KR101704118B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

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

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

This specification claims the benefit of Korean Patent Application No. 10-2013-0106085 filed on September 4, 2013, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

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

International Patent Publication No. WO 2010/021524

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

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

[Chemical Formula 1]

In formula (1)

m, n and o are each an integer of 0 to 4,

R1 to R4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted imine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or may be bonded to adjacent groups to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, Lt; / RTI >

R5 and R6 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or R5 and R6 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring or a spiro bond.

In addition, in one embodiment of the present specification, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound do.

Heterocyclic compounds according to embodiments of the present disclosure have suitable energy levels and are excellent in electrochemical stability and thermal stability. Thus, the organic light emitting device comprising the compound provides high efficiency and / or high driving stability.

1 to 5 are cross-sectional views illustrating the structure of an organic light emitting device according to an embodiment of the present invention.

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

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

The heterocyclic compound according to one embodiment of the present invention has a structure in which a substituted or unsubstituted indene group is condensed at carbon positions 5 and 6 of the 1,2-benzocarbazole group; Or a benzene ring at positions 5 and 6, and a substituted or unsubstituted fluorenyl group is condensed.

The heterocyclic compound according to one embodiment of the present invention has triplet energy (triplet energy) in the case where an indene group is condensed on a benzocarbazole group in which a benzene ring is further condensed in a carbazole group, Is low, it is possible to provide appropriate triplet energy for the red phosphor element. Further, the energy gap is narrower, the emission wavelength is long, the molecular weight is large, and the thermal stability is large.

Further, the structure in which the indene group is condensed at the 5th and 6th positions of the 1,2-benzocarbazole group has a LUMO energy level lower than that in the case of condensation at the 3th and 4th positions, When a compound is introduced, electron transport is easy, and a low voltage can be provided.

The above heterocyclic compound having a core has an excellent thermal stability and / or excellent electron and hole mobility.

In one embodiment of the present specification, R1 to R4 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted aryl group; Or one of the following substituents.

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms,

R10 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted imine group, a substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or forms a substituted or unsubstituted hydrocarbon ring or substituted or unsubstituted heterocyclic ring with an adjacent group or forms a spiro bond .

In one embodiment of the present invention, at least one of R1 to R4 is any one of the substituents.

In one embodiment of the present invention, when at least one of R 1 to R 4 is any one of the above-described substituents, the compound has excellent thermal stability and / or electron and hole mobility.

Further, the above substituent functions as an n-type substituent. In the case of a bipolar host comprising a compound having an n-type substituent and a p-type substituent, the hole and / or electron mobility is excellent and the device has an excellent effect.

In one embodiment of the present specification, R 1 is any one of the substituents, and R 2 to R 4 are hydrogen; Or a substituted or unsubstituted aryl group.

In another embodiment, at least one of R 2 to R 4 is any one of the substituents, and R 1 is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, any one of R 2 to R 4 is any one of the substituents, and the other is hydrogen, and R 1 is a substituted or unsubstituted aryl group.

In one embodiment, any one of R 2 to R 4 is any one of the substituents, and the other is hydrogen, and R 1 is a substituted or unsubstituted phenyl group.

또는

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

or

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

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

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.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; Thiol group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; An aryl group; Arylalkyl groups; An arylalkenyl group; And a heterocyclic group containing at least one of N, O and S atoms, or unsubstituted or substituted with at least two substituents selected from the above-exemplified substituents, do. 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 ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 2 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, 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 25 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 aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted. In addition, an aryl group in the present specification may mean an aromatic ring.

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

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

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

,

,

및

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

,

,

And

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

In the present specification, the 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 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 at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

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

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the heterocyclic group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, and S, and the like. The number of carbon atoms of the heterocyclic ring 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 benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

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

In the present specification, the aryl groups in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group are the same as the aforementioned aryl groups. 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. However, 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.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other. In the present specification, the adjacent groups mean respective substituents in which R2, R3 and R4 are adjacent when m, n and o are 2 or more.

In the present specification, when the adjacent groups are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring or a spiro bond, R2, R3 and R4, when m, n and o are 2 or more, Means to form a 5- to 7-membered heterocycle containing one or more of O, N and S as a heterocyclic ring, a 5-membered to 7-membered hydrocarbon ring, and a heterocyclic ring.

As used herein, the hydrocarbon ring is a cycloalkyl group; A cycloalkenyl group; Aromatic ring group; Or an aliphatic cyclic group, which may be monocyclic or polycyclic, and includes all rings in which one or more of them are bonded and condensed.

The term "heterocycle" as used herein means that at least one carbon atom of the hydrocarbon ring is substituted with a hetero atom such as N, O, or S, and may be an aliphatic ring or an aromatic ring, and may be monocyclic or polycyclic.

In the present specification, the spiro bond means a structure in which two ring organic compounds are connected to one atom, and a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom can do.

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

In one embodiment of the present disclosure, m is one.

In one embodiment of the present disclosure, n is one.

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

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

(2)

In formula (2)

R1, R5 and R6 are the same as defined in Formula 1,

R2 ', R3' and R4 'are the same as or different from each other and are the same as defined for R2 to R4,

At least one of R 1, R 2 ', R 3' and R 4 'is one of the following substituents.

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms,

R10 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted imine group, a substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or forms a substituted or unsubstituted hydrocarbon ring or substituted or unsubstituted heterocyclic ring with an adjacent group or forms a spiro bond .

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

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

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

In one embodiment of the present specification, R1 is a phenyl group.

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

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

이다. In one embodiment of the present disclosure, R2 is

to be.

이다. In one embodiment of the present disclosure, R2 is

to be.

이다. In one embodiment of the present disclosure, R2 is

to be.

이다. In one embodiment of the present disclosure, R2 is

to be.

이다. In one embodiment of the present disclosure, R2 is

to be.

이다. In one embodiment of the present disclosure, R2 is

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

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

to be.

In one embodiment of the present disclosure, L1 is a direct bond; Or a substituted or unsubstituted arylene 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 invention, L1 is a substituted or unsubstituted phenylene group.

또는

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

or

to be.

In one embodiment of the present invention, L1 is a substituted or unsubstituted biphenylene group.

또는

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

or

to be.

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

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

to be.

In one embodiment of the present specification, R10 to R13 are hydrogen; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R10 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R10 is a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, R10 is a phenyl group.

In one embodiment of the present disclosure, R10 is hydrogen.

In one embodiment of the present specification, R11 is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, R11 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R11 is a phenyl group.

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

In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, R12 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R12 is a phenyl group.

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 invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-1 to 1-19.

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

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of 3-1 to 3-19 below.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following 4-1 to 4-19.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following 5-1 to 5-3.

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

The reaction product obtained by reacting alpha tetralone with 1-phenylhydrazinium chloride was reacted with acetonitrile and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to obtain 11H-benzo [a] Carbazole. After the 11H-benzo [a] carbazole is halogenated, 2- (2-hydroxypropan-2-yl) phenylboronic acid is added to conduct a ring-closing reaction. Thereafter, the halogenated R 1 to R 4 are reacted to form a compound represented by the above-mentioned Formulas 1-1 to 1-19, Formulas 2-1 to 2-20, Formulas 3-1 to 3-19, Formulas 4-1 to 4-19, The heterocyclic compound represented by the general formula (1) can be prepared as well as the general formulas (5-1) to (5-3).

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And an organic layer formed of one or more layers including a light emitting layer provided between the first electrode and the second electrode,

Wherein at least one of the organic material layers comprises the heterocyclic compound.

In one embodiment of the present disclosure, a hole transporting layer, a hole injecting layer, or a layer simultaneously injecting holes and transporting holes, wherein the hole transporting layer, the hole injecting layer, or the layer simultaneously injecting holes and transporting holes, ≪ / RTI >

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 contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant.

When the heterocyclic compound according to one embodiment of the present invention is used as a host, the hole and / or electron mobility is improved as a bipolar host, thereby providing a high voltage, high efficiency and / or long life organic light emitting device.

In one embodiment of the present invention, the phosphorescent dopant compound is represented by the following formula (3).

(3)

In formula (3)

M ₁ is Ir or Os,

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

d ', f', g ', h', j, j ', and q', p, q, q ', r, s, t, u', v ', w', x ', a, b', c ' k is an integer of 0 to 4,

each of r ', s', t', u, v, w, x, y, y 'and e'

b, e, h, i, k 'and 1 are integers of 0 to 3,

c and g 'each represent an integer of 0 to 2,

f 'is an integer of 0 to 5,

z is an integer of 0 to 8,

R ₁₁₀ to R ₁₆₅ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C ₂ ~ _10; A substituted or unsubstituted C ₆ ~ ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C _1-10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; Alkoxy group, a substituted or unsubstituted C ₁ ~ ₁₀ ring; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or groups adjacent to each other form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

In one embodiment of the present invention, the phosphorescent dopant compound represented by Formula 3 is any one of the following compounds.

,

,

,

,

,

,

,

,

,

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In one embodiment of the present disclosure, the content of the dopant relative to the total weight of the light emitting layer is 4 wt% to 15 wt%. The lifetime of the device can be increased in the above range.

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

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

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

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

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

2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 shows a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

The organic light-emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the heterocyclic compound.

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

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

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.

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

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

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

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

PREPARATION EXAMPLE 1 Synthesis of Compound of Formula 1-1

[Formula 1-1A]

[Formula 1-1B]

[Formula 1-1C]

[Chemical Formula 1D]

[Formula 1-1E]

[Formula 1-1]

Preparation of Formula 1-1A

A mixture of alpha-tetralone (14.6 g, 100 mmol) and 1-phenylhydrazinium chloride (19.5 g, 100 mmol) was added to ethanol and 2-3 drops of acetic acid was added thereto, followed by boiling and stirring. After boiling for 3 hours, water was added and the resulting solid was filtered off and dried to give a brown solid (18.7 g, 85%). MS: [M + H] < ⁺ > = 220

Preparation of Formula 1-1B

(22.0 g, 100 mmol) was dissolved in acetonitrile (MeCN), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone , 6-dicyano-1,4-benzoquinone, DDQ) (22.7 g, 100 mmol) was slowly added thereto and stirred at room temperature for 3 hours. The resulting solid was filtered, washed with an aqueous solution of potassium carbonate and dried to obtain the compound of Formula 1-1B (20 g, yield 90%). MS: [M + H] < ⁺ > = 219

Preparation of Formula 1-1C

1B (22 g, 100 mmol) was dissolved in tetrahydrofuran (100 ml), N-bromosuccinimide (24.6 g, 100 mmol) was added thereto, and the mixture was stirred for 10 hours. After stirring for 1 hour, filtration gave a brown solid (26.6 g, 90%). MS: [M + H] < ⁺ > = 296

Preparation of Formula 1-1D

2- (2-hydroxypropan-2-yl) phenylboronic acid (18.1 g, 100 mmol) was added to a solution of 2- (2-hydroxypropan- was dissolved in tetrahydrofuran (tetrahydrofuran, THF), the addition of calcium carbonate solution, palladium (a _{(phenyl) 3) 4) (Pd (} P (Ph) 3) 4) boiling put 0.01 equivalents of the catalyst, and the mixture was stirred. The mixture was stirred for 12 hours and then cooled to room temperature. The organic layer was separated and recrystallized from chloroform and ethanol to obtain a yellow solid (27.5 g, yield 78%) of the formula 1-1D. MS: [M + H] < ⁺ > = 352

Preparation of Formula 1-1E

1-1D (35.2 g, 100 mmol) was dissolved in acetic acid, followed by addition of 2-3 drops of sulfuric acid, followed by boiling. After cooling to room temperature, water was added and stirred for about 1 hour, followed by filtration to obtain structural formula 1-1E. MS: [M + H] < ⁺ > = 334

Preparation of Formula 1-1

1E (33.4 g, 100 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine ( 26.7 g, 100 mmol) was dissolved in toluene -t- butoxy sodium (after boil put 14.4 g, 150 mmol) Pd ( P (t-Bu) ₃ side 0.1 equiv) ₂ catalyst into the mixture 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 (41.2 g, yield 73%). MS: [M + H] < ⁺ > = 565

PREPARATION EXAMPLE 2 Synthesis of Compound (1-2)

[Formula 1-2A]

[Formula 1-2]

Preparation of Formula 1-2A

2-chloro-4,6-diphenyl-1,3,5-triazine (26.7 g, 100 mmol) and 4-chlorophenyl after the acid (4-chlorophenyl boronic acid) ( 15. 6 g, 100 mmol) was dissolved in tetrahydrofuran (THF), and stirred under boiling was added to the calcium carbonate aqueous solution, Pd (PPh _{3) 4} catalyst into 0.01 eq. . After stirring for 12 hours, the mixture was cooled to room temperature, and the organic layer was separated, and then recrystallized from chloroform and ethanol to obtain a 1-2A white solid (31 g, yield 88%). MS: [M + H] < + > = 344

Preparation of Formulas 1-2

Except that 1-2A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. (1-2) was obtained in the same manner as in the production method of 1-1. MS: [M + H] < ⁺ > = 641

PREPARATION EXAMPLE 3 Synthesis of Compound (1-4)

[Formula 1-4]

Preparation of Formulas 1-4

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4,6-diphenyl (1-4) was obtained in the same manner as in the preparation of (1-1) except that 2-chloro-4,6-diphenylpyrimidine was used. MS: [M + H] < ⁺ > = 564

PREPARATION EXAMPLE 4 Synthesis of Compound (1-5)

[Formula 1-5]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 4-chloro-2,6-diphenyl (1-5) was obtained in the same manner as in the production method of the formula (1-1), except that 4-chloro-2,6-diphenylpyrimidine was used. MS: [M + H] < ⁺ > = 564

PREPARATION EXAMPLE 5 Synthesis of Compound (1-10)

[Chemical Formula 1-10A]

[Chemical Formula 1-10]

Preparation of Formulas 1-10A

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in place of 2-chloro-4,6-diphenyl- (1-10A) was obtained in the same manner as in the preparation of the compound of the formula (1-2A), except that 2-chloro-4,6-diphenylpyridine was used. MS: [M + H] < ⁺ > = 342

Preparation of Formulas 1-10

Except that 1-10A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1. ≪ / RTI > MS: [M + H] < ⁺ > = 639

PREPARATION EXAMPLE 6 Synthesis of Compound of Formula 1-16

[Formula 1-16A]

[Chemical Formula 1-16]

Preparation of Formula 1-16A

Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and cooled to -78 ° C. n-BuLi (2.5 M, 37 ml, 93 mmol) was slowly added dropwise thereto, followed by stirring 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. The reaction mixture was poured into MgSO ₄ and stirred to remove water, followed by filtration, followed by concentration and recrystallization from hexane to obtain the compound of Formula 1-16A (18 g, yield 85%). MS: [M + H] < ⁺ > = 357

Preparation of Formula 1-16

(1-16) was obtained in the same manner as in the preparation of compound (1-1), except that 1-16A was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

MS: [M + H] < ⁺ > = 610

PREPARATION EXAMPLE 7 Synthesis of Compound of Formula 1-17

[Chemical Formula 1-17A]

[Formula 1-17]

Preparation of Formula 1-17A

Except that 1-16A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6- -2A, the compound of the formula 1-17A was obtained. MS: [M + H] < ⁺ > = 389

Preparation of Formulas 1-17

2-chloro-4,6-diphenyl-1,3,5-triazine

(1-157) was obtained in the same manner as in the preparation of compound (1-1), except that 1-17A was used instead of compound (1-12). MS: [M + H] < ⁺ > = 686

PREPARATION EXAMPLE 8 Synthesis of Compound of Formula 2-1

[Formula 2-1A]

[Formula 2-1B]

[Chemical Formula 2-1C]

[Formula 2-1]

Preparation of Formula 2-1A

Except that bromophenyl was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 < / RTI > was obtained in the same manner as in the production method of < RTI ID = 0.0 > MS: [M + H] < ⁺ > = 410

Preparation of Formula 2-1B

2-1B was obtained in the same manner as in the process for producing the compound of the formula 1-1C, except that 2-1A was used instead of 1-1B. MS: [M + H] < ⁺ > = 488

Preparation of Formula 2-1C

(25.8 g, 100 mmol), bis (pinacolato) diboron (25.4 g, 200 mmol) and potassium acetate (25 g, 200 mmol) were dissolved in dioxane (300 mL) Pd (DBA) ₂ (1.2 g, 1 mmol) and P (Cy) ₃ (1.5 g, 2 mmol) were added thereto, followed by heating and stirring 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 the structural formula 2-1C (32 g, yield 60%). MS: [M + H] < ⁺ > = 536

Preparation of Formula 2-1

(2-1) was obtained in the same manner as in the preparation of compound of formula (1-2A), except that 2-1C was used instead of 4-chlorophenylboronic acid. MS: [M + H] < ⁺ > = 641

PREPARATION EXAMPLE 9 Synthesis of Compound of Formula 2-3

[Formula 2-3]

Preparation of Formula 2-3

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4,6-diphenylpyridine 3- (2-chloro-4,6-diphenylpyrimidine) was used instead of 2-chloro-4,6-diphenylpyrimidine. MS: [M + H] < ⁺ > = 640

PREPARATION EXAMPLE 10 Synthesis of Compound of Formula 2-10

[Chemical Formula 2-10]

Preparation of 2-10

Except that 1-10A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 > was obtained in the same manner as in the production method of < 1 > MS: [M + H] < ⁺ > = 715

PREPARATION EXAMPLE 11 Synthesis of Compound of Formula 2-17

[Formula 2-17]

Preparation of Formula 2-17

Except that 1-16A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 < / RTI > MS: [M + H] < ⁺ > = 686

≪ Example 1 >

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 angstroms was placed in distilled water containing a dispersing agent 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]

[ET1]

≪ Example 2 >

In the same manner as in Example 1 except that the compound represented by Formula 1-16 was used as the light emitting layer host in Formula 1-1.

≪ Example 3 >

The same experiment was conducted except that the light emitting layer host in Example 1 was used in place of the compound 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.

Example
(5 mA / cm ² ) Host material Voltage
(V) efficiency
(cd / A) Comparative Example 1 CBP 5.29 20.34 Example 1 (1-1) 5.03 21.17 Example 2 (1-16) 4.99 22.71 Example 3 2-1 5.22 21.51 Example 4 (2-17) 4.68 23.23

From the results of Table 1, it can be seen that the heterocyclic compound according to one embodiment of the present invention has low driving voltage and high efficiency and can be used as an appropriate material in an organic light emitting device.

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

Claims (19)

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

In formula (1)
m, n and o are each an integer of 0 to 4,
At least one of R1 and R4 is a substituent shown below,
And the rest is hydrogen or a substituted or unsubstituted aryl group,

L1 is a substituted or unsubstituted arylene group,
R10 and R11 are substituted or unsubstituted aryl groups,
R2, R3, R5 and R6 are hydrogen. delete delete The method according to claim 1,
The heterocyclic compound represented by the formula (1) is represented by the following formula (2).
(2)

In formula (2)
R1, R5 and R6 are the same as defined in Formula 1,
R2 ', R3' and R4 'are the same as or different from each other and are the same as defined for R2 to R4,
At least one of R1 and R4 'is a substituent shown below,
L1 is a substituted or unsubstituted arylene group,
R10 and R11 are substituted or unsubstituted aryl groups. delete delete delete delete delete delete delete delete A first electrode; A second electrode facing the first electrode; And at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises the heterocyclic compound according to any one of claims 1 and 4. 14. The method of claim 13,
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 that simultaneously transports electrons and injects electrons comprises the heterocyclic compound. 14. The method of claim 13,
Wherein the light emitting layer comprises the heterocyclic compound. 14. The method of claim 13,
Wherein the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant. 18. The method of claim 16,
Wherein the phosphorescent dopant compound is represented by the following Formula 3:
(3)

In formula (3)
M ₁ is Ir or Os,
L ₁₀ , L ₁₁ and L ₁₂ are the same or different and independently of each other are any one of the following structures,

d ', f', g ', h', j, j ', and q', p, q, q ', r, s, t, u', v ', w', x ', a, b', c ' k is an integer of 0 to 4,
each of r ', s', t', u, v, w, x, y, y 'and e'
b, e, h, i, k 'and 1 are integers of 0 to 3,
c and g 'each represent an integer of 0 to 2,
f 'is an integer of 0 to 5,
z is an integer of 0 to 8,
R ₁₁₀ to R ₁₆₅ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C ₂ ~ _10; A substituted or unsubstituted C ₆ ~ ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C _1-10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; Alkoxy group, a substituted or unsubstituted C ₁ ~ ₁₀ ring; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or groups adjacent to each other form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. 18. The method of claim 17,
Wherein the phosphorescent dopant compound represented by Formula 3 is any one of the following compounds:

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

. 14. The method of claim 13,
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously injecting holes and transporting holes,
Wherein the hole transport layer, the hole injection layer, or the layer that simultaneously injects holes and transports the hole transport layer includes the heterocyclic compound.

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