KR101654420B1 - Heterocyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to an organic light emitting device comprising a heterocyclic compound and an organic material layer including at least one layer including a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode, Wherein the organic compound is a compound represented by formula (I).

Description

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

The present invention relates to heterocyclic compounds and organic light emitting devices using the same.

This specification claims the benefit of Korean Patent Application No. 10-2013-0114643, filed on September 26, 2013, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable state in oxidation and in a reduced state can be used, and when excitons are formed, .

Therefore, there is a need in the art to develop new organic materials.

Korean Patent Publication No. 2006-0023046

An object of the present invention is to provide a heterocyclic compound and an organic light emitting device using the heterocyclic compound.

In one embodiment of the present specification, there is provided a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In formula (1)

A and B are the same or different and are each independently a benzene ring or a naphthalene ring,

m is an integer of 0 to 4 when A is a benzene ring and 0 to 6 when A is a naphthalene ring,

n is an integer from 0 to 4 when B is a benzene ring and is an integer from 0 to 6 when B is a naphthalene ring,

m + n is 1 or more,

X and Y are the same or different from each other, and each independently hydrogen or cyano group,

At least one of X and Y is a cyano group,

L is a direct bond; An arylene group which is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic and nitrile groups; Or a divalent heterocyclic ring substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic, However,

Ar is represented by the following general formula (2) or (3)

(2)

(3)

In formulas (2) and (3)

Cy 1 to Cy 4 are the same or different from each other and each independently represent a benzene ring substituted or unsubstituted with an aryl group; Or a naphthalene ring substituted or unsubstituted with an aryl group,

Ar ₁ represents a substituted or unsubstituted alkyl group having 1 to 4 substituents selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, An aryl group; Or a heterocyclic ring substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic, .

According to an embodiment of the present invention, there is provided an organic light emitting device comprising a first electrode, a second electrode, and an organic layer including one or more layers including a light emitting layer provided between the first electrode and the second electrode, And the light emitting layer comprises the heterocyclic compound.

The heterocyclic compound according to one embodiment of the present invention can be used as a light emitting material. The compound according to one embodiment of the present specification has an appropriate energy level, and is excellent in electrochemical stability and thermal stability. Thus, the organic light emitting device comprising the compound provides high efficiency and / or high driving stability.

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 detail.

In one embodiment of the present invention, X and Y are the same or different from each other, and each independently hydrogen or cyano group, and at least one of X and Y is a cyano group.

In one embodiment of the present specification, at least two of X and Y are cyano groups.

When at least one of X and Y is a cyano group, the electron mobility of a carbazole derivative substituted with a cyano group increases, and a bipolar host (host) in which a hole transport unit and an electron transport unit are simultaneously present in one molecule ), And when used as a phosphorescent light-emitting layer, the driving voltage of the organic light emitting element can be lowered.

In one embodiment of the present invention, Ar in Formula 1 is the Formula 2 or Formula 3.

In one embodiment of the present specification, a carbazole group substituted with at least one cyano group or a structure in which a nitrogen atom of a benzocarbazole group substituted with at least one cyano group is linked with a carbazole group or a benzocarbazole group through L .

In one embodiment of the present specification, a carbazole group substituted with at least one cyano group or a structure wherein a nitrogen atom of a benzocarbazole group substituted with at least one cyano group is linked to a benzene ring of a carbazole group or a benzocarbazole group through L .

In one embodiment of the present specification, a carbazole group substituted with at least one cyano group, or a structure in which the nitrogen atom of the benzocarbazole group substituted with at least one cyano group is linked to the nitrogen atom of the carbazole group or the benzocarbazole group through L .

L is a direct bond; An arylene group which is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic and nitrile groups; Or a divalent heterocyclic ring substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic, .

In one embodiment of the present invention, A and B in Formula 1 are the same or different from each other and each is a benzene ring.

In one embodiment of the present invention, A in Formula 1 is a naphthalene ring.

In one embodiment of the present invention, B in Formula 1 is a benzene ring.

In one embodiment of the present specification, Cy1 to Cy4 are the same or different and each independently represents a benzene ring substituted or unsubstituted with an aryl group; Or a naphthalene ring substituted or unsubstituted with an aryl group.

In another embodiment, the Cy1 is a benzene ring substituted with an aryl group.

In another embodiment, the Cy1 is an unsubstituted benzene ring.

In another embodiment, the Cy1 is a naphthalene ring substituted with an aryl group.

In one embodiment of the present specification, Cy1 is a naphthalene ring substituted with a phenyl group.

In another embodiment, the Cy1 is an unsubstituted naphthalene ring.

In one embodiment of the present specification, Cy2 is a benzene ring substituted with an aryl group.

In another embodiment, the Cy2 is an unsubstituted benzene ring.

In another embodiment of the present specification, Cy2 is a naphthalene ring substituted with an aryl group.

In one embodiment of the present specification, Cy2 is a naphthalene ring substituted with a phenyl group.

In another embodiment, the Cy2 is an unsubstituted naphthalene ring.

In another embodiment, Cy3 is a benzene ring substituted with an aryl group.

In another embodiment, the Cy3 is an unsubstituted benzene ring.

In another embodiment, Cy3 is a naphthalene ring substituted with an aryl group.

In one embodiment of the present specification, Cy3 is a naphthalene ring substituted with a phenyl group.

In another embodiment, the Cy3 is an unsubstituted naphthalene ring.

In one embodiment of the present specification, Cy4 is a benzene ring substituted with an aryl group.

In another embodiment, the Cy4 is an unsubstituted benzene ring.

In another embodiment of the present specification, Cy4 is a naphthalene ring substituted with an aryl group.

In one embodiment of the present specification, Cy4 is a naphthalene ring substituted with a phenyl group.

In another embodiment, the Cy4 is an unsubstituted naphthalene ring.

In the present specification, the naphthalene ring is a naphthalene ring in which a benzene ring forms a condensed ring at positions 2 and 3 of the carbazole group.

In the present specification, the naphthalene ring is a naphthalene ring in which a benzene ring forms a condensed ring at the 3 and 4 positions of the following carbazole groups.

In one embodiment of the present invention, B in Formula 1 is a benzene ring.

In one embodiment of the present invention, the compound represented by the formula (1) is represented by any one of the following formulas (4) to (24).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

≪ EMI ID =

In formulas (4) to (24)

L is the same as defined in Chemical Formula 1,

Ar ₁ is the same as defined in formula (2)

a and b each represent an integer of 0 to 4,

c is an integer of 0 to 6,

a + b and b + c are at least 1,

X ₁ and X ₂ are the same or different from each other and are each hydrogen or a cyano group,

Y ₁ is hydrogen or cyano group,

At least one of X ₁ and Y ₁ is a cyano group, or at least one of X ₂ and Y ₁ is a cyano group,

A carbazole group which is not substituted by X ₁ and Y ₁ or X ₂ and Y ₁ , or a benzocarbazole group which is not substituted by X ₁ and Y ₁ or X ₂ and Y ₁ is further substituted or unsubstituted as an aryl group.

In one embodiment of the present specification, at least one of A, B, and Cy1 to Cy4 is a naphthalene ring, and when at least one of Cy1 to Cy4 is a naphthalene ring, the naphthalene ring is substituted or unsubstituted with an aryl group.

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

As used herein, the term "substituted or unsubstituted" means 1 or 2 selected from the group consisting of halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, Means that at least two of the substituents substituted with the above-described substituents or substituted with at least one of the above-exemplified substituents are substituted with a connected substituent, or have no substituent. 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. Means that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent connected thereto. 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.

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

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, branched or cyclic, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl But are not limited to, pentyl, heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, cyclohexyl and cyclopentyl.

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 20 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.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted. In addition, an aryl group in the present specification may mean an aromatic ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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

,

,

및

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

,

,

And

And the like. However, the present invention is not limited thereto.

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. 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, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, the number of carbon atoms of the arylalkyl group is not particularly limited, but in one embodiment of the present specification, the arylalkyl group has 7 to 50 carbon atoms. Specifically, the aryl moiety has 6 to 49 carbon atoms and the alkyl moiety has 1 to 44 carbon atoms. Specific examples thereof include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, Group, an?,? -Methylphenylbenzyl group, a 1-naphthylbenzyl group, a 2-naphthylbenzyl group, a p-fluorobenzyl group, a 3,5-difluorobenzyl group, , p-methoxybenzyl group, m-methoxybenzyl group,? -phenoxybenzyl group,? -benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, But are not limited to, an ethyl group, an aminobenzyl group, a nitrobenzyl group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group and the like.

In the present specification, the number of carbon atoms of the arylalkenyl group is not particularly limited, but in one embodiment of the present specification, the arylalkenyl group has 8 to 50 carbon atoms. Specifically, the aryl moiety has 6 to 49 carbon atoms, and the alkenyl moiety has 2 to 44 carbon atoms.

In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N Se and S, and the like. The number of carbon atoms of the heterocyclic group 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 benzoxazole 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, a dibenzofuranyl group, and the like, but are not limited thereto.

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

In one embodiment of the present specification, L is a substituted or unsubstituted arylene group.

In one embodiment of the present invention, L represents one or two or more selected from the group consisting of phenyl, biphenyl, terphenyl, and fluorene, and the phenyl, biphenyl, terphenyl, Substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group and a nitrile group.

In one embodiment of the present specification, L represents a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L comprises a phenylene group.

In one embodiment of the present specification, L represents a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, L comprises a biphenylene group.

In one embodiment of the present specification, L represents a substituted or unsubstituted terphenylene group.

In another embodiment, L comprises a terphenylene group.

In one embodiment of the present specification, L represents a substituted or unsubstituted fluorenylene group.

In one embodiment, L comprises a fluorenylene group substituted with an alkyl group.

In one embodiment of the present disclosure, L is selected from the group consisting of phenylene; Biphenylene; Terphenylene; Fluorenylene substituted with an alkyl group; Or fluorenylene substituted with a phenylene-alkyl group.

In one embodiment of the present specification, Ar is formula (2).

In one embodiment of the present specification, Ar is the formula (3).

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, Ar ₁ is a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, Ar ₁ is a phenyl group.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, Ar ₁ is a biphenyl group.

In one embodiment of the present specification, X is a cyano group.

In one embodiment of the present specification, Y is a cyano group.

In one embodiment of the present invention, the heterocyclic compound containing A and B in the formula (1) may be represented by the following structure. In addition, an asterisk (*) in the following structure may represent a portion connected to L.

In one embodiment of the present invention, Formula (2) may be represented by any one of the following structures.

In one embodiment of the present invention, the formula (3) may be represented by any one of the following structures.

In one embodiment of the present invention, the compound represented by Formula 1 is represented by any one of the following Formulas 1-1 to 1-20.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 2-1 to 2-20.

The compound of formula (1) may be prepared based on the preparation examples described below.

Ar and Ar 'are the same as or different from each other and can correspond to the definition of L in formula (1), wherein C and D are the same or different from each other , And Cy1 to Cy4 in formulas (2) and (3), respectively.

Specifically, the ring group of A and B may be subjected to a bromination process to replace the cyano group after substitution with a bromine atom. The carbazole group or the benzocarbazole group substituted with the cyano group is reacted with a carbazole group or a benzocarbazole group substituted with a boronic acid or a borolane group to obtain a heterocycle of the above formulas 1-1 to 1-20 and 2-1 to 2-20 The heterocyclic compound of formula (1) can be prepared, but not limited thereto.

In one embodiment of the present disclosure, the carbazole group or the benzocarbazole group has a core linked to the carbazole group or the benzocarbazole group through L. Thus, as the nitrogen atom is located between aryl groups, the core structure of the heterocyclic compound includes limited conjugation.

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. As described above, since the core of the compound of Formula 1 contains limited conjugation, the energy band gap has a large property.

In this specification, compounds having various energy bandgaps can be synthesized by introducing various substituents to Ar ₁ and L to a core structure having a large energy band gap as described above. According to one embodiment of the present invention, the heterocyclic compound has a large energy band gap, so that it is easier to control the energy band gap by introducing a substituent than when the energy band gap is small.

Further, in one embodiment of the present specification, the HOMO and LUMO energy levels of a compound can be controlled by introducing various substituents at positions of Ar ₁ and L.

Accordingly, the organic light emitting device including the compound of Formula 1 according to one embodiment of the present invention can provide a high efficiency long life organic light emitting device.

Since the compound according to one embodiment of the present disclosure includes an amine structure in the core structure, it can have an appropriate energy level as a hole injecting and / or hole transporting material in an organic light emitting device. In this specification, by selecting a compound having an appropriate energy level according to the substituent among the above compounds and using the compound in an organic light emitting device, a device having a low driving voltage and a high light efficiency can be realized.

The heterocyclic compound of Formula 1 according to one embodiment of the present disclosure has appropriate hole or electron mobility. Therefore, when the heterocyclic compound is applied to an organic light emitting device, it is possible to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer.

By introducing various substituents to the core structure according to one embodiment of the present invention, the energy bandgap can be finely adjusted, and the characteristics at the interface between the organic materials can be improved, thereby making it possible to diversify the use of the material.

In addition, the compound represented by the formula (1) has a high glass transition temperature (T _g ) and thus is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

The present invention also provides an organic light emitting device using the compound of formula (1).

According to an embodiment of the present disclosure, there is provided an organic light emitting device comprising a first electrode, a second electrode, and an organic layer including one or more layers including a light emitting layer provided between the first electrode and the second electrode, And a heterocyclic compound represented by the formula (1).

In one embodiment of the present invention, the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant.

In another embodiment, the nitrogen-containing heterocyclic compound is included as a host of the light-emitting layer, and includes a phosphorescent dopant compound represented by the following formula (26) as a dopant.

(26)

In Formula 26,

M ₁ is Ir or Os,

L ₁₀ , L ₁₁ and L ₁₂ are the same or different and independently of each other are any one of the following structures,

p, r, s, t, v, y, b, d, f, h and l are each an integer of 0 to 4,

each of u, w, z, a, c, e, g, i and j is an integer of 0 to 6,

k is an integer of 0 to 8,

R ₁₀ to R ₄₁ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C ₂ ~ _10; A substituted or unsubstituted C ₆ ~ ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C _1-10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; Alkoxy group, a substituted or unsubstituted C ₁ ~ ₁₀ ring; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or adjacent groups form a condensed ring of monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic rings.

In one embodiment of the present invention, the phosphorescent dopant compound represented by Formula 26 is any one of the following compounds.

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 in this specification may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In 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.

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

The structure of the organic light emitting device of the present specification is illustrated in Figs. 1 and 2, but is not limited thereto.

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

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

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.

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.

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

The substrate can be selected in consideration of optical properties and physical properties as required. For example, the substrate is preferably transparent. The substrate may be of a rigid material, but may also be of a flexible material such as plastic.

As the material of the substrate, besides glass and quartz plate, a material such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (acrylonitrile butadiene styrene copolymer), TAC (triacetyl cellulose), and PAR (polyarylate), but the present invention is not limited thereto.

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 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 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 hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. The hole injecting material preferably has a highest occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic material, phthalocyanine derivative, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, Perylene-based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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 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, perylene tetracarboxylic 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 electron transporting layer 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. Do. 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 hole blocking layer is a layer for preventing the triplet excitons or holes from diffusing into the electron transporting layer, and may have electron transporting ability in a broad sense. The hole blocking layer is preferably a material having a function of transporting electrons and a capability of transporting holes, which is remarkably small. The probability of recombination of electrons and holes can be improved by blocking holes while transporting electrons. As the material of the hole blocking layer, the material of the electron transporting layer can be used as needed.

In one embodiment of the present invention, the organic light emitting diode may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The method for synthesizing the organic compound represented by Formula 1 and the preparation of the organic light emitting device using the same will be described in more detail with reference to the following Examples and Comparative Examples. However, these embodiments are for the purpose of illustrating the specification, and the scope of the present specification is not limited thereto.

Production Example 1. Synthesis of Formula 1-1

(20 mmol) of 1-chloro-4-iodobenzene and 4.77 g (20 mmol) of 11H-benzo (a) carbazole, 1.9 g (10 mmol) of copper iodide, 1.34 ml (20 mmol) of ethylenediamine was added to 250 ml of toluene and the mixture was stirred under reflux for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate, concentrated under reduced pressure, and subjected to column purification to obtain 5.88 g of A-1.

5.88 g (18 mmol) of A-1 and dimethylformamide were added, and 6.37 g (36 mmol) of N-bromosuccinimide was slowly dropped from the ice bath and stirred for 3 hours. The reaction mixture was poured into distilled water, extracted with methylene chloride, concentrated under reduced pressure, and purified by column purification to obtain 6.9 g of A-2.

A solution of 6.9 g (14.3 mmol) of A-2 and 2.8 g (31.5 mmol) of cuprous cyanide in 100 ml of N-methylpyrrolidone (NMP) was heated and stirred at 200 ° C for 5 hours. After the reaction was completed, the solution was cooled to room temperature, and then 180 ml of water was poured, followed by filtration and washing with ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was separated with water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered through celite. This was concentrated under reduced pressure to give a column. After drying, 2.72 g of intermediate A was obtained.

(7.2 mmol) of Intermediate A and 2.1 g (7.2 mmol) of 4- (9H-carbazol-9-yl) phenylboronic acid were dissolved in 50 ml of tetrahydrofuran, and 2.99 g (21.6 mmol) of potassium carbonate 30 ml of water was added. The solution was stirred at an elevated temperature, and when refluxing started, 0.04 g (0.07 mmol) of bis (tri-t-butylphosphine) palladium was added and reacted for 24 hours. After cooling, the water and the organic layer were separated, the organic layer was taken, dried over anhydrous magnesium sulfate, and filtered through celite. This was concentrated under reduced pressure to obtain a column. After drying, 3.79 g of the compound of formula (1-1) was obtained.

Production example 2. Synthesis of formula 1-8

The same reaction as in the synthesis of A-1 was carried out except that 4.76 g (20 mmol) of chloro-4-iodobenzene and 4.34 g (20 mmol) of 7H-benzo (c) carbazole were used and 5.97 g of B- . The same reaction as in the synthesis of A-2 was carried out except that 5.97 g (18.3 mmol) of B-1 and 6.48 g (36.6 mmol) of N-bromosuccinimide were used and 7.9 g of B-2 was obtained.

The reaction was carried out in the same manner as in the synthesis of Intermediate A except that 7.9 g (16.4 mmol) of B-2 and 3.21 g (36.1 mmol) of cuprous cyanide were used and 2.86 g of Intermediate B was obtained.

(7.58 mmol) of Intermediate B and 3.06 g (7.58 mmol) of 9,9-dimethyl-7- (9H-9-carbazolyl) Followed by purification to obtain 4.78 g of 1-8.

Production Example 3. Synthesis of Compound (1-15)

Except that 3.77 g (10 mmol) of Intermediate A and 3.37 g (10 mmol) of (4- (11H-benzo (a) carbazol-11-yl) ≪ / RTI > and 5.71 g of Formula 1-15 was obtained.

Production example 4. Synthesis of formula 1-16

The same reaction as in the synthesis of the compound of the formula 1-1 was carried out except that 3.77 g (10 mmol) of Intermediate A and 3.37 g (10 mmol) of (4- (7H-benzo (c) carbazol- And purified to obtain 6.03 g of the compound of Formula 1-16.

Preparation Example 5. Synthesis of Compound (1-18)

The same reaction as in the synthesis of A-2 was carried out except that 2.17 g (10 mmol) of 11H-benzo (a) carbazole and 3.54 g (20 mmol) of N-bromosuccinimide were used to purify 3.36 g of C- .

1.2 g (4.5 mmol) of Intermediate C was obtained by proceeding in the same manner as in the synthesis of Intermediate A except that 3.36 g (9 mmol) of C-1 and 1.76 g (19.8 mmol) of cuprous cyanide were used .

(10 mmol) of 2-bromo-7-iodo-9,9-dimethylfluorene, 1.26 g (20 mmol) of copper powder, 0.53 g (2 mmol) of crown-6 and 4.15 g (30 mmol) of potassium carbonate were added in this order, 200 ml of 1,2-dichlorobenzene was added thereto, and the mixture was refluxed at 180 ° C for 24 hours and stirred. After the completion of the reaction, the solution was concentrated and subjected to column purification to obtain 3.9 g of Intermediate D.

Was dissolved in 100 ml of toluene along with 3.9 g (6.7 mmol) of Intermediate D, 1.79 g (6.7 mmol) of Intermediate C and 0.84 g (8.7 mmol) of t-butoxysodium. The mixture was stirred at an elevated temperature. When refluxing began, 0.36 g (0.7 mmol) of bis (tri-t-butylphosphine) palladium was slowly added dropwise. The reaction was continued under reflux conditions for 24 hours. After cooling, the mixture was filtered through celite, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a column. After drying, 3.84 g of a compound represented by the formula 1-18 was obtained.

Preparation Example 6. Synthesis of 1-20

Except that 3.78 g (10 mmol) of Intermediate B and 3.37 g (10 mmol) of (4- (11H-benzo (a) carbazol-11-yl) And purified to give 5.4 g of 1-20.

Production Example 7. Synthesis of Formula 2-1

The same reaction as in the synthesis of A-2 was carried out except that 2.7 g (10 mmol) of 9- (4-chlorophenyl) -9H-carbazole and 3.54 g (20 mmol) of N-bromosuccinimide were used, g of E-1 was obtained.

E-1 (3.5 g, 8.1 mmol) and cuprous cyanide (1.58 g, 17.8 mmol). The reaction was carried out in the same manner as in the synthesis of Intermediate A to obtain 1.32 g of Intermediate E.

(10 mmol) of 8-bromo-11-phenyl-11H-benzo (a) carbazole was dissolved in 100 ml of tetrahydrofuran, followed by 2.5M n-butyllithium (hexane) Respectively. Thereafter, (5- (diethoxymethyl) furan-2-yl) boronic acid was stirred for 2 hours while slowly adding thereto. Then, 2M hydrochloric acid was added, and the mixture was immersed in water and extracted with water and ethyl acetate. The organic layer was collected, concentrated under reduced pressure, and subjected to column purification to obtain 2.87 g of Intermediate F. The same reaction as in the synthesis of the compound of the formula 1-1 was carried out except that 2.87 g (8.5 mmol) of the intermediate compound F and 2.78 g (8.5 mmol) of the intermediate compound E were used and 4.47 g of the compound of the formula (2-1) was obtained.

Production Example 8. Synthesis of Formula 2-3

The same reaction as in Intermediate F was carried out except that 3.7 g (10 mmol) of 8-bromo-7-phenyl-7H-benzo (c) carbazole was used to purify 2.97 g of Intermediate G. Intermediate G 2.97 g (8.8 mmol) of Intermediate E and 2.88 g (8.8 mmol) of Intermediate E, the reaction was carried out in the same manner as in the synthesis of the compound of the formula 1-1 and purification was conducted to obtain 4.37 g of 2-3.

Production Example 9. Synthesis of Formula 2-13

The same reaction as in the synthesis of the compound of the formula 1-1 was carried out except that 3.77 g (10 mmol) of Intermediate B and 3.63 g (10 mmol) of 6,9-diphenyl-9H-carbazole- g < / RTI > of formula (2-13).

<Examples>

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

[LINE]

N, N-bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1-biphenyl) -4,4-diamine) compound having the following structure was deposited on the hole injection layer to a thickness of 400 Å The hole transport layer was formed by thermal vacuum deposition.

[NPB]

Then, the compound of Formula 1-1 prepared in Preparation Example 1 was vacuum deposited on the hole transport layer to a film thickness of 300 Å at a concentration of 10% with Ir (ppy) _{3 as a} dopant to form a light emitting layer.

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

[Electron transport material]

Lithium fluoride (LiF) and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

<Experimental Example 2>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-8 was used instead of the compound of Formula 1-1.

<Experimental Example 3>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-1 was used instead of the compound of Formula 1-1.

<Experimental Example 4>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-16 was used instead of the compound of Formula 1-1.

<Experimental Example 5>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-18 was used in place of the compound of Formula 1-1.

<Experimental Example 6>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-20 was used in place of the compound of Formula 1-1.

<Experimental Example 7>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-1 was used instead of the compound of Formula 1-1.

<Experimental Example 8>

In the same manner as in Experimental Example 1, except that the compound of Formula 2-3 was used instead of the compound of Formula 1-1.

<Experimental Example 9>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-1 was used instead of the compound of Formula 1-1.

&Lt; Comparative Example 1 &

In the same manner as in Experimental Example 1, the following H1 was used in place of the compound of Formula 1-1.

[H1]

&Lt; Comparative Example 2 &

In the same manner as in Experimental Example 1, except that the following H2 was used in place of the compound of Formula 1-1.

[H2]

The results shown in Table 1 were obtained when current was applied to the organic light-emitting device manufactured by Experimental Examples 1 to 8 and Comparative Examples 1 and 2.

Host Dopant Doping concentration (%) Voltage (V)
@ 5,000 cd / m ² efficiency
(cd / A) Relative life
(T ^95% ) Experimental Example 1 (1-1) Ir (ppy) ₃ 10 4.7 35 2.4 Experimental Example 2 1-8 Ir (ppy) ₃ 10 4.6 34 2.2 Experimental Example 3 Formula 1-15 Ir (ppy) ₃ 10 4.6 38 2.2 Experimental Example 4 (1-16) Ir (ppy) ₃ 10 4.8 40 3.3 Experimental Example 5 (1-18) Ir (ppy) ₃ 10 4.5 38 1.7 Experimental Example 6 1-20 Ir (ppy) ₃ 10 4.7 34 3.7 Experimental Example 7 2-1 Ir (ppy) ₃ 10 4.3 37 4.5 Experimental Example 8 (2-3) Ir (ppy) ₃ 10 4.5 35 4.1 Experimental Example 9 2-13 Ir (ppy) ₃ 10 4.7 34 3.9 Comparative Example 1 H1 Ir (ppy) ₃ 10 5.2 32 One Comparative Example 2 H2 Ir (ppy) ₃ 10 5.1 28 0.8

The results of Table 1 indicate that the heterocyclic compound according to one embodiment of the present invention can be included in the organic light emitting device as a host of the phosphorescent light emitting layer and can exhibit a driving voltage lower than that of Comparative Examples 1 and 2 which does not include a cyano group, An organic light emitting device having an efficiency and a long life can be manufactured.

Claims (11)

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

In formula (1)
A and B are the same or different and are each independently a benzene ring or a naphthalene ring,
m is an integer of 1 to 4 when A is a benzene ring and is an integer of 1 to 6 when A is a naphthalene ring,
n is an integer from 1 to 4 when B is a benzene ring and is an integer from 1 to 6 when B is a naphthalene ring,
m + n is 2 or more,
X and Y are the same or different from each other, and each independently hydrogen or cyano group,
At least one of X and at least one of Y is a cyano group,
L is an arylene group substituted or unsubstituted with an alkyl group,
Ar is represented by the following general formula (2) or (3)
(2)

(3)

In formulas (2) and (3)
Cy1 to Cy4 are the same or different and are benzene rings each independently substituted or unsubstituted with an aryl group; Or a naphthalene ring substituted or unsubstituted with an aryl group,
Ar ₁ is an aryl group,
In the above Formulas 1 to 3,
At least one of A, B and Cy1 to Cy4 is a naphthalene ring. The method according to claim 1,
The compound represented by the formula (1) is represented by the following formulas (5) to (15), and
Heterocyclic compound represented by any one of &lt; RTI ID = 0.0 &gt;
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

In formulas (5) to (15) and (17) to (24)
L is the same as defined in Chemical Formula 1,
Ar ₁ is the same as defined in formula (2)
a and b are each an integer of 1 to 4,
c is an integer of 1 to 6,
X ₁ and X ₂ are the same or different from each other and are each hydrogen or a cyano group,
Y ₁ is hydrogen or cyano group,
At least one of X ₁ , at least one of X ₂ , and at least one of Y ₁ is a cyano group. The method according to claim 1,
And at least one of Cy1 to Cy4 is a naphthalene ring, the naphthalene ring is substituted or unsubstituted with an aryl group. The method according to claim 1,
L is one or two or more selected from the group consisting of phenyl, biphenyl, terphenyl and fluorene,
Wherein said phenyl, biphenyl, terphenyl and fluorene are substituted or unsubstituted with an alkyl group. delete The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-20):

. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (2-1) to (2-20):

. An organic light emitting device comprising: a first electrode, a second electrode, and an organic layer including at least one layer including a light emitting layer provided between the first electrode and the second electrode,
Wherein the light emitting layer comprises the heterocyclic compound according to any one of claims 1 to 4, 6 and 7. The method of claim 8,
Wherein the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant. The method of claim 9,
Wherein the phosphorescent dopant compound is represented by the following Chemical Formula 26:
(26)

In Formula 26,
M ₁ is Ir or Os,
L ₁₀ , L ₁₁ and L ₁₂ are the same or different and independently of each other are any one of the following structures,

p, r, s, t, v, y, b, d, f, h and l are each an integer of 0 to 4,
each of u, w, z, a, c, e, g, i and j is an integer of 0 to 6,
k is an integer of 0 to 8,
R ₁₀ to R ₄₁ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C ₂ ~ _10; A substituted or unsubstituted C ₆ ~ ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C _1-10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; Alkoxy group, a substituted or unsubstituted C ₁ ~ ₁₀ ring; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or adjacent groups form a condensed ring of monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic rings. The method of claim 10,
Wherein the phosphorescent dopant compound represented by Formula 26 is any one of the following compounds:

.

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