3: M < 3 of  Produce

(1) Preparation of compound of formula A-2

Figure 112015123932651-pat00051

A solution of 20 g (83 mmol) of formula A-1 and 11.8 g (75.45 mmol) of (3-chlorophenyl) boronic acid 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium in tetrahydrofuran 180 ml and mixed with 70 ml of an aqueous solution of 31.3 g (226 mmol) of potassium carbonate, and the mixture was heated under reflux for 18 hours. The impurities were removed using chloroform and water, and anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized with chloroform and ethanol to obtain 19 g (80%) of the compound of formula A-2.

(2) Preparation of the compound of the formula M <

Figure 112015123932651-pat00052

M-3 and 18.2 g (yield 75%) were obtained in the same manner as in the preparation of M 1-1, except that the compound of formula A-2 was used instead of the compound of formula A-1.

Compounds M 1-4 to M 1-6 were prepared according to the method for preparing Compound M 1-1 of Preparation Example 1 and Compound M 1-3 of Preparation Example 3

Figure 112015123932651-pat00053

Manufacturing example  7: 1 of  Produce

Figure 112015123932651-pat00054

20 g (118 mmol) of diphenylamine, 33.4 g (118 mmol) of 1-bromo-4-iodobenzene and 13.2 g (236 mmol) of potassium hydroxide were added to a 1 L round bottom flask in 400 ml of xylene And stirred. After 5 minutes, 7 g (35.5 mmol) of 1,10-phenanthroline was added and stirred. When the materials were dissolved to some extent, 6.75 g (35.5 mmol) of cupric iodide was added and the temperature was raised to reflux for 18 hours. The impurities were removed using ethyl acetate and water, and anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized with ethyl acetate and ethanol to obtain 24 g (63%) of a compound represented by the formula M 2-1.

Compounds M 2-2 to M 2-24 were prepared according to the process for the preparation of compound M 2-1 in Production Example 7.

Figure 112015123932651-pat00055

Figure 112015123932651-pat00056

Figure 112015123932651-pat00057

Figure 112015123932651-pat00058

Manufacturing example  31 < / RTI > 1 of  Produce

Figure 112015123932651-pat00059

To a 0.25 L round bottom flask were added 6.57 g (26.7 mmol) of 2-bromocarbazole, 8.45 g (25.4 mmol) of formula M 1-1 and 0.587 g (0.5 mmol) of tetrakistriphenylphosphine palladium in 64 mL of tetrahydrofuran And the mixture was mixed with 20 ml of an aqueous solution of potassium carbonate (10.5 g, 76.2 mmol), and the mixture was heated under reflux for 15 hours. The impurities were removed using chloroform and water, and anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized with chloroform and ethanol to obtain 7.36 g (78%) of a compound of the formula M 3-1.

Compounds M3-2 to M3-12 were prepared according to the method for preparation of compound M3-1 of Preparation Example 31. [

Figure 112015123932651-pat00060

Figure 112015123932651-pat00061

Figure 112015123932651-pat00062

Manufacturing example  43: 1- 1 of  Produce

Figure 112015123932651-pat00063

To a 0.25 L round bottom flask was added 7 g (18.8 mmol) of the formula M 3-1, 6.11 g (18.8 mmol) of the formula M 2-1, 0.14 g (0.28 mmol) of bis (tri-t- butylphosphine) palladium, 3.6 g (37.6 mmol) of t-butoxide was added to 65 ml of xylene and refluxed for 3 hours. The impurities were removed using chloroform and water, and anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized using chloroform and ethyl acetate to obtain 8.57 g (74%) of the compound of Formula 1-1.

The following compounds were prepared according to the method for the preparation of Compound 1-1 of Production Example 43:

Figure 112015123932651-pat00064

Figure 112015123932651-pat00065

Figure 112015123932651-pat00066

Figure 112015123932651-pat00067

Figure 112015123932651-pat00068

Figure 112015123932651-pat00069

Figure 112015123932651-pat00070

Figure 112015123932651-pat00071

Figure 112015123932651-pat00072

Figure 112015123932651-pat00073

Figure 112015123932651-pat00074

Figure 112015123932651-pat00075

Figure 112015123932651-pat00076

Figure 112015123932651-pat00077

Figure 112015123932651-pat00078

Figure 112015123932651-pat00079

Figure 112015123932651-pat00080

Figure 112015123932651-pat00081

Example

< Experimental Example 1 >

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried and transferred to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator. On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

Figure 112015123932651-pat00082

(N, N-bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1- biphenyl) -4,4-diamine) compound of the following structure A thick hole transport layer was formed by thermal vacuum deposition.

[NPB]

Figure 112015123932651-pat00083

Subsequently, the compound of Formula 1-2 prepared in Example 1 was vacuum deposited on the hole transport layer to a film thickness of 300 Å at a concentration of 10% (weight ratio Wt%) of Ir (ppy) 3 dopant to form a light emitting layer.

The following electron transporting material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injecting and transporting layer.

[Electron transport material]

Figure 112015123932651-pat00084

Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and a thickness of 2000 Å to form a cathode.

<Experimental Example 2>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-9 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 3>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-34 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 4>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-1 was used instead of the compound of Formula 1-2 in Experimental Example 1.

<Experimental Example 5>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-14 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 6>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-26 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 7>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-33 was used in place of the compound of Formula 1-2 in Experimental Example 1.

<Experimental Example 8>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-41 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 9>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 3-2 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 10>

An organic light emitting device was prepared in the same manner as in Experimental Example 1 except that Compound 3-21 was used instead of Compound 1-2 in Experimental Example 1.

&Lt; Experimental Example 11 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 3-26 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 12>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 3-33 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 13>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 4-26 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 14>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 4-38 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 15>

An organic light emitting device was prepared in the same manner as in Experimental Example 1 except that Compound 5-26 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 16>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 5-29 was used instead of Compound 1-2 in Experimental Example 1.

<Experiment 17>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 5-30 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 18>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 6-3 was used instead of the compound of Formula 1-2 in Experimental Example 1.

<Experimental Example 19>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 6-26 was used instead of Compound 1-2 in Experimental Example 1.

<Experimental Example 20>

An organic light emitting device was prepared in the same manner as in Experimental Example 1 except that the compound 6-36 was used instead of the compound of the formula 1-2 in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compound A was used instead of the compound of the formula 1-2 in Experimental Example 1.

Figure 112015123932651-pat00085

&Lt; Comparative Example 2 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1 except that Compound B was used instead of Compound 1-2 in Experimental Example 1.

Figure 112015123932651-pat00086

&Lt; Comparative Example 3 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compound C was used instead of the compound of the formula 1-2 in Experimental Example 1.

Figure 112015123932651-pat00087

Table 1 shows the device results obtained by using the compounds of Experimental Examples 1 to 20, Comparative Examples 1 and 3 as a light emitting layer.

Host The driving voltage (V) Current efficiency (cd / A) Power Efficiency (lm / W) Experimental Example 1 1-2 5.0 42.5 26.7 Experimental Example 2 1-9 6.2 43.5 22.0 Experimental Example 3 1-34 5.7 42.6 23.46 Experimental Example 4 2-1 5.6 47.8 26.8 Experimental Example 5 2-14 4.8 45.8 30.0 Experimental Example 6 2-26 4.3 43.3 31.6 Experimental Example 7 2-33 5.3 42.9 25.4 Experimental Example 8 2-41 5.2 43.7 26.4 Experimental Example 9 3-2 4.9 45.6 29.3 Experimental Example 10 3-21 5.4 49.0 28.5 Experimental Example 11 3-26 4.3 45.6 33.3 Experimental Example 12 3-33 5 42.9 27.0 Experimental Example 13 4-26 4.5 43.8 30.6 Experimental Example 14 4-38 4.9 46.5 29.8 Experimental Example 15 5-26 4.4 42.5 30.3 Experimental Example 16 5-29 5.2 44.6 26.9 Experimental Example 17 5-30 5 43.6 27.4 Experimental Example 18 6-3 5.6 45.8 25.7 Experimental Example 19 6-26 4.8 43.2 28.3 Experimental Example 20 6-36 4.9 45.5 29.2 Comparative Example 1 Compound A 6.4 41.2 20.2 Comparative Example 2 Compound B 7.1 42 18.6 Comparative Example 3 Compound C 6.8 42.5 19.6

As can be seen from Table 1, the luminescent characteristics of the hosts prepared in Experimental Examples 1 to 20 are significantly lower in driving voltage and higher in power efficiency than the compounds of Comparative Example 1, Comparative Example 2 and Comparative Example 3 .

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

1: substrate
2: anode
3: light emitting layer
4: Cathode
5: Hole injection layer
6: hole transport layer
7:
8: Electron transport layer

Claims (13)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]
Figure 112017067626829-pat00088

In Formula 1,
Ar 1 and Ar 2 are the same or different from each other and are each independently a phenyl group; A biphenyl group; Naphthyl group; A 9,9-dimethylfluorenyl group; Or a dibenzothiophene group,
Ar 3 is a phenyl group or a biphenyl group,
R 1 and R 2 are hydrogen,
L 1 is a phenylene group,
L 2 is a direct bond or a phenylene group,
n, m and p are the same or different from each other and each is an integer of 0 to 4,
q is an integer of 0 to 7,
When n, m, p and q are 2 or more, the substituents in parentheses are the same or different. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)
Figure 112015123932651-pat00089

(3)
Figure 112015123932651-pat00090

In the general formulas (2) and (3)
Ar 1 to Ar 3 , L 1 to L 2, and R 1 and R 2 have the same meanings as in formula (1)
The definitions of n, m, p and q are as shown in formula (1). delete delete delete delete The method according to claim 1,
L 1 is
Figure 112015123932651-pat00091
or
Figure 112015123932651-pat00092
ego,
L 2 is a direct bond;
Figure 112015123932651-pat00093
or
Figure 112015123932651-pat00094
Lt; / RTI &gt; delete The method according to claim 1,
Wherein the compound of formula 1 is selected from the following formulas:
Figure 112017067626829-pat00123

Figure 112017067626829-pat00124

Figure 112017067626829-pat00125

Figure 112017067626829-pat00126

Figure 112017067626829-pat00127

Figure 112017067626829-pat00128

Figure 112017067626829-pat00129

Figure 112017067626829-pat00130

Figure 112017067626829-pat00131

Figure 112017067626829-pat00132

Figure 112017067626829-pat00133

Figure 112017067626829-pat00134

Figure 112017067626829-pat00135

Figure 112017067626829-pat00136

Figure 112017067626829-pat00137
 An organic light emitting device comprising an anode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a compound according to any one of claims 1, 2, 7 and 9 . [Claim 11] The organic light emitting device according to claim 10, wherein the organic compound layer containing the compound is at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. The organic light emitting device according to claim 10, wherein the organic compound layer containing the compound is a light emitting layer. 11. The organic light emitting device according to claim 10, wherein the organic light emitting element is a flexible organic light emitting element.
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