KR101919932B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a heterocyclic compound of formula (I) and an organic light emitting device including 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. 10-2016-0015688 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 enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered 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,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 is a polycyclic heteroaryl group containing at least two substituted or unsubstituted N,

R1 to R13 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.

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.

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.
Figure 3 shows LC / MS values of compounds 1-3 according to one embodiment of the present disclosure.
Figure 4 shows the LC / MS values of compounds 1-30 according to one embodiment of the present disclosure.
Figure 5 shows the LC / MS values of compounds 1-68 according to one embodiment of the present disclosure.

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

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

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, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- Pentyl, neopentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2- Methylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 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 ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. 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-phenylnaphthalenamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-dimethylfluorenyltriphenyleneamine group, N-triphenylenyldibenzofuran An amine group, an N-triphenylenyldibenzothiophenamine group, an N-phenyltriphenyleneamine group, an N-biphenyldimethylfluoreneamine group, an N-biphenyldibenzofuranamine group, A thiophene amine group, an N-biphenylphenylcarbazoleamine group, an N-biphenyltriphenyleneamine group, an N-naphthyltriphenylenamine group, an N-phenyldiphenylfluoreneamine group, Fluorenylamine group, N-phenyl spirobifluorene amine group, N-naphthyl spirobifluorene amine group, N-naphthyldiphenylfluorene amine group, N- A phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, a phenyldimethylfluorene group, Naphthyldibenzothiophenamine group, N-phenyldibenzothiophenamine group, N-phenylphenylcarbazolamine group, dinaphthylamine group, N-phenylphenylcarbazolium group, Naphthalene amine group, and the like, 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 heteroaryl 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 , wherein R ₁₀₀ and R ₁₀₁ 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, a dinaphthylphosphine oxide group, 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, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with 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, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl, and dibenzofuranyl.

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, 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, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means 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.

In the present specification, the term " polycyclic " means two or three or more rings. Specifically, it may be a bicyclic to tenth ring, more specifically, a bicyclic to tenth ring, and more specifically, a bicyclic or tricyclic ring.

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

(3)

In Formula 3,

The definition of L1 and Ar1 is the same as that of the above formula (1).

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted quinolinylene group; Or a substituted or unsubstituted pyridyl group.

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A phenylene group; Biphenyllylene groups; Naphthylene group; A quinolinylene group; Or a pyridyl group.

According to one embodiment of the present invention, in the general formula (1), Ar 1 is a polycyclic heteroaryl group having 2 to 30 carbon atoms and containing at least two substituted or unsubstituted N atoms.

According to one embodiment of the present invention, in the general formula (1), Ar 1 is a polycyclic heteroaryl group having 2 to 20 carbon atoms containing at least two substituted or unsubstituted N atoms.

According to one embodiment of the present invention, in the general formula (1), Ar1 is a divalent or tricyclic heteroaryl group containing at least 2 N atoms.

According to one embodiment of the present invention, Ar 1 in Formula 1 is represented by any one of the following formulas A-6, A-23, and F.

[A-6]

[A-23]

[Chemical Formula F]

In the above formulas A-6, A-23 and F,

W1 and W2 are the same or different and are each independently N or CRa,

X1 to X4 are the same or different and each independently N or CRb,

Y1 to Y3 are the same or different and are each independently N or CRd,

Z1 to Z4 are the same or different and each independently N or CRc,

G is O; S; Or CRxRy,

R201, Ra, Rb, Rc, Rd, Rx and Ry are the same or different 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 may be bonded to adjacent groups to form a substituted or unsubstituted ring,

는 상기 화학식 1 또는 L1에 연결되는 부위이다.

Is a moiety connected to Formula 1 or L1.

According to one embodiment of the present invention, the formula (A-6) is represented by any one of the following formulas A-7 to A-9 and A-11.

[A-7]

[A-8]

[A-9]

[A-11]

In Formulas A-7 to A-9 and A-11,

The definition of Y1 and Y2 is the same as that of the above formula (A-6)

R202 to R205 are the same or different 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, the formula (A-6) is represented by any one of the following formulas (A-12) to (A-19).

[A-12]

[A-13]

[Chemical formula A-14]

[A-15]

[A-16]

[A-17]

[A-18]

[A-19]

In the above formulas A-12 to A-19,

R202 to R207 are the same or different 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, the formula (A-23) is represented by any one of the following formulas A-24 to A-27.

[A-24]

[A-25]

[A-26]

[A-27]

In Formulas A-24 to A-27,

The definition of R201 is the same as that of the above formula (A-23)

R202 to R205 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, the formula (A-6) is represented by the following formula (A-28) or (A-29).

[A-28]

[A-29]

In the above formulas A-28 and A-29,

The definitions of Y1 and Y2 are the same as those of the formula (A-6)

R202 to R205 and R208 to R211 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, the formula (A-6) is represented by the following formula (A-30) or (A-31).

[A-30]

[A-31]

In the above formulas A-30 and A-31,

R202 to R205 and R207 to R211 are the same or different 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, Formula (F) is represented by Formula (F-1) below.

[Formula F-1]

In the above formula (F-1)

G, W1 and W2 are the same as in the above formula (F)

R401 to R404 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, the formula (F-1) is represented by any one of the following formulas (F-2) to (F-4).

[Formula F-2]

[Formula F-3]

[Formula F-4]

In the formulas (F-2) to (F-4)

The definitions of R401 to R404 are the same as those of the above formula (F)

R405 to R407 are the same or different 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 is bonded to an adjacent group to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, each of R202 to R205 is independently hydrogen.

According to one embodiment of the present invention, each of R208 to R211 is independently hydrogen.

According to one embodiment of the present invention, R401 to R404 each independently represent hydrogen.

According to one embodiment of the present invention, R406 and R407 are the same or different and each independently a substituted or unsubstituted alkyl group.

According to one embodiment of the present invention, R406 and R407 are the same or different from each other and each independently an alkyl group.

According to one embodiment of the present invention, R406 and R407 are each independently a methyl group.

According to one embodiment of the present invention, R201 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, R201 is a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, R201 is a phenyl group or a naphthyl group.

According to one embodiment of the present invention, R206 and R207 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, R206 and R207 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heteroaryl group.

According to one embodiment of the present invention, R206 and R207 are the same or different and each independently represents an aryl group substituted or unsubstituted with an aryl group or a heteroaryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group or a heteroaryl group.

According to one embodiment of the present invention, R206 and R207 are the same or different and each independently represent a phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A naphthyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A pyridine group substituted or unsubstituted with an aryl group or a heteroaryl group; A quinolinyl group substituted or unsubstituted with an aryl group or a heteroaryl group; Or a carbazole group substituted or unsubstituted with an aryl group or a heteroaryl group.

According to one embodiment of the present invention, R206 and R207 are the same or different and each independently represent a phenyl group substituted or unsubstituted with a phenyl group or a pyridine group; Naphthyl group; Biphenyl group; A pyridine group; A quinoline group; Or a carbazol group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, R405 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, R405 is a substituted or unsubstituted C6-C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.

According to one embodiment of the present invention, R405 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted pyridine group.

According to one embodiment of the present disclosure, R405 is a phenyl group; Naphthyl group; Biphenyl group; Or a pyridine group.

According to one embodiment of the present disclosure, at least one of Y1 and Y2 is N.

According to one embodiment of the present disclosure, Y3 is N.

According to one embodiment of the present disclosure, at least one of W1 and W2 is N.

According to one embodiment of the present invention, Ar 1 in Formula 1 is represented by any one of the following Group X structures.

[Group X]

According to one embodiment of the present invention, the formula (1) may be 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 an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of 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 stacked in this order on a transparent 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 material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound represented by the 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).

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 material layer contains the heterocyclic compound represented by the formula (1) as a host of the light emitting layer, and includes another organic compound, metal or metal compound as a dopant.

The dopant may be represented by any one of the following compounds, but is not limited thereto.

Dp - 1 Dp - 2 Dp -3

Dp - 4 Dp - 5 Dp -6

Dp - 7 Dp - 8 Dp -9

Dp - 10 Dp - 11 Dp -12

DP-13 Dp-14 Dp-15

Dp - 16 Dp - 17 Dp -18

Dp - 19 Dp - 20 Dp -21

Dp - 22 Dp - 23 Dp -24

Dp-25 Dp-26 Dp-27

According to one embodiment of the present invention, the content of the host may be 90 to 99% by weight and the content of the dopant may be 1 to 10% by weight based on the total content of the host and the dopant.

According to one embodiment of the present invention, the content of the host and the dopant may be 95 to 97% by weight and 3 to 5% by weight, respectively, based on the total content of the host and the dopant.

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) .

The compounds of the present invention can be prepared by using Buchwald-Hartwig coupling reaction, Heck coupling reaction, Ullmann coupling reaction or the like as a typical reaction.

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 by 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 that can be used in the present invention 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 an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. 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 aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

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

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

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

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole 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.

≪ Preparation Example > Preparation of compound 1

The compounds of the present invention were prepared by using Buchwald-Hartwig coupling reaction, Heck coupling reaction, Ullmann coupling reaction and the like as typical reactions.

1) Preparation of compound 1-a

A solution of 200.00 g (1.0 eq) of 11,12-dihydroindolo [2,3-a] carbazole, 2.05 eq of Copper powder and 2.0 eq of K ₂ CO _{3 was} added to 1 L of DMAC (dimethylacetamide) And the mixture was stirred. At the beginning of reflux, 149.80 g (1.0 eq) of 1-bromo-2-chlorobenzene was added dropwise. After the reaction was completed, the mixture was cooled to room temperature and then the copper powder was removed by filtration. The solution in which the product was dissolved was depressurized to remove all of the solvent. The solution was completely dissolved in CHCl ₃ , washed with water, and again decompressed to remove the solvent, which was purified by column chromatography. To obtain Compound 1-a (202.98 g, yield 71%). [M + H] = 367

2) Preparation of compound 1

Compound 1-a 202.98 g Pd (dba ) to _{(1.0 eq) 2 3.18 g (} 0.01 eq), PCy 3 4.66 g (0.03 eq), K 3 PO 4 235.38 g (2.00 eq) of diethyl acetamide (Dimethylacetamide) 1.4 L, refluxed and stirred. After 3 hours, the reaction mixture was poured into water, and the crystals were dropped and filtered. The filtered solid was completely dissolved in ethyl acetate and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. Compound 1 (133.61 g, yield 73%) was obtained. [M + H] < + > = 331

<Synthesis Example>

Synthesis Example 1 Synthesis of Compound 1-3

Compound 1 10.0 g (1.0 eq), 2- (4-bromophenyl) -3-phenylquinoxaline 11.99 g (1.1 eq), K 3 PO 4 12.86 g (2.0 eq), Pd (t-Bu 3 P) 2 0.07 g ( 0.005 eq) was dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain Compound 1-3 (16.08 g, yield 87%). [M + H] &lt; / RTI &gt; = 611

Figure 3 shows the LC / MS values of compounds 1-3.

Synthesis Example 2 Synthesis of Compound 1-5

Compound 1 10.0 g (1.0 eq), 2-chloro-3-phenylquinoxaline 6.94 g (1.1 eq), K 3 to _{PO 4 12.86 g (2.0 eq)} , Pd (t-Bu 3 P) 2 0.07 g (0.005 eq) Was dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, the crystals were dropped, and the solution was cooled and filtered. This was subjected to column chromatography to obtain Compound 1-5 (12.45 g, yield 77%). [M + H] &lt; + &gt; = 535

Synthesis Example 3 Synthesis of Compound 1-29

Compound 1 10.0 g (1.0 eq), 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine 9.14 g (1.1 eq), K ₃ PO ₄ 12.86 g t-Bu ₃ P) ₂ (0.07 g, 0.005 eq) was dissolved in 80 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, the crystals were dropped, and the solution was cooled and filtered. This was subjected to column chromatography to obtain Compound 1-29 (15.37 g, yield 86%). [M + H] = 591

Synthesis Example 4 Synthesis of Compound 1-30

Compound 1 10.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) benzo [4,5] thieno [3,2-d] pyrimidine 8.39 g (1.1 eq), K 3 PO 4 12.86 g (2.0 eq) and 0.07 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, the crystals were dropped, and the solution was cooled and filtered. This was subjected to column chromatography to obtain Compound 1-30 (16.09 g, yield 83%). [M + H] &lt; / RTI &gt; = 640

Figure 4 shows LC / MS values for compounds 1-30.

Synthesis Example 5 Synthesis of Compound 1-39

Compound 1 10.0 g (1.0 eq), 2- (4-bromophenyl) -4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine 8.39 g (1.1 eq), K 3 PO 4 12.86 g (2.0 eq ) And 0.07 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain Compound 1-39 (15.74 g, yield 78%). [M + H] &lt; + &gt; = 667

Synthesis Example 6 Synthesis of Compound 1-57

Compound 1 10.0 g (1.0 eq), 2-chloro-4-phenylquinazoline 9.89 g (1.1 eq), K 3 to _{PO 4 12.86 g (2.0 eq)} , Pd (t-Bu 3 P) 2 0.07 g (0.005 eq) Was dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, the crystals were dropped, and the solution was cooled and filtered. This was subjected to column chromatography to obtain Compound 1-57 (11.81 g, yield 73%). [M + H] &lt; + &gt; = 535

Synthesis Example 7 Synthesis of Compound 1-61

Compound 1 10.0 g (1.0 eq), 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline 6.13 g (1.1 eq), K 3 PO 4 12.86 g (2.0 eq), Pd (t -Bu ₃ P) ₂ (0.07 g, 0.005 eq) was dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, the crystals were dropped, and the solution was cooled and filtered. This was subjected to column chromatography to obtain Compound 1-61 (14.41 g, yield 78%). [M + H] &lt; / RTI &gt; = 612

Synthesis Example 8 Synthesis of Compound 1-68

Compound 1 10.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 7.41 g (1.1 eq), K 3 PO 4 12.86 g (2.0 eq), Pd (t-Bu 3 P) 2 0.07 g (0.005 eq) was dissolved in 80 ml of xylene, refluxed and stirred. After 1 hour, the reaction was terminated and the solvent was removed under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, the crystals were dropped, and the solution was cooled and filtered. This was subjected to column chromatography to obtain Compound 1-68 (13.27 g, yield 75%). [M + H] = 685

Figure 5 shows LC / MS values for compounds 1-68.

<Examples>

&Lt; Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying. Hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 50 Å on the thus-prepared ITO transparent electrode to form a hole injection layer. HT1 (700 Å) for transporting holes was vacuum deposited thereon and HT2 (200 Å) was deposited thereon. Compound 1-3 and dopant Dp-7 compound were vacuum-deposited as a host to a thickness of 300 Å in the light emitting layer. The amount of the dopant was 3 wt% based on the total amount of the host and the dopant. Then, an E1 compound (300 ANGSTROM) was sequentially vacuum-deposited by electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device. In the above procedure, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of LiF was 0.2 Å / sec, and the deposition rate of aluminum was 3 Å / sec to 7 Å / sec.

&Lt; Example 2 >

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-5 was used instead of Compound 1-3 in Example 1.

&Lt; Example 3 >

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-29 was used instead of Compound 1-3 in Example 1,

<Example 4>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-30 was used instead of Compound 1-3 in Example 1.

&Lt; Example 5 >

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-39 was used instead of Compound 1-3 in Example 1.

&Lt; Example 6 >

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1-57 was used instead of Compound 1-3 in Example 1.

&Lt; Example 7 >

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-61 was used instead of Compound 1-3 in Example 1.

&Lt; Example 8 >

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-68 was used instead of Compound 1-3 in Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Example 1, except that H-1 was used instead of the compound 1-9 in Example 1.

&Lt; Comparative Example 2 &

An organic luminescent device was fabricated in the same manner as in Example 1, except that H-2 was used instead of the compound 1-9 in Example 1.

The results of the organic luminescent devices manufactured by the above Examples 1 to 8 and Comparative Examples 1 and 2 are shown in Table 1 below. Voltage, efficiency, and emission color are data at 5000 nit brightness. The lifetime was 100% of the initial photocurrent value, and the time was 98% of the photocurrent value.

division matter The driving voltage (V) Efficiency (cd / A) Life span T98 (hr) Luminous color Example 1 Compound 1-3 3.9 32.7 43 Red Example 2 Compound 1-5 3.8 34.5 41 Red Example 3 Compound 1-29 4.1 31.7 55 Red Example 4 Compound 1-30 4.0 32.0 57 Red Example 5 Compound 1-39 4.1 31.5 48 Red Example 6 Compound 1-57 4.3 30.1 63 Red Example 7 Compound 1-61 4.2 30.5 60 Red Example 8 Compound 1-68 4.2 31.0 67 Red Comparative Example 1 H-1 4.0 31.5 17 Red Comparative Example 2 H-2 3.9 31.0 13 Red

As can be seen from the results of Table 1, the organic light emitting device using the compound of the present invention exhibited improved luminescence efficiency while lowering the driving voltage and all emitted red light. Although the voltage was similar to that of the comparative materials H-1 and H-2, they were generally good in terms of efficiency. In addition, the lifetime advantages of red light emission were all exhibited and showed a long life effect of up to 5 times. Therefore, the compound of the present invention can be considered to have the advantages of high efficiency, low driving voltage and long life in an organic light emitting device.

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 (16)

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

In Formula 1,
L1 is a direct bond; Or an arylene group,
Ar 1 is a polycyclic heteroaryl group substituted or unsubstituted with R 'and containing 2 or more N, R' is an aryl group substituted or unsubstituted with a heteroaryl group,
R1 to R13 are each independently hydrogen. delete delete [2] The compound according to claim 1, wherein L1 is a direct bond; A phenylene group; Biphenylene group; Or a naphthylene group. The heterocyclic compound according to claim 1, wherein Ar1 is represented by any one of the following formulas A-6, A-23 and F:
[A-6]

[A-23]

[Chemical Formula F]

In the above formulas A-6, A-23 and F,
W1 and W2 are the same or different and are each independently N or CRa,
X1 to X4 are the same or different and each independently N or CRb,
Y1 to Y3 are the same or different and are each independently N or CRd,
Z1 to Z4 are the same or different and each independently N or CRc,
In formula (A-6), at least one of Y1, Y2 and Z1 to Z4 is N,
In formula (A-23), at least one of Y3 and Z1 to Z4 is N,
In formula (F), at least one of W1, W2 and X1 to X4 is N,
G is O; S; Or CRxRy,
R201, Ra, Rb, Rc, Rd, Rx and Ry are the same or different and each independently hydrogen; Or an aryl group which is substituted or unsubstituted with a heteroaryl group or is bonded to an adjacent group to form a ring substituted or unsubstituted with R ", R" is an aryl group substituted or unsubstituted with a heteroaryl group,

Is a moiety connected to Formula 1 or L1. The heterocyclic compound according to claim 5, wherein the formula (A-6) is represented by any one of formulas (A-7) to (A-
[A-7]

[A-8]

[A-9]

[A-11]

In Formulas A-7 to A-9 and A-11,
The definition of Y1 and Y2 is the same as that of the above formula (A-6)
R202 to R205 are the same or different and each independently hydrogen; Or an aryl group which is substituted or unsubstituted with a heteroaryl group, or is bonded to an adjacent group to form a ring substituted or unsubstituted with R ", and R" is an aryl group substituted or unsubstituted with a heteroaryl group. The heterocyclic compound according to claim 5, wherein the formula (A-6) is represented by any one of formulas (A-12) to
[A-12]

[A-13]

[Chemical formula A-14]

[A-15]

[A-16]

[A-17]

[A-18]

[A-19]

In the above formulas A-12 to A-19,
R202 to R207 are the same or different and each independently hydrogen; Or an aryl group which is substituted or unsubstituted with a heteroaryl group, or is bonded to an adjacent group to form a ring substituted or unsubstituted with R ", and R" is an aryl group substituted or unsubstituted with a heteroaryl group. The heterocyclic compound according to claim 5, wherein the formula (A-23) is represented by any one of the following formulas A-24 to A-27:
[A-24]

[A-25]

[A-26]

[A-27]

In Formulas A-24 to A-27,
The definition of R201 is the same as that of the above formula (A-23)
R202 to R205 are the same or different from each other, and each independently hydrogen; Or an aryl group which is substituted or unsubstituted with a heteroaryl group, or is bonded to an adjacent group to form a ring substituted or unsubstituted with R ", and R" is an aryl group substituted or unsubstituted with a heteroaryl group. The heterocyclic compound according to claim 5, wherein the formula (A-6) is represented by the following formula (A-28) or (A-
[A-28]

[A-29]

In the above formulas A-28 and A-29,
The definitions of Y1 and Y2 are the same as those of the formula (A-6)
R202 to R205 and R208 to R211 are the same or different from each other, and each independently hydrogen; Or an aryl group substituted or unsubstituted with a heteroaryl group. The heterocyclic compound according to claim 5, wherein the formula (A-6) is represented by the following formula (A-30) or (A-31)
[A-30]

[A-31]

In the above formulas A-30 and A-31,
R202 to R205 and R207 to R211 are the same or different and each independently hydrogen; Or an aryl group substituted or unsubstituted with a heteroaryl group. The heterocyclic compound according to claim 5, wherein the formula (F) is represented by the following formula (F-1):
[Formula F-1]

In the above formula (F-1)
G, W1 and W2 are the same as in the above formula (F)
R401 to R404 are the same or different from each other, and each independently hydrogen; Or an aryl group substituted or unsubstituted with a heteroaryl group. The heterocyclic compound according to claim 11, wherein the formula (F-1) is represented by any one of the following formulas (F-2) to
[Formula F-2]

[Formula F-3]

[Formula F-4]

In the formulas (F-2) to (F-4)
The definitions of R401 to R404 are the same as those of the above formula (F-1)
R405 to R407 are the same or different and each independently hydrogen; Or an aryl group substituted or unsubstituted with a heteroaryl group. 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 material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is a heterocycle according to any one of claims 1 and 4 to 13 Wherein the compound is a compound represented by the following formula. 15. The organic light emitting device according to claim 14, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound. [16] The organic light emitting device according to claim 14, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the heterocyclic compound.

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