KR101957788B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Heterocyclic compound and organic light emitting device comprising the same Download PDF

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KR101957788B1
KR101957788B1 KR1020160022659A KR20160022659A KR101957788B1 KR 101957788 B1 KR101957788 B1 KR 101957788B1 KR 1020160022659 A KR1020160022659 A KR 1020160022659A KR 20160022659 A KR20160022659 A KR 20160022659A KR 101957788 B1 KR101957788 B1 KR 101957788B1
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차용범
곽지원
홍성길
이성재
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주식회사 엘지화학
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    • 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
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    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • 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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Abstract

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

Description

TECHNICAL FIELD [0001] The present invention relates to a heterocyclic compound and an organic light emitting device including the heterocyclic compound. [0002]

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

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

Korean Patent Laid-Open Publication No. 2013-0007441

Heterocyclic compounds and organic light emitting devices containing them are described in this specification.

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

[Chemical Formula 1]

Figure 112016018715261-pat00001

In Formula 1,

R 1 and R 2 are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R 1 and R 2 are bonded to each other to form a substituted or unsubstituted ring,

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

m is an integer of 0 to 5,

When m is 2 or more, L < 1 >

Ar 1 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted thioalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar 2 and Ar 3 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

One embodiment of the present disclosure is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And a compound represented by the general formula (1).

The compound described in this 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. In particular, the compounds described in this specification can be used as hole injecting, hole transporting, hole injecting and hole transporting, electron blocking, luminescence, hole blocking, electron transporting, or electron injecting materials.

Fig. 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. Fig.
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 3, an electron transporting layer 7 and a cathode 4 It is.
Figure 3 shows a general formula of the compounds of the present invention.

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

An embodiment of the present invention provides a compound represented by the above formula (1).

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, the "substituent group to which at least two substituents are connected" can be interpreted as an aryl group substituted with a heterocyclic group. Further, as a more specific example, " biphenyl group " may be an aryl group, and the phenyl group may be interpreted as a substituted phenyl group.

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

Figure 112016018715261-pat00002

In the present specification, the ester group may be substituted with an ester group oxygen by a straight-chain, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

Figure 112016018715261-pat00003

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

Figure 112016018715261-pat00004

In the present specification, the silyl group may be represented by the formula of -SiR a R b R c , wherein R a , R b and R c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BR a R b , wherein R a and R b are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, Group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are 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 containing two or more 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.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole, and a triphenylamine group.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group containing at least two heterocyclic groups may contain a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, the arylheteroarylamine group means an aryl group and an amine group substituted with a heterocyclic group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine 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.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. 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, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

When the fluorenyl group is substituted,

Figure 112016018715261-pat00005
,
Figure 112016018715261-pat00006
, A spirofluorenyl group
Figure 112016018715261-pat00007
(9,9-dimethylfluorenyl group), and
Figure 112016018715261-pat00008
(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 1 to 30. [ Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group. A benzoimidazoquinazolinyl group, a benzoimidazophenanthridin group, and the like, but are not limited thereto.

In one embodiment of the present invention, the heterocyclic group has 3 to 60 ring members. In another embodiment, the heterocyclic group has 3 to 40 ring members. In one embodiment, the heterocyclic group has 3 to 20 ring members.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylheteroarylamine group, The description of one aryl group may be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group can be applied to the alkyl group described above.

In the present specification, the heteroaryl group in the heteroaryl group, the heteroarylamine group and the arylheteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.

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

In the present specification, the description of the above-mentioned heterocyclic group can be applied, except that the heteroarylene group is an aromatic divalent group.

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. But are not limited to these.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Specific examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, klysene, pentacene, fluorene, indene, Thienyl, benzofluorene, spirofluorene, etc., but are not limited thereto.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom. Specific examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, Azokane, thiocane, and the like, but are not limited thereto.

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom. Specifically, examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinoline, quinazoline 4, quinoxaline, And examples thereof include acridine, phenanthridine, diazanaphthalene, triazainene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, But are not limited to, sol, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

In one embodiment of the present disclosure, L < 1 > is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

Also, in the present specification, L 1 represents a direct bond; Or any one of the following groups selected from the group below, but the present invention is not limited thereto, and the following structures may be further substituted.

Figure 112016018715261-pat00009

The structures include deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; An arylheteroarylamine group; Arylphosphine groups; And a heterocyclic group, which may be substituted or unsubstituted.

In one embodiment, L < 1 > is a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment, L < 1 > is a direct bond; Or a phenylene group.

In one embodiment, L < 1 > is a direct bond.

In one embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 2 below.

(2)

Figure 112016018715261-pat00010

In Formula 2,

The definitions of R 1 , R 2 and Ar 1 to Ar 3 are the same as those in formula (1).

According to one embodiment of the present invention, R 1 and R 2 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R 1 and R 2 may be bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, R 1 and R 2 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment, R 1 and R 2 are the same or different and are each independently an alkyl group or an aryl group, or combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, R 1 and R 2 are the same or different and are each independently a methyl group or a phenyl group, or combine with each other to form a fluorene ring.

In one embodiment of the present invention, the compound represented by Formula 1 may be represented by any of Formula 3 to Formula 5 below.

(3)

Figure 112016018715261-pat00011

[Chemical Formula 4]

Figure 112016018715261-pat00012

[Chemical Formula 5]

Figure 112016018715261-pat00013

In the above Chemical Formulas 3 to 5,

The definitions of Ar 1 to Ar 3 are the same as those in formula (1).

According to one embodiment of the present disclosure, Ar < 1 > is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Ar < 1 > is hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

Further, according to one embodiment of the present specification, Ar 1 may be any one selected from the following structures, and the following structures may be further substituted.

Figure 112016018715261-pat00014

Figure 112016018715261-pat00015

Figure 112016018715261-pat00016

Figure 112016018715261-pat00017

Figure 112016018715261-pat00018

Figure 112016018715261-pat00019

Figure 112016018715261-pat00020

Figure 112016018715261-pat00021

Figure 112016018715261-pat00022

Figure 112016018715261-pat00023

Specifically, the structures include deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; An arylheteroarylamine group; Arylphosphine groups; And a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment, Ar 1 is a phenyl group; A biphenyl group; Naphthyl group; A fluorenyl group; A fluorenyl group substituted with a methyl group; A dibenzofuranyl group; A dibenzofuranyl group substituted with a phenyl group; A dibenzothiophene group; A dibenzothiophen group substituted with a phenyl group; Carbazole group; Or a carbazole group substituted with a phenyl group.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different and each independently represents an aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a heterocyclic ring; A fluorenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group and an aryl group; An arylamine group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group and an aryl group; Or a heterocyclic group substituted or unsubstituted with an aryl group.

In the present state of the specification, Ar 2 and Ar 3 may be the same or different from each other, and each independently may be any one selected from the following structures.

Figure 112016018715261-pat00024

Figure 112016018715261-pat00025

Figure 112016018715261-pat00026

Figure 112016018715261-pat00027

Figure 112016018715261-pat00028

Figure 112016018715261-pat00029

Figure 112016018715261-pat00030

Figure 112016018715261-pat00031

Specifically, the structures include deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; An arylheteroarylamine group; Arylphosphine groups; And a heterocyclic group, which may be substituted or unsubstituted.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different and each independently represents an aryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of a methyl group, a phenyl group and a biphenyl group; Or a fluorenyl group substituted or unsubstituted with a methyl group.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different from each other and are each independently a phenyl group; A phenyl group substituted with at least one substituent selected from the group consisting of a methyl group, a phenyl group and a biphenyl group; A biphenyl group; A terphenyl group; A triphenylrenyl group; A fluorenyl group; A fluorenyl group substituted with a methyl group.

In one embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.

Figure 112016018715261-pat00032

Figure 112016018715261-pat00033

Figure 112016018715261-pat00034

Figure 112016018715261-pat00035

Figure 112016018715261-pat00036

Figure 112016018715261-pat00037

Figure 112016018715261-pat00038

Figure 112016018715261-pat00039

Figure 112016018715261-pat00040

Figure 112016018715261-pat00041

Figure 112016018715261-pat00042

Figure 112016018715261-pat00043

Figure 112016018715261-pat00044

Figure 112016018715261-pat00045

Figure 112016018715261-pat00046

Figure 112016018715261-pat00047

Figure 112016018715261-pat00048

Figure 112016018715261-pat00049

Figure 112016018715261-pat00050

Figure 112016018715261-pat00051

Figure 112016018715261-pat00052

Figure 112016018715261-pat00053

Figure 112016018715261-pat00054

Figure 112016018715261-pat00055

Figure 112016018715261-pat00056

Figure 112016018715261-pat00057

Figure 112016018715261-pat00058

Figure 112016018715261-pat00059

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents to the core structure. In the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure.

The compound represented by Formula 1 may be synthesized using a reaction represented by the following general formula, but is not limited thereto.

Figure 112016018715261-pat00060

In the above reaction formula, the definitions of R 1 , R 2 , L 1 , m, and Ar 1 to Ar 3 are as shown in Chemical Formula (1).

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Also, the organic light emitting device according to the present invention is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers Which comprises the above compound.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

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

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.

Therefore, in the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, Lt; / RTI >

In one embodiment, the organic material layer may include at least one of a hole injecting layer, an electron blocking layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes. Lt; / RTI >

As another example, the organic material layer may include an electron blocking layer, and the electron blocking layer may include a compound represented by the above formula (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1). As one example, the compound represented by Formula 1 may be included as a host of the light emitting layer. As another example, the compound represented by Formula 1 may be included as a phosphorescent host in the light emitting layer.

As another example, the organic compound layer containing the compound represented by Formula 1 may include a compound represented by Formula 1 as a host, and may include another organic compound, metal, or metal compound as a dopant.

As another example, the organic material layer containing the compound represented by Formula 1 may include a compound represented by Formula 1 as a host, and may be used together with an iridium (Ir) dopant.

The organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports electrons and electron injection, and at least one of the layers may include the compound.

In another embodiment, the organic material layer of the organic electronic device includes a hole transporting layer, and the hole transporting layer includes a compound represented by the above formula (1).

In such an organic layer having a multi-layer structure, the compound may be included in a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports light and electrons, or a layer that simultaneously transports electrons and emits light.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, or the electron transporting layer 7.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (PEDT), polypyrrole and polyaniline.

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

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, 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 iridium complex used as a dopant in the light emitting layer is as follows.

[Ir (piq) 3 ] [Btp 2 Ir (acac)]

Figure 112016018715261-pat00061

[Ir (ppy) 3 ] [Ir (ppy) 2 (acac)]

Figure 112016018715261-pat00062

[Ir (mpyp) 3 ] [F 2 Irpic]

Figure 112016018715261-pat00063

[(F 2 ppy) 2 Ir (tmd)] [Ir (dfppz) 3 ]

Figure 112016018715261-pat00064
　　　
Figure 112016018715261-pat00065

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include 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 organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The compound according to the present invention may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

The method for preparing the compound of Formula 1 and the preparation of the organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention and the scope of the present invention is not limited thereto.

< Synthetic example  1> Synthesis of intermediate

(1) Synthesis of intermediate A

According to the following reaction scheme, Intermediate A was synthesized.

Figure 112016018715261-pat00066

(2) Synthesis of intermediate B

Intermediate B was synthesized according to the following scheme.

Figure 112016018715261-pat00067

(3) Synthesis of intermediate C

Intermediate C was synthesized according to the following reaction formula.

Figure 112016018715261-pat00068

(4) Synthesis of intermediate D

Intermediate D was synthesized according to the following reaction scheme.

Figure 112016018715261-pat00069

(5) Synthesis of intermediate E

According to the following reaction scheme, Intermediate E was synthesized.

Figure 112016018715261-pat00070

(3) Synthesis of intermediate F

According to the following reaction scheme, Intermediate F was synthesized.

Figure 112016018715261-pat00071

< Synthetic example  2> Synthesis of compounds 1 to 7

Manufacturing example  One: Synthesis of Compound (1)

                                                  [Compound 1]

Figure 112016018715261-pat00072

Compound A (15.57 g, 25.86 mmol) and Iodobenzene (5.0 g, 24.63 mmol) were dissolved in 140 ml of xylene in a 500 ml round bottom flask under nitrogen atmosphere and sodium tert-butoxide -butoxide (3.08 g, 32.02 mmol) was added and bis (tri-tert-butylphosphine) palladium (0) (0.13 g, 0.25 mmol) And the mixture was heated and stirred for 2 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain Compound 1 (11.62 g, yield 69%).

MS [M + H] &lt; + &gt; = 679

Manufacturing example  2: Synthesis of Compound 2 below

                                                  [Compound 2]

Figure 112016018715261-pat00073

Compound A (11.29 g, 18.75 mmol) and 4-iodobiphenyl (5.0 g, 17.86 mmol) were dissolved in 250 ml of xylene in a 500 ml round-bottomed flask under nitrogen atmosphere and sodium tert- Was added sodium tert-butoxide (2.23 g, 23.21 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 150 ml of tetrahydrofuran to obtain Compound 2 (10.78 g, yield: 80%).

MS [M + H] &lt; + &gt; = 755

Manufacturing example  3: Synthesis of Compound 3 below

                                                [Compound 3]

Figure 112016018715261-pat00074

Compound A (11.78 g, 26.17 mmol) and 3-bromo-9-phenyl-9H-carbazole (8.0 g, 24.92 mmol) in a 500 ml round- ) Was completely dissolved in 210 ml of xylene and sodium tert-butoxide (3.11 g, 32.40 mmol) was added thereto and bis (tri-tert-butylphosphine) palladium (0) (tri-tert-butylphosphine) palladium (0)) (0.13 g, 0.25 mmol) were added and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 210 ml of ethyl acetate to obtain Compound 3 (10.78 g, yield: 80%).

MS [M + H] &lt; + &gt; = 755

Manufacturing example  4: Synthesis of Compound 4 below

                                                 [Compound 4]

Figure 112016018715261-pat00075

In a nitrogen atmosphere, Compound B (19.06 g, 25.86 mmol) and Iodobenzene (5.0 g, 24.63 mmol) were dissolved in 140 ml of xylene in a 500 ml round-bottomed flask and sodium tert-butoxide -butoxide (3.08 g, 32.02 mmol) was added and bis (tri-tert-butylphosphine) palladium (0) (0.13 g, 0.25 mmol) And the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to obtain Compound 4 (14.47 g, yield: 73%).

MS [M + H] &lt; + &gt; = 803

Manufacturing example  5: Synthesis of Compound 5 below

                                                   [Compound 5]

Figure 112016018715261-pat00076

To a 500 ml round bottom flask in a nitrogen atmosphere was added compound C (14.23 g, 19.30 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.0 g, 18.38 mmol) was completely dissolved in 140 ml of xylene, sodium tert-butoxide (3.08 g, 32.02 mmol) was added and bis (tri-tert-butylphosphine) palladium 0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.13 g, 0.25 mmol) were added and the mixture was heated with stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to prepare the above compound 5 (12.53 g, yield: 74%).

MS [M + H] &lt; + &gt; = 917

Manufacturing example  6: Synthesis of Compound 6 below

                                                  [Compound 6]

Figure 112016018715261-pat00077

Compound E (12.30 g, 21.43 mmol), 2-bromodibenzo [b, d] furan (5.0 g, 20.41 mmol) was added to a 500 ml round- (Tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) was added to a solution of sodium tert-butoxide -butylphosphine palladium (0)) (0.10 g, 0.20 mmol) was added thereto, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain Compound 6 (11.05 g, yield: 73%).

MS [M + H] &lt; + &gt; = 741

Manufacturing example  7: Synthesis of the following compound 7

                                                 [Compound 7]

Figure 112016018715261-pat00078

In a nitrogen atmosphere, Compound F (11.46 g, 20.04 mmol) and 2-bromodibenzo [b, d] thiophene (5.0 g, 19.08 mmol) After dissolving in 170 ml of xylene, sodium tert-butoxide (2.38 g, 24.81 mmol) was added and bis (tri- tert-butylphosphine) palladium (0) tert-butylphosphine) palladium (0)) (0.10 g, 0.19 mmol) were added and the mixture was heated with stirring for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 230 ml of ethyl acetate to obtain Compound 6 (9.26 g, yield: 65%).

MS [M + H] &lt; + &gt; = 755

< Experimental Example  1-1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene hexanitrile (HAT-CN) of the following formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[HAT-CN]

Figure 112016018715261-pat00079

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

[NPB]

Figure 112016018715261-pat00080

Subsequently, the following compound 1 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form an electron blocking layer.

[Compound 1]

Figure 112016018715261-pat00081

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

[BH]

Figure 112016018715261-pat00082

[BD]

Figure 112016018715261-pat00083

[ET 1]

Figure 112016018715261-pat00084

[LiQ]

Figure 112016018715261-pat00085

The compound ET 1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 Å and a thickness of 2000 Å on the electron injection and transport layer sequentially to form a cathode.

Was maintained at the deposition rate 0.4 ~ 0.7Å / sec for organic material in the above process, lithium ply lifting 0.3Å / sec, the aluminum cathode was deposited at a rate of 2Å / sec, During the deposition, a vacuum 10 2 ⅹ -7 To 5 x 10 &lt; -6 &gt; torr, thereby fabricating an organic light emitting device.

< Experimental Example  1-2>

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

< Experimental Example  1-3>

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

< Experimental Example  1-4>

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

< Experimental Example  1-5>

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

< Experimental Example  1-6>

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

< Experimental Example  1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1-1.

< Comparative Example  1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of EB 1 was used instead of the compound 1 in Experimental Example 1-1.

[EB 1]

Figure 112016018715261-pat00086

< Comparative Example  2>

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

[EB 2]

Figure 112016018715261-pat00087

The results shown in Table 1 were obtained when current was applied to the organic light-emitting device manufactured in Experimental Example 1, Experimental Examples 1-1 to 1-7, and Comparative Examples 1 and 2.

compound
(Electronic blocking layer) Voltage
(V @ 10 mA / cm 2 ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1-1 Compound 1 3.68 6.64 (0.138, 0.127) Experimental Example 1-2 Compound 2 3.73 6.56 (0.139, 0.127) Experimental Example 1-3 Compound 3 3.65 6.64 (0.138, 0.126) Experimental Examples 1-4 Compound 4 3.50 6.71 (0.138, 0.127) Experimental Examples 1-5 Compound 5 3.68 6.68 (0.138, 0.127) Experimental Example 1-6 Compound 6 3.89 6.45 (0.138, 0.125) Experimental Example 1-7 Compound 7 3.79 6.50 (0.138, 0.127) Comparative Example 1 EB 1 4.23 6.07 (0.136, 0.127) Comparative Example 2 EB 2 4.05 6.24 (0.136, 0.127)

As shown in Table 1, the organic luminescent device manufactured using the compound of the present invention as an electron blocking layer was prepared in the same manner as in Comparative Example 2 in which substituents were connected to other positions of the core of the present invention and Comparative Example 1 The compound of the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of an organic light emitting device because it acts as an electron blocking function.

In Experimental Examples 1-1 to 1-7, the voltage was 10% to 12% lower than that of Comparative Examples 1 and 2, and the efficiency was higher than 8-10%.

As shown in Table 1, it was confirmed that the compounds according to the present invention are excellent in electron blocking ability and applicable to organic light emitting devices.

< Experimental Example  2-1 to Experimental Example  2-7>

The same experiment was conducted except that the following EB 3 material was used in place of the compound 1 as the electron blocking layer in Experimental Example 1 and the compounds of Experimental Examples 1-1 to 1-7 were used instead of NPB as the hole transporting layer.

[EB 3]

Figure 112016018715261-pat00088

< Comparative Example  3>

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

[HT 1]

Figure 112016018715261-pat00089

< Comparative Example  4>

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

[HT 2]

Figure 112016018715261-pat00090

The results shown in Table 2 were obtained when current was applied to the organic light-emitting devices manufactured in Experimental Examples 2-1 to 2-7 and Comparative Examples 3 to 4.

compound
(Hole transport layer) Voltage
(V @ 10 mA / cm 2 ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 2-1 Compound 1 4.58 5.35 (0.138, 0.127) EXPERIMENTAL EXAMPLE 2-2 Compound 2 4.56 5.25 (0.139, 0.127) Experimental Example 2-3 Compound 3 4.57 5.36 (0.138, 0.126) Experimental Example 2-4 Compound 4 4.41 5.55 (0.138, 0.127) Experimental Example 2-5 Compound 5 4.37 5.56 (0.138, 0.126) Experimental Examples 2-6 Compound 6 4.62 5.24 (0.138, 0.126) Experimental Example 2-7 Compound 7 4.68 5.20 (0.138, 0.127) Comparative Example 3 HT 1 5.12 4.82 (0.137, 0.127) Comparative Example 4 HT 2 5.06 4.93 (0.137, 0.127)

As shown in Table 2, Comparative Example 2 in which a substituent was connected to another position of the core of the present invention of the organic light emitting device manufactured using the compound of the present invention as a hole transport layer, and Comparative Example 1 in which the amine group was not substituted Compared with the case where the material is used, the compound of the present invention plays a role of transporting holes, and thus exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Specifically, in Experimental Examples 2-1 to 2-7, the voltage was decreased by 10% or more and the efficiency was 7 to 10% or more higher than that of Comparative Examples 3 and 4.

As shown in Tables 1 and 2, it was confirmed that the compounds according to the present invention are excellent in electron blocking ability and hole transporting ability, and are applicable to organic light emitting devices.

Although the preferred embodiments (electron blocking layer, hole transporting layer) of the present invention have been described above, the present invention is not limited thereto and can be variously modified within the scope of the claims and the detailed description of the invention And this also belongs to the category of invention.

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

Claims (12)

A compound represented by the following formula (1):
[Chemical Formula 1]
Figure 112018121377217-pat00091

In Formula 1,
R 1 and R 2 are the same or different and are each independently a phenyl group or a methyl group, or R 1 and R 2 are bonded to each other to form a ring,
L &lt; 1 &gt; is a direct bond,
m is 0,
Ar 1 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Or a heterocyclic group having 3 to 30 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms,
Ar 2 and Ar 3 are the same or different and each independently represent an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms. [2] The compound according to claim 1, wherein Ar &lt; 1 &gt; A biphenyl group; Naphthyl group; A fluorenyl group; A fluorenyl group substituted with a methyl group; A dibenzofuranyl group; A dibenzofuranyl group substituted with a phenyl group; A dibenzothiophene group; A dibenzothiophen group substituted with a phenyl group; Carbazole group; Or a carbazole group substituted with a phenyl group. 2. The compound according to claim 1, wherein Ar 2 and Ar 3 are the same or different from each other and are each independently a phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; A fluorenyl group; Lt; / RTI &gt; is a fluorenyl group substituted with a methyl group. delete delete The compound according to claim 1, wherein R 1 and R 2 are the same or different from each other, and each independently is a methyl group. The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structures:
Figure 112016018715261-pat00094

Figure 112016018715261-pat00095

Figure 112016018715261-pat00096

Figure 112016018715261-pat00097

Figure 112016018715261-pat00098

Figure 112016018715261-pat00099

Figure 112016018715261-pat00100

Figure 112016018715261-pat00101

Figure 112016018715261-pat00102

Figure 112016018715261-pat00103

Figure 112016018715261-pat00104

Figure 112016018715261-pat00105

Figure 112016018715261-pat00106

Figure 112016018715261-pat00107

Figure 112016018715261-pat00108

Figure 112016018715261-pat00109

Figure 112016018715261-pat00110

Figure 112016018715261-pat00111

Figure 112016018715261-pat00112

Figure 112016018715261-pat00113

Figure 112016018715261-pat00114

Figure 112016018715261-pat00115

Figure 112016018715261-pat00116

Figure 112016018715261-pat00117

Figure 112016018715261-pat00118

Figure 112016018715261-pat00119

Figure 112016018715261-pat00120

Figure 112016018715261-pat00121
. 1. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers is a compound of any one of claims 1 to 3, 6, and 7 Wherein the organic compound comprises a compound according to any one of claims 1 to 12. [Claim 9] The organic electroluminescent device according to claim 8, wherein the organic material layer comprises at least one of an electron transport layer, an electron injection layer, and a layer simultaneously performing electron transport and electron injection, device. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer. The organic electroluminescent device according to claim 8, wherein the organic material layer includes at least one of a hole injecting layer, an electron blocking layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, &Lt; / RTI &gt; 9. The organic light emitting device according to claim 8, wherein the organic compound layer contains the compound as a host and contains another organic compound, metal or metal compound as a dopant.
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