KR101828653B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Hetero-cyclic compound and organic light emitting device comprising the same Download PDF

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KR101828653B1
KR101828653B1 KR1020150136598A KR20150136598A KR101828653B1 KR 101828653 B1 KR101828653 B1 KR 101828653B1 KR 1020150136598 A KR1020150136598 A KR 1020150136598A KR 20150136598 A KR20150136598 A KR 20150136598A KR 101828653 B1 KR101828653 B1 KR 101828653B1
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곽지원
하재승
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주식회사 엘지화학
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    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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    • 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
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Abstract

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

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

This application claims the benefit of Korean Patent Application No. 10-2014-0131968, filed on September 30, 2014, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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 increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer 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 Publication No. 2000-0051826

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

One embodiment of the present disclosure provides a heterocyclic compound represented by the following Formula 1:

[Chemical Formula 1]

Figure 112015093886576-pat00001

In Formula 1,

R 1 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

Provided that at least two adjacent groups of R 1 to R 12 are bonded to each other to form a substituted or unsubstituted ring,

Ar 1 to Ar 3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group.

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first 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 comprises a heterocyclic compound represented by Formula 1, Lt; / RTI >

The heterocyclic compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The heterocyclic compound according to at least one of the embodiments can not easily crystallize, thereby improving the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. In particular, the heterocyclic compounds described herein can be used as hole injecting, hole transporting, hole injecting and transporting, light emitting, 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 7, an electron transporting layer 8 and a cathode 4 It is.

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

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

In the present specification,

Figure 112015093886576-pat00002
Quot; means a bond connected to another substituent.

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; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or other substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

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 112015093886576-pat00003

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

Figure 112015093886576-pat00004

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 112015093886576-pat00005

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

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

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, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

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 this 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 30 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 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 112015093886576-pat00006
,
Figure 112015093886576-pat00007
,
Figure 112015093886576-pat00008
And
Figure 112015093886576-pat00009
And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, S and Si as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane 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 pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl 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 aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.

In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.

In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.

In the present specification, arylene means having two bonding positions in an aryl group, that is, divalent. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, heteroarylene means having two bonding positions in the heterocyclic group, that is, divalent. The description of the above-mentioned heterocyclic group can be applied except that each of these is 2 groups.

In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.

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.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more of the N, O, or S atoms as heteroatoms.

As used herein, aromatic heterocycle refers to an aromatic ring comprising at least one heteroatom of N, O or S atoms.

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.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (4).

(2)

Figure 112015093886576-pat00010

(3)

Figure 112015093886576-pat00011

[Chemical Formula 4]

Figure 112015093886576-pat00012

In the above Formulas 2 to 4,

The definitions of R 1 to R 12 and Ar 1 to Ar 3 are the same as those of formula (1)

R 21 to R 24 and R 31 to R 36 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine 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 aryl group; Or a substituted or unsubstituted heterocyclic 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 aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

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 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 aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic 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 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

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 aryl group having 1 to 5 rings; Or a substituted or unsubstituted heterocyclic group of 1 to 5 rings.

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 aryl group having 1 to 4 rings; Or a substituted or unsubstituted heterocyclic group of 1 to 4 rings.

According to one embodiment of the present specification, Ar 1 to Ar 3 are the same or different from each other and each independently represents a substituted or unsubstituted aryl group having 1 to 3 rings; Or a substituted or unsubstituted heterocyclic group of 1 to 3 rings.

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

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a monocyclic substituted or unsubstituted aryl group; Or a monocyclic substituted or unsubstituted heterocyclic group containing at least one N atom.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; Or a substituted or unsubstituted triazine group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and are each independently a phenyl group; A pyridyl group; Pyrimidyl; Or triazine group.

According to one embodiment of the present invention, Ar 1 to Ar 3 may be the same or different from each other, and may be independently represented by the following formula (5).

[Chemical Formula 5]

Figure 112015093886576-pat00013

In Formula 5,

X 1 to X 3 are the same or different and are each independently CR or N,

R is hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent two or more substituents may be bonded to each other to form a substituted or unsubstituted ring,

L 1 to L 3 are the same or different from each other and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

A 1 and A 2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent two or more substituents may be bonded to each other to form a substituted or unsubstituted ring,

a, b and c are the same or different and each independently an integer of 0 to 5,

when a is 2 or more, L < 1 >

when b is 2 or more, L < 2 > are the same or different from each other,

When c is 2 or more, L < 3 >

According to another embodiment of the present invention, in Formula 5, X 1 to X 3 are CR.

According to another embodiment of the present invention, in Formula 5, at least one of X 1 to X 3 is N and the remainder is CR.

According to another embodiment of the present invention, in Formula 5, one of X 1 to X 3 is N and the remaining is CR.

According to another embodiment of the present invention, in Formula 5, two of X 1 to X 3 are N and the remainder is CR.

According to another embodiment of the present invention, in the general formula (5), X 1 to X 3 are N.

According to one embodiment of the present disclosure, A 1 and A 2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, A 1 and A 2 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, A 1 and A 2 are the same or different and each independently represents a substituted or unsubstituted 1 to 3 ring aryl group; Or a substituted or unsubstituted 1-to 3-membered heterocyclic group.

According to one embodiment of the present invention, A 1 and A 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthryl group.

According to one embodiment of the present disclosure, A 1 and A 2 are the same or different from each other and are each independently a phenyl group; A biphenyl group; A pyridyl group; A fluorenyl group; Or a phenanthryl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted perylenyl group; A substituted or unsubstituted crecenyl group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar 1 to 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; Anthracenyl group; A phenanthryl group; Pyrenyl; A perylenyl group; A crycenyl group; Or a fluorenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted aryl group having 3 to 5 rings.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each independently substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted pyrenyl group; Or a substituted or unsubstituted perylenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other, and each independently anthracenyl group; A phenanthryl group; A triphenylrenyl group; Pyrenyl; Perylenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 may be the same or different and each independently represent any one of the following formulas (6) to (10).

[Chemical Formula 6]

Figure 112015093886576-pat00014

(7)

Figure 112015093886576-pat00015

[Chemical Formula 8]

Figure 112015093886576-pat00016

[Chemical Formula 9]

Figure 112015093886576-pat00017

[Chemical formula 10]

Figure 112015093886576-pat00018

In Formulas 6 to 10,

B 1 to B 10 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent two or more substituents may be bonded to each other to form a substituted or unsubstituted ring,

b1 is an integer of 0 to 9,

b2, b5 and b7 are the same or different and independently of one another are an integer of 0 to 5,

b3, b4, b8 and b9 are the same or different and each independently represents an integer of 0 to 4,

b6 is an integer of 0 to 6,

b10 is an integer of 0 to 3,

When each of b1 to b10 is 2 or more, the structures in parentheses are the same or different from each other.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted heterocyclic group containing at least one N atom.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each a divalent substituted or unsubstituted heterocyclic group containing at least one N atom.

According to one embodiment of the present invention, Ar 1 to Ar 3 may be the same or different from each other, and each independently may be represented by the following formula (11) or (12).

(11)

Figure 112015093886576-pat00019

[Chemical Formula 12]

Figure 112015093886576-pat00020

In the above formulas (11) and (12)

C 1 and C 2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent two or more substituents may be bonded to each other to form a substituted or unsubstituted ring,

c1 is an integer of 0 to 6, c2 is an integer of 0 to 5,

If more than c1 is 2, C 1 is the same as or different from each other, and

c2 is not less than 2, C 2 is the same as or different from each other.

According to one embodiment of the present invention, C 1 and C 2 are the same or different from each other, and two or more mutually adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, Ar 1 to Ar 3 may be the same or different from each other, and each independently may be represented by the following formula (13).

[Chemical Formula 13]

Figure 112015093886576-pat00021

In the above formula (13)

Z is CR a R b , N-Ar, S or O,

R a , R b , Y 1 and Y 2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent two or more substituents may be bonded to each other to form a substituted or unsubstituted ring,

Ar is the same or different and is independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group,

L 11 is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

y1 is an integer of 0 to 4, y2 is an integer of 0 to 3, p11 is an integer of 0 to 5,

If more than y1 is 2 and Y 1 are the same as or different from each other,

If y2 is not less than 2, and Y 2 are the same as or different from each other,

When p11 is 2 or more, L < 11 >

According to one embodiment of the present invention, Ar 1 to Ar 3 may be the same or different from each other and each independently selected from the following substituted or unsubstituted structural formulas.

Figure 112015093886576-pat00022

Figure 112015093886576-pat00023

Figure 112015093886576-pat00024

Figure 112015093886576-pat00025

Figure 112015093886576-pat00026

Figure 112015093886576-pat00027

Figure 112015093886576-pat00028

Figure 112015093886576-pat00029

Figure 112015093886576-pat00030

Figure 112015093886576-pat00031

Figure 112015093886576-pat00032

Figure 112015093886576-pat00033

Figure 112015093886576-pat00034

Figure 112015093886576-pat00035

Figure 112015093886576-pat00036

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (14) to (16).

[Chemical Formula 14]

Figure 112015093886576-pat00037

[Chemical Formula 15]

Figure 112015093886576-pat00038

[Chemical Formula 16]

Figure 112015093886576-pat00039

In Formulas 14 to 16 above,

The definitions of R 1 to R 12 are the same as those of formula (1)

R 21 to R 24 and R 31 to R 36 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group,

X 1 to X 9 are the same or different and are each independently CR or N,

R is hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, adjacent two or more substituents are bonded to each other to form a substituted or unsubstituted ring,

S 1 to S 3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two adjacent or more adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,

p, q and r are the same or different and each independently represents an integer of 0 to 2,

when p is 2, S 1 are the same or different from each other,

when q is 2, S 2 are the same or different from each other,

When r is 2, S 3 is equal to or different from each other.

According to another embodiment of the present invention, in the above formulas (14) to (16), X 1 to X 3 are CR.

According to another embodiment of the present invention, in the general formulas (14) to (16), at least one of X 1 to X 3 is N and the remainder is CR.

According to another embodiment of the present invention, in the general formulas (14) to (16), one of X 1 to X 3 is N and the remaining is CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), two of X 1 to X 3 are N and the remainder is CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), X 1 to X 3 are N.

According to another embodiment of the present invention, in the above formulas (14) to (16), X 4 to X 6 are CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), at least one of X 4 to X 6 is N and the remainder is CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), one of X 4 to X 6 is N and the remaining is CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), two of X 4 to X 6 are N, and the remainder is CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), X 4 to X 6 are N.

According to another embodiment of the present invention, in the above formulas (14) to (16), X 7 to X 9 are CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), at least one of X 7 to X 9 is N and the remainder is CR.

According to another embodiment of the present specification, in the above formulas (14) to (16), one of X 7 to X 9 is N and the remaining is CR.

According to another embodiment of the present invention, in the above formulas 14 to 16, two of X 7 to X 9 are N, and the remainder is CR.

According to another embodiment of the present invention, in the above formulas (14) to (16), X 7 to X 9 are N.

According to one embodiment of the present disclosure, R 1 to R 12 are the same or different and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, and adjacent substituents of R 1 to R 12 are bonded to each other to form a benzene ring.

According to one embodiment of the present disclosure, R 1 to R 4 combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, R 5 to R 8 combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, R 9 to R 12 combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, Ar 1 to Ar 3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen 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 heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine 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 aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted aryl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group.

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

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and are each independently a substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each independently a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other, and each independently represents a fluorenyl group; Or a phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other and are each independently a naphthyl group; Or a phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different from each other, and each independently is a biphenyl group; Or a phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are the same or different and each is a phenyl group substituted with carbazole; Or an unsubstituted phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 3 are unsubstituted phenyl groups.

According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be any one selected from the following structural formulas.

Figure 112015093886576-pat00040

Figure 112015093886576-pat00041

Figure 112015093886576-pat00042

Figure 112015093886576-pat00043

Figure 112015093886576-pat00044

Figure 112015093886576-pat00045

Figure 112015093886576-pat00046

Figure 112015093886576-pat00047

Figure 112015093886576-pat00048

Figure 112015093886576-pat00049

Figure 112015093886576-pat00050

Figure 112015093886576-pat00051

Figure 112015093886576-pat00052

Figure 112015093886576-pat00053

Figure 112015093886576-pat00054

The heterocyclic compound represented by the formula (1) can be prepared based on the following production example. According to one embodiment, it can be prepared in the following manner.

[Reaction Scheme 1] Preparation of Formula 2

Figure 112015093886576-pat00055

[Reaction Scheme 2] Preparation of Formula 4

Figure 112015093886576-pat00056

In the above reaction formula,

The definitions of the substituents are the same as in the formulas (2) and (4).

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

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first 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 comprises a heterocyclic compound represented by Formula 1, Lt; / RTI >

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, an electron blocking layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers. 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, And a heterocyclic compound represented by the general formula (1).

In one embodiment of the present invention, the organic material layer includes an electron blocking layer, and the electron blocking layer includes a heterocyclic compound represented by the general formula (1).

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

In one embodiment of the present invention, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a heterocyclic compound represented by 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 heterocyclic compound represented by 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 a heterocyclic compound represented by the above formula (1).

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, 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 compound 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.

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. 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 heterocyclic compound represented by 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 one or more layers of the organic material layer include the heterocyclic compound, i.e., the heterocyclic compound represented by the formula (1).

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode 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 depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The heterocyclic compound represented by Formula 1 may be formed into an organic 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, 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 a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

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-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), 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.

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be 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 porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples 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 electron blocking layer is a layer which can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emission layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

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.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. 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. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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 organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

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

The heterocyclic compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Production Example 1. Preparation of Compound 2

1) Preparation of compound 2-b

Figure 112015093886576-pat00057

20 g (78 mmol) of 5,12-dihydro-indolo [3,2-a] carbazole, 50 ml of iodobenzene, 5 g of Cu powder (80 mmol) and K 3 PO 4 (24.8 g, 117 mmol) were added, and the mixture was stirred at 200 ° C. The reaction solution was cooled to room temperature, and the precipitated solid was reduced in pressure to obtain a powder, which was then dissolved in an organic solvent to separate the Cu powder. The obtained organic layer was dried under reduced pressure and purified by column chromatography. 18 g (54 mmol) of the obtained compound 2-a was treated with 12.2 g (59 mmol) of 2-bromonaphthalene instead of iodobenzene in the same manner and stirred at 200 DEG C using dimethylformamide as a solvent. The reaction product was dissolved in an organic solution to separate Cu powder, and the obtained organic solution was dried under reduced pressure and purified by column chromatography to obtain 19 g (41 mmol, yield 75%) of the compound 2-b.

2) Preparation of compound 2-c

Figure 112015093886576-pat00058

19 g (41 mmol) of the compound 2-b was completely dissolved in 70 ml of CHCl 3 at room temperature. Then, the temperature is maintained at 0 ° C using ice. 7.3 g (41 mmol) of N-Bromosuccinimide was slowly added while stirring at 0 ° C. After stirring for 1 hour, the mixture was warmed to room temperature and dried under reduced pressure to obtain 20 g (37 mmol, yield 90%) of the compound 2-c using column chromatography.

3) Preparation of compound 2-d

Figure 112015093886576-pat00059

(39 mmol) of benzophenone hydrazone, 0.12 g (0.56 mmol) of Pd (OAc) 2 , (+) - 2,2'-bis (diphenylphosphino) 0. 1 5-binaphthyl (0.35 g, 0.56 mmol) and NaOtBu (5.3 g, 56 mmol) were added, and toluene was used as a solvent. The temperature was lowered to room temperature, followed by drying under reduced pressure to obtain 21 g (32 mmol, yield 86%) of the compound 2-d by column chromatography.

4) Preparation of compound 2-e

Figure 112015093886576-pat00060

21 g (32 mmol) of the compound 2-d, 7 g (48 mmol) of alpha -tetralone, and toluenesulfonic acid . 15.2 g (80 mmol) of H 2 O was added, and 150 ml of ethanol was used as a solvent, followed by reflux and stirring. The temperature was lowered to room temperature, followed by drying under reduced pressure to obtain 18 g (30 mmol, yield 93%) of the compound 2-e by column chromatography.

5) Preparation of compound 2-f

Figure 112015093886576-pat00061

18 g (30 mmol) of the compound 2-e and 1.8 g of 10% Pd / Charcoal were refluxed for 3 hours using xylene. After cooling to room temperature, the catalyst was removed by filtration, and 13 g (21 mmol, 70% yield) of Compound 2-f was obtained by column chromatography.

6) Preparation of compound 2

Figure 112015093886576-pat00062

13 g (21 mmol) of the compound 2-f, 50 ml of iodobenzene, 2 g (31.5 mmol) of Cu powder and 6.68 g (31.5 mmol) of K 3 PO 4 were stirred while heating at 180 ° C. After cooling to room temperature, the catalyst and K 3 PO 4 were removed by filtration. And dried under reduced pressure to obtain Compound 2 (10 g, 14.8 mmol, yield 70%) by column chromatography. (m / z = 673)

Production Example 2. Preparation of Compound 1

1) In Production Example 1, Compound 1 was prepared in the same manner as in Production Example 1 except that iodobenzene was used instead of 2-bromonaphthalene in the production of Compound 2-b. (m / z = 623)

Production Example 3. Preparation of Compound 9

In the preparation of Compound 2-a in Production Example 1, 1) Compound 2-a was prepared by using 9- (4-bromophenyl) -carbazole instead of iodobenzene and 1) Compound 9 was prepared in the same manner as in Preparation Example 1 except that iodobenzene was used in place of naphthalene. (m / z = 788)

Production Example 4. Preparation of Compound 11

1) of Production Example 1, 2-bromonaphthalene was used instead of iodobenzene in the production of the compound 2-a in the production of the compound 2-b, and 6) 2-bromonaphthalene instead of iodobenzene The compound 11 was prepared in the same manner as in Preparation Example 1 except that the compound 11 was used. (m / z = 773)

Production Example 5. Preparation of Compound 36

1) Preparation of compound 36-b

Figure 112015093886576-pat00063

In Production Example 1, 1) Compound 4-bromo-9,9'-dimethylfluorene was used instead of 2-bromonaphthalene in the production of compound 2-b, -b.

2) Preparation of compound 36-c

Figure 112015093886576-pat00064

2) The compound 2-c was prepared in the same manner as in Production Example 1, except that 38-b was used in place of the compound 2-b in Production Example 2-c.

3) Preparation of compound 36-d

Figure 112015093886576-pat00065

3) In Production Example 1, except that 36-c was used instead of Compound 2-c in the production of Compound 2-d, Compound 36-d was obtained in the same manner as in Production Example 1, 3).

4) Preparation of compound 36-e

Figure 112015093886576-pat00066

4) In Production Example 1, 4), except that 36-d was used instead of the compound 2-d in the production of the compound 2-e and B-tetralone was used in place of the a-teteralone, To obtain Compound 36-e.

5) Preparation of compound 36-f

Figure 112015093886576-pat00067

5) In Production Example 1, Compound 36-f was obtained in the same manner as in 5) of Production Example 1, except that 36-e was used instead of Compound 2-e in the production of Compound 2-f.

6) Preparation of compound 36

Figure 112015093886576-pat00068

6) 6) The compound 2 of Preparation Example 1 was prepared in the same manner as in 6) of Preparation Example 1, except that 36-f was used instead of the compound 2-f. Thus, 36 was obtained. (m / z < / RTI > = 739)

Production Example 6. Preparation of Compound 32

In Production Example 1, except that 1) 2-bromonaphthalene was used instead of iodobenzene in the production of the compound 2-a, and 6) 2-bromonaphthalene was used in place of iodobenzene in the production of the compound 2. [ The compound 32 was prepared in the same manner as in Preparation Example 1. (m / z = 773)

Preparation 7. Preparation of Compound 38

In Preparative Example 11) Compound 2-a factory-iodo-benzene instead of in the preparation of 3- (3-bromophenyl) -9,9- dimethyl-9 H -Fluorene use, and 1) the compound 2-b, 2 -Bromonaphthalene was used instead of bromonaphthalene, and 6) 1-bromonaphthalene was used instead of iodobenzene in the production of compound 2. Compound 38 was prepared in the same manner as Preparation Example 1, except that iodobenzene was used instead of iodobenzene. (m / z = 865)

Preparation 8. Preparation of 46

1) Preparation of compound 46-a

Figure 112015093886576-pat00069

9-bromo-11 H -Benzo [ a] carbazole 20g (67.53mmol), 2- (3-bromophenyl) -naphthalene 19.1g (67.53mmol), K 3 PO 4 21.50g (101.30mmol), Cu powder 6.4g ( 101.30 mmol), and 100 ml of dimethylformamide was stirred under reflux. After cooling to room temperature, the catalyst and K 3 PO 4 were removed by filtration. Dried under reduced pressure, and 27.9 g (59.43 mmol, 88% yield) of Compound 46-a was obtained by column chromatography.

2) Preparation of compound 46-b

Figure 112015093886576-pat00070

Compound 46-a 27.9g (59.43mmol), B - (2-nitrophenyl) -Boronic acid 10.9g (65.4mmol), dissolved Pd (PPh3) 4 1.3g (1.2mmol ) in tetrahydrofuran, 300ml, K 2 CO 3 (aq) (12.3 g, 89.1 mmol), and the mixture was refluxed and stirred. After cooling to room temperature, the organic layer was separated and the solvent was removed by distillation under reduced pressure. And recrystallized with ethanol to obtain 28.9 g (53.48 mmol, yield 90%) of the compound 46-b.

3) Preparation of compound 46-c

Figure 112015093886576-pat00071

50 ml of triethylphosphite was added to 28.9 g (53.48 mmol) of the compound 46-b, and the mixture was stirred under reflux. After the reaction was completed, all triethylphosphite was removed by vacuum distillation. After cooling to room temperature, 16.5 g (32.6 mmol, yield: 61%) of the compound 46-c was obtained by column chromatography.

4) Preparation of compound 46-d

Figure 112015093886576-pat00072

Preparative Example the preparation of: 1) 46-a of 8 9-bromo-11 H -Benzo [a] carbazole in place of the compound 46-c 16.5g (32.6mmol, except that a) the Preparative Example 81) and of 19.0 g (26.7 mmol, yield 82%) of the compound 46-d was obtained in the same manner.

5) Preparation of compound 46-e

Figure 112015093886576-pat00073

19 g (26.7 mmol) of the compound 46-d was completely dissolved in 70 ml of CHCl 3 at room temperature. The temperature was maintained at 0 ° C using ice. 4.8 g (26.7 mmol) of N-Bromosuccinimide was stirred at 0 ° C and then slowly added. After stirring for 1 hour, the mixture was warmed to room temperature, dried under reduced pressure, and 18.8 g (23.8 mmol, yield 89%) of Compound 46-e was obtained by column chromatography.

6) Preparation of compound 46-f

Figure 112015093886576-pat00074

(2) of Production Example 8) The procedure of Production Example 8-2) was repeated except for using 18.8 g (23.8 mmol) of 46-e instead of 46-a in the production of 46-b, (21.7 mmol, yield: 91%).

7) Preparation of Compound 46

Figure 112015093886576-pat00075

18 g (21.7 mmol, yield: 91%) of the compound 46-f and 30 ml of triethylphosphite were placed and stirred under reflux. After the reaction was completed, all triethylphosphite was removed by vacuum distillation. After cooling to room temperature, 9.9 g (12.4 mmol, yield: 57%) of the compound 46-g was obtained by column chromatography.

8) Preparation of Compound 46

Figure 112015093886576-pat00076

In Preparative Example 81) Compound 46-a 9-bromo-11 H -Benzo the preparation of [a] carbazole in place of the compound 46-g 9.9g (12.4mmol), and a, 2- (3-bromophenyl) -naphthalene using (10.2 mmol, yield: 82%) was obtained in the same manner as in Production Example 8, except that iodobenzene was used. (m / z = 875)

Production Example 9. Preparation of Compound 49

2) instead of 2- (3-bromophenyl) -naphthalene was used in the preparation of Compound 46-b, except that iodobenzene was used instead of 2- (3-bromophenyl) 8) Compound 46 was prepared in the same manner as in Preparation Example 8 except that 9- (4-bromophenyl-carbazole was used instead of iodobenzene in the preparation of Compound 46 to prepare Compound 49. (m / z = 864)

Production Example 10. Preparation of Compound 1-1

Figure 112015093886576-pat00077

Except that 2-bromonaphthalene (2eq.) Was used instead of iodobenzene in the preparation of compound 2-a in the preparation of Compound 1-b), and 6) 2-bromonaphthalene was used instead of iodobenzene Was prepared in the same manner as in Preparation Example 1 to obtain Compound 1-1. (m / z = 773)

Production Example 11. Preparation of Compound 1-3

Figure 112015093886576-pat00078

Except that 4-bromobiphenyl (2eq.) Was used instead of iodobenzene in the preparation of compound 2-a in the preparation of 1) compound 2-b of Production Example 1, and 6) 4-bromobiphenyl was used instead of iodobenzene in the preparation of compound 2. Was prepared in the same manner as in Preparation Example 1 to obtain Compound 1-3. (m / z = 851)

Production Example 12. Preparation of Compound 1-5

Figure 112015093886576-pat00079

Except that 2-bromobiphenyl (2eq.) Was used instead of iodobenzene in the preparation of compound 2-a in the preparation of 1) compound 2-b of Production Example 1, and 6) 2-bromobiphenyl was used instead of iodobenzene in the preparation of compound 2. Was prepared in the same manner as in Preparation Example 1 to obtain Compound 1-5. (m / z = 851)

Production Example 13. Preparation of Compound 1-16

Figure 112015093886576-pat00080

(2e) was used instead of iodobenzene in the preparation of compound 2-a in the preparation of compound 1-b of Example 1, and N-phenyl-3-bromocarbazole 3-bromocarbazole was used instead of 3-bromocarbazole. Compound 1-16 was obtained. (m / z = 1118)

Production Example 14. Preparation of Compound 1-18

Figure 112015093886576-pat00081

A) 9,9-dimethyl-3-bromofluorene (2eq.) Was used instead of iodobenzene in the preparation of compound 2-a in the preparation of Compound 1-b) 9-dimethyl-3-bromofluorene was used instead of 3-bromo-4-methyl-3-bromo-fluorene. (m / z = 971)

Production Example 15. Preparation of Compound 2-1

Figure 112015093886576-pat00082

2-bromonaphthalene (2eq.) Was used instead of iodobenzene and 4-bromo-9,9'-dimethylfluorene in the preparation of compound 36-b, and 6-bromonaphthalene Was prepared in the same manner as in Preparation Example 5, except that the compound 2-1 was used. (m / z = 773)

Preparation 16. Preparation of Compound 2-3

Figure 112015093886576-pat00083

4-bromobiphenyl (2eq.) Was used instead of iodobenzene and 4-bromo-9,9'-dimethylfluorene in the preparation of Compound 36-b, and 6) 4-bromobiphenyl Was prepared in the same manner as in Preparation Example 5 to obtain Compound 2-3. (m / z = 851)

Preparation 17. Preparation of compound 2-5

Figure 112015093886576-pat00084

2-bromobiphenyl (2eq.) Was used instead of iodobenzene and 4-bromo-9,9'-dimethylfluorene in the preparation of Compound 36-b, and 6) 2-bromobiphenyl The compound was prepared in the same manner as in Preparation Example 5 except that the compound 2-5 was used. (m / z = 851)

Preparation 18. Preparation of compound 2-16

Figure 112015093886576-pat00085

(2eq.) Was used instead of iodobenzene and 4-bromo-9,9'-dimethylfluorene in the preparation of Compound 36-b, and 6) in place of iodobenzene N-phenyl-3-bromocarbazole was used in place of N-phenyl-3-bromocarbazole. Compound 2-16 was obtained. (m / z = 1118)

Preparation 19. Preparation of compound 2-18

Figure 112015093886576-pat00086

1) 9,9-dimethyl-3-bromofluorene (2eq.) Was used instead of iodobenzene and 4-bromo-9,9'-dimethylfluorene in the preparation of Compound 36-b, was prepared in the same manner as in Preparation Example 5, except that 9,9-dimethyl-3-bromofluorene was used instead of iodobenzene. Compound 2-18 was thus obtained. (m / z = 971)

Production Example 20. Preparation of Compound 3-1

Figure 112015093886576-pat00087

2-bromonaphthalene was used instead of 2- (3-bromophenyl) -naphthalene in the preparation of Compound 46-a, and 6) 2-bromonaphthalene (2 eq.) Was used instead of iodobenzene in the preparation of Compound 46 , 3), 5) and 6) of Preparation Example 5, to give Compound 3-1. (m / z = 773)

Preparation 21. Preparation of 3-3

Figure 112015093886576-pat00088

4-bromobiphenyl was used instead of 2- (3-bromophenyl) -naphthalene in the preparation of Compound 46-a, and 6) 4-bromobiphenyl (2 eq.) Was used in the preparation of Compound 46 instead of iodobenzene 3), 5) and 6) of Preparation Example 5, to obtain Compound 3-3. (m / z = 851)

Preparation 22. Preparation of 3-5

Figure 112015093886576-pat00089

2-bromobiphenyl was used instead of 2- (3-bromophenyl) -naphthalene in the preparation of Compound 46-a, and 6) 2-bromobiphenyl (2 eq.) Was used instead of iodobenzene in the preparation of Compound 46 3), 5) and 6) of Production Example 5 to obtain Compound 3-5. (m / z = 851)

Preparation 23. Preparation of Compound 3-16

Figure 112015093886576-pat00090

1) In Production Example 8, N-phenyl-3-bromocarbazole was used instead of 2- (3-bromophenyl) -naphthalene in the preparation of Compound 46-a. 6) N-phenyl-3-bromocarbazole (2eq.) Was used instead of 2-ethylhexylcarbodiimide. Compound 3-16 was obtained in the same manner as in 1) to 3), 5) and 6) of Preparation Example 5 above. (m / z = 1118)

Preparation 24. Preparation of compound 3-18

Figure 112015093886576-pat00091

1) 9,9-methyl-3-bromofluorene was used instead of 2- (3-bromophenyl) -naphthalene in the preparation of Compound 46-a, and 6) 9,9-methyl -3-bromofluorene (2eq.) Was used in place of 3-bromoethylamine, to thereby obtain the compound 3-18. (m / z = 971)

≪ Comparative 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 (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

Figure 112015093886576-pat00092

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 112015093886576-pat00093

Subsequently, an electron blocking layer was formed on the hole transport layer by vacuum evaporation of the following compound tris (4- (9H-carbazol-9-yl) phenyl) amine (TCTA) to a thickness of 100 angstroms.

[TCTA]

Figure 112015093886576-pat00094

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 112015093886576-pat00095

[BD]

Figure 112015093886576-pat00096

[ET1]

Figure 112015093886576-pat00097

[LiQ]

Figure 112015093886576-pat00098

The compound ET1 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 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at a vapor deposition rate of 0.4 to 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 -7 To 5 x 10 < -6 > torr, thereby fabricating an organic light emitting device.

<Experimental Example 1-1>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 1 was used instead of Compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-2>

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

<Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 11 was used instead of Compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that Compound 38 was used instead of Compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 46 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 49 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 1-1 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 1-3 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-9>

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

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 1-16 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 1-18 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 2-1 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 2-3 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 2-5 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 2-16 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-16>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 2-18 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-17>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 3-1 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-18>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 3-3 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-19>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1 except that the compound 3-5 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-20>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 3-16 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

<Experimental Example 1-21>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound 3-18 was used instead of the compound TCTA as the electron blocking layer in Comparative Example 1-1.

When current was applied to the organic light emitting device manufactured by Comparative Example 1-1 and Experimental Examples 1-1 to 1-21, the results shown in Table 1 were obtained.

compound
(Electron blocking layer) Voltage
(V @ 10 mA / cm 2 ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Comparative Example 1-1 Compound TCTA 4.19 5.25 (0.138, 0.127) Experimental Example 1-1 Compound 1 4.05 5.30 (0.139, 0.122) Experimental Example 1-2 Compound 2 3.84 5.45 (0.138, 0.126) Experimental Example 1-3 Compound 11 3.89 5.42 (0.138, 0.127) Experimental Examples 1-4 Compound 38 3.88 5.40 (0.137, 0.125) Experimental Examples 1-5 Compound 46 3.87 5.47 (0.136, 0.125) Experimental Example 1-6 Compound 49 3.85 5.45 (0.135, 0.127) Experimental Example 1-7 Compound 1-1 3.82 5.43 (0.131, 0.128) Experimental Examples 1-8 Compound 1-3 3.83 5.42 (0.134, 0.125) Experimental Examples 1-9 Compound 1-5 3.80 5.44 (0.132, 0.126) Experimental Example 1-10 Compound 1-16 3.82 5.46 (0.134, 0.122) Experimental Example 1-11 Compound 1-18 3.85 5.43 (0.133, 0.123) Experimental Example 1-12 Compound 2-1 3.87 5.40 (0.136, 0.127) Experimental Example 1-13 Compound 2-3 3.86 5.42 (0.137, 0.128) Experimental Example 1-14 Compound 2-5 3.84 5.43 (0.135, 0.126) Experimental Example 1-15 Compound 2-16 3.85 5.44 (0.138, 0.122) Experimental Example 1-16 Compound 2-18 3.86 5.42 (0.132, 0.124) Experimental Example 1-17 Compound 3-1 3.84 5.46 (0.133, 0.125) Experimental Example 1-18 Compound 3-3 3.85 5.42 (0.138, 0.126) Experimental Example 1-19 Compound 3-5 3.86 5.43 (0.139, 0.126) Experimental Example 1-20 Compound 3-16 3.87 5.47 (0.137, 0.127) Experimental Example 1-21 Compound 3-18 3.83 5.44 (0.136, 0.122)

The heterocyclic compound represented by Formula 1 according to one embodiment of the present invention exhibits low voltage and high efficiency due to its excellent electron blocking ability, and can be applied to organic light emitting devices.

&Lt; Experimental Examples 2-1 to 2-19 >

In Comparative Example 1-1, compounds 1, 9, 32, 36, 1-1, 1-3, 1-5, 1-16, 1-18, 2-1, 2-3, 2-5, 2-16, 2-18, 3-1, 3-3, 3-5, 3-16 or 3-18 were used in place of the organic light- Respectively.

When current was applied to the organic light-emitting device manufactured in Comparative Example 1-1 and Experimental Examples 2-1 to 2-19, the results shown in the following Table 2 were obtained.

compound
(Hole transport layer) Voltage
(V @ 10 mA / cm 2 ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Comparative Example 1-1 Compound NPB 4.69 5.45 (0.138, 0.127) Experimental Example 2-1 Compound 1 4.43 5.70 (0.139, 0.123) EXPERIMENTAL EXAMPLE 2-2 Compound 9 4.44 5.78 (0.138, 0.126) Experimental Example 2-3 Compound 32 4.45 5.73 (0.136, 0.124) Experimental Example 2-4 Compound 36 4.40 5.71 (0.135, 0.125) Experimental Example 2-5 Compound 1-1 4.42 5.69 (0.137, 0.121) Experimental Examples 2-6 Compound 1-3 4.43 5.68 (0.136, 0.123) Experimental Example 2-7 Compound 1-5 4.40 5.65 (0.132, 0.125) Experimental Examples 2-8 Compound 1-16 4.41 5.64 (0.138, 0.126) Experimental Examples 2-9 Compound 1-18 4.43 5.63 (0.134, 0.128) Experimental Example 2-10 Compound 2-1 4.47 5.54 (0.135, 0.121) Experimental Example 2-11 Compound 2-3 4.48 5.56 (0.136, 0.122) Experimental Examples 2-12 Compound 2-5 4.43 5.59 (0.138, 0.123) Experimental Example 2-13 Compound 2-16 4.46 5.60 (0.138, 0.125) Experimental Example 2-14 Compound 2-18 4.46 5.62 (0.136, 0.126) Experimental Example 2-15 Compound 3-1 4.49 5.82 (0.132, 0.127) Experimental Example 2-16 Compound 3-3 4.50 5.78 (0.134, 0.121) Experimental Example 2-17 Compound 3-5 4.51 5.79 (0.135, 0.125) Experimental Example 2-18 Compound 3-16 4.48 5.75 (0.133, 0.128) Experimental Example 2-19 Compound 3-18 4.47 5.72 (0.132, 0.126)

The heterocyclic compound represented by Formula 1 according to one embodiment of the present invention has excellent hole transporting ability and exhibits characteristics of low voltage and high efficiency and can be applied to organic light emitting devices.

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

Claims (15)

A first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the one or more organic material layers include a hole transporting layer containing a heterocyclic compound represented by any one of the following Chemical Formulas 2 to 4 , A hole injection layer, and an electron blocking layer.
(2)
Figure 112017128354061-pat00147

(3)
Figure 112017128354061-pat00148

[Chemical Formula 4]
Figure 112017128354061-pat00149

In the above formulas 2 to 4,
R 1 to R 12, R 21 to R 24, and R 31 to R 36 are the same or different and each independently hydrogen or deuterium,
Ar 1 to Ar 3 are the same or different from each other, and each independently represents an alkyl group; An aryl group, or an aryl group substituted or unsubstituted with an aryl group. delete delete The organic electroluminescent device according to claim 1, wherein Ar 1 to Ar 3 are the same or different from each other,
[Chemical Formula 5]
Figure 112017128354061-pat00150

In Formula 5,
X 1 to X 3 are the same or different from each other and are each independently CR,
R is hydrogen; An alkyl group; An aryl group substituted or unsubstituted with an alkyl group or an aryl group, or an adjacent two or more substituents bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group or an aryl group,
L 1 to L 2 , which are the same or different from each other, are each independently a direct bond; Or arylene substituted or unsubstituted with an alkyl group or an aryl group,
L 3 is a direct bond; Or arylene substituted or unsubstituted with an alkyl group or an aryl group,
A 1 and A 2 are the same or different and each independently hydrogen; An alkyl group; Or an aryl group substituted or unsubstituted with an alkyl group or an aryl group, or an adjacent two or more substituents may be bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group or an aryl group,
a and b are the same or different, and each independently represents an integer of 0 to 5,
c is an integer of 0 to 5,
when a is 2 or more, L &lt; 1 &gt;
when b is 2 or more, L &lt; 2 &gt; are the same or different from each other,
When c is 2 or more, L &lt; 3 &gt; The organic electroluminescent device according to claim 1, wherein Ar 1 to Ar 3 are the same or different from each other and each independently represent any one of the following formulas (6) to (10)
[Chemical Formula 6]
Figure 112017128354061-pat00151

(7)
Figure 112017128354061-pat00152

[Chemical Formula 8]
Figure 112017128354061-pat00153

[Chemical Formula 9]
Figure 112017128354061-pat00154

[Chemical formula 10]
Figure 112017128354061-pat00155

In Formulas 6 to 10,
B 1 to B 10 are the same or different from each other, and each independently hydrogen; An alkyl group; An aryl group substituted or unsubstituted with an alkyl group or an aryl group, or an adjacent two or more substituents bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group or an aryl group,
b1 is an integer of 0 to 9,
b2, b5 and b7 are the same or different and independently of one another are an integer of 0 to 5,
b3, b4, b8 and b9 are the same or different and each independently represents an integer of 0 to 4,
b6 is an integer of 0 to 6,
b10 is an integer of 0 to 3,
When each of b1 to b10 is 2 or more, the structures in parentheses are the same or different from each other. delete The organic electroluminescent device according to claim 1, wherein Ar 1 to Ar 3 are the same or different from each other,
[Chemical Formula 13]
Figure 112017128354061-pat00156

In the above formula (13)
Z is CR a R b ,
R a , R b , Y 1 and Y 2 are the same or different from each other, and each independently hydrogen; An alkyl group; An aryl group which is substituted or unsubstituted with an alkyl group or an aryl group, or an adjacent two or more substituents are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group or an aryl group,
L 11 is a direct bond or arylene substituted or unsubstituted with an alkyl group or an aryl group,
y1 is an integer of 0 to 4, y2 is an integer of 0 to 3, p11 is an integer of 0 to 5,
If more than y1 is 2 and Y 1 are the same as or different from each other,
If y2 is not less than 2, and Y 2 are the same as or different from each other,
When p11 is 2 or more, L &lt; 11 &gt; The organic electroluminescent device according to claim 1, wherein Ar 1 to Ar 3 are the same or different from each other and each independently selected from the following substituted or unsubstituted structural formulas:
Figure 112017128354061-pat00157

Figure 112017128354061-pat00158

Figure 112017128354061-pat00159

Figure 112017128354061-pat00160

Figure 112017128354061-pat00161

Figure 112017128354061-pat00162
. The organic electroluminescent device according to claim 1, wherein the compounds represented by Chemical Formulas 2 to 4 are represented by Chemical Formulas 14 to 16:
[Chemical Formula 14]
Figure 112017128354061-pat00163

[Chemical Formula 15]
Figure 112017128354061-pat00164

[Chemical Formula 16]
Figure 112017128354061-pat00165

In Formulas 14 to 16 above,
The definitions of R 1 to R 12, R 21 to R 24 and R 31 to R 36 are the same as those of formulas (2) to (4)
X 1 to X 9 are the same or different from each other, and are each independently CR,
R is hydrogen; An alkyl group; An aryl group which is substituted or unsubstituted with an alkyl group or an aryl group, or an adjacent two or more substituents are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group or an aryl group,
S 1 to S 3 are the same or different from each other, and each independently hydrogen; An alkyl group; An aryl group which is substituted or unsubstituted with an alkyl group or an aryl group, or an adjacent two or more substituents are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group or an aryl group,
p, q and r are the same or different and each independently represents an integer of 0 to 2,
when p is 2, S 1 are the same or different from each other,
when q is 2, S 2 are the same or different from each other,
When r is 2, S 3 is equal to or different from each other. The organic electroluminescent device according to claim 1, wherein the compound represented by any one of Chemical Formulas 2 to 4 is selected from the following structural formulas:
Figure 112017128354061-pat00166

Figure 112017128354061-pat00167

Figure 112017128354061-pat00168

Figure 112017128354061-pat00169
Figure 112017128354061-pat00170
Figure 112017128354061-pat00171

Figure 112017128354061-pat00172

Figure 112017128354061-pat00173

Figure 112017128354061-pat00174

Figure 112017128354061-pat00175

Figure 112017128354061-pat00176

Figure 112017128354061-pat00177

Figure 112017128354061-pat00178

Figure 112017128354061-pat00179

Figure 112017128354061-pat00180
. delete delete delete delete delete
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TW201827425A (en) * 2016-09-14 2018-08-01 德商麥克專利有限公司 Compounds having carbazole structures
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US10662196B2 (en) 2016-11-17 2020-05-26 Universal Display Corporation Organic electroluminescent materials and devices
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Organic Letters, 17(17), 4164-4167, 2015

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