KR20160062603A - Hetero-cyclic compound and organic electronic device comprising the same - Google Patents

Abstract

Provided are a heterocyclic compound and an organic electronic device in which the compound is contained in an organic substance layer. According to the present invention, the compound can be used as a material for organic electronic devices.

Description

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

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 the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like. These devices may be used as a hole injecting or transporting material, an electron injecting or transporting material, need. 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. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not yet been sufficiently developed. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

Korean Patent Publication No. 2007-0078724 Korean Patent Publication No. 1074193

Therefore, the present inventors have found that a compound capable of satisfying the conditions required for a material usable in an organic electronic device, for example, an appropriate energy level, an electrochemical stability, and a thermal stability, Structure and an organic electronic device comprising the heterocyclic compound derivative.

An embodiment of the present disclosure provides a heterocyclic compound represented by any one of the following formulas (1) to (3):

[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,

X is CAr1Ar2, NAr3, O, S, SO, SO 2 or SiAr4Ar5,

R1 to R14, Y and Ar1 to Ar5 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; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a ring.

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound.

The compound according to the present invention can be used as an organic layer material of an organic electronic device. Such a compound can serve as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic electronic device such as an organic light emitting device. The compound according to one embodiment may be used as a light emitting host material of an organic light emitting element, such as a phosphorescent host material. The compound according to another embodiment may be used as an electron transport layer material of an organic light emitting device.

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

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

The present invention provides a heterocyclic compound represented by any of the above formulas (1) to (3).

또는

는 다른 치환기에 연결되는 부위를 의미한다.In this specification

or

Quot; refers to a moiety that is connected to another substituent.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; A heteroarylamine group; An arylamine group; Or a heterocyclic group, or that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent to which they are linked. 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 carbon number of the carbonyl group is not particularly limited,

40 < / RTI > Specifically, it may be a compound having the following structure,

.

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

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 alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylhexyl, 4-methylhexyl and 5-methylhexyl.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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

,

,

,

,

,

,

, 및

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

,

,

,

,

,

,

, And

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

In the present specification, the heterocyclic group 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 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 aryl groups in the aryloxy group, arylthioxy group, arylsulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group and arylamine group are exemplified by the above- same.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group is the same as the above-mentioned alkyl group.

In the present specification, the heteroaryl group in the heteroaryl group and the heteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

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

In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group.

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

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 group in which the substituent is substituted with an atom directly bonded to the atom to which the substituted atom is substituted, a substituent having the closest stereostructure to 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.

The heterocyclic compound according to one embodiment of the present disclosure has X at R < 1 > or R < 3 >. When X is located at R1 or R3, the characteristics such as lifetime and efficiency of the organic electronic device including X are excellent, as compared with the case where X is located at R2. In general, when the molecular structure is deflected, the efficiency is high when it is used in a light emitting layer, an electron transporting layer, a hole transporting layer, etc., and in the case of X in which R3 is located at R3, As a result, the efficiency of the organic electronic device including the same can be increased. When X is located at R1 or R3, it has a condensed structure in the ortho and para directions based on N atoms, while when X is located at R2, And has a condensed structure in the meta direction. The inventors of the present invention have found that when the organic electroluminescent device has a condensed structure in the ortho or para direction, the characteristics such as lifetime and efficiency of the organic electronic device including the condensed structure are improved.

In one embodiment of the present invention, the heterocyclic compound is represented by the above formula (1) or (2).

In one embodiment of the present invention, the heterocyclic compound is represented by Formula 1 or Formula 2, and two or more adjacent groups out of R 11 to R 14 may be bonded to each other to form at least one ring. For example, R11 and R12 may bond to form a ring, R12 and R13 may bond to each other to form a ring, or R13 and R14 may bond to each other to form a ring, and R11 and R12 may form a ring. R12 and R13 and R14 may be bonded to each other at the same time to form two rings.

In one embodiment of the present invention, the heterocyclic compound is represented by the general formula (1) or (2), and two or more adjacent groups out of the R 11 to R 14 bond to each other to form a condensed ring, and the condensed ring may be benzene ring have.

In one embodiment of the present disclosure, the heterocyclic compound may be represented by any one of the following formulas (4) to (7):

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,

a is an integer of 0 to 4,

When a is an integer of 2 or more, plural R < 15 > are the same as or different from each other,

R15 is the same as R1,

The definitions of X, Y and R1 to R14 are the same as described above.

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

In one embodiment of the present invention, the heterocyclic compound is represented by Formula 3, and two or more adjacent groups out of R 11 to R 14 may bond to each other to form at least one ring. For example, R11 and R12 may bond together to form a ring, R12 and R13 may bond to each other to form a ring, or R13 and R14 may bond to each other to form a ring. R12 and R13 and R14 may be bonded to each other at the same time to form two rings.

In one embodiment of the present invention, the heterocyclic compound is represented by Formula 3, and two or more adjacent groups out of R 11 to R 14 may bond to each other to form a condensed ring, and the condensed ring may be a benzene ring.

In another embodiment, the heterocyclic compound may be represented by the following formula (8) or (9): < EMI ID =

[Chemical Formula 8]

[Chemical Formula 9]

In formulas (8) and (9)

b is an integer of 0 to 4,

When b is an integer of 2 or more, the plural R < 16 > s are the same as or different from each other,

R16 is the same as R1,

The definitions of X, Y and R1 to R14 are the same as described above.

In one embodiment of the present specification, Y is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present invention, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present invention, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heterocyclic group containing at least one N atom as a hetero atom.

이다. In one embodiment of the present specification, Y is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted isoquinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted

to be.

In another embodiment, Y is a substituted or unsubstituted phenyl group, and when the phenyl group is substituted, the substituent may be a nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y is a substituted or unsubstituted phenyl group, and when the phenyl group is substituted, the substituent may be a nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted C2-C30 heterocyclic group, and a substituted or unsubstituted C2-C30 heterocyclic group. At this time, the heterocyclic group is not limited thereto, but may include one or more N as a hetero atom.

; 치환 또는 비치환된

; 치환 또는 비치환된

; 치환 또는 비치환된

; 및 치환 또는 비치환된

이루어진 군에서 선택되는 1종 이상일 수 있다.In one embodiment of the present invention, Y is a substituted or unsubstituted phenyl group, and when the phenyl group is substituted, the substituent is a substituted or unsubstituted heterocyclic group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted alkyl group; A nitrile group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted triphenylene group; Substituted or unsubstituted

; Substituted or unsubstituted

; Substituted or unsubstituted

; Substituted or unsubstituted

; And substituted or unsubstituted

And may be at least one selected from the group consisting of

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

In one embodiment of the present invention, Y is a phenyl group substituted or unsubstituted with a triazine group substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Y is a phenyl group substituted or unsubstituted with an aryl group-substituted triazine group.

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

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

to be.

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

to be.

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

to be.

In one embodiment of the present specification, Y is a substituted or unsubstituted triazine group.

In another embodiment, Y is a triazine group substituted or unsubstituted with a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Y is a substituted or unsubstituted triazine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

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

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

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

to be.

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

In another embodiment, Y is a phenyl group; And a triazine group substituted or unsubstituted with a biphenyl group.

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

to be.

In one embodiment of the present specification, Y is a triazine group substituted or unsubstituted with a naphthylene group.

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

to be.

In one embodiment of the present disclosure, X is NAr3, O, S or SO _2, the definition of Ar3 is the same as described above.

In one embodiment of the present disclosure, X is NAr3 and the definition of Ar3 is the same as described above.

In one embodiment of the present disclosure, X is NAr3, Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, X is NAr3, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

이다.In one embodiment of the present disclosure, X is NAr3, Ar3 is a phenyl group; A phenyl group substituted with a substituted or unsubstituted triazine group; A phenyl group substituted with a dibenzothiophene group; A phenyl group substituted with a dibenzofurane group; A phenyl group substituted with an arylphosphine group; A phenyl group substituted with a substituted or unsubstituted imidazole group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; or

to be.

In one embodiment of the present disclosure, X is O.

In another embodiment, X is S.

In one embodiment of the present disclosure, X is SO ₂ .

In one embodiment of the present disclosure, X is CAr1Ar2, and the definitions of Ar1 and Ar2 are the same as described above.

In one embodiment of the present specification, X is CAr1Ar2, Ar1 and Ar2 are each independently a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, X is CAr1Ar2, Ar1 and Ar2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present disclosure, X is CAr1Ar2, and Ar1 and Ar2 are methyl groups.

In one embodiment of the present disclosure, X is SiAr4Ar5, and the definitions of Ar4 and Ar5 are the same as described above.

In one embodiment of the present specification, X is SiAr4Ar5, and Ar4 and Ar5 are each independently a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, X is SiAr4Ar5, and Ar4 and Ar5 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present disclosure, X is SiAr4Ar5, and Ar4 and Ar5 are methyl groups.

In one embodiment of the present specification, at least one of R5 to R10 is deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen; An arylamine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; An arylphosphine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; A silyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present invention, at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen or any one of substituents of the following [A-1].

[A-1]

In one embodiment of the present specification, at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen or any of substituents of the following [A-2].

[A-2]

In one embodiment of the present specification, at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen or any one of substituents of the following [A-3].

[A-3]

In one embodiment of the present invention, at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen or any of substituents of the following [A-4], but is not limited thereto.

[A-4]

In one embodiment of the present invention, at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen or any one of substituents of the following [A-5].

 [A-5]

In one embodiment of the present invention, the Y may be represented by any one of the substituents of the above [A-1] to [A-5].

In another embodiment, X may be NAr3, and Ar3 may be represented by any of the substituents of the above [A-1] to [A-5].

In one embodiment of the present disclosure, R 1 to R 14 are hydrogen.

_In one embodiment herein, the heterocyclic compound represented by Formula 1 may be selected from the following structural formulas:

_

In one embodiment herein, the heterocyclic compound represented by Formula 2 may be selected from the following structural formulas:

In one embodiment herein, the heterocyclic compound represented by Formula 3 may be selected from the following structural formulas:

The above heterocyclic compound can be produced based on the following production example. According to one embodiment, the heterocyclic compound represented by Formula 1 may be prepared in the following manner.

[Reaction Scheme 1]

According to another embodiment, the heterocyclic compound represented by Formula 2 may be prepared in the following manner.

[Reaction Scheme 2]

According to an embodiment of the present invention, the heterocyclic compound represented by Formula 3 may be prepared in the following manner.

[Reaction Scheme 3]

By introducing various substituents to the core structure having the above structure, it is possible to synthesize a compound having the intrinsic properties of the introduced substituent. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic electronic device into the core structure, a material meeting the requirements of each organic layer is synthesized .

In this specification, a compound having an appropriate energy level according to a substituent among the above compounds is selected and used in an organic electronic device, thereby realizing a device having a low driving voltage and a high light efficiency.

Further, by introducing various substituent groups into the core structure, it is possible to finely control the energy band gap, and the characteristics at the interface between the organic materials can be improved and the use of the materials can be diversified.

An embodiment of the present invention also provides an organic electronic device using the heterocyclic compound. Specifically, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises the heterocyclic compound.

In one embodiment of the present invention, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor.

In one embodiment of the present disclosure, at least one organic layer is disposed between a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And a heterocyclic compound.

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.

Therefore, in another embodiment of the present disclosure, the organic material layer of the organic light emitting device may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, Layer may contain the above heterocyclic compound.

Specifically, the organic material layer of the organic light emitting device may include a hole injection layer, and the hole injection layer may include the heterocyclic compound.

In another example, the organic material layer of the organic light emitting device may include a hole transporting layer, and the hole transporting layer may include the heterocyclic compound.

In another example, the organic material layer of the organic light emitting device may include a hole transporting layer and a hole injecting layer, and the hole transporting layer and the hole injecting layer may include the heterocyclic compound.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.

As one example, the heterocyclic compound may be included as a host of the light emitting layer.

As another example, the organic compound layer containing the heterocyclic compound may include the heterocyclic compound as a host, and may include another organic compound, metal, or metal compound as a dopant.

In addition, the organic material layer may include at least one of an electron transporting layer, an electron injection layer, and a layer that simultaneously transports electrons and electron injection, and at least one of the layers may include the heterocyclic compound. Specifically, the organic material layer of the organic light emitting device may include an electron injection layer, and the electron injection layer may include the heterocyclic compound.

In another example, the organic material layer of the organic light emitting device includes an electron transporting layer, and the electron transporting layer includes the heterocyclic compound.

In another embodiment, the organic material layer of the organic light emitting device may include an electron injection layer, and the electron injection layer may include the heterocyclic compound.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and one or more layers of the electron transporting layer include the heterocyclic compound.

In the organic compound layer having such a multi-layer structure, the heterocyclic compound may include a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports light and electrons, or a layer that simultaneously transports electrons and emits light.

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

The organic electronic device according to the present invention may have a structure as shown in Figs. 1 to 5, but the present invention is not limited thereto.

1 shows an organic electronic device in which a substrate 1, 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 Structure is illustrated.

2 illustrates the structure of an organic electronic device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a cathode 7 are sequentially stacked.

3 illustrates the structure of an organic electronic device in which a substrate 1, an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked.

4 shows a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated.

5 illustrates a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated.

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. (International Patent Application Publication No. 2003/012890)

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.

The substrate may be a glass substrate or a plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto and is not limited as long as it is a substrate commonly used in an organic electronic device.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

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

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic electronic device according to the present invention may be a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

1 substrate
2 anodes
3 hole injection layer
4 hole transport layer
5 Light emitting layer
6 electron transport layer
7 cathode

Claims (22)

A heterocyclic compound represented by any one of the following formulas (1) to (3):
[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,
X is CAr1Ar2, NAr3, O, S, SO, SO 2 or SiAr4Ar5,
R1 to R14, Y and Ar1 to Ar5 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; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a ring. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by the formula (1) or (2). The method according to claim 2, To R < 14 > are bonded to each other to form at least one ring. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by any one of the following formulas (4) to (7):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,
a is an integer of 0 to 4,
When a is an integer of 2 or more, plural R < 15 > are the same as or different from each other,
R15 is the same as R1,
X, Y and R1 to R14 are the same as defined in claim 1. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by the formula (3). The method according to claim 5, To R < 14 > are bonded to each other to form at least one ring. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by the following formula (8) or (9):
[Chemical Formula 8]

[Chemical Formula 9]

In formulas (8) and (9)
b is an integer of 0 to 4,
When b is an integer of 2 or more, the plural R < 16 > s are the same as or different from each other,
R16 is the same as R1,
X, Y and R1 to R14 are the same as defined in claim 1. The compound according to claim 1, wherein Y is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The compound according to claim 1, wherein Y is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted isoquinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted

≪ / RTI > The compound according to claim 1, wherein at least one of R5 to R10 is deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The compound according to claim 1, wherein at least one of R1 to R14, Y and Ar1 to Ar5 is hydrogen; Or a substituent selected from the following [A-1] to [A-5]:
[A-1]

[A-2]

[A-3]

[A-4]

[A-5]

The heterocyclic compound of claim 1, wherein said heterocyclic compound is selected from the following structural formulas:

_

The heterocyclic compound of claim 1, wherein said heterocyclic compound is selected from the following structural formulas:

The heterocyclic compound of claim 1, wherein said heterocyclic compound is selected from the following structural formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound according to any one of claims 1 to 14 Organic electronic device. 16. The organic electronic device according to claim 15, 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. 16. The organic electroluminescent device according to claim 15, wherein the organic electronic device is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And an organic material layer containing the heterocyclic compound. The organic electronic device according to claim 17, wherein the organic compound layer including the compound is a light emitting layer. [Claim 17] The organic electronic device according to claim 17, wherein the organic compound layer containing the compound is an electron injection layer, an electron transport layer, or an electron injection and transport layer. The organic electronic device according to claim 17, wherein the organic compound layer containing the compound is a hole injection layer, a hole transport layer, or a hole injection and transport layer. 18. The organic electronic device according to claim 17, wherein the compound is a phosphorescent host material or a fluorescent host material. [Claim 17] The organic electronic device according to claim 17, wherein the organic material layer comprises two or more electron transporting layers, and one or more of the electron transporting layers include the heterocyclic compound.

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