KR20180131963A - 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 having the same. According to one embodiment of the present disclosure, provided is the organic light emitting device which comprises: a first electrode; a second electrode facing the first electrode; and at least one organic material layer provided between the first electrode and the second electrode. At least one layer of the organic material layers includes the heterocyclic compound represented by the chemical formula 1.

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. 10-2017-0068460 filed on June 1, 2017, 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,

At least one of R 1 to R 3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group, and the rest is hydrogen,

At least one of R 4 to R 6 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group, and the rest is hydrogen,

When R 2 is an unsubstituted phenyl group, R 5 is a substituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group,

When R5 is an unsubstituted phenyl group, R2 is a substituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic 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 compound according to one embodiment of the present disclosure 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.
Figure 3 is a mass spectrometry (MS) spectrum of Compound 5 herein.
4 is a mass spectrometry (MS) spectrum of Compound 7 of the present specification.
5 is a mass spectrometry (MS) spectrum of Compound 13 of the present specification.
Figure 6 is a mass spectrometry (MS) spectrum of Compound 17 herein.
7 is a mass spectrometry (MS) spectrum of Compound 30 herein.
8 is a mass spectrometry (MS) spectrum of Compound 57 of the present specification.
Figure 9 is a mass spectrometry (MS) spectrum of Compound 59 herein.
10 is a mass spectrometry (MS) spectrum of compound 18 herein.
11 is a mass spectrometry (MS) spectrum of Compound 27 of the present specification.
12 is a mass spectrometry (MS) spectrum of Compound 33 of the present specification.
13 is a mass spectrometry (MS) spectrum of compound 38 herein.
14 is a mass spectrometry (MS) spectrum of Compound 41 of the present specification.
15 is a mass spectrometry (MS) spectrum of compound 47 of the present specification.
16 is a mass spectrometry (MS) spectrum of Compound 53 of the present 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 substituted with anthracene at positions 2 and 8 of dibenzofurane. Therefore, electron transfer is facilitated as the conjugation length increases, Also, since the substituents are bonded to the R1 to R6 positions of the anthracene, the interaction of the anthracene and the substituents located at R1 to R6 is reduced, and the interaction of the electrons is reduced to maintain the independent characteristics of the substituents. The voltage of the organic light emitting device is low, the lifetime characteristics are improved, and the efficiency can be improved.

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; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are 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, , But is not limited thereto.

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 isoquinolyl 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, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but the present invention is not limited thereto.

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.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the above Formulas 1-1 to 1-3, the definitions of R 1 to R 6 are the same as those defined in Formula 1 above.

According to one embodiment of the present disclosure, at least one of R 1 to R 3 is a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or an alkyl group, or a polycyclic heteroaryl group substituted or unsubstituted with an aryl group, and the remainder is hydrogen.

According to one embodiment of the present invention, at least one of R 1 to R 3 is a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrenyl group; A fluoranthenyl group; An alkyl group, or a fluorenyl group substituted or unsubstituted with an aryl group; A spirobifluorenyl group; An alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group; A dibenzothiophene group; Or dibenzofuranyl group, and the remainder is hydrogen.

According to one embodiment of the present invention, at least one of R 1 to R 3 is substituted with deuterium, methyl, t-butyl, trimethylsilyl, phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophene Or an unsubstituted phenyl group; A biphenyl group substituted or unsubstituted with a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; A phenanthrenyl group; A fluoranthenyl group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A spirobifluorenyl group; A carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A dibenzothiophene group; Or dibenzofuranyl group, and the remainder is hydrogen.

According to one embodiment of the present disclosure, at least one of R4 to R6 is a phenyl group substituted or unsubstituted with deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or an alkyl group, or a polycyclic heteroaryl group substituted or unsubstituted with an aryl group, and the remainder is hydrogen.

According to one embodiment of the present invention, at least one of R 4 to R 6 is a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrenyl group; A fluoranthenyl group; An alkyl group, or a fluorenyl group substituted or unsubstituted with an aryl group; A spirobifluorenyl group; An alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group; A dibenzothiophene group; Or dibenzofuranyl group, and the remainder is hydrogen.

According to one embodiment of the present invention, at least one of R 4 to R 6 is substituted with deuterium, methyl, t-butyl, trimethylsilyl, phenyl, biphenyl, naphthyl, dibenzofuranyl or dibenzothiophene Or an unsubstituted phenyl group; A biphenyl group substituted or unsubstituted with a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; A phenanthrenyl group; A fluoranthenyl group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A spirobifluorenyl group; A carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A dibenzothiophene group; Or dibenzofuranyl group, and the remainder is hydrogen.

According to one embodiment of the present invention, R 2 and R 5 are the same or different and are each independently a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or a polycyclic heteroaryl group substituted or unsubstituted with an alkyl group or an aryl group, and when R5 is an unsubstituted phenyl group, R2 is a phenyl group substituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or a polycyclic heteroaryl group substituted or unsubstituted with an alkyl group or an aryl group, and when R 2 is an unsubstituted phenyl group, R 5 is a phenyl group substituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or an alkyl group, or a polycyclic heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, R 2 and R 5 are the same or different and are each independently a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrenyl group; A fluoranthenyl group; An alkyl group, or a fluorenyl group substituted or unsubstituted with an aryl group; A spirobifluorenyl group; An alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group; A dibenzothiophene group; Or a dibenzofuranyl group, and when R5 is an unsubstituted phenyl group, R2 is a phenyl group substituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrenyl group; A fluoranthenyl group; An alkyl group, or a fluorenyl group substituted or unsubstituted with an aryl group; A spirobifluorenyl group; An alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group; A dibenzothiophene group; Or a dibenzofuranyl group, and when R 2 is an unsubstituted phenyl group, R 5 is a phenyl group substituted with a deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrenyl group; A fluoranthenyl group; An alkyl group, or a fluorenyl group substituted or unsubstituted with an aryl group; A spirobifluorenyl group; An alkyl group, or a carbazolyl group substituted or unsubstituted with an aryl group; A dibenzothiophene group; Or a dibenzofuranyl group.

According to one embodiment of the present invention, R2 and R5 are the same or different from each other, and each independently represents a group selected from the group consisting of deuterium, methyl, t-butyl, trimethylsilyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, A phenyl group substituted or unsubstituted with a dibenzothiophene group; A biphenyl group substituted or unsubstituted with a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; A phenanthrenyl group; A fluoranthenyl group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A spirobifluorenyl group; A carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A dibenzothiophene group; Or a dibenzofuranyl group, and when R5 is an unsubstituted phenyl group, R 2 is a group selected from the group consisting of deuterium, methyl, t-butyl, trimethylsilyl, phenyl, biphenyl, dibenzofurancyl, A phenyl group substituted with a group; A biphenyl group substituted or unsubstituted with a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; A phenanthrenyl group; A fluoranthenyl group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A spirobifluorenyl group; A carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A dibenzothiophene group; Or a dibenzofuranyl group and R 2 is an unsubstituted phenyl group, R 5 is a group selected from the group consisting of deuterium, methyl, t-butyl, trimethylsilyl, phenyl, biphenyl, dibenzofuranyl, A phenyl group substituted with a group; A biphenyl group substituted or unsubstituted with a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; A phenanthrenyl group; A fluoranthenyl group; A methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group; A spirobifluorenyl group; A carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A dibenzothiophene group; Or a dibenzofuranyl group.

According to one embodiment of the present invention, R 2 and R 5 may be the same or different and each independently selected from Substituents 1-1 to 1-71 shown below, but are not limited thereto.

According to one embodiment of the present invention, R 1, R 3, R 4, and R 6 are the same or different and are each independently a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, or an aryl group; A biphenyl group; A polycyclic aryl group; Or a monocyclic or polycyclic heteroaryl group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present invention, R 1, R 3, R 4, and R 6 are a phenyl group substituted or unsubstituted with a deuterium, an alkyl group, a silyl group, or an aryl group; A biphenyl group; Naphthyl group; A fluorenyl group substituted with an alkyl group; A carbazolyl group substituted with an alkyl group; A dibenzothiophene group; Or a dibenzofuranyl group.

According to one embodiment of the present invention, R 1, R 3, R 4 and R 6 are a phenyl group substituted or unsubstituted with a deuterium, a methyl group, a t-butyl group, a trimethylsilyl group or a phenyl group; A biphenyl group; Naphthyl group; A fluorenyl group substituted with a methyl group; A methyl group, or a carbazolyl group substituted with an ethyl group; A dibenzothiophene group; Or a dibenzofuranyl group.

According to one embodiment of the present invention, R 1, R 3, R 4, and R 6 are the same or different and independently selected from Substituents 2-1 to 2-35, but are not limited thereto.

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 compound described above.

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 more organic layers.

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

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

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

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

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

According to an embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes at least one host and at least one dopant, and the at least one host includes a heterocyclic compound represented by the formula do.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer contains the heterocyclic compound represented by the formula (1) as a host of the light emitting layer, and another organic compound, metal or metal compound is used as a dopant .

According to one embodiment of the present invention, the light emitting layer comprises a heterocyclic compound represented by Formula 1 as a host of the light emitting layer, and includes an organic compound, a metal or a metal compound as a dopant in the light emitting layer, 99 to 99: 1.

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.

When the organic light emitting device includes an additional light emitting layer other than the light emitting layer including the compound represented by Formula 1, the light emitting layer may further include a hole transporting layer and a hole transporting layer from the electron transporting layer. A material capable of emitting light in a visible light region by transporting and receiving electrons, respectively, and the light emitting layer is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; 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 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 layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material 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.

According to one embodiment of the present invention, Formula 1 can be prepared by the following Formula 1 and Formula 2, and in Formula 1, when the substituents bonded to both sides of the dibenzofuran core of Formula 1 are the same, The general formula 2 corresponds to the case where the substituents bonded to both sides of the dibenzofuran core of the formula 1 are different from each other, but the production of the heterocyclic compound represented by the formula 1 is not limited thereto.

[Formula 1]

[Formula 2]

Synthesis Example 1. Synthesis of Intermediate 1

A solution of 2,8-dibromodibenzofuran (20 g, 61.35 mmol), bis (pinacol) diboron (38.95 g, 153.37 mmol) and potassium acetate (30.1 g, 306.7 mmol) mL and refluxed. Bis (dibenzylideneacetone naphthyridin-acetone) palladium (0) (Pd (dba) 2; 705 mg, 1.22 mmol) and tricyclohexylphosphine _{(PCy 3; 668 mg, 2.45} mmol) the mixture was stirred for 30 minutes, dissolved in dioxane, 30 mL Respectively. After refluxing for 24 hours, it was cooled, filtered, and then 500 mL of water was added. The mixture was extracted three times with 300 mL of toluene, and the organic layer was concentrated under reduced pressure. Column chromatography afforded Intermediate 1 (21.9 g, 52.2 mmol).

Production Example 1. Preparation of Compound 5

Intermediate 1 (8.52 g, 20.27 mmol) and 9- (1-naphthyl) -10-bromoanthracene (17.88 g, 46.63 mmol) were dissolved in 500 mL of dioxane. Calcium carbonate (14 g, 101.4 mmol) was dissolved in 100 mL of pure water and bis (tri-t-butylphosphine) palladium (0) (BTP; 51.8 mg, 0.101 mmol) was added. Refluxed for 2 hours, cooled and filtered. The filtered solid was recrystallized from toluene to give compound 5 (12.1 g, 15.64 mmol).

Fig. 3 is a mass spectrometry (MS) spectrum of the above compound 5. Fig.

Production Example 2. Preparation of Compound 7

Intermediate 1 (7 g, 16.66 mmol) and 9- (1-naphthyl) -10-bromoanthracene were used in place of Intermediate 1 (8.52 g, 20.27 mmol) and 9- 4-biphenyl) -10-bromoanthracene (15 g, 36.65 mmol) was used to give compound 7 (10.1 g, 12.28 mmol).

Fig. 4 is a mass spectrometry (MS) spectrum of the above compound 7. Fig.

Production Example 3. Preparation of Compound 13

Intermediate 1 (10.44 g, 24.85 mmol) and 9- (1-naphthyl) -10-bromoanthracene were used in place of Intermediate 1 (8.52 g, 20.27 mmol) and 9- 2-naphthyl) -10-bromoanthracene (20 g, 52.18 mmol) was used to obtain Compound 13 (15.2 g, 19.67 mmol).

5 is a mass spectrometry (MS) spectrum of the compound 13.

Production Example 4. Preparation of Compound 17

Intermediate 1 (7 g, 16.66 mmol) and 9- (1-naphthyl) -10-bromoanthracene were used in place of Intermediate 1 (8.52 g, 20.27 mmol) and 9- Dibenzofuranyl) -10-bromoanthracene (15 g, 35.44 mmol) was used to obtain Compound 17 (11.0 g, 12.89 mmol).

FIG. 6 is a mass spectrometry (MS) spectrum of the compound 17.

Production Example 5. Preparation of Compound 30

Compound 30

Intermediate 1 (11.83 g, 28.16 mmol) and 9-bromoaniline were used in place of Intermediate 1 (8.52 g, 20.27 mmol) and 9- (1-naphthyl) (15.58 g, 22.81 mmol) was obtained in the same manner as in Example 1, except that 10-phen-10- (phenyl-d5) anthracene (20 g, 59.13 mmol) was used.

7 is a mass spectrometry (MS) spectrum of the compound 30.

Production Example 6. Preparation of Compound 57

Compound 57

(8.10 g, 19.3 mmol) instead of Intermediate 1 (8.52 g, 20.27 mmol) and 9- (1-naphthyl) -10-bromoanthracene (17.88 g, 46.63 mmol) (13.8 g, 13.90 mmol), except that 10-bromo-1,8-dimesitylanthracene (20.0 g, 40.53 mmol) .

8 is a mass spectrometry (MS) spectrum of the compound 57. FIG.

Preparation 7. Preparation of Compound 59

  Compound 59

(7.85 g, 18.69 mmol) instead of Intermediate 1 (8.52 g, 20.27 mmol) and 9- (1-naphthyl) -10-bromoanthracene (17.88 g, 46.63 mmol) (16.57 g, 14.21 mmol) was obtained in the same manner as in Example 1, except for using 1,6-di (naphthalen-1-yl) anthracene (20.0 g, 39.26 mmol).

9 is a mass spectrometry (MS) spectrum of the compound 59. FIG.

Synthesis Example 2. Synthesis of Intermediates 2 and 3

A solution of 8-bromodibenzofuran-2-ol (40 g, 152.04 mmol), bis (pinacol) diboron (46.33 g, 182.44 mmol) and potassium acetate (37.3 g, 380.1 mmol) 800 mL, and refluxed. Bis (dibenzylideneacetone naphthyridin-acetone) palladium (0) (Pd (dba) 2; 874 mg, 1.52 mmol) and tricyclohexylphosphine _{(PCy 3; 853 mg, 3.04} mmol) the mixture was stirred for 30 minutes, dissolved in dioxane, 30 mL Respectively. After refluxing for 24 hours, it was cooled, filtered, and then 700 mL of water was added. The mixture was extracted three times with 600 mL of toluene and the organic layer was concentrated under reduced pressure. Column chromatography afforded Intermediate 2 (41.0 g, 132.3 mmol).

Intermediate 2 (30.72 g, 99.03 mmol) and 9-bromo-10-phenylanthracene (30 g, 90.03 mmol) were dissolved in dioxane (500 mL). Calcium carbonate (31.1 g, 225.07 mmol) was dissolved in 100 mL of pure water, and bis (trimethylbutylphosphine) palladium (0) (BTP: 92 mg, 0.18 mmol) was added. Refluxed for 2 hours, cooled and filtered. The filtered solid was recrystallized from toluene to give intermediate 3 (32.22 g, 73.82 mmol).

Synthesis Example 3. Synthesis of Intermediates 4 and 5

Intermediate 3 (25 g, 57.27 mmol) was added to 600 mL of acetonitrile, and calcium carbonate (19.8 g, 143 mmol) was dissolved in 150 mL of pure water while stirring. The reaction mixture was cooled to 0 C and nonafluoropentane-1-sulfonyl fluoride (24.20 g, 68.73 mmol) was slowly added dropwise. After stirring for 4 hours, 400 mL of toluene was added, the organic layer was separated, and the water layer was washed twice with 300 mL of toluene. The organic layer was collected, concentrated under reduced pressure, and recrystallized with hexane to obtain Intermediate 4 (40.5 g, 52.69 mmol).

Except that Intermediate 4 (40 g, 52.04 mmol) was used instead of 8-bromodibenzofuran-2-ol in the synthesis of Intermediate 2 in Synthesis Example 2 to obtain Intermediate 5 (22.18 g, 40.59 mmol).

Synthesis Example 4. Synthesis of Intermediate 6

Intermediate 2 was prepared in the same manner as Intermediate 2 except that (4- (10-phenylanthracen-9-yl) phenyl) trimethylsilane (35.0 g, 86.33 mmol) was used in place of 9-bromo- 5, intermediate 6 was obtained (22.97 g, 37.12 mmol).

Synthesis Example 5. Synthesis of Intermediate 7

The synthesis method of Intermediates 2 to 5 was repeated except that 10-bromo-1,8-diphenylanthracene (36.0 g, 87.95 mmol) was used in place of 9-bromo- The same synthesis was carried out to obtain Intermediate 7 (21.90 g, 35.18 mmol).

Preparation 8. Preparation of Compound 18

Intermediate 5 Compound 18

(19.63 g, 35.92 mmol) was used in the synthesis of Intermediate 3 instead of Intermediate 2 (30.72 g, 99.03 mmol) and 9-bromo-10-phenylanthracene (30 g, (21.91 g, 27.43 mmol) was obtained in the same manner as in Example 1, except that -10- (4-phenylnaphthalen-1-yl) anthracene (15.0 g, 32.65 mmol) was used.

10 is a mass spectrometry (MS) spectrum of the compound 18.

Production Example 9. Preparation of Compound 27

  Intermediate 6 Compound 27

Intermediate 3 (20.4 g, 33.00 mmol) was used in the synthesis of Intermediate 3 instead of Intermediate 2 (30.72 g, 99.03 mmol) and 9-bromo-10-phenylanthracene (30 g, -10- (phenanthrene-9-yl) anthracene (13.0 g, 30.00 mmol) was used to obtain the compound 27 (18.5 g, 21.90 mmol).

11 is a mass spectrometry (MS) spectrum of the compound 27. FIG.

Production Example 10. Preparation of Compound 33

Intermediate 5 Compound 33

Intermediate 3 was prepared in the same manner as Intermediate 3 except that Intermediate 5 (17.70 g, 32.39 mmol) was used instead of Intermediate 2 (30.72 g, 99.03 mmol) and 10-bromo -1,2-di (naphthalen-1-yl) anthracene (15.0 g, 29.44 mmol) was used to obtain Compound 33 (17.25 g, 20.32 mmol).

12 is a mass spectrometry (MS) spectrum of the compound 33. FIG.

Production Example 11. Preparation of Compound 38

Intermediate 7 Compound 38

Intermediate 3 was prepared in the same manner as Intermediate 3 except that Intermediate 7 (26.5 g, 42.56 mmol) was used instead of Intermediate 2 (30.72 g, 99.03 mmol) and 9-bromo-10-phenylanthracene (30 g, (Dibenzothiophen-2-yl) anthracene (17.0 g, 38.69 mmol) was used to obtain the compound 38 (22.17 g, 25.92 mmol).

13 is a mass spectrometry (MS) spectrum of the compound 38. FIG.

Production Example 12. Preparation of Compound 41

Intermediate 5 Compound 41

Bromo-10-phenylanthracene (30 g, 90.03 mmol) instead of Intermediate 2 (30.72 g, 99.03 mmol) in the synthesis of Intermediate 3 above, Intermediate 5 (18.36 g, 33.59 mmol) (Dibenzofuran-2-yl) anthracene (18.0 g, 30.53 mmol) was used in place of 1,8-di (dibenzofuran-2-yl) anthracene. 21.48 g (23.20 mmol) of the compound 41 was obtained.

14 is a mass spectrometry (MS) spectrum of the compound 41. FIG.

Production Example 13. Preparation of Compound 47

Intermediate 7 Compound 47

Intermediate 3 was prepared in the same manner as Intermediate 3 except that Intermediate 7 (22.27 g, 35.77 mmol) was used instead of Intermediate 2 (30.72 g, 99.03 mmol) and 9-bromo-10-phenylanthracene (30 g, (11.3 g, 32.52 mmol) was used in place of 10- (phenyl-d5) anthracene (19.37 g, 25.69 mmol).

15 is a mass spectrometry (MS) spectrum of the compound 47. FIG.

Production Example 14. Preparation of Compound 53

Intermediate 7 Compound 53

Intermediate 3 was prepared in the same manner as Intermediate 3 except that Intermediate 7 (21.51 g, 34.55 mmol) was used instead of Intermediate 2 (30.72 g, 99.03 mmol) and 10-bromo -1,2-di (naphthalen-1-yl) anthracene (16.0 g, 31.41 mmol) was used to obtain the compound 53 (20.63 g, 22.30 mmol).

16 is a mass spectrometry (MS) spectrum of the compound 53. FIG.

Fabrication of organic light emitting device

Comparative Example 1

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent 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.

Hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on the ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

(HAT)

(HAT)

(4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400A) as a hole transporting material was vacuum deposited on the hole injection layer to form a hole transport layer .

(NPB)

(NPB)

Next, 9- (naphthalene-1-yl) -10- (naphthalen-2-yl) anthracene (BH1) was vacuum deposited on the hole transport layer to a thickness of 300 Å as a light emitting layer host to form a light emitting layer.

(BH1)

(BH1)

4% by weight of Compound N4, N9-bis (dibenzofuran-4-yl) -N4 and N9-di-m-tolylpyrene-4,9-diamine (BD1) was used as a blue light emitting dopant, Respectively.

(BD1)

(BD1)

Alq ₃ (aluminum tris (8-hydroxyquinoline)) of the following formula was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

(Alq₃)

(Alq ₃₎

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 Å on the electron injection and transport layer sequentially to form a cathode.

Was maintained at a vapor deposition rate of 0.4 to 0.7 Å / sec for organic material in the above process, the lithium fluoride of the cathode-fluoro is 0.3 Å / sec, the aluminum is 2 Å / sec was maintained at a deposition rate of, During the deposition, a vacuum 2Х10 ^-7 ~ 5 × 10 ^-8 torr.

Comparative Example 2

(10-phenylanthracene-9-yl) di (naphthalen-2-yl) anthracene (BH1) was used instead of the 9- (BH2) was used instead of benzofuran (BH2).

(BH2)

(BH2)

Examples 1 to 14

The compound prepared in Preparation Examples 1 to 14 was used instead of the 9- (naphthalen-1-yl) -10- (naphthalen-2-yl) anthracene (BH1) as a light emitting layer host in the above- An organic light emitting device was fabricated in the same manner as in Comparative Example 1,

The organic light emitting devices of Comparative Examples 1 and 2 and Examples 1 to 14 were subjected to measurement of voltage, efficiency, color coordinates and lifetime at a current density of 20 mA / cm ² . At this time, T97 means the time required for the luminance to be reduced to 97% when the initial luminance at a light density of 20 mA / cm ² is taken as 100%.

Device example Host material The driving voltage (V) The luminous efficiency (Cd / A) Color coordinate CIE_y Lifetime T97% (hours) Comparative Example 1 BH1 5.29 6.75 0.046 130 Comparative Example 2 BH2 5.20 6.53 0.047 82 Example 1 Compound 5 5.17 6.89 0.044 152 Example 2 Compound 7 5.10 6.80 0.045 167 Example 3 Compound 13 5.20 6.85 0.046 140 Example 4 Compound 17 5.05 6.87 0.047 149 Example 5 Compound 18 5.20 6.88 0.046 137 Example 6 Compound 27 5.12 7.02 0.044 128 Example 7 Compound 30 5.11 6.73 0.047 147 Example 8 Compound 33 5.08 6.83 0.049 156 Example 9 Compound 38 5.01 6.71 0.048 112 Example 10 Compound 41 4.97 6.81 0.049 153 Example 11 Compound 47 5.07 6.86 0.048 146 Example 12 Compound 53 5.13 6.72 0.050 139 Example 13 Compound 57 5.06 6.87 0.049 140 Example 14 Compound 59 5.11 6.86 0.049 141

In Table 1, the heterocyclic compound of the present invention has an anthracene substitution at positions 2 and 8 of dibenzofurane. Therefore, the electron transfer is easy as the conjugation length increases, and the anthracene R1 to R6 positions The substituents are bonded to each other, and the interaction between the anthracene and the substituents located at R 1 to R 6 is minimized by the conjugation of the electrons, so that the substituents can maintain their independent characteristics. Therefore, the organic light- , The lifetime characteristics were improved, and the efficiency was improved. In particular, Comparative Example 2 in which a compound in which the R2 and R5 positions of anthracene are unsubstituted phenyl groups is applied to an organic light emitting device has a shorter conjugation length than the compound of Formula 1, The efficiency and lifetime characteristics of the organic light emitting diode are lower than those of the organic light emitting diode.

Therefore, when the heterocyclic compound of Formula 1 was applied to the host of the blue light emitting layer of the organic light emitting device, the device exhibited excellent characteristics of low voltage, 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,
At least one of R 1 to R 3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group, and the rest is hydrogen,
At least one of R 4 to R 6 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group, and the rest is hydrogen,
When R 2 is an unsubstituted phenyl group, R 5 is a substituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group,
When R5 is an unsubstituted phenyl group, R2 is a substituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted polycyclic aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by the following formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the above Formulas 1-1 to 1-3, the definitions of R 1 to R 6 are the same as those defined in Formula 1 above. [4] The compound according to claim 1, wherein at least one of R1 to R3 is a phenyl group substituted or unsubstituted with deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or an alkyl group, or a polycyclic heteroaryl group substituted or unsubstituted with an aryl group, and the remainder is hydrogen. [4] The compound according to claim 1, wherein at least one of R4 to R6 is a phenyl group substituted or unsubstituted with deuterium, an alkyl group, a silyl group, an aryl group, or a heteroaryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group; An alkyl group, or a polycyclic aryl group substituted or unsubstituted with an aryl group; Or an alkyl group, or a polycyclic heteroaryl group substituted or unsubstituted with an aryl group, and the remainder is hydrogen. The heterocyclic compound according to claim 1, wherein R 2 and R 5 are the same or different from each other and each independently selected from Substituent 1-1 to 1-71:

The heterocyclic compound according to claim 1, wherein R1, R3, R4 and R6 are the same or different from each other and each independently selected from Substituents 2-1 to 2-35:

The compound according to claim 1, wherein the compound of 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 7, device. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer.

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