KR20150030616A - Hetero-cyclic compound and organic electronic device comprising the same - Google Patents

Abstract

In the present invention, provided are a hetelcyclic compound and an organic electronic device including the same. In the present invention, provided are a heterocyclic compound denoted by chemical formula 1 and an organic electronic device including the same wherein the heterocyclic compound can be used as materials of organic layers from an organic light-emitting device and an organic electronic device, thereby improving efficiency, low driving voltage and/or longevity property in the organic light-emitting device and the organic electronic device.

Description

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

This specification claims the benefit of Korean Patent Application No. 10-2013-0110000 filed on September 12, 2013 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

An organic electronic device means an element requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electric device. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor that interfaces with an electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of organic electronic devices include organic light emitting devices, organic solar cells, and organic transistors, all of which require hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials for driving the devices. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

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, and the necessity of developing such materials is the same in other organic electronic devices described above.

Journal fuer Praktische Chemie (Leipzig), 1940, vol. 156, p. 27

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

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

[Chemical Formula 1]

In Formula 1,

n and m are the same as or different from each other, each independently an integer of 1 to 5,

When n is an integer of 2 or more, a plurality of S1's are the same or different from each other,

When m is an integer of 2 or more, a plurality of S2s are the same or different from each other,

S1 and S2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two or more groups adjacent to each other may be connected to form a ring,

R1 is any one of the following formulas (2) and (3)

(2)

(3)

In formulas (2) and (3)

L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

X1 to X5 are the same or different from each other and each independently N or CR,

At least one of X1 to X5 is N,

R is hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

B1 and B2 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

The present invention also relates to an organic electronic device comprising a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the heterocyclic compound And an organic electroluminescent device.

The novel heterocyclic compound according to the present invention can be used as a material for an organic material layer of an organic electronic device including an organic light emitting device and by using the same, it is possible to improve efficiency, low driving voltage and / Can be improved.

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

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

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

As used herein, the term "substituted or unsubstituted" A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; An arylamine group; An aryl group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group and a heterocyclic group. 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.

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, 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 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.

The length of the alkyl group, alkenyl group and alkoxy group contained in the compound does not affect the conjugation length of the compound but affects the application of the compound to the organic electronic device, for example, the vacuum deposition method or the solution application method. The number of carbon atoms is not particularly limited.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

,

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 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 naphthyl, binaphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, tetracenyl, And the like, but the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N and S as a heteroatom. The number of carbon atoms is not particularly limited, but is preferably 2 to 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, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having two or more of the 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 silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, Naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the aryl sulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group, but the present invention is not limited thereto.

In the present specification, the alkyl group in the alkylthio group and the alkylsulfoxy group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present specification, the arylene group, the alkenylene group and the fluorenylene group are each a divalent group of an aryl group, an alkenyl group and a fluorenyl group. The descriptions of the above-mentioned aryl group, alkenyl group and fluorenyl group can be applied, except that they are each 2 groups.

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

As used herein, the term "adjacent group" means a substituent in which the substituent is substituted with an atom directly bonded to a substituted atom, a substituent located closest to the substituent, or a substituent substituted with an atom substituted with the substituent It can mean. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent groups ".

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

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

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

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

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

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is provided.

In one embodiment of the present specification, R1 is substituted with a heterocyclic group containing 6-membered monocyclic N represented by the general formula (2) or a phosphine oxide represented by the general formula (3). Substituting the formula (2) or (3) for the R 1 position is easier to synthesize than other positions and is advantageous in terms of time and / or economy.

When the formula (1) is substituted with the formula (2) or the formula (3), the substituent represented by the formula (2) or the formula (3) functions as an n-type substituent. Thus, a p-type compound containing an n-type substituent can exhibit the properties of a bipolar host. Therefore, the hole and / or electron mobility can be improved, and the device can have excellent properties.

In addition, the compound represented by Formula 1 has excellent thermal stability and can provide high efficiency when it is included in an organic electronic device including an organic light emitting device.

In one embodiment of the present invention, the formula (1) may be represented by the following formula (1-1). [Formula 1-1]

In Formula 1-1,

a and b are each independently an integer of 1 to 7,

When a is an integer of 2 or more, a plurality of R < 10 > are the same as or different from each other,

When b is an integer of 2 or more, plural R < 11 > are the same as or different from each other,

The definitions of R10 and R11 are the same as those of R2 to R9,

The definitions of R1, S1, S2, n and m are the same as described above.

In one embodiment of the present invention, the formula (1) may be represented by the following formula (1-2).

[Formula 1-2]

In Formula 1-2,

c and d are each independently an integer of 1 to 4,

When c is an integer of 2 or more, plural R < 12 > are the same as or different from each other,

When d is an integer of 2 or more, plural R < 13 > are the same or different from each other,

The definitions of R12 and R13 are the same as those of R2 to R9,

R 1 to R 3, R 9, R 10, S 1, S 2, m and n are as defined above.

In one embodiment of the present specification, X 1 to X 5 are the same or different from each other, and each independently N or CR, and at least one of X 1 to X 5 is N.

In one embodiment of the present disclosure, X1 is N.

In one embodiment of the present disclosure, X1 is CR.

In one embodiment of the present specification, X1 is CH.

In one embodiment of the present disclosure, X2 is N.

In one embodiment of the present disclosure, X2 is a CR.

In one embodiment of the present disclosure, X3 is N.

In one embodiment of the present disclosure, X3 is CR.

In one embodiment of the present disclosure, X3 is CH.

In one embodiment of the present disclosure, X4 is N.

In one embodiment of the present disclosure, X4 is CR.

In one embodiment of the present disclosure, X5 is N.

In one embodiment of the present disclosure, X5 is a CR.

In one embodiment of the present specification, X5 is CH.

In one embodiment of the present invention, the compound represented by Formula 2 is represented by any one of the following Formulas 2-1 to 2-5.

In formulas (2-1) to (2-5)

Wherein L1 is the same as defined in Chemical Formula 2,

A1 and A2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

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

In one embodiment of the present disclosure, R 1 is Formula 3.

In one embodiment of the present specification, R 2 to R 9 are hydrogen.

In one embodiment of the present disclosure, R 2 is hydrogen.

In one embodiment of the present disclosure, R3 is hydrogen.

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

In one embodiment of the present disclosure, R5 is hydrogen.

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

In one embodiment of the present specification, R7 is hydrogen.

In one embodiment of the present disclosure, R8 is hydrogen.

In one embodiment of the present specification, R9 is hydrogen.

In another embodiment, R10 is hydrogen.

In one embodiment of the present specification, R11 is hydrogen.

In one embodiment of the present specification, R12 is hydrogen.

In one embodiment of the present specification, R13 is hydrogen.

In one embodiment of the present disclosure, S1 is hydrogen.

In one embodiment of the present disclosure, S2 is hydrogen.

In one embodiment of the present specification, R, B1 and B2 are the same or different and each independently hydrogen; Or a substituted or unsubstituted aryl group.

In one embodiment of the present disclosure, R is the same as defined above for A1 or A2.

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

In one embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In one embodiment of the present specification, R is a substituted or unsubstituted phenyl group.

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

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

In one embodiment of the present invention, R is a naphthyl group.

이다. In one embodiment of the present specification, R is a naphthyl group,

to be.

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

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

이다.In another embodiment, R is a biphenyl group,

to be.

In one embodiment of the present invention, B1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In one embodiment of the present invention, B1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, B1 is a phenyl group.

In one embodiment of the present invention, B1 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, B1 is a naphthyl group.

In one embodiment of the present invention, B2 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In one embodiment of the present invention, B2 is a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, B2 is a phenyl group.

In one embodiment of the present invention, B2 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, B2 is a naphthyl group.

In one embodiment of the present specification, B1 and B2 are substituted or unsubstituted aryl groups.

In another embodiment, each of B1 and B2 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In one embodiment of the present invention, each of B1 and B2 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, L 1 and L 2 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthalene group.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group.

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

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

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

to be.

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

to be.

In one embodiment of the present specification, L1 is a substituted or unsubstituted naphthalene group.

In one embodiment of the present specification, L1 is a naphthalene group.

이다. In another embodiment, L1 is a naphthalene group,

to be.

In one embodiment of the present specification, L2 is a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L2 is a substituted or unsubstituted phenylene group.

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

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

to be.

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

to be.

In one embodiment of the present specification, L2 is a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, L2 is a biphenylene group.

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

to be.

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

to be.

In one embodiment of the present specification, L2 is a substituted or unsubstituted naphthalene group.

In one embodiment of the present specification, L2 is a naphthalene group.

이다. In one embodiment of the present disclosure, L2 is a naphthalene group,

to be.

In one embodiment of the present specification, L2 is a substituted or unsubstituted fluorenylene group.

In one embodiment of the present specification, L2 is a fluorenylene group substituted or unsubstituted with an alkyl group.

In another embodiment, L2 is a fluorenylene group substituted or unsubstituted with an alkyl group having 10 or less carbon atoms.

In one embodiment of the present specification, L2 is a fluorenylene group substituted or unsubstituted with a methyl group.

이다.In one embodiment of the present disclosure, L2 is

to be.

In one embodiment of the present invention, the compound represented by Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-34.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-35 to 1-48.

The compound represented by the above formula (1) can be produced based on the following production example. According to one embodiment, it can be prepared in the same manner as in the following Schemes 1 to 4.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

[Reaction Scheme 4]

The A compound obtained through the above-mentioned Reaction Scheme 1 and the B compound obtained through the above Reaction Scheme 2 are reacted to obtain a C compound, which is then reacted with the D compound to obtain an E compound represented by the above formula (1).

However, the process for synthesizing the compound represented by Formula 1 is not limited to the reaction conditions of Reaction Schemes 1 to 4, and any conditions may be used as long as reaction conditions are known in the art.

In addition, the compound represented by Formula 1 may have various substituents using methods and materials known in the art.

The compounds represented by Formula 1 may have properties suitable for use as organic layers used in organic electronic devices by introducing various substituents into the core structure represented by the formula.

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

In one embodiment of the present specification, an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers And the above heterocyclic compound.

The organic electronic device may be selected from the group consisting of an organic light emitting device, an organic solar cell, and an organic transistor.

The organic material layer of the organic electronic device in this specification may have a single layer structure, but may have a multi-layer 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, 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 another embodiment, the organic electronic device may be a normal type organic electronic device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

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

The organic electronic 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 electronic device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form 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 electronic device can be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode 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 deposition method in the production of an organic electronic 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 one embodiment of the present invention, the organic electronic device may be an organic light emitting device.

In one embodiment of the present disclosure, an organic light emitting device comprising at least one organic layer including a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, More than one layer includes the above heterocyclic compound.

In one embodiment of the present disclosure, the layer including the hole injection layer, the hole transport layer, or the hole injection and hole transport at the same time, and the hole injection layer, the hole transport layer, or the hole injection and hole transport at the same time, .

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, And the above heterocyclic compound.

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound.

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound as a host of the light emitting layer.

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound as a host of the light emitting layer, and the dopant may be selected by a person skilled in the art from known dopant materials according to properties required in the organic light emitting device, .

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

In another embodiment, the organic material layer of the organic light emitting device may include a hole injecting layer containing a compound containing an arylamino group, a carbazole group, or a benzoxazole group, in addition to an organic material layer containing a heterocyclic compound represented by the formula Or a hole transporting layer.

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.

For example, the organic electronic device according to the present embodiment may have the structure as shown in Figs. 1 and 2, but the present invention is not limited thereto.

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 one embodiment of the present invention, the organic electronic device may be an organic solar cell.

In one embodiment of the present disclosure, the first electrode; A second electrode; And a photoactive layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes the heterocyclic compound, Lt; / RTI >

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transporting and electron injection, and the electron transporting layer, the electron injecting layer, Include the above heterocyclic compounds.

In another embodiment, the photoactive layer may comprise the heterocyclic compound.

In another embodiment, the organic layer includes an electron donor and an electron acceptor, and the electron donor or electron acceptor includes the heterocyclic compound.

In the embodiment of the present invention, when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron beams and the electron acceptors. The generated holes are transported to the anode through the electron donor layer.

In an embodiment of the present disclosure, the organic solar cell may further include an additional organic layer. The organic solar cell can reduce the number of organic layers by using organic materials having various functions at the same time.

In one embodiment of the present disclosure, the organic electronic device may be an organic transistor.

In one embodiment of the present specification, an organic transistor including a source, a drain, a gate, and one or more organic layers, wherein at least one of the organic layers includes the heterocyclic compound.

In one embodiment of the present disclosure, the organic transistor may comprise a charge generating layer, and the charge generating layer may comprise the heterocyclic compound.

In another embodiment, the organic transistor may comprise an insulating layer, and the insulating layer may be located on the substrate and the gate.

When the organic electronic device includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

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

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

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.

In addition to glass and quartz, the material of the substrate may be selected from the group consisting of polyethyleneterephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (acrylonitrile butadiene styrene copolymer), TAC (triacetyl cellulose) and PAR (polyarylate), but are 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.

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

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 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 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 an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

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

The preparation of the compound represented by Formula 1 and the organic electronic device including the same will be described in detail in the following Examples, Preparation Examples and Comparative Examples. However, the following examples and preparative examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

PREPARATION EXAMPLE 1 Synthesis of Compound of Formula 1-1

Preparation of Formula 1-1A

Pyrrole (6.7 g, 0.1 mol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -10 ° C. N-Bromosuccinimide (24.6 g, 0.1 mol) was added thereto, and the mixture was stirred for 3 hours. Ethanol was added thereto, followed by stirring for 1 hour, followed by filtration to obtain a brown solid (15.3 g, 69%).

MS: [M + H] < ⁺ > = 223

Preparation of Formula 1-1B

1-1A 22.3 g, and the mixture was stirred under boiling 0.1 mol) and phenyl Bornholm acid (24.4 g, 0.2 mol) and then dissolved in tetrahydrofuran, it was added to the calcium carbonate aqueous solution, Pd (PPh _{3) 4} catalyst into 0.02 eq. After stirring for 12 hours, the mixture was cooled to room temperature, and the organic layer was separated. The organic layer was recrystallized from chloroform and ethanol to obtain a brown solid (16.4 g, yield 75%).

MS: [M + H] < ⁺ > = 220

Preparation of Formula 1-1C

1-1C was obtained in the same manner as in the production method of the compound of the formula 1-1A, except that 1-1B was used instead of pyrrole.

MS: [M + H] < ⁺ > = 375

Preparation of Formula 1-1D

After dissolving dibromobiphenyl (30.9 g, 0.1 mol), bis (pinacolato) diboron (127 g, 0.5 mol) and potassium acetate (126 g, 0.6 mol) in dioxane (300 mL) , Pd (DBA) ₂ (2.3 g, 0.005 mol) and P (Cy) ₃ (3.2 g, 0.01 mol) were added and the mixture was heated and stirred for 12 hours. After the reaction solution was cooled to room temperature, distilled water (100 mL) was added and extracted with methylene chloride (100 mL x 3). The organic layer was concentrated and recrystallized from ethanol to obtain structural formula 1-1D (24 g, yield 60%).

MS: [M + H] < ⁺ > = 407

Preparation of Formula 1-1E

1-1C was used in place of 1-1A, and 1-1D was used in place of phenylboronic acid.

MS: [M + H] < ⁺ > = 370

Preparation of Formula 1-1

1-1E (37.3 g, 0.1 mol) and 2-chloro-4,6-diphenyl-1,3,5-triazine ( 26.7 g, 0.1 mol) was dissolved in toluene -t- butoxy sodium (after boil put 14.4 g, 150 mmol) Pd ( P (t-Bu) ₃ side) the _second catalyst into 0.2 equivalents was stirred for 3 hours. After the solution was cooled to room temperature, water was added and stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to obtain the compound of Formula 1-1 (43.8 g, yield 73%).

MS: [M + H] < ⁺ > = 601

PREPARATION EXAMPLE 2 Synthesis of Compound (1-2)

Preparation of Formulas 1-2

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4,6-diphenylpyridine (1-2) was obtained in the same manner as in the preparation of compound (1-1), except that 2-chloro-4,6-diphenylpyrimidine was used.

MS: [M + H] < ⁺ > = 600

PREPARATION EXAMPLE 3 Synthesis of Compound (1-3)

Preparation of Formulas 1-3

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 4-chloro-2,6-diphenylpyridine 3- (4-chloro-2,6-diphenylpyrimidine) was used instead of 4-chloro-2,6-diphenylpyrimidine.

MS: [M + H] < ⁺ > = 600

PREPARATION EXAMPLE 4 Synthesis of Compound (1-4)

Preparation of Formulas 1-4

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in place of 2-chloro-4,6-diphenyl- (1-4) was obtained in the same manner as in the preparation of compound (1-1), except that 2-chloro-4,6-diphenylpyridine was used instead of 2-chloro-4,6-diphenylpyridine.

MS: [M + H] < ⁺ > = 600

PREPARATION EXAMPLE 5 Synthesis of Compound of Formula 1-6 below

Preparation of 1-6

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl- (2-chloro-4,6- (1-dinaphthyl) -1,3,5-triazine) was used instead of 2- 1-6 was obtained in the same manner.

MS: [M + H] < ⁺ > = 701

PREPARATION EXAMPLE 6 Synthesis of Compound (1-11)

Preparation of Formula 1-11A

2-chloro-4,6-diphenyl-1,3,5-triazine (26.7 g, 100 mmol) and 4-chlorophenyl 4-chlorophenyl boronic acid (15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF), an aqueous solution of calcium carbonate was added, and 0.01 equivalent of Pd (PPh ₃ ) ₄ catalyst was added and boiled. After stirring for 12 hours, the mixture was cooled to room temperature, and the organic layer was separated. The organic layer was recrystallized from chloroform and ethanol to obtain a 1-11A white solid (31 g, yield 88%).

MS: [M + H] < ⁺ > = 344

Preparation of Formula 1-11

Except that 1-11A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6- -1 < / RTI > was obtained in the same manner as the production method of < RTI ID = 0.0 >

MS: [M + H] < ⁺ > = 677

PREPARATION EXAMPLE 7 Synthesis of Compound (1-26)

Preparation of Formula 1-26A

(1-26A) was obtained in the same manner as in the preparation of the compound of the formula (1-1D), except that dibromobanaphthyl was used instead of dibromobiphenyl.

MS: [M + H] < ⁺ > = 507

Preparation of Formula 1-26B

1-26B was obtained in the same manner as in the preparation of the compound of the formula 1-1E, except that 1-26A was used instead of 1-1D.

MS: [M + H] < ⁺ > = 470

Preparation of Formulas 1-26

1-26B was obtained in the same manner as in the preparation of compound (1-1), except that 1-26B was used instead of 1-1E.

MS: [M + H] < ⁺ > = 701

PREPARATION EXAMPLE 8 Synthesis of Compound of Formula 1-35

Preparation of Formula 1-35A

Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-BuLi (2.5 M, 37 ml, 93 mmol) was slowly added dropwise and stirred for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise, stirred for 3 hours, then warmed to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized from hexane to obtain a white solid. The residue was dissolved in trichloromethane (200 ml), and hydrogen peroxide solution (20 ml) was added thereto, followed by stirring for 12 hours. MgSO ₄ and stirred to remove water, followed by filtration, concentration and recrystallization from hexane to obtain the compound 1-35A (18 g, yield 85%).

MS: [M + H] < ⁺ > = 357

Preparation of 1-35

(1-35) was obtained in the same manner as in the preparation of compound (1-1), except that 1-35A was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

MS: [M + H] < ⁺ > = 646

≪ Example 1 >

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. The detergent was a product of Fischer Co., and the distilled water was distilled water secondarily filtered with a filter manufactured by Millipore Co. 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, ultrasonic washing was performed in the order of solvent of isopropyl alcohol, acetone, and methanol, and dried.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. NPB (400 Å), which is a hole transporting material, was vacuum-deposited thereon. Then, the compound represented by Formula 1-1 synthesized in Preparation Example 1 and the dopant D1 compound was vacuum deposited to a thickness of 300 Å as a light emitting layer. E1 and LiQ were then thermally vacuum deposited with (200 A) electron injection and transport layer. Lithium quinolate (LiQ) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium quinolate was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

[Hexanitrile hexaazatriphenylene] [NPB]

 [CBP] [D1]

 [E1]

≪ Example 2 >

The same experiment was carried out as in Example 1 except that the light emitting layer host was used in place of the compound of Formula 1-1.

≪ Example 3 >

The same experiment was carried out as in Example 1 except that the compound represented by Formula 1-11 was used as a light emitting layer host instead of Formula 1-1.

<Example 4>

The same experiment was carried out as in Example 1 except that the light emitting layer host was used in place of the compound of Formula 1-1.

&Lt; Comparative Example 1 &

In the same manner as in Example 1 except that CBP was used instead of the compound of Formula 1-1 as a light emitting layer host.

Table 1 shows the results of an experiment on an organic light emitting device manufactured by using each compound as a light emitting layer host as in the above embodiment.

Experimental Example
(5 mA / cm ² ) Host material Voltage
(V) efficiency
(cd / A) Comparative Example 1 CBP 5.29 22.09 Example 1 (1-1) 3.23 22.17 Example 2 1-6 3.55 23.71 Example 3 (1-11) 4.00 23.01 Example 4 1-35 4.68 24.16

As can be seen from Table 1, the organic electronic device including the compound represented by Chemical Formula 1 exhibits excellent characteristics in terms of efficiency and driving voltage as compared with the case of using a conventional material.

Specifically, organic light emitting devices manufactured by using the compound represented by the formula (1) as a host of a light emitting layer exhibit excellent characteristics in terms of efficiency and driving voltage when compared with the case of using a conventional material.

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

Claims (18)

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

In Formula 1,
n and m are the same as or different from each other, each independently an integer of 1 to 5,
When n is an integer of 2 or more, a plurality of S1's are the same or different from each other,
When m is an integer of 2 or more, a plurality of S2s are the same or different from each other,
S1 and S2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R2 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two or more groups adjacent to each other may be connected to form a ring,
R1 is any one of the following formulas (2) and (3)
(2)

(3)

In the general formulas (2) and (3)
L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
X1 to X5 are the same or different from each other and each independently N or CR,
At least one of X1 to X5 is N,
R is hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
B1 and B2 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1,
Wherein the formula (2) is represented by any one of the following formulas (2-1) to (2-5):

In the general formulas (2-1) to (2-5)
Wherein L1 is the same as defined in Chemical Formula 2,
A1 and A2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1,
Wherein said R2 to R9 are hydrogen. The method according to claim 1,
R, B1 and B2 are the same or different from each other and each independently hydrogen; Or a substituted or unsubstituted aryl group. The method according to claim 1,
And L &lt; 2 &gt; are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthalene group. The heterocyclic compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-1:
[Formula 1-1]

In Formula 1-1,
a and b are each independently an integer of 1 to 7,
When a is an integer of 2 or more, a plurality of R &lt; 10 &gt; are the same as or different from each other,
When b is an integer of 2 or more, plural R &lt; 11 &gt; are the same as or different from each other,
The definitions of R10 and R11 are the same as those of R2 to R9,
The definitions of R1, S1, S2, n and m are the same as in claim 1. 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 (1-34)

The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-35 to 1-48:

1. An organic electronic device comprising a first electrode, a second 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 is provided in any one of claims 1 to 8 &Lt; / RTI &gt; wherein said heterocyclic compound comprises a heterocyclic compound. The method of claim 9,
Wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, and an organic transistor. The method of claim 9,
Wherein the organic electronic device includes at least one organic layer including a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes And said heterocyclic compound. The method of claim 11,
Wherein the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transport and electron injection,
Wherein the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons comprises the heterocyclic compound. The method of claim 11,
Wherein the light emitting layer comprises the heterocyclic compound as a host of the light emitting layer. The method of claim 11,
Wherein the organic material layer includes a hole transporting layer or a hole injecting layer,
Wherein the hole transport layer or the hole injection layer comprises the heterocyclic compound. The method of claim 11,
Wherein the organic material layer 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. The method of claim 9,
Wherein the organic electronic device includes at least one organic layer including a first electrode, a second electrode, and a photoactive layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes And said heterocyclic compound. 18. The method of claim 16,
Wherein the organic layer comprises a photoactive layer, and the photoactive layer comprises the heterocyclic compound. The method of claim 9,
Wherein the organic electronic device is an organic transistor including a source, a drain, a gate and one or more organic layers, and at least one of the organic layers includes the heterocyclic compound.

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