KR101914854B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present application claims the benefit of Korean Patent Application No. 10-2016-0015683 filed on February 11, 2016 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

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

According to one embodiment of the present invention, there is provided a heterocyclic compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R <1> and R <4> to R <7> are hydrogen; heavy hydrogen; 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 amine 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 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

R 2 is the following formula 2 or 3, and R 3 is the following formula 4 or 5; R2 is represented by the following formula 4 or 5, R3 is represented by the following formula 2 or 3,

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

X1 is N or CR8, X2 is N or CR9, X3 is N or CR10, X4 is N or CR11, X5 is N or CR12,

At least one of X1 to X3 is N,

At least one of X &lt; 4 &gt; and X &lt; 5 &gt; is N,

Y1 and Y2 are the same or different and each independently NR13, CR14R15, O or S,

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

Z1 to Z8 and R8 to R15 are the same or different from each other, and each independently hydrogen; heavy hydrogen; 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 amine 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 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

When one of X1 to X3 is N, Z1 and Z2 are not simultaneously hydrogen,

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

b is an integer of 1 to 3,

When a, b, c, and d are two or more, the structures in parentheses two or more are the same or different,

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.

Is a moiety connected to R2 or R3 of formula (1).

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a heterocyclic compound represented by Formula 1, to provide.

The organic light emitting device including the heterocyclic compound according to one embodiment of the present invention is excellent in thermal stability, and can improve the efficiency, the driving voltage and / or the lifetime characteristics.

In particular, when the heterocyclic compound according to one embodiment of the present invention is used as a host of the light emitting layer, it is possible to improve the lifetime of the device by increasing the stability of holes and electrons by appropriately separating HOMO and LUMO, In particular, efficiency can be improved in a phosphorescent device.

1 shows an organic light emitting device 10 according to an embodiment of the present invention.
2 shows an organic light emitting element 11 according to another embodiment of the present invention.

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

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

In the heterocyclic compound represented by Formula 1 according to an embodiment of the present invention, the electron-transport substituent and the hole-soluble substituent are spatially separated from each other around the indole core. Therefore, when the organic light- And LUMO are appropriately separated to improve the stability of holes and electrons, thereby improving the lifetime of the device. In addition, since the triplet energy is large, it is possible to improve the efficiency particularly in the phosphorescent device.

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

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

Examples of substituents in the present specification are described 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; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

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

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 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 substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 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 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, 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 30. 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 is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is 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 30 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 this specification, the amine group is -NH ₂ ; An alkylamine group; N-arylalkylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group and triphenylamine group, but are not limited thereto.

In the present specification, the N-alkylarylamine amine group means an amine group in which N in the amine group is substituted with an alkyl group and an aryl group.

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine 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, And the like, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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 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, However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 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 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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.

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 in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is 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. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the above heteroaryl groups.

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

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.

In this specification, the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.

According to one embodiment of the present invention, in the above formula (1), adjacent groups among R4 to R7 are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, in the general formula (1), adjacent groups among R4 to R7 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, in the above formula (1), adjacent groups among R4 to R7 are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, in the above formula (1), adjacent groups among R4 to R7 are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, in the above formula (1), adjacent groups of R4 to R7 are bonded to each other to form a benzene ring substituted with (R20) e.

According to another temporary state, R20 is hydrogen; heavy hydrogen; 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 amine 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 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

e is an integer of 1 to 4,

When e is 2 or more, two or more R &lt; 20 &gt; s are the same or different from each other.

According to one embodiment of the present invention, in the above formula (1), R4 and R5 are bonded to each other to form a benzene ring substituted with (R20) e.

According to one embodiment of the present invention, in the general formula (1), R 5 and R 6 combine with each other to form a benzene ring substituted with (R 20) e.

According to one embodiment of the present invention, in Formula 1, R6 and R7 are bonded to each other to form a benzene ring substituted with (R20) e.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 through 1-3,

R 1 to R 7 have the same definitions as in the above formula (1), R 20 represents hydrogen; heavy hydrogen; 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 amine 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 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

e is an integer of 1 to 4,

When e is 2 or more, two or more R &lt; 20 &gt; s are the same or different from each other.

According to one embodiment of the present invention, in the general formulas 1-1 to 1-3, R20 represents hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in the general formulas 1-1 to 1-3, R20 represents hydrogen; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in the general formulas 1-1 to 1-3, R20 represents hydrogen; A phenyl group; Or a carbazolyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, the formula 1 is represented by any one of the following formulas 1-4 to 1-11.

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

[Formula 1-11]

In Formulas 1-4 to 1-11,

R 1 and R 4 to R 7 have the same meanings as defined in formula (1), X 1 to X 3, Z 1 and Z 2 have the same definitions as in formula (2), and X 4, X 5, Z 3, Z 4 and a have the same meanings as in formula The definitions of L1, Y1, Z5, Z6, b and c are the same as those of the above formula (4), and the definitions of L2, Y2, Z7, Z8 and d are the same as those of the above formula (5).

According to one embodiment of the present invention, in the general formula (1), R1 is a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in the general formula (1), R 1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in the general formula (1), R 1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R1 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, in the general formula (1), R1 is a phenyl group.

According to one embodiment of the present disclosure, in the general formula (1), R4 to R7 represent hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, in the general formula (1), R4 to R7 represent hydrogen; An aryl group substituted or unsubstituted with an alkyl group; Or a heteroaryl group.

According to one embodiment of the present disclosure, in the general formula (1), R4 to R7 represent hydrogen; A phenyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; Or a dibenzofuranyl group.

According to one embodiment of the present disclosure, in the general formula (1), R4 to R7 represent hydrogen; A phenyl group; A fluorenyl group substituted or unsubstituted with a methyl group; Or a dibenzofuranyl group.

According to one embodiment of the present invention, the formula (2) is represented by any one of the following formulas (2-1) to (2-7).

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

[Chemical Formula 2-7]

In the general formulas (2-1) to (2-7)

Z1, Z2 and R9 to R10 are as defined in the above formula (2)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.

Is a moiety connected to R2 or R3 of formula (1).

According to one embodiment of the present invention, in the general formula (2), Z 1 to Z 2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in Formula 2, Z 1 to Z 2 are the same or different and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, in the general formula (2), Z 1 to Z 2 are the same or different and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 2, Z 1 to Z 2 are the same or different and each independently represents an aryl group substituted or unsubstituted with a nitrile group, an aryl group, or a heteroaryl group; Or a heteroaryl group.

According to one embodiment of the present invention, in Formula 2, Z 1 to Z 2 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted dibenzofurane group.

According to one embodiment of the present invention, in the general formula (2), Z 1 to Z 2 are phenyl groups substituted or unsubstituted with a nitrile group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; Or a dibenzofurane group.

According to one embodiment of the present invention, in the general formula (2), Z1 to Z2 represent a phenyl group substituted or unsubstituted with a nitrile group, a phenyl group, a biphenyl group or a pyridyl group; A biphenyl group substituted or unsubstituted with a phenyl group; A terphenyl group; Or a dibenzofurane group.

According to one embodiment of the present invention, in the general formulas (2-1) to (2-7), R8 to R10 are the same or different and each independently hydrogen; halogen; Or a nitrile group.

According to one embodiment of the present invention, in the general formulas (2-1) to (2-7), R8 to R10 are the same or different and each independently hydrogen; Fluorine; Goat; bromine; iodine; Or a nitrile group.

According to one embodiment of the present invention, in the general formulas (2-1) to (2-7), R8 to R10 are hydrogen.

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

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In the above formulas (3-1) to (3-3)

Z3, Z4, a, R11 and R12 are as defined in the above formula (3)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.

Is a moiety connected to R2 or R3 of formula (1).

According to one embodiment of the present invention, in Formula 3, Z3 represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in Formula 3, Z3 represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 3, Z3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 3, Z3 is a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in Formula 3, Z3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 3, Z3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 3, Z3 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, in Formula 3, Z3 is a phenyl group.

According to one embodiment of the present invention, in Formula 3, Z4 is hydrogen.

According to one embodiment of the present invention, in the general formulas (3-1) to (3-3), R11 and R12 are the same or different and each independently hydrogen; halogen; Or a nitrile group.

According to one embodiment of the present invention, in the general formulas (3-1) to (3-3), R11 and R12 are the same or different and each independently hydrogen; Fluorine; Goat; bromine; iodine; Or a nitrile group.

According to one embodiment of the present invention, in the general formulas (3-1) to (3-3), R11 and R12 are hydrogen.

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

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

In the general formulas (4-1) to (4-4)

L1, Y1, Z5, Z6, b and c are the same as in the above formula (4)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.

Is a moiety connected to R2 or R3 of formula (1).

According to one embodiment of the present invention, in the formula (4), when Z6 is 2 or more, two or more Z6 are bonded to adjacent groups to form

According to one embodiment of the present invention, the formula (4) is represented by any one of the following formulas (4-5) to (4-8).

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-8]

In the above formulas 4-5 to 4-8,

L1, Z5, Z6, b, c and R13 to R15 are as defined in the above formula (4)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.본 명세서의 일 실시상태에 따르면, 상기 화학식 4에 있어서, L1은 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.

According to one embodiment of the present invention, in Formula 4, L1 is a direct bond; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, in Formula 4, L1 is a direct bond; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 4, L1 is a direct bond; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 4, L1 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene ring.

According to one embodiment of the present invention, in Formula 4, L1 is a direct bond; A phenylene group; Or wait for naphthylene.

According to one embodiment of the present invention, in the general formula (4), Z5 and Z6 are hydrogen.

According to one embodiment of the present invention, in the general formulas (4-7) and (4-8), R13 to R15 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in the formulas (4-7) and (4-8), R13 to R15 are the same or different and each independently represents a substituted or unsubstituted straight or branched alkyl group having 1 to 30 carbon atoms ; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in the formulas (4-7) and (4-8), R13 to R15 are the same or different and each independently represents a substituted or unsubstituted straight or branched alkyl group having 1 to 20 carbon atoms ; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in the general formulas (4-7) and (4-8), R13 to R15 are the same or different and are each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, in Formulas (4-7) and (4-8), R13 to R15 are the same or different from each other, and each independently represents a methyl group; Or a phenyl group.

According to one embodiment of the present invention, in the above Formula 4-7, R13 is a phenyl group.

According to one embodiment of the present invention, in the above Formula 4-8, R14 and R15 are methyl groups.

According to one embodiment of the present invention, in the above Formula 4-8, R14 and R15 are phenyl groups.

According to one embodiment of the present invention, the formula (4) is represented by any one of the following formulas (4-9) to (4-14).

[Chemical Formula 4-9]

[Formula 4-10]

[Formula 4-11]

[Formula 4-12]

[Formula 4-13]

[Chemical Formula 4-14]

In Formulas 4-9 to 4-14,

L1, Z5, Z6 and b are the same as in the above formula (4)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이며,

Is a moiety connected to R2 or R3 of the above formula (1)

Z62 to Z64 are the same or different from each other, and each independently hydrogen; heavy hydrogen; 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 amine 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 heteroaryl group,

f is 1 or 2,

g and h are each an integer of 1 to 4,

When there are a plurality of f, g, and h, the structures in the plurality of parentheses are equal to or different from each other.

According to one embodiment of the present invention, in Formulas 4-9 to 4-14, Y1 is NR13 and R13 is a phenyl group.

According to one embodiment of the present specification, in the formulas 4-9 to 4-14, Z5, Z6, Z61 and Z62 are hydrogen.

According to one embodiment of the present invention, in the general formulas (4-12) to (4-14), Z63 and Z64 are the same or different and are each independently an alkyl group; Or an aryl group.

According to one embodiment of the present invention, in the general formulas (4-12) to (4-14), Z63 and Z64 are the same or different and are each independently a methyl group; Or a phenyl group.

According to one embodiment of the present invention, the formula (5) is represented by the following formula (5-1) or (5-2).

[Formula 5-1]

[Formula 5-2]

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

L2, Y2, Z7, Z8 and d are as defined in the above formula (5)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.

Is a moiety connected to R2 or R3 of formula (1).

According to one embodiment of the present invention, the formula 5 is represented by any one of the following formulas 5-3 to 5-6.

[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

[Formula 5-6]

In the above formulas 5-3 to 5-6,

L2, R16 to R18, Z7, Z8 and d are as defined in the above formula (5)

는 상기 화학식 1의 R2 또는 R3에 연결되는 부위이다.

Is a moiety connected to R2 or R3 of formula (1).

According to one embodiment of the present invention, in Formula 5, L2 is a direct bond.

According to one embodiment of the present invention, in Formula 5, Z7 represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in Formula 5, Z7 is a substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 5, Z7 is a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 5, Z7 is a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, in Formula 5, Z7 represents a methyl group; Or a phenyl group.

According to one embodiment of the present invention, in Formula 5, Z8 is hydrogen.

According to one embodiment of the present invention, in Formulas 5-5 and 5-6, R16 to R18 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in Formulas 5-5 and 5-6, R16 to R18 are the same or different and each independently represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms ; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in Formulas 5-5 and 5-6, R16 to R18 are the same or different and each independently represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms ; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in formulas 5-5 and 5-6, R16 to R18 are the same or different and each independently represents a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, in the formulas 5-5 and 5-6, R16 to R18 are the same or different and each independently represents a methyl group; Or a phenyl group.

According to one embodiment of the present invention, in the above formula (5-5), R16 is a phenyl group.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following compounds.

According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the above-described heterocyclic compound.

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

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.

2 shows a structure in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90 and a second electrode 50) are successively laminated on a substrate. 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1).

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1) as a host of the light emitting layer.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a phosphorescent host of the light emitting layer.

According to one embodiment of the present invention, the organic compound layer containing the heterocyclic compound represented by Formula 1 includes the compound represented by Formula 1 as a host of the light emitting layer, and the organic compound, metal, . According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer is formed of a heterocyclic compound represented by the general formula (1) as a phosphorescent host of the light emitting layer And includes an iridium-based metal complex as a phosphorescent dopant in the light-emitting layer.

According to an embodiment of the present invention, the organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

The organic light emitting device of the present invention is manufactured by materials and methods known in the art except that one or more of the organic layers include the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above formula (1) .

When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

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, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition 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.

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

According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.

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

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

The hole injecting layer is a layer for injecting holes from the electrode as a hole injecting material and a hole injecting effect for injecting holes in the anode as a hole injecting material and an excellent hole injecting effect for a light emitting layer or a light emitting material , The migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also the ability to form thin films is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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

The electron blocking layer is a layer which can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The light emitting material of the light emitting layer 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 high 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; Benzoxazole, benzothiazole and benzimidazole compounds; 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 may be 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 heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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

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

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

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

In addition, the organic light emitting diode according to the present invention may be an inverted type in which the lower electrode is a cathode, the upper electrode is a cathode, the lower electrode is a cathode, and the upper electrode is an anode.

According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

Production Example 1. Preparation of Compound 1

1) Preparation of Compound 1-1

(0.056 mol) of 1-phenyl-1H-indol-3-yl) boronic acid and 13.0 g (0.056 mol) of 4-chloro-2,6-diphenylpyrimidine were dissolved in 150 mL of 1,4- 35 g (0.17 mol) of post potassium phosphate are added. 0.9 g of dibenzylidene acetone palladium and 0.9 g of tricyclohexylphosphine were added thereto while warming the mixed solution, and the mixture was stirred under reflux for 12 hours. When the reaction is complete, the reaction is cooled to room temperature, washed with water and extracted with 300 mL of ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. A small amount of ethyl acetate and excess ethanol were added to the concentrated compound to precipitate a solid, which was then stirred at room temperature for 2 hours and filtered to obtain 19 g (81%) of Compound 1-1.

2) Preparation of Compound 1-2

Compound (1-1) (15 g, 0.035 mol) is dissolved in 100 mL of anhydrous tetrahydrofuran and cooled to 0 ° C. 6.3 g (0.035 mol) of N-bromosuccinimide is slowly added to this solution. After the reaction was completed by stirring at room temperature for 4 hours, the reaction mixture was washed with 20% sodium thiosulfate aqueous solution and extracted with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 50 mL of ethyl acetate was added to the concentrated compound, and the mixture was stirred at room temperature to precipitate a solid. The solid was filtered to obtain 15.3 g (86%) of pale brown Compound 1-2.

3) Preparation of compound 1-3

15 g (0.03 mol) of Compound 1-2 was dissolved in 100 mL of 1,4-dioxane, and 10.3 g (0.036 mol) of bis (pitacolato) diboron was added. 5.9 g (0.06 mol) of potassium acetate was added while stirring the mixture and the mixture was heated to reflux. 0.5 g (0.9 mmol) of dibenzylidene acetone palladium and 0.5 g (0.9 mmol) of tricyclohexylphosphine were added under reflux and stirring, and the mixture was stirred under reflux for 12 hours. After completion of the reaction, the reaction product was cooled to room temperature, washed with water and then extracted twice with chloroform. The collected organic layer was washed once with water, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration. The concentrated material was stirred with heating in a small amount of ethyl acetate and an excess of ethanol solution and filtered to obtain 13.6 g (83%) of pale yellow Compound 1-3.

4) Preparation of compound 1

7.7 g (0.02 mol) of the compound 1-3 and 12 g (0.02 mol) of 3- (4-chlorophenyl) -9-pentyl-9H- carbazole were diluted in 80 mL of 1,4- 13.9 g (0.066 mol) of K ₃ PO ₄ ) was added to the mixed solution, which was then heated and stirred under reflux. 380 mg of dibenzylidene acetone palladium and 370 mg of tricyclohexylphosphine were added to the mixture, followed by stirring under reflux for 12 hours. After completion of the reaction, the reaction product was cooled to room temperature, and the precipitated solid was filtered. The precipitated solid was dissolved in chloroform and washed twice with water. The combined organic layer was dried over anhydrous magnesium sulfate, filtered, and recrystallized using ethyl acetate as a mixed solution To give 11.8 g (73%) of Compound 1 as pale yellow.

MS: [M + H] &lt; ⁺ &gt; = 741

(D, 2H), 7.94 (d, 2H), 7.50-7.90 (m, 3H), 8.17 (m, 2H), 7.33 (t, IH), 7.25-7.27 (m, 4H)

Production Example 2. Preparation of Compound 2

1) Preparation of Compound 2-1

(0.056 mol) of 1-phenyl-2- (indol-3-yl) boronic acid and 13.0 g (0.056 mol) of 4-chloro-2,6-diphenylpyrimidine were dissolved in 150 mL of 1,4- 35 g (0.17 mol) of post potassium phosphate are added. 0.9 g of dibenzylidene acetone palladium and 0.9 g of tricyclohexylphosphine were added thereto while warming the mixed solution, and the mixture was stirred under reflux for 12 hours. When the reaction is complete, the reaction is cooled to room temperature, washed with water and extracted with 300 mL of ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. A small amount of ethyl acetate and excess ethanol were added to the concentrated compound to precipitate a solid, which was stirred at room temperature for 2 hours and then filtered to obtain 19 g (81%) of Compound 2-1.

2) Preparation of compound 2-2

2) in Production Example 1 Compound 2-2 was prepared in the same manner except that Compound 1-2 was used instead of Compound 1-1 in the production of Compound 1-2.

3) Preparation of Compound 2

Compound 2-2, 15 g (0.03mol) and (9,9-dimethyl -9-H- fluorene -2-yl) boronic acid was charged into a 7.8 g (0.033mol) in 90 mL of tetrahydrofuran K ₂ An aqueous solution in which 12.3 g (0.09 mol) of CO ₃ was dissolved in 30 mL of water was charged and warmed. 340 mg (3 mmol) of tetrakis- (triphenylphosphine) palladium was added to the refluxed mixture, and the mixture was refluxed and stirred for 12 hours. When the reaction was completed, the tetrahydrofuran was concentrated. The precipitated solid was cooled to room temperature, filtered, washed again with chloroform, washed with water, treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Recrystallization from chloroform and ethyl acetate gave 14 g (76%) of light yellow compound 2.

MS: [M + H] &lt; ⁺ &gt; = 617

(D, 1H), 7.89 (d, 1H), 7.84 (s, 1H), 7.7-7.8 (m, 4H), 8.14 2H), 7.28-7.62 (m, 16H), 1.70 (s, 6H)

Production Example 3. Preparation of Compound 3

1) Preparation of compound 3-3

Production Example 3 3) Compound 3-3 was prepared in the same manner except that Compound 2-2 was used instead of Compound 1-2 in the production of Compound 1-3.

2) Preparation of Compound 3

4) In Production Example 1, 15 g (0.027 mol) of Compound 3-3 was used instead of Compound 1-3 in the production of Compound 1, and 10 g (0.027 mol) of 3- -bromo-3,3-dimethyl-1-phenyl-1,3-dihydroindeno [2,1-b] carbazole.

MS: [M + H] &lt; ⁺ &gt; = 782

(D, IH), 7.89 (s, IH), 7.87 (s, IH), 8.24-8.36 (m, 6H) 1H), 7.67 (d, 1H), 7.48-7.62 (m, 18H), 7.35-7.38 (m,

Production Example 4. Preparation of Compound 4

1) Preparation of compound 4-1

(1-phenyl -1H- indole - 2 Days) after the acid 15g (0.063mol) and 2-chloro-4-phenyl-quinazolin 15.0g (0.063mol) in 1,4-dioxane In a 150mL K ₂ CO ₃ And an aqueous solution in which 12.3 g (0.09 mol) of the compound was dissolved in 30 mL of water was added and warmed. 340 mg (3 mmol) of tetrakis- (triphenylphosphine) palladium was added to the refluxed mixture, and the mixture was refluxed and stirred for 12 hours. When the reaction was completed, the tetrahydrofuran was concentrated. The precipitated solid was cooled to room temperature, filtered, washed again with chloroform, washed with water, treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Recrystallization from chloroform and ethyl acetate gave 20 g (81%) of yellow compound 4-1.

2) Preparation of compound 4-2

16 g (0.04 mol) of the compound 4-1 is dissolved in 100 mL of N, N-dimethylformamide, and then cooled to 0 deg. 7.1 g (0.04 mol) of N-bromosuccinimide is slowly added to this solution. When the reaction is completed by stirring at room temperature for 8 hours, the mixture is slowly poured into 300 ml of water to precipitate a solid. The precipitated solid was filtered and dissolved in chloroform (300 mL), washed with 20% sodium thiosulfate aqueous solution, and the organic layer was separated. The separated organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Ethyl acetate (30 mL) was added to the concentrated compound, and the mixture was stirred at room temperature to precipitate a solid. The solid was filtered to obtain 14.6 g (76%) of yellow compound 4-2.

3) Preparation of Compound 4

7.4 g (0.022 mol) of 7-phenyl-7H-benzo [c] carbazol-10-yl) boronic acid were added to 70 mL of tetrahydrofuran, and then K ₂ CO ₃ 8.7 g (0.06 mol) of triethylamine was dissolved in 20 mL of water, and the solution was warmed. 240 mg (0.2 mmol) of tetrakis- (triphenylphosphine) palladium was added to the refluxed mixture, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the tetrahydrofuran was concentrated and ethyl acetate was added. The precipitated solid was cooled to room temperature, filtered, washed again with chloroform, washed with water, treated with anhydrous magnesium sulfate, filtered and then recrystallized with ethyl acetate to obtain yellow Of compound 4 (69%).

MS: [M + H] &lt; ⁺ &gt; = 689

(M, 5H), 7.50 (d, IH), 7.30 (d, IH) 7.65 (m, 20 H), 7.30 (t, 1 H)

<Experimental Example 1>

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer.

The HT-1 compound was thermally vacuum-deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and an HT-2 compound was vacuum deposited on the HT-1 deposition layer to a thickness of 50 Å to form an electron blocking layer.

Subsequently, a host compound 1 and phosphorescent dopant GD-1 were co-deposited on the HT-2 deposited film at a weight ratio of 12% to form a 400 Å thick light emitting layer. ET-1 was vacuum deposited on the light-emitting layer to a thickness of 250 ANGSTROM, and ET-2 was co-deposited with a 2 wt% LiQ to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Respectively.

Experimental Example 2

The experiment was carried out in the same manner as in Experimental Example 1, except that Compound 2 was used instead of Compound 1 in Experimental Example 1.

Experimental Example 3

The experiment was carried out in the same manner as in Experimental Example 1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1.

Experimental Example 4

Experiments were carried out in the same manner as in Experimental Example 1, except that Compound 4 was used instead of Compound 1 in Experimental Example 1

Comparative Example 1

The experiment was carried out in the same manner as in Experimental Example 1, except that H1 was used instead of Compound 1 in Experimental Example 1.

Comparative Example 2

Experiments were carried out in the same manner as in Experimental Example 1, except that H2 was used instead of Compound 1 in Experimental Example 1.

Table 1 shows the evaluation results of the organic light emitting device manufactured by using each compound as a host in the light emitting layer in Experimental Examples 1 to 4 and Comparative Examples 1 and 2

Voltage (V) (@ 10mA / cm2) Efficiency (Cd / A)
(@ 10mA / cm2) The color coordinates (x, y) Life span (h)
T ₉₅ at 20 mA / cm ² Comparative Example 1 4.8 42 0.37, 0.61 24 h Comparative Example 2 5.1 35 0.35, 0.62 15 h Experimental Example 1 3.8 50 0.36, 0.60 40 h Experimental Example 2 4.2 48 0.37, 0.61 43 h Experimental Example 3 3.7 55 0.36, 0.60 45 h Experimental Example 4 4.5 43 0.38, 0.59 35 h

As can be seen in Table 1, Experimental Examples 1 to 4 show that the heterocyclic compound of the present invention is used as a host of a green light emitting layer and can exhibit lower voltage characteristics and improved lifetime than Comparative Examples 1 and 2.

Particularly, in the case of Comparative Example 2 in which one of X1 to X3 of Formula 2 according to one embodiment of the present invention is N, and Z1 and Z2 are simultaneously hydrogen, the driving voltage is higher than those of Experiments 1 to 4, Or more.

10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron transport layer
90: electron injection layer

Claims (8)

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

In Formula 1,
R1 is an aryl group,
R4 to R7 are the same or different from each other, and each independently hydrogen; An aryl group substituted or unsubstituted with an alkyl group; Or a heteroaryl group, or adjacent groups may combine with each other to form a benzene ring substituted with (R &lt; 20 &_gt;) _e ,
R20 is hydrogen; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group,
e is an integer of 1 to 4,
When e is 2 or more, two or more R &lt; 20 &gt; s are the same or different from each other,
R 2 is the following formula 2 or 3, and R 3 is the following formula 4; R2 is the following formula 4, R3 is the following formula 2 or 3,
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
X1 is N or CR8, X2 is N or CR9, X3 is N or CR10, X4 is N or CR11, X5 is N or CR12,
At least one of X1 to X3 is N,
At least one of X &lt; 4 &gt; and X &lt; 5 &gt; is N,
Y1 is NR13, CR14R15, O or S,
L1 is a direct bond; Or an arylene group,
Z1 and Z2 are the same or different and each independently represents an aryl group substituted or unsubstituted with a nitrile group, an aryl group, or a heteroaryl group; Or a heteroaryl group,
Z3 is an aryl group,
Z4, Z5 and R8 to R12 are hydrogen,
Z6 may be hydrogen or may combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring with an alkyl group or aryl group,
R13 to R15 are the same or different from each other and each independently represents an alkyl group; Or an aryl group,
a and c are each an integer of 1 to 4,
b is an integer of 1 to 3,
When a, b, and c are two or more, the structures in parentheses two or more are the same or different,

Is a moiety connected to R2 or R3 of formula (1). The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 through 1-3,
The definitions of R 1 to R 7 are the same as those of the above formula (1)
R20 is hydrogen; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group,
e is an integer of 1 to 4,
When e is 2 or more, two or more R &lt; 20 &gt; s are the same or different from each other. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-4, 1-6, 1-8, and 1-10:
[Formula 1-4]

[Chemical Formula 1-6]

[Chemical Formula 1-8]

[Chemical Formula 1-10]

In Formulas 1-4, 1-6, 1-8, and 1-10,
R 1 and R 4 to R 7 have the same meanings as defined in formula (1), X 1 to X 3, Z 1 and Z 2 have the same definitions as in formula (2), and X 4, X 5, Z 3, Z 4 and a have the same meanings as in formula The definitions of L1, Y1, Z5, Z6, b and c are the same as those of the above formula (4). delete The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following compounds:

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 of any one of claims 1 to 3 and 5 Organic light emitting device. 7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. 7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer.

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