KR20170109430A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound and an organic light emitting device comprising the same. The heterocyclic compound of the present specification is represented by chemical formula 1. The novel compound according to the present invention can be used as a material for an organic material layer of an organic light emitting device, and by using the compound, the efficiency, low driving voltage and/or lifetime characteristics of the organic light emitting device can be improved.

Description

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

The present invention relates to heterocyclic compounds and organic light emitting devices containing them.

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.

International Patent Application Publication No. 2003/012890

Therefore, the present inventors aim to provide a heterocyclic compound having a chemical structure capable of performing various functions required in an organic light emitting device according to a substituent, and an organic light emitting device including the heterocyclic compound.

The present invention provides a heterocyclic compound represented by the following formula (1).

[Chemical Formula 1]

In formula (1)

Cy1 and Cy2 are the same or different and are each independently a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring; or a substituted or unsubstituted benzene ring substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted nitrogen-containing heterocyclic ring; Or a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, said naphthalene ring being unsubstituted or substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted nitrogen-

At least one of Cy1 and Cy2 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, wherein said naphthalene ring is unsubstituted or substituted with one or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-

X1 to X3 are the same or different from each other and each independently CR or N,

At least one of X1 to X3 is N,

L is a substituted or unsubstituted arylene group having 10 to 30 carbon atoms,

R, Ar1 and Ar2 are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

Also, the present specification discloses a plasma display panel comprising 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 new compound according to the present invention can be used as a material of an organic material layer of an organic light emitting device, and by using it, it is possible to improve the efficiency, the driving voltage and / or the lifetime characteristic of the organic light emitting device.

Fig. 1 shows an example of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated.
2 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked FIG.

Hereinafter, the present specification will be described in detail.

The present invention provides a compound represented by the above formula (1).

In one embodiment of the present invention, at least one of Cy1 and Cy2 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, or a naphthalene ring substituted or unsubstituted with one or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-containing heterocyclic rings.

According to one embodiment of the present specification, the substituent of Cy1 and Cy2 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, the balance of the bipolar characteristics of the molecule itself, that is, the HOMO energy level or the HOMO energy level, while maintaining an appropriate balance between the n-type portion and the p- The LUMO energy level can be appropriately adjusted.

In addition, when Cy1 and Cy2 include a nitrogen-containing heterocyclic ring below the heterocyclic ring, the HOMO energy level can be sufficiently lowered to effectively block holes passing from the hole-transporting layer, It can be expected to serve as an electron transport layer and / or an electron injection layer which can expect an increase in efficiency and a synergistic effect of lifetime.

In addition, the heterocyclic compound according to one embodiment of the present invention simultaneously contains a nitrogen-containing ring group including X1 to X3 and a nitrogen-containing ring group including Cy1 and Cy2. In this case, the heterocyclic compound according to one embodiment of the present invention has a bipolar characteristic, so that the charge mobility can be controlled by a single substance, and the effect of reducing the interfacial barrier with the organic material layer can be expected.

In one embodiment of the present invention, the naphthalene ring is formed by condensing an additional benzene ring on the carbon at positions 1 and 2 of the benzene ring adjacent to the pyrrole group of formula (1).

In one embodiment, the naphthalene ring is formed by condensing an additional benzene ring on the carbon at positions 2 and 3 of the benzene ring adjacent to the pyrrole group of formula (I).

In another embodiment, the naphthalene ring is formed by condensing an additional benzene ring on the carbon at positions 3 and 4 of the benzene ring adjacent to the pyrrole group of formula (1).

In one embodiment of the present invention, the heterocyclic compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-3).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

L, X1 to X3, Ar1 and Ar2 are the same as defined in formula (1)

a, c and e are each an integer of 1 to 4,

b, d and f are each an integer of 1 to 6,

When a, b, c, d, e and f are each an integer of 2 or more, each of at least two of R 1 to R 6 is the same or different,

R1 to R6 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, an aryl group, a nitrogen-containing monocyclic ring and a nitrogen-containing heterocyclic ring; A substituted or unsubstituted nitrogen-containing monocyclic ring substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, an aryl group, a nitrogen-containing monocyclic ring and a nitrogen-containing heterocyclic ring; Or a heterocyclic ring of nitrogen which is substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, an aryl group, a nitrogen-containing monocyclic ring and a nitrogen-containing heterocyclic ring.

As used herein, the term "substituted or unsubstituted" A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two 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, "a substituent to which at least two 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.

The aryl group may be a monocyclic or polycyclic aryl group, and when it is a polycyclic aryl group, it may be a monocyclic, tricyclic or polycyclic aryl group.

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. Specifically, monocyclic aryl groups include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, and quarter-phenyl groups.

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 anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

When the aryl group is a bicyclic aryl group, the number of carbon atoms is preferably 6 to 12. Specifically, an example of this aryl group is a naphthyl 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 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, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, a thiazolyl group, 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 nitrogen-containing monocyclic ring is a monocyclic ring group containing at least one N, and includes pyridine, pyrimidine, pyridazine, pyrazine, triazine, tetrazine, pentacene, But is not limited thereto.

In the present specification, the nitrogen-containing heterocyclic ring is a ring group in which two monocyclic rings containing at least one N are condensed, and examples thereof include a quinoline group, an isoquinoline group, a quinazoline group, a quinoxaline group and a naphthyridine group. But is not limited thereto.

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

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 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, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted on the N atom with an aryl group, an alkyl group, an arylalkyl group, and a heterocyclic group. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, An anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, And the like, but the present invention is not limited thereto.

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

In one embodiment of the present specification, L is an arylene group having 10 to 30 carbon atoms. Specifically, in one embodiment, L is an arylene group having 12 to 25 carbon atoms.

When L is less than 10 carbon atoms, steric hindrance occurs between the nitrogen-containing heterocyclic ring containing X1 to X3 and the nitrogen-containing ring containing Cy1 and Cy2, and the energy band gap may become excessively large. Specifically, when L is less than 10 carbon atoms, the physical distance between the n-type portion and the p-type portion becomes too close to each other, so that charge transfer within the molecule is facilitated due to steric hindrance and short conjugation, Which may cause a decrease in efficiency. This phenomenon may be particularly serious when used as an electron transporting, electron injection or hole blocking layer of a blue light emitting device. When L is less than 10 carbon atoms, the LUMO energy level is excessively high. Therefore, when a compound having L less than 10 carbon atoms is included in the device, the energy barrier between the cathode and the electron transport layer becomes large, leading to a reduction in the driving voltage and / or efficiency of the device.

When an arylene group having 10 or more carbon atoms according to one embodiment of the present invention is included as L, the steric hindrance between the nitrogen containing ring including X1 to X3 and the nitrogen containing ring including Cy1 and Cy2 is prevented, And the bipolar characteristics can be maintained, thereby maximizing the efficiency. In addition, the carbon number of L can be appropriately adjusted to adjust the energy band gap as needed, and the charge transfer ability can be controlled accordingly.

Therefore, the organic light emitting device including the heterocyclic compound according to one embodiment of the present invention can expect excellent charge injection ability and high charge mobility.

The carbon number of L in the present specification includes not only one divalent carbon number but also a structure in which a plurality of divalent groups are connected to each other.

In one embodiment of the present invention, L is represented by the following formula (2).

(2)

In formula (2)

o, p, q and r are each an integer of 0 or 1,

1? O + p + q + r? 4,

L1 to L4 are the same or different from each other and each independently represent a phenylene group; Or a naphthalene group,

The total sum of the carbon numbers of L1 to L4 is 10 to 30.

는 화학식 1과 연결되는 부위를 의미한다.In the present specification,

Means a moiety connected to the formula (1).

In one embodiment of the present disclosure, o + p + q + r = 2.

In one embodiment of the present disclosure, o + p + q + r = 3.

In another embodiment, o + p + q + r = 4.

In one embodiment of the present invention, L1 is a phenylene group.

In one embodiment, L1 is a naphthalene group.

In another embodiment, L1 is a fluorenylene group.

In one embodiment of the present invention, L2 is a phenylene group.

In another embodiment, L2 is a naphthalene group.

In another embodiment, L2 is a fluorenylene group.

In one embodiment of the present specification, L3 is a phenylene group.

In another embodiment, L3 is a naphthalene group.

In another embodiment, L3 is a fluorenylene group.

In one embodiment of the present invention, L4 is a phenylene group.

In another embodiment, L4 is a naphthalene group.

In another embodiment, L4 is a fluorenylene group.

이다. In one embodiment of the present disclosure, the phenylene group is

to be.

이다. In another embodiment, the phenylene group is

to be.

이다.In one embodiment of the present disclosure, the naphthalene group is

to be.

이다. In another embodiment, the naphthalene group is

to be.

이다.In one embodiment of the present disclosure, the fluorenylene group is

to be.

In one embodiment of the present disclosure, o is zero.

In another embodiment, o is one.

In one embodiment of the present disclosure, p is zero.

In another embodiment, p is one.

In one embodiment of the present disclosure, q is zero.

In another embodiment, q is 1.

In one embodiment of the present disclosure, r is zero.

In another embodiment, r is 1.

In one embodiment of the present invention, Formula (2) is any one of the following structures. In one embodiment of the present specification, L is any one of the following structures.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted phenanthrenyl group.

In one embodiment, Ar1 and Ar2 are the same.

In another embodiment, Ar1 and Ar2 are different from each other.

In one embodiment, Ar1 is a substituted or unsubstituted phenyl group.

In another embodiment, Ar1 is a phenyl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted naphthyl group.

In another embodiment, Ar1 is a naphthyl group.

In one embodiment of the present specification, Ar1 is a 1-naphthyl group.

In another embodiment, Ar1 is a 2-naphthyl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted biphenyl ring.

In another embodiment, Arl is biphenyl.

In one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenanthrenyl group.

In another embodiment, Ar1 is a 9-phenanthrenyl group.

In one embodiment, Ar2 is a substituted or unsubstituted phenyl group.

In another embodiment, Ar2 is a phenyl group.

In one embodiment of the present specification, Ar2 is a substituted or unsubstituted naphthyl group.

In another embodiment, Ar2 is a naphthyl group.

In one embodiment of the present invention, Ar2 is a 1-naphthyl group.

In another embodiment, Ar2 is a 2-naphthyl group.

In one embodiment of the present specification, Ar2 is a substituted or unsubstituted biphenyl ring.

In another embodiment, Ar2 is biphenyl.

In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenanthrenyl group.

In another embodiment, Ar2 is a 9-phenanthrenyl group.

In one embodiment of the present specification, Cy1 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, or a benzene ring substituted or unsubstituted with one or two or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-containing heterocyclic rings.

In one embodiment of the present specification, Cy1 is an unsubstituted benzene ring.

In another embodiment, Cy1 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, or a naphthalene ring substituted or unsubstituted with one or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-containing heterocyclic rings.

In one embodiment of the present specification, Cy1 is an unsubstituted naphthalene ring.

In one embodiment of the present specification, Cy2 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, or a benzene ring substituted or unsubstituted with one or two or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-containing heterocyclic rings.

In one embodiment of the present specification, Cy2 is an unsubstituted benzene ring.

In one embodiment, Cy2 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, or a naphthalene ring substituted or unsubstituted with one or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-containing heterocyclic rings.

In one embodiment of the present specification, Cy2 is an unsubstituted naphthalene ring.

In one embodiment of the present specification, Cy1 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, and Cy2 is a benzene ring.

In one embodiment of the present specification, at least one of Cy1 and Cy2 is a naphthyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A biphenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; And a quinoline group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group, or a naphthalene ring substituted or unsubstituted with a substituent selected from the group consisting of

In one embodiment of the present specification, Cy1 is a naphthalene ring substituted with one or more substituents selected from the group consisting of cyano,

In one embodiment, the Cy1 is a naphthalene ring substituted with a naphthyl group.

In another embodiment, Cy1 is a naphthalene ring substituted with a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group.

In another embodiment, the Cy1 is a naphthalene ring substituted with a phenyl group substituted with a pyridine group.

In another embodiment, the Cy1 is a naphthalene ring substituted with a phenyl group substituted with a quinoline group.

In another embodiment, the Cy1 is a naphthalene ring substituted with a phenyl group substituted with a cyano group.

In one embodiment of the present specification, Cy1 is a naphthalene ring substituted with a biphenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group.

In another embodiment, the Cy1 is a naphthalene ring substituted with a biphenyl group substituted with a cyano group.

In another embodiment, Cy1 is a naphthalene ring substituted with a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group.

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

Is a naphthalene ring substituted with a quinoline group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group in another embodiment.

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

In one embodiment, R1 is hydrogen.

In one embodiment of the present disclosure, R < 2 > is hydrogen; A naphthyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A biphenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; Or a quinoline group substituted or unsubstituted with one or two or more substituents selected from the group consisting of cyano, pyridine, phenyl and quinoline groups.

In another embodiment, R < 2 > is hydrogen.

In one embodiment of the present invention, R 2 is a naphthyl group substituted or unsubstituted with one or more substituents selected from the group consisting of cyano, pyridine, phenyl, and quinoline groups.

In another embodiment, R2 is a naphthyl group.

In another embodiment, R 2 is a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group.

In another embodiment, R 2 is a phenyl group substituted with a pyridine group.

In another embodiment, R 2 is a phenyl group substituted with a quinoline group.

In another embodiment, R 2 is a phenyl group substituted or unsubstituted with cyano group.

In another embodiment, R 2 is a biphenyl ring substituted or unsubstituted with one or more substituents selected from the group consisting of cyano, pyridine, phenyl and quinoline groups.

In another embodiment, R < 2 > is a biphenyl radical substituted with a cyano group.

In one embodiment of the present invention, R 2 is a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group.

In one embodiment, R2 is a pyridine group.

In another embodiment, R 2 is a quinolinyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group.

In another embodiment, R < 2 > is a quinoline group.

In another embodiment, R3 is hydrogen.

In one embodiment of the present disclosure, R4 is hydrogen.

In another embodiment, R5 is hydrogen.

In one embodiment of the present disclosure, R6 is hydrogen.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is any one of the following Formulas 1-1-1 to 1-1-90. Specifically, the heterocyclic compound represented by Formula 1-1 is any one of the following Formulas 1-1-1 to 1-1-90.

.

.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is any one of the following Formulas 1-2-1 to 1-2-82. Specifically, the heterocyclic compound represented by Formula 1-2 is any one of the following Formulas 1-2-1 to 1-2-82.

.

.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is any one of the following Formulas 1-3-1 to 1-3-90. Specifically, the heterocyclic compound represented by Formula 1-3 is any one of the following Formulas 1-3-1 to 1-3-90.

ㄴ

N

.

.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is any one of the following Formulas 1-4-1 to 1-4-9. Specifically, the heterocyclic compound represented by Formula 1-1 is any one of the following Formulas 1-4-1 to 1-4-9.

The present invention also 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 includes the heterocyclic compound.

In this specification, when a member is located on another member, it includes not only when a member is in contact with another member but also when there is another member between the two members.

In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.

In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer.

In one embodiment of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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

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

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, one or more organic compound layers and an anode are sequentially stacked on a substrate

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

1 shows a structure of an organic electronic 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 heterocyclic compound may be included in the light emitting layer (3).

2 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked Structure is illustrated. In such a structure, the heterocyclic compound may be contained in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

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.

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 of the organic layers include the heterocyclic compound, i.e., the compound represented by Formula 1 above.

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

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and 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 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 Alq ₃ ; 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 hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

The 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 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising 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.

< Synthetic example  1> Preparation of the compound represented by the formula 1-1-1

[Formula 1A] &lt; EMI ID =

The compound of formula IA (10.6 g, 25.2 mmol) and a-benzocarbazole (5.5 g, 25.2 mmol) were dissolved in 300 ml of xylene and sodium-tertiary- butoxide (4.8 g, 50.4 mmol) (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.4 g (0.76 mmol) of triethylamine were added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-1-1 (8 g, 53%).

MS: [M + H] &lt; ⁺ &gt; = 600

< Synthetic example  2> Preparation of the compound represented by the formula 1-1-5

[Chemical Formula 1B] [Formula 1-1-5]

(4.6 g, 21.4 mmol) was dissolved in 300 ml of xylene and sodium-tertiary-butoxide (4.1 g, 42.8 mmol), bis [(tri- (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.32 g (0.64 mmol) was added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform and then distilled under reduced pressure. The residue was recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-1-5 (9 g, 63%).

MS: [M + H] &lt; ⁺ &gt; = 676

< Synthetic example  3> Preparation of the compound represented by the formula 1-1-12

[Chemical Formula 1C] [Chemical Formula 1-1-12]

(4.6 g, 21.4 mmol) was dissolved in 300 ml of xylene and sodium-tertiary-butoxide (4.1 g, 42.8 mmol), bis (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.32 g (0.64 mmol) was added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-1-12 (10 g, 69%).

MS: [M + H] &lt; ⁺ &gt; = 676

< Synthetic example  4> Preparation of the compound represented by the formula 1-1-6

[Chemical Formula 1D] [Chemical Formula 1-1-6]

(1. 6 g, 21.4 mmol) and a-benzocarbazole (4.6 g, 21.4 mmol) were dissolved in 300 ml of xylene and sodium-tertiary-butoxide (4.1 g, 42.8 mmol), bis [ (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.32 g (0.64 mmol) was added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, and the residue was distilled off under reduced pressure. The residue was recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-1-6 (8.5 g, 59%).

MS: [M + H] &lt; ⁺ &gt; = 676

< Synthetic example  5> Preparation of the compound represented by the formula 1-1-11

[Chemical Formula 1E] [Chemical Formula 1-1-11]

The compound of the formula 1E (10 g, 18.3 mmol) and a-benzocarbazole (4 g, 18.3 mmol) were dissolved in 300 ml of xylene and sodium-tertiary-butoxide (3.5 g, 36.6 mmol), bis [ -Butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.25 g (0.55 mmol) was added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-1-11 (7 g, 53%).

MS: [M + H] &lt; ⁺ &gt; = 726

< Synthetic example  6> Preparation of the compound represented by the formula 1-2-1

[Chemical Formula 1A] [Chemical Formula 1-2-1]

The compound of formula 1A (10.6 g, 25.2 mmol) and b-benzocarbazole (5.5 g, 25.2 mmol) were dissolved in 300 ml of xylene and sodium- tertiary- butoxide (4.8 g, 50.4 mmol), bis [ (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.4 g (0.76 mmol) of triethylamine were added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-2-1 (10 g, 69%).

MS: [M + H] &lt; ⁺ &gt; = 600

< Synthetic example  7> Preparation of the compound represented by the formula 1-3-1

[Chemical Formula 1A] [Formula 1-3-1]

The compound of formula 1A (10.6 g, 25.2 mmol) and c-benzocarbazole (5.5 g, 25.2 mmol) were dissolved in 300 ml of xylene and sodium-tertiary- butoxide (4.8 g, 50.4 mmol) (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.4 g (0.76 mmol) of triethylamine were added, and the mixture was refluxed in a nitrogen stream for 12 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-3-1 (9.2 g, 64%).

MS: [M + H] &lt; ⁺ &gt; = 600

< Synthetic example  8> Preparation of the compound represented by the general formula 1-3-69

[Chemical Formula 3A] [Chemical Formula 1-3-69]

The compound of formula 3A (10 g, 18.3 mmol) and c-benzocarbazole (4 g, 18.3 mmol) were dissolved in 300 ml of xylene and sodium-tertiary- butoxide (3.5 g, 36.6 mmol), bis [ -Butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.25 g (0.55 mmol) of triethylamine were added, and the mixture was refluxed in a nitrogen stream for 12 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-3-69 (11 g, 83%).

MS: [M + H] &lt; ⁺ &gt; = 726

< Synthetic example  9> Preparation of the compound represented by the formula 1-1-68

[Chemical Formula 1F] [Chemical Formula 1-1-68]

The compound of Formula 1F (10.6 g, 25.2 mmol) and a-benzocarbazole (5.5 g, 25.2 mmol) were dissolved in 300 ml of xylene and sodium- tertiary- butoxide (4.8 g, 50.4 mmol) (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.4 g (0.76 mmol) of triethylamine were added, and the mixture was refluxed in a nitrogen stream for 4 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, distilled under reduced pressure, and recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-1-68 (11.2 g, 78%).

MS: [M + H] &lt; ⁺ &gt; = 599

< Synthetic example  10> Preparation of the compound represented by the general formula 1-3-68

[Formula 3B] [Formula 1-3-68]

The compound of Formula 3B (10.6 g, 25.2 mmol) and c-benzocarbazole (5.5 g, 25.2 mmol) were dissolved in 300 ml of xylene and sodium- tertiary-butoxide (4.8 g, 50.4 mmol) (Tert-butyl) phosphine] palladium (Pd [P (t-Bu) ₃ ] ₂ ) 0.4 g (0.76 mmol) of triethylamine were added, and the mixture was refluxed in a nitrogen stream for 12 hours. After completion of the reaction, the temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was dissolved in chloroform, and the residue was distilled off under reduced pressure. The residue was recrystallized from tetrahydrofuran and ethanol to obtain the compound of Formula 1-3-68 (10.2 g, 71%).

MS: [M + H] &lt; ⁺ &gt; = 599

< Example  1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water in which dispersant was dissolved and ultrasonically cleaned. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. HT1 (400 Å), which is a hole transporting material, was vacuum deposited on the hole transporting layer, and a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. On the light emitting layer, LiQ (Lithium Quinolate) and 1-11-1 prepared in Preparation Example 1 were vacuum deposited at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 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. Thereby preparing an organic light emitting device.

Was maintained at the deposition rate was 0.4 ~ 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 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

[Hexanitrile hexaazatriphenylene] [LiQ]

[HT1]

[H1]

[D1]

< Example  2>

The same experiment was carried out except that the electron transport layer in Example 1 was used in place of the compound represented by the formula 1-1-1.

< Example  3>

The same experiment was carried out except that the electron transport layer in Example 1 was used in place of the compound represented by the formula 1-1-1.

< Example  4>

The same experiment was carried out except that the electron transport layer in Example 1 was used in place of the compound represented by the formula 1-1-1.

< Example  5>

The same experiment was carried out except that the electron transport layer in Example 1 was used in place of the compound represented by the formula 1-1-1.

< Example  6>

The same experiment was conducted except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by the general formula 1-2-1 instead of the electron transport layer 1-1-1.

< Example  7>

The same experiment was conducted except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by Formula 1-3-1 instead of Formula 1-1-1.

< Example  8>

The same experiment was conducted except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by Chemical Formula 1-3-67 instead of Chemical Formula 1-1-1.

< Example  9>

The same experiment was carried out except that the electron transport layer in Example 1 was used in place of the compound represented by the formula 1-1-1.

< Example  10>

The same experiment was conducted except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by Chemical Formula 1-3-68 instead of Chemical Formula 1-1-1.

< Comparative Example  1>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of ET1 was used in place of the compound of Formula 1-1-1 in Example 1.

[ET1]

< Comparative Example  2>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of ET2 was used in place of the compound of Formula 1-1-1 in Example 1.

[ET2]

< Comparative Example  3>

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of ET3 was used in place of the compound of Formula 1-1-1 in Example 1.

[ET3]

< Comparative Example  4>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of ET4 was used instead of the compound of Formula 1-1-1 in Example 1.

[ET4]

< Comparative Example  5>

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound of ET5 was used in place of the compound of Formula 1-1-1 in Example 1.

[ET5]

< Comparative Example  6>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of ET6 was used in place of the compound of Formula 1-1-1 in Example 1.

[ET6]

< Comparative Example  7>

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of ET7 was used in place of the compound of Formula 1-1-1 in Example 1.

[ET7]

The Examples 1 to 10 and Comparative Examples 1 to were measured drive voltage and luminous efficiency of each of the compounds, such as 7, and the organic light emitting device produced by using as an electron transporting layer material at a current density of 10mA / cm ^2, 20mA / cm (LT98) at 98% of the initial luminance at the current density of ² was measured. The results are shown in Table 1 below.

Example
(Condition of 10 mA / cm 2) compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) LT98
(20 mA / cm ² Condition) Example 1 Formula 1-1-1 3.81 5.47 (0.137, 0.124) 53 Example 2 Formula 1-1-5 3.90 5.31 (0.139, 0.124) 61 Example 3 (1-1-12) 3.85 5.42 (0.138, 0.127) 55 Example 4 Formula 1-1-6 3.71 5.55 (0.138, 0.129) 42 Example 5 Formula 1-1-11 3.71 5.45 (0.137, 0.162) 41 Example 6 1-2-1 3.88 5.35 (0.137, 0.124) 47 Example 7 1-3-1 3.85 5.47 (0.137, 0.162) 59 Example 8 1-3-67 3.77 5.54 (0.137, 0.162) 49 Example 9 Formula 1-1-68 3.69 5.22 (0.137, 0.162) 49 Example 10 1-3-68 3.69 5.35 (0.137, 0.162) 44 Comparative Example 1 ET1 4.00 5.01 (0.140, 0.129) 32 Comparative Example 2 ET2 4.18 5.15 (0.140, 0.129) 15 Comparative Example 3 ET3 4.21 5.22 (0.139, 0.129) 19 Comparative Example 4 ET4 4.22 4.7 (0.137, 0.162) 31 Comparative Example 5 ET5 4.27 5.10 (0.140, 0.126) 29 Comparative Example 6 ET6 4.29 5.01 (0.139, 0.127) 37 Comparative Example 7 ET7 3.70 5.61 (0.140, 0.129) 20

It can be seen from the above Examples and Comparative Examples that the organic light emitting device having high efficiency, low driving voltage and long life can be provided when the heterocyclic compound according to one embodiment of the present invention is used.

Comparing Examples 1 to 10 and Comparative Examples 4 to 5 of Table 1, it can be seen that when L is 10 or more carbon atoms, the organic light emitting device having lower voltage and / or higher efficiency than phenylene or less than 10 carbon atoms of direct bond .

On the other hand, when Examples 1 to 10 and Comparative Examples 2 to 3 in Table 1 are compared with each other, it is found that when Ar1 and Ar2 are substituted with aryl groups, any one of Ar1 and Ar2 is advantageous in terms of life Respectively. The 6-membered heterocyclic group such as triazine or pyrimidine is a typical n-type structure group lacking electrons. When Ar1 and Ar2 of the present invention are not substituted with an aryl group, they are reduced by the charge supplied from the electrode, This is because the probability of becoming unstable is very high.

As can be seen from Comparative Examples 6 to 7, the benzocarbazole group introduced in the present invention is an electrochemically suitable p-type structure group, and it can be confirmed that the lifetime is maximized while minimizing a voltage rise.

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

Claims (15)

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

In formula (1)
Cy1 and Cy2 are the same or different and are each independently a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, or a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, said naphthalene ring being unsubstituted or substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted nitrogen-
At least one of Cy1 and Cy2 is a substituted or unsubstituted monocyclic aryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted nitrogen-containing monocyclic ring; And a substituted or unsubstituted nitrogen-containing heterocyclic ring, wherein said naphthalene ring is unsubstituted or substituted with one or more substituents selected from the group consisting of substituted or unsubstituted nitrogen-
X1 to X3 are the same or different from each other and each independently CR or N,
At least one of X1 to X3 is N,
L is a substituted or unsubstituted arylene group having 10 to 30 carbon atoms,
R, Ar1 and Ar2 are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The method according to claim 1,
The heterocyclic compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-3):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
L, X1 to X3, Ar1 and Ar2 are the same as defined in formula (1)
a, c and e are each an integer of 1 to 4,
b, d and f are each an integer of 1 to 6,
When a, b, c, d, e and f are each an integer of 2 or more, each of at least two of R 1 to R 6 is the same or different,
R1 to R6 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, an aryl group, a nitrogen-containing monocyclic ring and a nitrogen-containing heterocyclic ring; A substituted or unsubstituted nitrogen-containing monocyclic ring substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, an aryl group, a nitrogen-containing monocyclic ring and a nitrogen-containing heterocyclic ring; Or a heterocyclic ring of nitrogen which is substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, an aryl group, a nitrogen-containing monocyclic ring and a nitrogen-containing heterocyclic ring. The method according to claim 1,
Wherein L is a heterocyclic compound represented by the following formula (2): &lt; EMI ID =
(2)

In formula (2)
o, p, q and r are each an integer of 0 or 1,
1? O + p + q + r? 4,
L1 to L4 are the same or different from each other and each independently represent a phenylene group; Or a naphthalene group,
The total sum of the carbon numbers of L1 to L4 is 10 to 30. The method of claim 3,
Wherein L represented by the general formula (2) is any one of the following structures:

. The method according to claim 1,
Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted phenanthrenyl group. The method according to claim 1,
At least one of Cy1 and Cy2 is a naphthyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A biphenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; A pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group and a quinoline group; And a quinoline group substituted with one or more substituents selected from the group consisting of a cyano group, a pyridine group, a phenyl group, and a quinoline group, or a naphthalene ring substituted or unsubstituted with a substituent selected from the group consisting of a substituted or unsubstituted quinoline group. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-1-1 to 1-1-90:

. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-2-1 to 1-2-82:

.

. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-3-1 to 1-3-90:

. The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-4-1 to 1-4-9:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound according to any one of claims 1 to 10 Lt; / RTI &gt; [Claim 12] The organic light emitting diode according to claim 11, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the heterocyclic compound. 12. The organic light emitting device according to claim 11, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer. 12. The organic light emitting device according to claim 11, wherein the organic material layer comprises an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the heterocyclic compound. 12. The organic electroluminescent device according to claim 11, wherein the organic light emitting device further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer. Light emitting element.

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