WO2019107934A1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The specification relates to a compound of chemical formula 1 and an organic light emitting device comprising the same.

Description

Compounds and organic light emitting devices containing them

This application is a continuation-in-part of Korean Patent Application No. 10-2017-0160604 filed on November 28, 2017, and Korean Patent Application No. 10-2018-0147622 filed on November 26, 2018 The contents of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

In order to commercialize an organic light emitting device, it is necessary to improve the efficiency of a light emitting material. For this purpose, studies on phosphorescent and retarding fluorescent materials have been actively conducted. However, in the case of the above-mentioned phosphorescent material, there is a problem that the cost of the metal complex required to realize phosphorescence is high and the lifetime is short, although high efficiency can be achieved.

Recently, the introduction of the concept of thermally activated delayed fluorescence (TADF) in the case of the retarded fluorescent material has revealed a highly efficient green fluorescent material having a high external quantum efficiency as well as a fluorescent material. The concept of thermally activated delayed fluorescence (TADF) is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission. Generally, the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.

The present invention provides a compound and an organic light emitting device comprising the same.

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

[Chemical Formula 1]

In Formula 1,

A1 to A5 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,

R 1 to R 4 and R 11 to R 14 are the same or different and each independently represents hydrogen or a substituted or unsubstituted alkyl group,

R5 to R8 and R15 to R18 are the same or different and each independently represents hydrogen, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

n is 1 or 2,

When n is 2, the structures in the plurality of parentheses are equal to or different from each other,

When n is 1, and any one of A1 to A5 is a heteroaryl group, the remainder is hydrogen.

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 includes the compound described above.

The organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.

1 shows an organic light emitting device according to an embodiment of the present invention.

<Description of Symbols>

10: Organic light emitting device

20: substrate

30: first electrode

40: light emitting layer

50: second electrode

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

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

The compound represented by formula (1) according to an embodiment of the present invention binds two cyano groups at a meta position centering on a benzene core, so that light of a specific wavelength range is emitted, and an organic light emitting device including the compound .

Since the two carbazole derivatives and one or two aryl groups are bonded around the benzene core of Formula 1, the charge balance injected into the light emitting layer is controlled, and the organic light emitting device including the organic compound has low driving voltage, Can be improved.

When only one phenyl ring of the carbazole derivative bonded to the benzene core of Formula 1 is substituted with asymmetrically an aryl group, particularly a phenyl group, the HOMO region is enlarged and the hole transfer is improved in the light emitting layer, It is possible to improve the service life.

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.

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; Cyano; 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.

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 methylsulfoxy 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; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include 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.

When the fluorenyl group is substituted,

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, or a substituted or unsubstituted diarylamine 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, or a substituted or unsubstituted diheteroarylamine 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, 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 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 the following formula (1-1) or (1-2).

[Formula 1-1]

[Formula 1-2]

In the above formulas 1-1 and 1-2,

The definitions of A 1 to A 5, R 1 to R 8 and R 11 to R 18 are as defined in the above formula (1)

A11 to A15 are the same or different and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.

According to one embodiment of the present invention, in the general formula (1), R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or an alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a methyl group.

According to one embodiment of the present invention, in the general formula (1), adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.

According to one embodiment of the present invention, adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form an aromatic ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the above formula (1), adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form an indene ring substituted with at least one alkyl group.

According to one embodiment of the present invention, adjacent groups among R1 to R8 and R11 to R18 in the general formula (1) are bonded to each other to form an indene ring substituted with at least one methyl group.

According to one embodiment of the present invention, in the general formula (1), R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, in Formula 1, R 2 and R 3 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in Formula 1, R 2 and R 3 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one methyl group.

According to one embodiment of the present invention, any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted alkyl group; To form an unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted alkyl group; To form a ring-opened hydrocarbon ring.

According to one embodiment of the present invention, in Formula 1, R 3 is a substituted or unsubstituted phenyl group, R 2 is a substituted or unsubstituted alkyl group, and R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .

According to one embodiment of the present invention, in the general formula (1), R 3 is a phenyl group, R 2 is an isopropyl group, and R 2 and R 3 are bonded to each other to form an indene ring substituted with two methyl groups.

According to one embodiment of the present invention, in the general formula (1), R 6 and R 7 combine with each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, in Formula 1, R 6 and R 7 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the above formula (1), R 6 and R 7 combine with each other to form an aromatic ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 6 and R 7 combine with each other to form an indene ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the above formula (1), R 6 and R 7 combine with each other to form an indene ring substituted with at least one methyl group.

According to one embodiment of the present invention, any one of R6 and R7 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, any one of R6 and R7 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form a ring-opened hydrocarbon ring.

According to one embodiment of the present invention, R6 is a substituted or unsubstituted phenyl group, R7 is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .

According to one embodiment of the present invention, R6 is a phenyl group, R7 is an isopropyl group, and R6 and R7 are bonded to each other to form an indene ring substituted with two methyl groups.

According to one embodiment of the present invention, in the general formula (1), R 12 and R 13 combine with each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, R12 and R13 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the above formula (1), R 12 and R 13 combine with each other to form an aromatic ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R12 and R13 are bonded to each other to form an indene ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 12 and R 13 combine with each other to form an indene ring substituted with at least one methyl group.

According to one embodiment of the present invention, any one of R12 and R13 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.

According to an embodiment of the present invention, any one of R12 and R13 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.

According to an embodiment of the present invention, R13 is a substituted or unsubstituted phenyl group, R12 is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .

According to one embodiment of the present invention, R13 is a phenyl group, R12 is an isopropyl group, and R12 and R13 are bonded to each other to form an indene ring substituted with two methyl groups.

According to one embodiment of the present invention, in the above formula (1), R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, R16 and R17 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the above Formula 1, R16 and R17 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R16 and R17 are bonded to each other to form an indene ring substituted with at least one alkyl group.

According to one embodiment of the present invention, in the general formula (1), R16 and R17 are bonded to each other to form an indene ring substituted with at least one methyl group.

According to one embodiment of the present invention, any one of R16 and R17 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.

According to one embodiment of the present invention, any one of R16 and R17 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.

According to one embodiment of the present invention, R16 is a substituted or unsubstituted phenyl group, R17 is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .

According to one embodiment of the present invention, R16 is a phenyl group, R17 is an isopropyl group, and R16 and R17 are bonded to each other to form an indene ring substituted with two methyl groups.

According to one embodiment of the present disclosure, A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group.

According to one embodiment of the present disclosure, A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; An aryl group which is substituted or unsubstituted with a fluorine atom, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a polycyclic heteroaryl group.

According to one embodiment of the present disclosure, A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; A phenyl group substituted or unsubstituted by fluorine, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a carbazolyl group.

According to one embodiment of the present specification, adjacent groups of A1 to A5 are bonded to each other to form an aromatic ring.

According to one embodiment of the present disclosure, adjacent groups of A1 to A5 combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A 1 and A 5 combine with each other to form an aromatic ring.

According to one embodiment of the present disclosure, A 1 and A 5 combine with each other to form a benzene ring.

According to one embodiment of the present invention, A1 and A5 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A1 and A5 are each ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A2 and A3 combine with each other to form an aromatic ring.

According to one embodiment of the present disclosure, A2 and A3 combine with each other to form a benzene ring.

According to one embodiment of the present invention, A2 and A3 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A2 and A3 are each an ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A3 and A4 are bonded to each other to form an aromatic ring.

According to one embodiment of the present disclosure, A3 and A4 are bonded to each other to form a benzene ring.

According to one embodiment of the present invention, A3 and A4 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A3 and A4 are each an ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A4 and A5 combine with each other to form an aromatic ring.

According to one embodiment of the present disclosure, A4 and A5 combine with each other to form a benzene ring.

According to one embodiment of the present invention, A4 and A5 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A4 and A5 are each ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A11 and A12 combine with each other to form an aromatic ring.

According to one embodiment of the present disclosure, A11 and A12 combine with each other to form a benzene ring.

According to one embodiment of the present invention, A11 and A12 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A11 and A12 are each ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A12 and A13 are bonded to each other to form an aromatic ring.

According to one embodiment of the present disclosure, A12 and A13 combine with each other to form a benzene ring.

According to one embodiment of the present invention, A12 and A13 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A12 and A13 are each ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A13 and A14 combine with each other to form an aromatic ring.

According to one embodiment of the present disclosure, A13 and A14 combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A13 and A14 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A13 and A14 are each an ethenyl group and combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A14 and A15 combine with each other to form an aromatic ring.

According to one embodiment of the present disclosure, A14 and A15 combine with each other to form a benzene ring.

According to one embodiment of the present disclosure, A14 and A15 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, A14 and A15 are each ethenyl and combine with each other to form a benzene ring.

According to one embodiment of the present invention, when n is 1 and either one of A1 to A5 is a polycyclic heteroaryl group in the general formula (1), the remainder is hydrogen.

According to one embodiment of the present invention, when n is 1 and one of A 1 to A 5 is a carbazolyl group in the general formula (1), the other is hydrogen.

According to one embodiment of the present disclosure, Formula 1 is selected from the following compounds.

.

According to one embodiment of the present invention, the compound represented by Formula 1 is a retardation fluorescent compound.

In the general organic light emitting device, the number of excitons generated in the singlet and triplet is generated at a ratio of 25:75 (monomodal: triplet), and depending on the type of emission due to exciton migration, fluorescence emission, It can be divided into luminescence. In the case of the phosphorescent light emission, it means that the exciton of the excited state moves to the ground state and emits light. In the case of the fluorescent emission, the exciton of the excited state is in the ground state ground state, and the light is emitted. The thermal activation delay fluorescent light emission is induced in the excited state from the excited state to the excited state, and the singlet excited state Means that the exciton moves to the ground state to cause fluorescent light emission.

The thermal activation delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time is long. The decay time is long, but the peak position of the emission spectrum differs from the phosphorescence spectrum and S ₁ -T ₁ &lt; / RTI &gt; energy difference. Here, S ₁ is a singlet energy level, and T ₁ is a triplet energy level.

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 FIG. 1, but 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.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant of the light emitting layer.

According to one embodiment of the present invention, the maximum emission wavelength of the dopant is from 450 nm to 570 nm.

According to one embodiment of the present disclosure, the dopant is a blue dopant.

According to one embodiment of the present disclosure, the dopant is a sky blue dopant.

According to one embodiment of the present disclosure, the dopant is a green dopant.

According to one embodiment of the present invention, the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the excited singlet energy and the excitation triplet energy has a higher value than the light emitting material of the compound and has a hole transporting ability and an electron transporting ability and also prevents a long wavelength of light emission, And may include an organic compound having a high glass transition temperature as a host.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a host.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.

According to one embodiment of the present invention, the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluorene derivative, a fluoranthene compound, Include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder furan compounds, and pyrimidine derivatives.

According to one embodiment of the present invention, the host may include any one or more selected from the following compounds, but is not limited thereto.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound represented by Formula 1 as a dopant of the light emitting layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound As a host of the light emitting layer.

According to one embodiment of the present disclosure, the light emitting layer contains the dopant and the host in a weight ratio of 1:99 to 50:50.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer may include at least one selected from the group consisting of the dopant including the compound represented by the above-mentioned formula (1), the condensed aromatic ring derivative, and the heterocyclic compound Containing host at a weight ratio of 1:99 to 50:50.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that the dopant of the light emitting layer contains the compound of the present specification, that is, the 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 by a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

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

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

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

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

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

The electron 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, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or 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.

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.

[Example]

[Production Example 1]

end. Preparation of Compound P2

27.2 g of 1,5-dibromo-2,4-difluorobenzene (P1) and 24 g of trimethylsilyl chloride (TMSCl) were mixed with 200 ml of tetrahydrofuran (THF) under nitrogen and cooled to -78 ° C . Next, 220 ml of lithium diisopropylamide (LDA, 2M) was slowly added dropwise, stirred at -78 캜 for 1 hour, and slowly heated to room temperature. After completion of the reaction, the reaction mixture was extracted with 3% diluted hydrochloric acid and dichloromethane, dried over anhydrous sodium sulfate and filtered. The dichloromethane was distilled off under reduced pressure, and then washed with cold methanol to obtain 32.8 g of a white solid.

Next, 32.8 g of the compound obtained in the above reaction was mixed with 1320 ml of chloroform, stirred under nitrogen for 30 minutes, and cooled to -78 캜. 317 ml of 1 mol of iodine monochloride (ICl) was slowly added dropwise and stirred at the same temperature for 1 hour, then the temperature was raised to room temperature and stirred for 8 hours. After completion of the reaction, the reaction was terminated with an aqueous solution of sodium thiosulfite (Na ₂ S ₂ O ₃ ), followed by extraction with anhydrous sodium sulfate and filtration. Recrystallization with ethanol and drying gave 37.0 g of compound P2.

I. Preparation of compound P3

The compound P2 (1,5.1-dibromo-2,4-difluoro-3,6-diiodobenzene) (26.18g, 50mmol) and phenylboronic acid (12.2g, 100mmol) were dissolved in tetrahydrofuran (THF) 800 ml. To this was added a ₂ M solution of sodium carbonate (Na ₂ CO ₃ ) (500 mL) and tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ , 4.6 g, 4 mmol) and refluxed for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure. The concentrated compound was separated by column chromatography using hexane and ethyl acetate in a volume ratio of 6: 1 to obtain 21.0 g of compound P3. After drying in a vacuum oven for 24 hours, the obtained solid was found to have a peak at M / Z = 422 by mass spectrometry.

All. Preparation of compound P4

The compound P3 (14.0 g, 33.1 mmol) was dissolved in 600 ml of N, N-dimethylformamide. To this was added copper cyanide (CuCN, 6 g, 67 mmol) and refluxed under nitrogen. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted with water and ethyl acetate. The ethyl acetate layer was separated and then vacuum distilled to concentrate the compound. Subsequently, recrystallization from tetrahydrofuran gave 11.0 g of compound P4. A peak was confirmed at M / Z = 316 by mass spectrum measurement of the obtained solid.

la. Preparation of Compound (1)

Carbazol (2.8 g, 17 mmol), potassium carbonate (2.4 g, 17 mmol) and dimethyl sulfoxide (40 ml) were mixed and stirred at room temperature and nitrogen for 1 hour. To the reaction mixture was added compound P4 (2.6 g, 8.3 mmol) and stirred at 50 &lt; 0 &gt; C for 12 h. The mixture was cooled to room temperature, distilled water was added dropwise, and the mixture was filtered. The organic layer was separated, dried over magnesium sulfate, filtered through silica gel, and concentrated. Recrystallization from dichloromethane and ethanol gave 2.2 g of compound 1. A peak was confirmed at M / Z = 610 by mass spectrum measurement of the obtained solid.

[Production Example 2]

Preparation of Compound 2

Carbazole was prepared in the same manner as in the case of Compound 1, except that 3.3 g (17 mmol) of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was confirmed at M / Z = 666 by mass spectrum measurement of the obtained solid.

[Production Example 3]

Preparation of Compound 3

1,7-dihydroindeno [2,1-b] carbazole was used instead of 4-tert-butyl-9H-carbazole in Example 1, 2.0 g Of Compound 3 was prepared. A peak was confirmed at M / Z = 842 by mass spectrum measurement of the obtained solid.

[Production Example 4]

end. Preparation of compound P5

20.8 g of compound P5 was prepared in the same manner as in the synthesis of the compound P3 except that [1,1'-biphenyl] -2-ylboronic acid (19.8 g, 100 mmol) was used instead of phenylboronic acid . The obtained solid had a peak at M / Z = 574 as determined by mass spectrometry.

I. Preparation of compound P6

Compound P4 was prepared in the same manner as in the synthesis of compound P4 except that P5 (19.1 g, 33.1 mmol) was used instead of P3. A peak was observed at M / Z = 468 by mass spectrum measurement of the obtained solid.

All. Preparation of compound 4

1.4 g of Compound 4 was obtained in the same manner as in the synthesis of Compound 1, except that P6 (3.9 g, 8.3 mmol) was used instead of P4. A peak was confirmed at M / Z = 762 by mass spectrum measurement of the obtained solid.

[Production Example 5]

Preparation of Compound 5

2.0 g of Compound 5 was prepared, except that 3.3 g, 17 mmol of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was observed at M / Z = 818 by mass spectrum measurement of the obtained solid.

[Production Example 6]

Preparation of Compound 6

1,7-dihydroindeno [2,1-b] carbazole was used instead of 4-tert-butyl-9H-carbazole as a starting material, 1.8 g Of Compound 6 was prepared. A peak was confirmed at M / Z = 994 by mass spectrum measurement of the obtained solid.

[Production Example 7]

end. Preparation of compound P7

18.6 g of the compound P7 was prepared in the same manner as in the synthesis of the compound P3 except that (4-fluorophenyl) boronic acid (14.0 g, 100 mmol) was used instead of phenylboronic acid. The obtained solid was confirmed by mass spectrometry to have a peak at M / Z = 458.

I. Preparation of compound P8

6.6 g of the compound P8 was obtained in the same manner as in the synthesis of the compound P4 except that P7 (15.2 g, 33.1 mmol) was used instead of P3. A peak was confirmed at M / Z = 352 by mass spectrum measurement of the obtained solid.

All. Preparation of Compound 7

0.8 g of Compound 7 was obtained in the same manner as in the synthesis of Compound 1, except that P8 (2.9 g, 8.3 mmol) was used instead of P4. A peak was confirmed at M / Z = 646 by mass spectrum measurement of the obtained solid.

[Production Example 8]

Preparation of Compound 8

1.4g of Compound 8 was prepared in the same manner as in Compound 7, except that 3.3g of 17mg of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was confirmed at M / Z = 702 by mass spectrum measurement of the obtained solid.

[Production Example 9]

Preparation of Compound 9

Carbazole was prepared in the same manner as in the compound 7 except that 4.8 g of 17 mmol of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole was used instead of 9H- Of Compound 9 was prepared. A peak was confirmed at M / Z = 878 by mass spectrum measurement of the obtained solid.

[Production Example 10]

end. Preparation of Compound P9

(4-cyanophenyl) boronic acid (14.7 g, 100 mmol) was used in place of the phenyl boronic acid, 16.0 g of the compound P9 was prepared. The obtained solid was confirmed by mass spectrometry to have a peak at M / Z = 472.

I. Preparation of compound P10

Compound P10 (8.4 g) was obtained in the same manner as in the synthesis of compound P4, except that P9 (15.7 g, 33.1 mmol) was used instead of P3. A peak was confirmed at M / Z = 366 by mass spectrum measurement of the obtained solid.

All. Preparation of Compound 10

0.8 g of Compound 10 was obtained in the same manner as in the synthesis of Compound 1, except that P10 (3.0 g, 8.3 mmol) was used instead of P4. A peak was confirmed at M / Z = 660 by mass spectrum measurement of the obtained solid.

[Production Example 11]

Preparation of Compound 11

Compound 9 was prepared in the same manner as Compound 10, except that 3.3 g, 17 mmol of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was confirmed at M / Z = 716 by mass spectrum measurement of the obtained solid.

[Production Example 12]

Preparation of Compound 12

Carbazole was prepared in the same manner as in Compound 10, except that 4.8 g, 17 mmol of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] Of Compound 12 was prepared. The peak of the obtained solid was confirmed by M / Z = 892 by mass spectrum measurement.

[Production Example 13]

end. Preparation of Compound P11

16.4 g of the compound P11 was prepared in the same manner as in the synthesis of the compound P3, except that (4- (tart-butyl) phenyl) boronic acid (17.8 g, 100 mmol) was used instead of phenylboronic acid. The obtained solid was confirmed by mass spectrometry to have a peak at M / Z = 534.

I. Preparation of compound P12

8.4 g of the compound P12 was obtained in the same manner as in the synthesis of the compound P4 except that P11 (15.7 g, 33.1 mmol) was used instead of P3. A peak was confirmed at M / Z = 428 by mass spectrum measurement of the obtained solid.

All. Preparation of Compound 13

1.0 g of Compound 13 was prepared in the same manner as in the synthesis of Compound 1, except that P12 (3.6 g, 8.3 mmol) was used instead of P4. A peak was confirmed at M / Z = 722 by mass spectrum measurement of the obtained solid.

[Production Example 14]

Preparation of Compound 14

Compound 14 was prepared in the same manner as Compound 13, except that 3.3 g (17 mmol) of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was observed at M / Z = 778 by mass spectrum measurement of the obtained solid.

[Production Example 15]

Preparation of compound 15

Compound 9 was prepared in the same manner as Compound 1 except that 17 mmol of 4.1-g of 3-phenyl-9H carbazole was used instead of 9H-carbazole to obtain 1.4 g of Compound 15. A peak was confirmed at M / Z = 762 by mass spectrum measurement of the obtained solid.

[Production Example 16]

Preparation of Compound 16

1.8 g of Compound 16 was prepared in the same manner as Compound 1, except that 4.1 mmol of 4-methyl-9H-carbazole was used instead of 4.1 g of 2-phenyl-9H-carbazole. A peak was confirmed at M / Z = 762 by mass spectrum measurement of the obtained solid.

[Production Example 17]

Preparation of Compound 17

Carbazole was used instead of 4-phenyl-9H-carbazole (4.1 g, 17 mmol) instead of 9H-carbazole, 1.8 g of Compound 17 was prepared. A peak was confirmed at M / Z = 762 by mass spectrum measurement of the obtained solid.

[Production Example 18]

Preparation of Compound 18

Compound 11 was prepared in the same manner as in Compound 10, except that 4.1 mmol of 3-phenyl-9H-carbazole was used instead of 9-carbazole, to obtain 1.6 g of Compound 18. A peak was confirmed at M / Z = 812 by mass spectrum measurement of the obtained solid.

[Production Example 19]

Preparation of Compound 19

2.0 g of Compound 19 was prepared in the same manner as Compound 10, except that 4.1 mmol of 4-phenyl-9H-carbazole was used instead of 9-carbazole. A peak was confirmed at M / Z = 812 by mass spectrum measurement of the obtained solid.

[Production Example 20]

Preparation of Compound 20

2.0 g of Compound 20 was prepared in the same manner as Compound 13, except that 4.1 mmol of 3-phenyl-9H-carbazole was used instead of 9-carbazole. A peak was confirmed at M / Z = 874 by mass spectrum measurement of the obtained solid.

[Example 1]

Organic Light Emitting Device Manufacturing

First, a glass substrate with a 40 mm x 40 mm x 0.5 mm thick ITO electrode was ultrasonically cleaned with isopropyl alcohol, acetone and DI water for 5 minutes, and then dried in an oven at 100 ° C. After the substrate was cleaned, it was subjected to an O ₂ plasma treatment in a vacuum for 2 minutes and transferred to a deposition chamber for deposition of other layers on the top. An organic layer was deposited on the ITO of the glass substrate by evaporation from a heated boat under a vacuum of about 10 ^-7 Torr in the following order. At this time, the deposition rate of the organic material was set at 10 nm / s.

1. Hole injection layer (HIL): HAT-CN, thickness 10 nm

2. Hole transport layer (HTL): NPB, thickness 75 nm

3. Electron barrier layer (EBL): mCBP, thickness 15 nm

4. Emissive material layer (EML): TH1 90 wt%, Compound 1 10 wt%, thickness 35 nm

5. Hole blocking layer (HBL): B3PYMPM, thickness 10 nm

6. Electron transport layer (ETL): TPBi, thickness 25 nm

7. Electron Injection Layer (EIL): LiF, thickness 80 nm

8. Cathode: Al, thickness 100 nm

A capping layer (CPL) was formed and encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a dry box for subsequent film formation and subsequently encapsulated using a UV cured epoxy and a getter.

[Example 2]

An organic light emitting diode was prepared using Compound 2 instead of Compound 1 as a dopant of the light emitting layer.

[Example 3]

An organic light emitting device was prepared using Compound 3 instead of Compound 1 as a dopant in the light emitting layer.

[Example 4]

An organic light emitting device was prepared using Compound 4 instead of Compound 1 as a dopant of the light emitting layer.

[Example 5]

An organic light emitting device was prepared using Compound 5 instead of Compound 1 as a dopant in the light emitting layer.

[Example 6]

An organic light emitting device was prepared by using Compound 6 instead of Compound 1 as a dopant in the light emitting layer.

[Example 7]

An organic light emitting device was prepared using Compound 8 instead of Compound 1 as a dopant in the light emitting layer.

[Example 8]

An organic light emitting device was prepared using Compound 9 instead of Compound 1 as a dopant in the light emitting layer.

[Example 9]

An organic light emitting device was prepared by using Compound 10 instead of Compound 1 as a dopant in the light emitting layer.

[Example 10]

An organic light emitting device was prepared using Compound 13 instead of Compound 1 as a dopant in the light emitting layer.

[Example 11]

An organic light emitting device was prepared by using Compound 14 instead of Compound 1 as a dopant of the light emitting layer.

[Example 12]

An organic light emitting device was prepared using Compound 15 instead of Compound 1 as a dopant in the light emitting layer.

[Example 13]

An organic luminescent device was prepared by using Compound 18 instead of Compound 1 as a dopant of the light emitting layer.

[Example 14]

An organic light emitting device was prepared by using Compound 20 instead of Compound 1 as a dopant in the light emitting layer.

[Comparative Example 1]

An organic luminescent device was prepared using the following Compound D1 instead of Compound 1 as a dopant in the light emitting layer.

[Comparative Example 2]

An organic luminescent device was prepared using the following compound D2 instead of compound 1 as a dopant in the light emitting layer.

[Comparative Example 3]

An organic light emitting device was prepared using the following compound D3 instead of Compound 1 as a dopant of the light emitting layer.

[Comparative Example 4]

An organic luminescent device was prepared using the following compound D4 instead of compound 1 as a dopant in the light emitting layer.

[Comparative Example 5]

An organic light emitting device was prepared using the following compound D5 instead of compound 1 as a dopant of the light emitting layer.

[Comparative Example 6]

An organic light emitting device was prepared using the following compound D6 instead of compound 1 as a dopant of the light emitting layer.

The properties of the organic luminescent devices prepared in Examples 1 to 14 and Comparative Examples 1 to 6, respectively, in which the thickness of the light emitting layer doped with the retardation fluorescent dopant of 10 wt% was 35 nm, were measured. The device characteristics were evaluated at room temperature using a current source (KEITHLEY) and a photometer (PR 650). (Cd / A), power efficiency (lm / W), luminance (cd / m &lt; ² &gt;) measured at a current density of 10 mA / cm & The time (T ₉₅ ) until the brightness was reduced to 95% was measured. The measurement results are shown in Table 1 below.

	compound	The driving voltage (V)	Current efficiency (cd / A)	Power Efficiency (lm / W)	Brightness (cd / m 2 )	T 95
Example 1	One	4	59.2	46.5	6020	380
Example 2	2	4.2	62.8	47.0	6180	460
Example 3	3	4.3	53.2	38.9	5530	240
Example 4	4	4.6	50.6	34.6	5560	300
Example 5	5	4.4	56	40.0	5200	260
Example 6	6	4.4	54.8	39.1	5280	240
Example 7	8	4.8	56.8	37.2	6000	260
Example 8	9	4	60.2	47.3	6000	420
Example 9	10	4.4	58.4	41.7	5640	300
Example 10	13	4.2	56.8	42.5	5480	280
Example 11	14	4.6	54.2	37.0	5320	300
Example 12	15	4.2	60.2	45.0	6020	480
Example 13	18	4.6	55.4	37.8	5540	360
Example 14	20	4.4	55	39.3	5500	340
Comparative Example 1	D1	6.8	46.2	21.3	4600	160
Comparative Example 2	D2	6.2	40.2	20.4	4000	160
Comparative Example 3	D3	6	41.8	21.9	4180	180
Comparative Example 4	D4	5.2	42.6	25.7	4800	180
Comparative Example 5	D5	5.6	44.8	25.1	4480	160
Comparative Example 6	D6	5.2	46.6	28.2	4660	190

The devices of Examples 1 to 14 using the heterocyclic compounds of the present invention had lower driving voltage, higher current efficiency, higher power efficiency, higher luminance, and higher lifetime characteristics than the devices of Comparative Examples 1 to 6 .

Claims (14)

1. A compound represented by the following formula (1):

   [Chemical Formula 1]

   

   In Formula 1,

   A1 to A5 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,

   R 1 to R 4 and R 11 to R 14 are the same or different and each independently represents hydrogen or a substituted or unsubstituted alkyl group,

   R5 to R8 and R15 to R18 are the same or different and each independently represents hydrogen, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

   n is 1 or 2,

   When n is 2, the structures in the plurality of parentheses are equal to or different from each other,

   When n is 1, and any one of A1 to A5 is a heteroaryl group, the remainder is hydrogen.
2. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-1 or 1-2:

   [Formula 1-1]

   

   [Formula 1-2]

   

   In the above formulas 1-1 and 1-2,

   The definitions of A 1 to A 5, R 1 to R 8 and R 11 to R 18 are as defined in the above formula (1)

   A11 to A15 are the same or different and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
3. The compound according to claim 1, wherein R1 to R8 and R11 to R18 are the same or different and each independently hydrogen; Or an alkyl group.
4. The compound according to claim 1, wherein adjacent groups of R5 to R8 and R15 to R18 are bonded to each other to form a hydrocarbon ring substituted with an alkyl group.
5. The compound according to claim 1, wherein the compound of formula (1) is selected from the following compounds:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
6. The compound according to claim 1, wherein the compound represented by Formula 1 is a retardation fluorescent compound.
7. 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 a compound according to any one of claims 1 to 6.
8. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.
9. 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 compound as a dopant of the light emitting layer.
10. [Claim 11] The organic light emitting device according to claim 9, wherein the maximum emission wavelength of the dopant is 450 nm to 570 nm.
11. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
12. 12. The organic electroluminescent device according to claim 11, wherein the host comprises at least one selected from the following compounds:

    

    

    

    

    

    
13. The organic electroluminescent device according to claim 7, wherein the organic material layer includes a light emitting layer, the light emitting layer contains the compound as a dopant of the light emitting layer, and includes at least one selected from a condensed aromatic ring derivative and a heterocyclic- Organic light emitting device.
14. 14. The organic light emitting device according to claim 13, wherein the light emitting layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.

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