KR20180093819A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1, and an organic light-emitting device including the same. The heterocyclic compound, according to an embodiment of the present invention, can be used as a material in an organic material layer of the organic light-emitting device.

Description

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

This application claims the benefit of Korean Patent Application No. 10- 2017-0019961 filed on February 14, 2017 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.

U.S. Patent Application Publication No. 2004-0251816

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,

X1 is O or S,

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

Y1 and Y3 are N, Y2 is CR13, Y4 is CR14, Y2 and Y4 are N, Y1 is CR14, Y3 is CR13,

R13 is a group which combines with L1,

R2 and R3, or R3 and R4 are groups which combine with * in the following formula (2)

R 2, R 3, R 4, R 5 and R 6 are the same or different and are each independently hydrogen; 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,

n is 1 or 2,

when n is 2, two L1s are the same or different from each other,

(2)

In Formula 2,

* Is a moiety bonded with R2 and R3, or R3 and R4 in the above formula (1)

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R15 to R18 are the same or different from each other, and each independently and independently hydrogen; 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.

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 heterocyclic compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device and by using it, it is possible to improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting 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.
3 is a mass spectrometry spectrum of Compound 1 prepared in Synthesis Example 1 of this specification.
4 is a mass spectrometry spectrum of Compound 2 prepared in Synthesis Example 2 of this specification.
5 is a mass spectrometry spectrum of Compound 3 prepared in Synthesis Example 3 of the present specification.
6 is a mass spectrometry spectrum of Compound 4 prepared in Synthesis Example 4 of the present specification.
7 is a mass spectrometry spectrum of Compound 5 prepared in Synthesis Example 5 of this specification.
8 is a mass spectrometry spectrum of Compound 6 prepared in Synthesis Example 6 of this specification.
9 is a mass spectrometry spectrum of Compound 7 prepared in Synthesis Example 7 of this specification.
10 is a mass spectrometry spectrum of Compound 8 prepared in Synthesis Example 8 of the present specification.
11 is a mass spectrometry spectrum of Compound 9 prepared in Synthesis Example 9 of this specification.
12 is a mass spectrometry spectrum of Compound 10 prepared in Synthesis Example 10 of the present specification.
13 is a mass spectrometry spectrum of Compound 11 prepared in Synthesis Example 11 of the present specification.
14 is a mass spectrometry spectrum of Compound 12 prepared in Synthesis Example 12 of the present specification.
15 is a mass spectrometry spectrum of Compound 13 prepared in Synthesis Example 13 of this specification.
16 is a mass spectrometry spectrum of Compound 14 prepared in Synthesis Example 14 of the present specification.
17 is a mass spectrometry spectrum of Compound 15 prepared in Synthesis Example 15 of this specification.
18 is a mass spectrometry spectrum of Compound 16 prepared in Synthesis Example 16 of this specification.
19 is a mass spectrometry spectrum of Compound 17 prepared in Synthesis Example 17 of this specification.
20 is a mass spectrometry spectrum of Compound 18 prepared in Synthesis Example 18 of this specification.
21 is a mass spectrometry spectrum of Compound 19 prepared in Synthesis Example 19 of this specification.
22 is a mass spectrometry spectrum of Compound 20 prepared in Synthesis Example 20 of this specification.
23 is a mass spectrometry spectrum of Compound 21 prepared in Synthesis Example 21 of this specification.
24 is a mass spectrometry spectrum of Compound 22 prepared in Synthesis Example 22 of this specification.
25 is a mass spectrometry spectrum of Compound 23 prepared in Synthesis Example 23 of this specification.
26 is a mass spectrometry spectrum of Compound 24 prepared in Synthesis Example 24 of this specification.

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

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

According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is selected from the group consisting of benzofura [3,4- d ] pyrimidine, benzofura [2,3-d] pyrimidine, benzothieno [ 4- d ] pyrimidine or benzothieno [2,3-d] pyrimidine is bonded to N of indolecarbazole through L 1, the flow of electrons is smooth, Since the steric hindrance of Formula 1 is reduced and the structure is stable since the compound of Formula 2 is bonded to R2 and R3 or R3 and R4 of Formula 1, the organic light emitting device of Formula 1 has low driving voltage, Excellent efficiency and long lifetime.

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, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine 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, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of 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, 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, triphenyl, pyrenyl, phenalenyl, perylenyl, no.

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, 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, 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 an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the heteroaryl group or the heterocyclic group except that the monocyclic group is not monovalent.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 through 1-4,

X1, L1, n, Y1 to Y4, R1, R2 and R4 to R12 are the same as in the above formula (1)

The definition of Ar1 and R15 to R18 is the same as that of the above formula (2).

According to one embodiment of the present invention, in the formula 1, Y1 and Y3 are N, Y2 is CR13, and Y4 is CR14.

According to one embodiment of the present invention, in the above Formula 1, Y2 and Y4 are N, Y1 is CR14, and Y3 is CR13.

According to one embodiment of the present disclosure, R13 is a group which combines with L1.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (1-5) to (1-12).

[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]

[Formula 1-12]

In the above formulas (1-5) to (1-12)

X1, L1, n, R1, R2, R4 to R12 and R14 are as defined above,

The definition of Ar1 and R15 to R18 is the same as that of the above formula (2).

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (1-13) to (1-20).

[Formula 1-13]

[Chemical Formula 1-14]

[Chemical Formula 1-15]

[Chemical Formula 1-16]

[Formula 1-17]

[Chemical Formula 1-18]

[Chemical Formula 1-19]

[Chemical Formula 1-20]

In Formulas 1-13 to 1-20,

L1, n, R1, R2, R4 to R12 and R14 are as defined above,

The definition of Ar1 and R15 to R18 is the same as that of the above formula (2).

According to one embodiment of the present invention, Formula 1 is represented by any one of Formulas 1-21 to 1-28.

[Formula 1-21]

[Formula 1-22]

[Formula 1-23]

[Formula 1-24]

[Chemical Formula 1-25]

[Chemical Formula 1-26]

[Chemical Formula 1-27]

[Chemical Formula 1-28]

In Formulas 1-21 to 1-28,

L1, n, R1, R2, R4 to R12 and R14 are as defined above,

The definition of Ar1 and R15 to R18 is the same as that of the above formula (2).

According to one embodiment of the present invention, R14 is a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R14 is an aryl group.

According to one embodiment of the present disclosure, R14 is a phenyl group; Or a naphthyl group.

According to one embodiment of the present disclosure, Ar1 is an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar1 represents a phenyl group; A biphenyl group; Naphthyl group; A phenanthryl group; Fluoranthene group; A triphenylrenyl group; Pyrenyl; A pyridyl group; Pyrimidyl; A triazinyl group substituted with an aryl group; Or a quinazolyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar1 represents a phenyl group; A biphenyl group; Naphthyl group; A phenanthryl group; Fluoranthene group; A triphenylrenyl group; Pyrenyl; A pyridyl group; Pyrimidyl; A triazinyl group substituted with a phenyl group; Or a quinazolyl group substituted or unsubstituted with a phenyl group or a naphthyl group.

According to one embodiment of the present disclosure, Formula 1 is selected from 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 material layer includes a hole transporting layer, and the hole transporting layer includes the heterocyclic compound represented by the general formula (1).

According to one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer which simultaneously transports and injects electrons, and the electron transporting layer, the electron injecting layer, And the above-mentioned heterocyclic compounds.

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.

In one embodiment of the present invention, the organic material layer includes the heterocyclic compound represented by Formula 1 as a host, and may include other organic compound, metal or metal compound as a dopant.

The dopant may be at least one selected from the following compounds, but is not limited thereto.

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 that can prevent electrons injected from the electron injection layer from entering the hole injection layer through the light emission 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 hole blocking layer prevents 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 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 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.

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.

The heterocyclic compound according to one embodiment of the present invention can be prepared by a basic synthesis scheme of the following Reaction Schemes 1 to 8, but is not limited thereto.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

[Reaction Scheme 4]

[Reaction Scheme 5]

[Reaction Scheme 6]

[Reaction Scheme 7]

[Reaction Scheme 8]

In the above Reaction Schemes 1 to 8, the definitions of X1, R14, L1 and n are the same as those defined in Formula 1, and the definition of Ar1 is the same as defined in Formula 2 above.

According to one embodiment of the present disclosure, intermediates A-1 and A-2 may be prepared according to the following reaction schemes 9 and 10, but are not limited thereto.

[Reaction Scheme 9]

[Reaction Scheme 10]

In the above Reaction Schemes 9 and 10, the definitions of X1 and R14 are the same as defined in Formula 1 above.

Production Example 1. Synthesis of Compound A-1-1

Dichlorobenzo [4,5] thieno [3,4- d ] pyrimidine (10 g, 0.04 mol), phenylboronic acid (4.8 g, 0.04 mol) and calcium carbonate (8.3 g, 0.06 mol) and Pd (PPh ₃ ) ₄ (1.8 g, 4 mol%) were dissolved in anhydrous tetrahydrofuran and water, and the mixture was refluxed at 80 ° C for 4 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature and extracted with chloroform. The extracted organic layer was dried over anhydrous magnesium sulfate and then recrystallized with ethyl acetate to obtain Compound A-1-1 (9.53 g, 82%).

Production Example 2. Synthesis of Compound A-1-2

Compound A-1-2 was obtained in the same manner as in Preparation Example 1, except that 1-naphthylboronic acid was used instead of phenylboronic acid.

Production Example 3. Synthesis of Compound A-1-3

Compound A-1-3 was obtained in the same manner as in Preparation Example 1, except that 2-naphthylboronic acid was used instead of phenylboronic acid.

Production Example 4. Synthesis of Compound A-1-4

Compound A-1-4 was obtained in the same manner as in Preparation Example 1, except that [1,1'-biphenyl] -4-ylboronic acid was used instead of phenylboronic acid.

Production Example 5. Synthesis of Compound A-2-1

Except that 2,4-dichlorobenzofura [3,2-d] pyrimidine was used instead of 2,4-dichlorobenzo [4,5] thieno [3,4- d ] pyrimidine in Production Example 1 The compound A-2-1 was obtained.

Production Example 6. Synthesis of Compound A-2-2

Except that 2,4-dichlorobenzofuro [3,2- d ] pyrimidine was used instead of 2,4-dichlorobenzo [4,5] thieno [3,4- d ] pyrimidine in Preparation Example 1, Compound A-2-2 was obtained in the same manner except that 1-naphthylboronic acid was used in place of acid.

Production Example 7. Synthesis of Compound A-2-3

Except that 2,4-dichlorobenzofuro [3,2- d ] pyrimidine was used instead of 2,4-dichlorobenzo [4,5] thieno [3,4- d ] pyrimidine in Preparation Example 1, Compound A-2-3 was obtained in the same manner except that 2-naphthylboronic acid was used in place of acid.

Production Example 8. Synthesis of Compound A-2-4

Except that 2,4-dichlorobenzofuro [3,2- d ] pyrimidine was used instead of 2,4-dichlorobenzo [4,5] thieno [3,4- d ] pyrimidine in Preparation Example 1, Compound A-2-4 was obtained in the same manner except that [1,1'-biphenyl] -4-ylboronic acid was used in place of acid.

Production Example 9. Synthesis of Compound A-3-1

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of 2,4-dichloro-benzo [4,5] thieno [2,3- d] pyrimidine Was used, to obtain Compound A-3-1.

Production Example 10. Synthesis of Compound A-3-2

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of 2,4-dichloro-benzo [4,5] thieno [2,3- d] pyrimidine And 1-naphthylboronic acid was used in place of phenylboronic acid, Compound A-3-2 was obtained.

Preparation Example 11. Synthesis of Compound A-3-3

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of 2,4-dichloro-benzo [4,5] thieno [2,3- d] pyrimidine And 2-naphthylboronic acid was used instead of phenylboronic acid, Compound A-3-3 was obtained in the same manner.

Production Example 12. Synthesis of Compound A-3-4

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of 2,4-dichloro-benzo [4,5] thieno [2,3- d] pyrimidine And using [1,1'-biphenyl] -4-ylboronic acid in place of phenylboronic acid, Compound A-3-4 was obtained.

Production Example 13. Synthesis of Compound A-4-1

Except that 2,4-dichlorobenzofura [2,3- d ] pyrimidine was used instead of 2,4-dichlorobenzo [4,5] thieno [3,4- d ] pyrimidine in Production Example 1 The compound A-4-1 was obtained.

Production Example 14. Synthesis of Compound A-4-2

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of using [2,3- d] pyrimidine-2,4-dichlorobenzophenone Pew and phenylboronic Compound A-4-2 was obtained in the same manner except that 1-naphthylboronic acid was used in place of acid.

Preparation Example 15. Synthesis of Compound A-4-3

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of using [2,3- d] pyrimidine-2,4-dichlorobenzophenone Pew and phenylboronic Compound A-4-3 was obtained in the same manner except that 2-naphthylboronic acid was used instead of 2-naphthylboronic acid.

Production Example 16. Synthesis of Compound A-4-4

2,4-dichlorobenzophenone in Preparative Example 1 [4,5] thieno [3,4- d] pyrimidine instead of using [2,3- d] pyrimidine-2,4-dichlorobenzophenone Pew and phenylboronic Compound A-4-4 was obtained in the same manner except that [1,1'-biphenyl] -4-ylboronic acid was used in place of acid.

Production Example 17. Synthesis of Compound B- (a) -1

Compound A-1-1 (10 g, 0.034 mol), 5,6-dihydroindolo [2,3- b ] carbazole (8.6 g, 0.034 mol), potassium phosphate (14.3 g, 0.067 mol ) of N, N - dissolved in dimethylacetamide (N, N -Dimethylacetamide) 100ml was refluxed for 1 hour at 160 ℃ temperature conditions. When the reaction was completed, the temperature was cooled to room temperature, and the reaction mixture was poured into water to precipitate a solid, which was then filtered. The filtered solid was dissolved in chloroform and extracted. The extracted organic layer was dried over anhydrous magnesium sulfate and then recrystallized with ethyl acetate to obtain Compound B- (a) -1 (14.8 g, 85%).

Production Example 18. Synthesis of Compound B- (a) -2

Compound B- (a) -2 was obtained in the same manner as in Production Example 17, except that Compound A-2-2 was used instead of Compound A-1-1.

Production Example 19. Synthesis of Compound B- (b) -1

Dihydroindolo [3,2- b ] carbazole was used in place of 5,6-dihydroindolo [2,3- b ] Compound B- (b) -1 was obtained in the same manner except that Compound A-3-2 was used.

Production Example 20. Synthesis of Compound B- (b) -2

Dihydroindolo [3,2- b ] carbazole was used in place of 5,6-dihydroindolo [2,3- b ] Compound B- (b) -2 was obtained in the same manner except that Compound A-4-3 was used.

Production Example 21. Synthesis of Compound B- (c) -1

Dihydroindolo [2,3- c ] carbazole was used in place of 5,6-dihydroindolo [2,3- b ] Compound B- (c) -1 was obtained in the same manner except that Compound A-2-2 was used.

Production Example 22. Synthesis of Compound B- (c) -2

Dihydroindolo [2,3- c ] carbazole was used in place of 5,6-dihydroindolo [2,3- b ] Compound B- (c) -2 was obtained in the same manner except that Compound A-3-1 was used.

Production Example 23. Synthesis of Compound B- (d) -1

Dihydroindolo [3,2- a ] carbazole was used instead of 5,6-dihydroindolo [2,3- b ] Compound B- (d) -1 was obtained in the same manner except that Compound A-1-3 was used.

Production Example 24. Synthesis of Compound B- (d) -2

Dihydroindolo [3,2- a ] carbazole was used instead of 5,6-dihydroindolo [2,3- b ] Compound B- (d) -2 was obtained in the same manner except that Compound A-4-1 was used.

Synthesis Example 1 Synthesis of Compound 1

(10 g, 0.019 mol), 1-bromonaphthalene (4 g, 0.019 mol) and potassium phosphate (8.2 g, 0.038 mol) were placed in a round bottom flask and bis (trishurbutyl Phosphine) palladium (0.02 g, 0.2 mol%) was added, and the mixture was further refluxed for 4 hours. When the reaction was completed, the temperature was cooled to room temperature, and the precipitated solid was filtered. Thereafter, the filtered solid was dissolved in chloroform and extracted. The extracted organic layer was dried over anhydrous magnesium sulfate and then recrystallized with ethyl acetate to obtain 9.7 g (78%) of compound 1 (specific example 1-2). ([M + H] = 643)

3 is a mass spectrometry spectrum of Compound 1 prepared in Synthesis Example 1. FIG.

Synthesis Example 2. Synthesis of Compound 2

Compound 2 (Example 1-12) was obtained in the same manner as in Synthesis Example 1, except that 2-chloropyrimidine was used instead of 1-bromonaphthalene. ([M + H] = 595)

4 is a mass spectrometry spectrum of Compound 2 prepared in Synthesis Example 2. FIG.

Synthesis Example 3. Synthesis of Compound 3

Compound 3 (Example 1-17) was synthesized in the same manner as in Synthesis Example 1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used in place of 1-bromonaphthalene . ([M + H] < / RTI > = 748)

5 is a mass spectrometry spectrum of Compound 3 prepared in Synthesis Example 3. FIG.

Synthesis Example 4. Synthesis of Compound 4

Except that 1-bromobenzene was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (a) -2 was used in place of Compound B- (a) -1, Compound 4 Example 1-120) was obtained. ([M + H] = 628)

6 is a mass spectrometry spectrum of Compound 4 prepared in Synthesis Example 4. FIG.

Synthesis Example 5. Synthesis of Compound 5

Except that 9-bromophenanthrene was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (a) -2 was used in place of Compound B- (a) -1, Compound 5 ( Specific example 1-124) was obtained. ([M + H] = 727)

7 is a mass spectrometry spectrum of Compound 5 prepared in Synthesis Example 5. FIG.

Synthesis Example 6. Synthesis of Compound 6

Except that 2-chloro-4-phenylquinazoline was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (a) -2 was used in place of Compound B- (a) -1 Compound 6 (specific example 1-134) was obtained. ([M + H] = 755)

8 is a mass spectrometry spectrum of Compound 6 prepared in Synthesis Example 6. FIG.

Synthesis Example 7: Synthesis of Compound 7

Except that 3-chlorofluoranthene was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (b) -1 was used in place of Compound B- (a) -1. Specific example 2-74) was obtained. ([M + H] = 768)

9 is a mass spectrometry spectrum of Compound 7 prepared in Synthesis Example 7. FIG.

Synthesis Example 8. Synthesis of Compound 8

Except that 1-bromopyrene was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (b) -1 was used in place of Compound B- (a) -1. Specific example 2-76) was obtained. ([M + H] = 768)

10 is a mass spectrometry spectrum of Compound 8 prepared in Synthesis Example 8. FIG.

Synthesis Example 9 Synthesis of Compound 9

Except that 2-chloro-4- (naphthalen-2-yl) quinazoline was used instead of 1-bromonaphthalene and Compound B- (b) -1 was used in place of compound B- (a) -1 Was obtained in the same manner as in Example 9 (specific example 2-84). ([M + H] = 822)

11 is a mass spectrometry spectrum of the compound 9 prepared in Synthesis Example 9. FIG.

Synthesis Example 10. Synthesis of Compound 10

Except that 1-bromobenzene was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (b) -2 was used in place of Compound B- (a) -1. To give Compound 10 (Specific Example 2-188). ([M + H] = 628)

12 is a mass spectrometry spectrum of Compound 10 prepared in Synthesis Example 10.

Synthesis Example 11. Synthesis of Compound 11

Except that 2-bromotriphenylene was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (b) -2 was used in place of Compound B- (a) -1, Compound 11 (Specific Example 2-194) was obtained. ([M + H] = 778)

13 is a mass spectrometry spectrum of Compound 11 prepared in Synthesis Example 11.

Synthesis Example 12. Synthesis of Compound 12

Except that 4-chloropyrimidine was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (b) -2 was used in place of Compound B- (a) -1, Compound 12 Example 2-200) was obtained. ([M + H] = 629)

14 is a mass spectrometry spectrum of Compound 12 prepared in Synthesis Example 12. FIG.

Synthesis Example 13. Synthesis of Compound 13

Except that 2-bromonaphthalene was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (c) -1 was used in place of Compound B- (a) -1, Compound 13 Example 3-122) was obtained. ([M + H] = 678)

15 is a mass spectrometry spectrum of Compound 13 prepared in Synthesis Example 13.

Synthesis Example 14. Synthesis of Compound 14

Compound 14 (Example 3 (a)) was obtained in the same manner as in Synthesis Example 1, except that 3-chloropyridine was used instead of 1-bromonaphthalene and Compound B- (c) -1 was used in place of Compound B- -129). ([M + H] = 628)

16 is a mass spectrometry spectrum of the compound 14 prepared in Synthesis Example 14. FIG.

Synthesis Example 15. Synthesis of Compound 15

Except that 2-chloroquinazoline was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (c) -1 was used in place of Compound B- (a) -1, Compound 15 Example 3-133) was obtained. ([M + H] = 679)

17 is a mass spectrometry spectrum of the compound 15 prepared in Synthesis Example 15;

Synthesis Example 16. Synthesis of Compound 16

Except that 9-bromophenanthrene was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (c) -2 was used in place of Compound B- (a) -1, Compound 16 ( Example 3-56) was obtained. ([M + H] = 693)

18 is a mass spectrometry spectrum of Compound 16 prepared in Synthesis Example 16;

Synthesis Example 17. Synthesis of Compound 17

In the same manner as in the above Synthesis Example 1 except that 4-chloropyridine was used instead of 1-bromonaphthalene and Compound B- (c) -2 was used in place of Compound B- (a) -1, Compound 17 -62). ([M + H] = 595)

19 is a mass spectrometry spectrum of Compound 17 prepared in Synthesis Example 17;

Synthesis Example 18. Synthesis of Compound 18

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used in place of 1-bromonaphthalene in the above Synthesis Example 1 and Compound B- (c) -2 Was used to obtain Compound 18 (Specific Example 3-68). ([M + H] = 749)

20 is a mass spectrometry spectrum of Compound 18 prepared in Synthesis Example 18.

Synthesis Example 19. Synthesis of Compound 19

Except that 2-bromonaphthalene was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (d) -1 was used in place of Compound B- (a) -1, Compound 19 Example 4-37) was obtained. ([M + H] = 693)

21 is a mass spectrometry spectrum of Compound 19 prepared in Synthesis Example 19;

Synthesis Example 20: Synthesis of Compound 20

Except that 4-bromo-1,1'-biphenyl was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (d) -1 was used in place of Compound B- (a) -1. To obtain Compound 20 (Specific Example 4-38). ([M + H] = 719)

22 is a mass spectrometry spectrum of Compound 20 prepared in Synthesis Example 20;

Synthesis Example 21. Synthesis of Compound 21

Except that 2-chloro-4-phenylquinazoline was used instead of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (d) -1 was used in place of Compound B- (a) -1 Compound 21 (specific example 4-49) was obtained. ([M + H] = 772)

23 is a mass spectrometry spectrum of the compound 21 prepared in Synthesis Example 21;

Synthesis Example 22. Synthesis of Compound 22

Except that 4-bromo-1,1'-biphenyl was used in place of 1-bromonaphthalene in Synthesis Example 1 and Compound B- (d) -2 was used in place of Compound B- (a) -1. To obtain Compound 22 (Specific Example 4-157). ([M + H] = 654)

24 is a mass spectrometry spectrum of the compound 22 prepared in Synthesis Example 22;

Synthesis Example 23. Synthesis of Compound 23

In the same manner as in the above Synthesis Example 1 except that 2-chloropyridine was used instead of 1-bromonaphthalene and Compound B- (d) -2 was used in place of Compound B- (a) -1, Compound 23 4-162). ([M + H] < + > = 578)

25 is a mass spectrometry spectrum of the compound 23 prepared in Synthesis Example 23. FIG.

Synthesis Example 24. Synthesis of Compound 24

Compound 24 (a) was obtained in the same manner as in Synthesis Example 1, except that 2-chloropyrimidine was used instead of 1-bromonaphthalene and Compound B- (d) -2 was used instead of Compound B- Example 4-165) was obtained. ([M + H] < / RTI > = 579)

26 is a mass spectrometry spectrum of the compound 24 prepared in Synthesis Example 24;

≪ Fabrication of organic light emitting device &

Comparative Example 1

A glass substrate coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersant and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. 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.

After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to 1 × 10 ^-6 torr, DNTPD (700 Å), hole transporting and electron blocking layer (NPB 300 Å) , CBP (95 wt%), which is generally used as a red phosphorescent host material, is co-deposited (300 Å) as Dp-6 (5 wt%) as a dopant and Alq ₃ (350 ANGSTROM), LiF (5 ANGSTROM) and Al (1,000 ANGSTROM) as cathodes. In the above process, 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 to 7 Å / sec.

Comparative Examples 2 to 8

An organic light emitting device was fabricated in the same manner as in Comparative Example 1 except that the following compounds A to G were used instead of CBP, respectively.

Examples 1 to 24

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compounds 1 to 24 prepared in Synthesis Examples 1 to 24 were used in place of the CBP, respectively.

The driving voltage, the current efficiency, and the lifetime were measured by applying a current of 10 mA / cm ² to the organic light-emitting device manufactured in the above Comparative Examples 1 to 8 and Examples 1 to 24. The T95 was 95% Respectively. The results are shown in Table 1 below.

Host material Driving voltage
(V) Current efficiency
(cd / A) life span
(T95% @ 10 mA / cm ² ) Comparative Example 1 CBP 7.55 13.07 58 Comparative Example 2 Compound A 4.82 18.12 78 Comparative Example 3 Compound B 4.74 18.42 76 Comparative Example 4 Compound C 4.92 17.25 81 Comparative Example 5 Compound D 4.98 17.03 88 Comparative Example 6 Compound E 5.02 16.22 90 Comparative Example 7 Compound F 5.11 16.10 95 Comparative Example 8 Compound G 5.86 15.96 99 Example 1 Compound 1 4.27 22.87 189 Example 2 Compound 2 4.32 23.59 178 Example 3 Compound 3 4.15 24.00 170 Example 4 Compound 4 4.26 22.05 195 Example 5 Compound 5 4.16 23.77 181 Example 6 Compound 6 4.40 20.99 198 Example 7 Compound 7 4.24 24.53 156 Example 8 Compound 8 4.50 25.44 120 Example 9 Compound 9 4.10 19.22 201 Example 10 Compound 10 4.34 20.13 179 Example 11 Compound 11 4.12 22.10 165 Example 12 Compound 12 4.38 24.73 133 Example 13 Compound 13 4.13 22.15 176 Example 14 Compound 14 4.11 22.84 170 Example 15 Compound 15 4.16 23.00 162 Example 16 Compound 16 4.23 25.57 124 Example 17 Compound 17 4.28 25.88 119 Example 18 Compound 18 4.21 24.99 135 Example 19 Compound 19 3.87 27.90 245 Example 20 Compound 20 4.01 26.31 203 Example 21 Compound 21 4.11 27.10 184 Example 22 Compound 22 4.08 25.11 188 Example 23 Compound 23 4.13 26.20 172 Example 24 Compound 24 4.10 26.04 177

In Table 1, Comparative Example 1 is an organic light emitting device using CBP used as a conventional light emitting layer host, and Comparative Examples 2 and 3 are compounds in which R 1 and R 2 in Formula 1 are bonded to Formula 2 And is an organic light emitting element used as a host of a light emitting layer.

Comparative Examples 4 and 5 are organic light emitting devices using a compound in which a carbazole is bonded at the Y1 position of the present invention. In Comparative Examples 6 and 8, an aryl group substituted for indolocarbazole at the Y3 position of the present formula And is an organic light-emitting device using a bonded compound as a host of the light emitting layer.

In the organic luminescent devices of Examples 1 to 24, a compound in which indolocarbazole, that is, R 2 and R 3 or R 3 and R 4 of Formula 1 are bonded to Y 2 or Y 3 in Formula 1, Is an organic light emitting device used.

The organic light emitting devices of Examples 1 to 24 using the heterocyclic compounds of the present invention have a stable electron transporting structure and a small steric hindrance, Low efficiency, high efficiency, and long life.

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 (10)

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

In Formula 1,
X1 is O or S,
L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Y1 and Y3 are N, Y2 is CR13, Y4 is CR14, Y2 and Y4 are N, Y1 is CR14, Y3 is CR13,
R13 is a group which combines with L1,
R2 and R3, or R3 and R4 are groups which combine with * in the following formula (2)
R 2, R 3, R 4, R 5 and R 6 are the same or different and are each independently hydrogen; 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,
n is 1 or 2,
when n is 2, two L1s are the same or different from each other,
(2)

In Formula 2,
* Is a moiety bonded with R2 and R3, or R3 and R4 in the above formula (1)
Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R15 to R18 are the same or different from each other, and each independently and independently hydrogen; 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. The heterocyclic compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (1-1) to (1-4)
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 through 1-4,
X1, L1, n, Y1 to Y4, R1, R2 and R4 to R12 are the same as in the above formula (1)
The definition of Ar1 and R15 to R18 is the same as that of the above formula (2). The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-5 to 1-12:
[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]

[Formula 1-12]

In the above formulas (1-5) to (1-12)
X 1, L 1, n, R 1, R 2, and R 4 to R 12 are the same as those in Formula 1,
Ar1 and R15 to R18 are as defined in the above formula (2)
R14 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. 2. The heterocyclic compound of claim 1, wherein R < 14 > is an aryl group. 2. The compound according to claim 1, wherein Ar1 is an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group. 2. The heterocyclic compound according to claim 1, wherein the formula 1 is selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises the heterocyclic compound of any one of claims 1 to 6, device. [Claim 7] The organic light emitting device according to claim 7, wherein the organic material layer includes a hole transporting layer, and the hole transporting layer comprises the heterocyclic compound. [8] The organic EL device according to claim 7, wherein the organic material layer comprises an electron transporting layer, an electron injecting layer, or a layer which simultaneously transports electrons and injects the electron transporting layer, the electron injecting layer, And an organic light emitting layer. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.

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