KR102160860B1 - Compound and organic light-emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of Formula 1 and an organic light emitting device including the same.

Description

Compound and organic light-emitting device comprising the same TECHNICAL FIELD

This application claims the benefit of the filing date of Korean Patent Application No. 10-2017-0160604 filed with the Korean Intellectual Property Office on November 28, 2017, the entire contents of which are incorporated herein.

The present specification 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 light-emitting materials, and for this purpose, research on phosphorescent and delayed fluorescent materials is being actively conducted. However, in the case of the phosphorescent material, although it is possible to achieve high efficiency, there is a problem in that the price of the metal complex required to implement phosphorescence is high and the lifespan is short.

In the case of delayed fluorescent materials, the concept of thermally activated delayed fluorescence (TADF) was recently introduced to introduce a highly efficient green fluorescent material that is a fluorescent material and has high external quantum efficiency. The concept of thermally activated delayed fluorescence (TADF) represents a phenomenon leading to fluorescence emission by causing the reverse energy transfer from the excitation triplet state to the excitation singlet state by thermal activation, and since light emission occurs through the triplet, the lifespan is generally reduced. It is called delayed fluorescence in that long light emission occurs. Since the delayed fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of external quantum efficiency of the conventional fluorescent material can be solved, and the price problem of the phosphorescent material can be solved in that it does not need to contain a metal complex.

International Publication No. 2016-015810

Nature, 492, pp 234-238 J. Am. Chem. Soc., 2012, 134 (36), pp 14706-14709

The present specification provides a compound and an organic light emitting device including the same.

According to an exemplary embodiment of the present specification, a compound represented by the following Formula 1 is provided.

[Formula 1]

In Formula 1,

A1 to A5 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl group; Alkenyl group; Haloalkoxy group; An aryl group unsubstituted or substituted 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,

R1 to R4 and R11 to R14 are the same as or different from each other, and each independently hydrogen or a substituted or unsubstituted alkyl group,

R5 to R8 and R15 to R18 are the same as or different from each other, and each independently 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 the same as or different from each other,

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

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

The organic light-emitting device including the compound represented by Formula 1 according to the exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or improve lifespan characteristics.

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

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

According to an exemplary embodiment of the present specification, a compound represented by Formula 1 is provided.

In the compound represented by Formula 1 according to an exemplary embodiment of the present specification, since the two cyano groups are bonded to the meta position around the benzene core, light in a specific wavelength region is emitted, and the organic light emitting device including the same is highly efficient. There are characteristics of.

In addition, since two carbazole derivatives and one or two aryl groups are combined around the benzene core of Formula 1 herein, the charge balance injected into the light emitting layer is adjusted, so that the organic light emitting device including the same has low driving voltage, efficiency, and lifetime. The improvement of is possible.

In addition, when an aryl group, especially a phenyl group, is asymmetrically substituted only in one phenyl ring of the carbazole derivatives bonded to the benzene core of the present formula (1), the HOMO region is expanded and hole transport is improved in the light emitting layer, thereby including the organic light emitting device Can improve the lifespan.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

Examples of the 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 position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; 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 alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; 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 substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to 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 of the imide group is not particularly limited, but it 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 nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 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 number of carbon atoms of the carbonyl group is not particularly limited, but it 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 a C1-C25 linear, branched or cyclic alkyl group 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 a linear or branched chain, 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-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, 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, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. 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 it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but It is not limited.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of 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 group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

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

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group is a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, and butyl. There is a sulfoxy group, but is not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, 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, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it 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 group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of 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 it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, phenalenyl group, perylenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, etc. , But is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

,

,

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

And

Etc. However, it is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group among the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-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 a phenylthioxy group, 2- There are a methylphenyl thioxy group, a 4-tert-butylphenyl thioxy group, and the like, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but 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 containing two or more aryl groups may include 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 one or more atoms and heteroatoms other than carbon, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. 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 thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are 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 including 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 heteroaryl group described above.

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

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group except for the non-monovalent one.

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

In the present specification, the heterocycle includes one or more atoms and heteroatoms other than carbon, and specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group or heterocyclic group except that it is not monovalent.

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

Definitions of A1 to A5, R1 to R8, and R11 to R18 are the same as defined in Formula 1,

A11 to A15 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl group; Alkenyl group; Haloalkoxy group; An aryl group unsubstituted or substituted 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 an exemplary embodiment of the present specification, in Formula 1, R1 to R8 and R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R1 to R8 and R11 to R18 are the same as or different from each other, and each independently hydrogen; Or an alkyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R1 to R8 and R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a methyl group.

According to an exemplary embodiment of the present specification, in Formula 1, adjacent groups of R1 to R8 and R11 to R18 combine with each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, adjacent groups of R1 to R8 and R11 to R18 are bonded to each other to form a hydrocarbon ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, adjacent groups of R1 to R8 and R11 to R18 combine with each other to form an aromatic ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, adjacent groups of R1 to R8 and R11 to R18 combine with each other to form an indene ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, adjacent groups of R1 to R8 and R11 to R18 combine with each other to form an indene ring substituted with one or more methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R2 and R3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R2 and R3 are bonded to each other to form a hydrocarbon ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R2 and R3 are bonded to each other to form an aromatic ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R2 and R3 are bonded to each other to form an indene ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R2 and R3 are bonded to each other to form an indene ring substituted with one or more methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R2 and R3 is a substituted or unsubstituted aryl group, the other is a substituted or unsubstituted alkyl group, and R2 and R3 are bonded to each other to be substituted or It forms an unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R2 and R3 is a substituted or unsubstituted phenyl group, the other is a substituted or unsubstituted alkyl group, and R2 and R3 are bonded to each other to be substituted or unsubstituted. It forms a cyclic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R3 is a substituted or unsubstituted phenyl group, R2 is a substituted or unsubstituted alkyl group, and R2 and R3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring. To form.

According to an exemplary embodiment of the present specification, in Formula 1, R3 is a phenyl group, R2 is an isopropyl group, and R2 and R3 are bonded to each other to form an indene ring substituted with two methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R6 and R7 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R6 and R7 combine with each other to form a hydrocarbon ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R6 and R7 are bonded to each other to form an aromatic ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R6 and R7 are bonded to each other to form an indene ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R6 and R7 are bonded to each other to form an indene ring substituted with one or more methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R6 and R7 is a substituted or unsubstituted aryl group, the other is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to be substituted or It forms an unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R6 and R7 is a substituted or unsubstituted phenyl group, the other is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to be substituted or unsubstituted. It forms a cyclic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, 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. To form.

According to an exemplary embodiment of the present specification, in Formula 1, 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 an exemplary embodiment of the present specification, in Formula 1, R12 and R13 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R12 and R13 are bonded to each other to form a hydrocarbon ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R12 and R13 combine with each other to form an aromatic ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R12 and R13 combine with each other to form an indene ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R12 and R13 are bonded to each other to form an indene ring substituted with one or more methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R12 and R13 is a substituted or unsubstituted aryl group, the other is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to be substituted or It forms an unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R12 and R13 is a substituted or unsubstituted phenyl group, the other is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to be substituted or unsubstituted It forms a cyclic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, 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. To form.

According to an exemplary embodiment of the present specification, in Formula 1, 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 an exemplary embodiment of the present specification, in Formula 1, R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R16 and R17 are bonded to each other to form a hydrocarbon ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R16 and R17 are bonded to each other to form an aromatic ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R16 and R17 are bonded to each other to form an indene ring substituted with one or more alkyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R16 and R17 are bonded to each other to form an indene ring substituted with one or more methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R16 and R17 is a substituted or unsubstituted aryl group, the other is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to be substituted or It forms an unsubstituted hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, any one of R16 and R17 is a substituted or unsubstituted phenyl group, the other is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to be substituted or unsubstituted It forms a cyclic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, 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. To form.

According to an exemplary embodiment of the present specification, in Formula 1, 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 an exemplary embodiment of the present specification, A1 to A5 and A11 to A15 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl group; Alkenyl group; Haloalkoxy group; An aryl group unsubstituted or substituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group.

According to an exemplary embodiment of the present specification, A1 to A5 and A11 to A15 are the same as or different from each other, and each independently hydrogen; Fluorine; Cyano group; Trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; Trifluoromethoxy group; An aryl group unsubstituted or substituted with a fluorine, cyano group, trifluoromethyl group, methyl group, or trifluoromethoxy group; Or it is a polycyclic heteroaryl group.

According to an exemplary embodiment of the present specification, A1 to A5 and A11 to A15 are the same as or different from each other, and each independently hydrogen; Fluorine; Cyano group; Trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; Trifluoromethoxy group; Phenyl group unsubstituted or substituted with fluorine, cyano group, trifluoromethyl group, methyl group, or trifluoromethoxy group; Or a carbazolyl group.

According to an exemplary embodiment of the present specification, adjacent groups of A1 to A5 combine with each other to form an aromatic ring.

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

According to an exemplary embodiment of the present specification, A1 and A5 are bonded to each other to form an aromatic ring.

According to an exemplary embodiment of the present specification, A1 and A5 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A1 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 an exemplary embodiment of the present specification, A1 and A5 are each an ethenyl group, and are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A2 and A3 are bonded to each other to form an aromatic ring.

According to an exemplary embodiment of the present specification, A2 and A3 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A2 and A3 are each a substituted or unsubstituted alkenyl group, and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, A2 and A3 are each an ethenyl group, and are bonded to each other to form a benzene ring.

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

According to an exemplary embodiment of the present specification, A3 and A4 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, 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 an exemplary embodiment of the present specification, A3 and A4 are each an ethenyl group, and are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A4 and A5 are bonded to each other to form an aromatic ring.

According to an exemplary embodiment of the present specification, A4 and A5 combine with each other to form a benzene ring.

According to an exemplary embodiment of the present specification, 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 an exemplary embodiment of the present specification, A4 and A5 are each an ethenyl group, and are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A11 and A12 are bonded to each other to form an aromatic ring.

According to an exemplary embodiment of the present specification, A11 and A12 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, 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 an exemplary embodiment of the present specification, A11 and A12 are each an ethenyl group, and are bonded to each other to form a benzene ring.

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

According to an exemplary embodiment of the present specification, A12 and A13 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A12 and A13 are each a substituted or unsubstituted alkenyl group, and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, A12 and A13 are each an ethenyl group, and are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A13 and A14 are bonded to each other to form an aromatic ring.

According to an exemplary embodiment of the present specification, A13 and A14 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A13 and A14 are each a substituted or unsubstituted alkenyl group, and are bonded to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, A13 and A14 are each an ethenyl group, and are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, A14 and A15 are bonded to each other to form an aromatic ring.

According to an exemplary embodiment of the present specification, A14 and A15 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, 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 an exemplary embodiment of the present specification, A14 and A15 are each an ethenyl group, and are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, in Formula 1, when n is 1, and any one of A1 to A5 is a polycyclic heteroaryl group, the remainder is hydrogen.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, when n is 1 and any one of A1 to A5 is a carbazolyl group, the remainder is hydrogen.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is a delayed fluorescent compound.

In general organic light emitting devices, the number of excitons generated in singlet and triplet is generated at a ratio of 25:75 (singlet: triplet), and fluorescence, phosphorescence, and thermally activated delayed fluorescence according to the luminescence type according to exciton movement It can be divided into light emission. In the case of phosphorescent emission, excitons in a triplet excited state move to a ground state to emit light, and in the case of the fluorescence emission, excitons in a singlet excited state are in the ground state ( ground state) to emit light, and in the thermally activated delayed fluorescence emission, an inverse interphase transition is induced from a triplet excited state to a singlet excited state, and the singlet excited state It means that excitons move to the ground state and cause fluorescence emission.

The heat activated delayed fluorescence decay time is the peak position of the emission spectrum identical to the fluorescence (decay time) is longer are separated and fluorescence emission from the point, the decay time is long, but the peak position of the emission spectrum and phosphorescence spectrum S ₁ -T _It differs from phosphorescence in that it differs by the difference of ₁ energy. At this time, S ₁ is a singlet energy level, and T ₁ is a triplet energy level.

According to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

According to an exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may be formed in a single-layer structure, but may be formed in 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 injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like 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 specification 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 device according to an exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound as a dopant of the emission layer.

According to the exemplary embodiment of the present specification, the maximum emission wavelength of the dopant is 450nm to 570nm.

According to the exemplary embodiment of the present specification, the dopant is a blue dopant.

According to an exemplary embodiment of the present specification, the dopant is a sky blue dopant.

According to the exemplary embodiment of the present specification, the dopant is a green dopant.

According to an exemplary embodiment of the present specification, the light-emitting material of the light-emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, wherein the light-emitting layer comprises the aforementioned compound as a light-emitting layer. Contains as a dopant of, wherein at least one of the excitation singlet energy and the excitation triplet energy has a higher value than that of the light emitting material of the compound, has a hole transporting ability and an electron transporting ability, and also prevents a longer wavelength of light emission, An organic compound having a high glass transition temperature may be included as a host.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a host.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic-containing compound as a host of the emission layer.

According to an exemplary embodiment of the present specification, 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, and the like. Is a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.

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

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes a compound represented by Formula 1 as a dopant of the emission layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound Is included as a host of the light emitting layer.

According to the exemplary embodiment of the present specification, the emission layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer comprises at least one selected from the dopant including the compound represented by Formula 1 and the condensed aromatic ring derivative and the heterocyclic compound. The host to be included is included in a weight ratio of 1:99 to 50:50.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except for including the compound of the present specification, that is, the compound represented by Formula 1 as a dopant of the emission layer.

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition method (PVD) such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be manufactured by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

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

According to another exemplary embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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; There are a multilayered material such as LiF/Al or LiO ₂ /Al, and Mg/Ag, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of injecting electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include the 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 transport 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 having a low work function and followed by an aluminum layer or a silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification 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 conditions, and cooled to -78°C. . Next, 220ml of lithium diisopropylamide (LDA, 2M) was slowly added dropwise, stirred at -78°C for 1 hour, and then slowly heated to room temperature. After completion of the reaction, extraction was performed with 3% diluted hydrochloric acid and dichloromethane, dried over anhydrous sodium sulfate, and filtered. Dichloromethane was distilled under reduced pressure and washed with cold methanol to obtain 32.8 g of a white solid.

Next, 32.8 g of the compound obtained in the reaction was mixed with 1320 ml of chloroform, stirred for 30 minutes under nitrogen, and the temperature of the reaction product was cooled to -78°C. 317 ml of 1 mol iodine monochloride (ICl) was slowly added dropwise and stirred at the same temperature for 1 hour, and then heated to room temperature and stirred for 8 hours. After the reaction was completed, the reaction was terminated with an aqueous sodium thiosulfite (Na ₂ S ₂ O ₃ ) solution, extracted, dried over anhydrous sodium sulfate, and filtered. It recrystallized with ethanol and dried, and 37.0g of compound P2 was obtained.

I. Preparation of compound P3

Compound P2 (1,5-dibromo-2,4-difluoro-3,6-diodobenzene) (26.18 g, 50 mmol) and phenyl boronic acid (12.2 g, 100 mmol) in tetrahydrofuran (THF) Dissolved in 800 ml. Sodium carbonate (Na ₂ CO ₃ ) 2M solution (500 mL) and tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ , 4.6 g, 4 mmol) were added and refluxed for 8 hours. After the reaction was completed, the 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, and the filtered filtrate was distilled under reduced pressure. The concentrated compound was separated by column chromatography using a solution obtained by mixing 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 showed a peak at M/Z=422 by mass spectrum measurement.

All. Preparation of compound P4

The compound P3 (14.0g, 33.1mmol) was dissolved in 600ml of N,N-dimethylformamide. Here, copper cyanide (CuCN, 6g, 67 mmol) was added and refluxed under nitrogen conditions. After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted with water and ethyl acetate. The ethyl acetate layer was separated, distilled under reduced pressure, and the compound was concentrated. Next, it was recrystallized from tetrahydrofuran, and 11.0 g of compound P4 was obtained. A peak was confirmed at M/Z=316 by measuring the mass spectrum of the obtained solid.

la. Preparation of compound 1

9H-carbazole (2.8g, 17mmol), potassium carbonate (2.4g, 17mmol) and 40ml of dimethyl sulfoxide were mixed and stirred at room temperature and nitrogen conditions for 1 hour. Compound P4 (2.6g, 8.3mmol) was added to the reaction mixture, followed by stirring at 50°C for 12 hours. After cooling to room temperature, distilled water was added dropwise and filtered. The solid obtained after washing with distilled water was dissolved in dichloromethane, the organic layer was separated, dried over magnesium sulfate, filtered through silica gel, and concentrated. Recrystallized from dichloromethane and ethanol to prepare 2.2 g of compound 1. A peak was confirmed at M/Z=610 by measuring the mass spectrum of the obtained solid.

[Production Example 2]

Preparation of compound 2

Except that 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole, 3.3 g and 17 mmol were used, and 1.8 g of compound 2 was prepared. A peak was confirmed at M/Z=666 by measuring the mass spectrum of the obtained solid.

[Production Example 3]

Preparation of compound 3

Except for using 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole 4.8g, 17mmol instead of 9H-carbazole, prepared in the same manner as Compound 1, 2.0g Compound 3 of was prepared. A peak was confirmed at M/Z=842 by measurement of the mass spectrum of the obtained solid.

[Production Example 4]

end. Preparation of compound P5

Except that [1,1'-biphenyl]-2-yl boronic acid (19.8 g, 100 mmol) was used instead of phenyl boronic acid, 20.8 g of compound P5 was prepared by the same method as the synthesis of compound P3. . The obtained solid showed a peak at M/Z = 574 by mass spectrum measurement.

I. Preparation of compound P6

Except that P5 (19.1g, 33.1mmol) was used instead of P3, it was prepared in the same manner as in the synthesis of compound P4 to obtain 10.4 g of compound P6. A peak was confirmed at M/Z=468 by measurement of the mass spectrum of the obtained solid.

All. Preparation of compound 4

Except for using P6 (3.9g, 8.3mmol) instead of P4, it was prepared in the same manner as the synthesis of compound 1 to obtain 1.4g of compound 4. A peak was confirmed at M/Z=762 by measuring the mass spectrum of the obtained solid.

[Production Example 5]

Preparation of compound 5

Except that 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole, 3.3 g and 17 mmol were used, and 2.0 g of compound 5 was prepared in the same manner as compound 4. A peak was confirmed at M/Z=818 by measuring the mass spectrum of the obtained solid.

[Production Example 6]

Preparation of compound 6

9H-carbazole instead of 7,7-dimethyl-5,7-dihydroindeno[2,1-b] carbazole 4.8g, except for using 17mmol, prepared in the same manner as compound 4, 1.8g Compound 6 was prepared. A peak was confirmed at M/Z=994 by measuring the mass spectrum of the obtained solid.

[Production Example 7]

end. Preparation of compound P7

Except that (4-fluorophenyl) boronic acid (14.0 g, 100 mmol) was used instead of phenyl boronic acid, 18.6 g of compound P7 was prepared by the same method as the synthesis of compound P3. The obtained solid showed a peak at M/Z = 458 by mass spectrum measurement.

I. Preparation of compound P8

Except for using P7 (15.2g, 33.1mmol) instead of P3, 6.6g of compound P8 was obtained by using the same method as for the synthesis of compound P4. A peak was confirmed at M/Z=352 by measuring the mass spectrum of the obtained solid.

All. Preparation of compound 7

Except for using P8 (2.9g, 8.3mmol) instead of P4, it was prepared in the same manner as the synthesis of compound 1 to obtain 0.8g of compound 7. A peak was confirmed at M/Z=646 by measuring the mass spectrum of the obtained solid.

[Production Example 8]

Preparation of compound 8

Except that 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole, 3.3 g and 17 mmol were used, and 1.4 g of compound 8 was prepared. A peak was confirmed at M/Z=702 by measuring the mass spectrum of the obtained solid.

[Production Example 9]

Preparation compound 9

Prepared in the same manner as Compound 7 except for using 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole 4.8g, 17mmol instead of 9H-carbazole, 1.2g Compound 9 of was prepared. A peak was confirmed at M/Z=878 by measurement of the mass spectrum of the obtained solid.

[Production Example 10]

end. Preparation of compound P9

Except that (4-cyanophenyl) boronic acid (14.7 g, 100 mmol) was used instead of phenyl boronic acid, 16.0 g of compound P9 was prepared by the same method as the synthesis of compound P3. The obtained solid was confirmed to have a peak at M/Z=472 by mass spectrum measurement.

I. Preparation of compound P10

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

All. Preparation of compound 10

Except for using P10 (3.0g, 8.3mmol) instead of P4, it was prepared in the same manner as the synthesis of compound 1 to obtain 0.8 g of compound 10. A peak was confirmed at M/Z=660 by measuring the mass spectrum of the obtained solid.

[Production Example 11]

Preparation compound 11

Except that 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole, 3.3g and 17mmol were used. A peak was confirmed at M/Z=716 by measurement of the mass spectrum of the obtained solid.

[Production Example 12]

Preparation compound 12

Except that 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole was used instead of 9H-carbazole, 4.8 g and 17 mmol were used, and prepared in the same manner as compound 10, 1.6 g Compound 12 of was prepared. A peak was confirmed at M/Z=892 by measurement of the mass spectrum of the obtained solid.

[Production Example 13]

end. Preparation of compound P11

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

I. Preparation of compound P12

Except for using P11 (15.7g, 33.1mmol) instead of P3, it was prepared in the same manner as the synthesis of compound P4 to obtain 8.4g of compound P12. A peak was confirmed at M/Z=428 by measurement of the mass spectrum of the obtained solid.

All. Preparation compound 13

Except for using P12 (3.6g, 8.3mmol) instead of P4, it was prepared in the same manner as in the synthesis of compound 1 to obtain 1.0 g of compound 13. A peak was confirmed at M/Z=722 by measurement of the mass spectrum of the obtained solid.

[Production Example 14]

Preparation compound 14

Except that 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole, 3.3 g and 17 mmol were used, and 1.4 g of compound 14 was prepared. A peak was confirmed at M/Z=778 by measurement of the mass spectrum of the obtained solid.

[Production Example 15]

Preparation compound 15

Except for using 4.1g and 17mmol of 3-phenyl-9H-carbazole instead of 9H-carbazole, 1.4g of compound 15 was prepared in the same manner as Compound 1. A peak was confirmed at M/Z=762 by measuring the mass spectrum of the obtained solid.

[Production Example 16]

Preparation compound 16

Except for using 4.1g and 17mmol of 2-phenyl-9H-carbazole instead of 9H-carbazole, it was prepared in the same manner as Compound 1, and 1.8g of Compound 16 was prepared. A peak was confirmed at M/Z=762 by measuring the mass spectrum of the obtained solid.

[Production Example 17]

Preparation compound 17

Except for using 4.1g and 17mmol of 4-phenyl-9H-carbazole instead of 9H-carbazole, it was prepared in the same manner as Compound 1, and 1.8g of Compound 17 was prepared. A peak was confirmed at M/Z=762 by measuring the mass spectrum of the obtained solid.

[Production Example 18]

Preparation compound 18

Except for using 4.1g and 17mmol of 3-phenyl-9H-carbazole instead of 9H-carbazole, 1.6g of compound 18 was prepared in the same manner as compound 10. A peak was confirmed at M/Z=812 by measurement of the mass spectrum of the obtained solid.

[Production Example 19]

Preparation compound 19

Except for using 4.1g and 17mmol of 4-phenyl-9H-carbazole instead of 9H-carbazole, 2.0g of compound 19 was prepared in the same manner as compound 10. A peak was confirmed at M/Z=812 by measurement of the mass spectrum of the obtained solid.

[Production Example 20]

Preparation compound 20

Except for using 4.1g and 17mmol of 3-phenyl-9H-carbazole instead of 9H-carbazole, it was prepared in the same manner as Compound 13, and 2.0g of Compound 20 was prepared. A peak was confirmed at M/Z=874 by measurement of the mass spectrum of the obtained solid.

[Example 1]

Organic light emitting device manufacturing

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

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

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

3. Electron blocking layer (EBL): mCBP, 15 nm thick

4. Emitting material layer (EML): TH1 90% by weight, compound 1 10% by weight, thickness 35nm

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

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

7. Electron injection layer (EIL): LiF, thickness 80nm

8. Cathode: Al, thickness 100nm

After the CPL (capping layer) was formed, it was encapsulated with glass. After the deposition of these layers, they were transferred from the deposition chamber into a drying box for film formation, and subsequently encapsulated using a UV curing epoxy and a moisture getter.

[Example 2]

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

[Example 3]

An organic light-emitting device was manufactured using Compound 3 instead of Compound 1 as a dopant of the emission layer.

[Example 4]

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

[Example 5]

An organic light-emitting device was manufactured using Compound 5 instead of Compound 1 as a dopant of the emission layer.

[Example 6]

An organic light-emitting device was manufactured using Compound 6 instead of Compound 1 as a dopant of the emission layer.

[Example 7]

An organic light-emitting device was manufactured using Compound 8 instead of Compound 1 as a dopant of the emission layer.

[Example 8]

An organic light-emitting device was manufactured using Compound 9 instead of Compound 1 as a dopant of the emission layer.

[Example 9]

An organic light-emitting device was manufactured using compound 10 instead of compound 1 as a dopant of the emission layer.

[Example 10]

An organic light-emitting device was manufactured using Compound 13 instead of Compound 1 as a dopant of the emission layer.

[Example 11]

An organic light-emitting device was manufactured using Compound 14 instead of Compound 1 as a dopant of the emission layer.

[Example 12]

An organic light-emitting device was manufactured using Compound 15 instead of Compound 1 as a dopant of the emission layer.

[Example 13]

An organic light-emitting device was manufactured using Compound 18 instead of Compound 1 as a dopant of the emission layer.

[Example 14]

An organic light-emitting device was manufactured using Compound 20 instead of Compound 1 as a dopant of the emission layer.

[Comparative Example 1]

An organic light-emitting device was manufactured using Compound D1 below instead of Compound 1 as a dopant of the emission layer.

[Comparative Example 2]

An organic light-emitting device was manufactured using Compound D2 below instead of Compound 1 as a dopant of the emission layer.

[Comparative Example 3]

An organic light-emitting device was manufactured using Compound D3 below instead of Compound 1 as a dopant of the emission layer.

[Comparative Example 4]

An organic light-emitting device was manufactured using Compound D4 below instead of Compound 1 as a dopant of the emission layer.

[Comparative Example 5]

An organic light-emitting device was manufactured using Compound D5 below instead of Compound 1 as a dopant of the emission layer.

[Comparative Example 6]

An organic light-emitting device was manufactured using Compound D6 below instead of Compound 1 as a dopant of the emission layer.

Physical properties were measured for the organic light-emitting devices prepared in Examples 1 to 14 and Comparative Examples 1 to 6 each prepared by setting the thickness of the light emitting layer doped with 10% by weight of the delayed fluorescent dopant to 35 nm. Device properties were evaluated at room temperature using a current source (KEITHLEY) and a photometer (PR 650). Driving voltage (V), current efficiency (cd/A), power efficiency (lm/W), luminance (cd/m ² ), measured at a current density of 10 ㎃/㎠ for each organic light emitting device, at 3000 nit The time until the brightness decreases to 95% (T ₉₅ ) was measured. The measurement results are shown in Table 1 below.

compound Driving voltage (V) Current efficiency
(cd/A) Power efficiency
(lm/W) Luminance (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 compound of the present invention have low driving voltage, high current efficiency, high power efficiency, high luminance, and high lifespan characteristics compared to the devices of Comparative Examples 1 to 6 .

10: organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode

Claims (14)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
A1 to A5 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl group; Haloalkoxy group; Or a phenyl group unsubstituted or substituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group,
R1 to R4 and R11 to R14 are the same as or different from each other, and each independently hydrogen or an alkyl group,
R5 to R8 and R15 to R18 are the same as or different from each other, and each independently hydrogen, an alkyl group or an aryl group, or adjacent groups combine with each other to form an indene ring substituted or unsubstituted with an alkyl group,
n is 1 or 2,
When n is 2, the structures in the plurality of parentheses are the same as or different from each other. The compound of claim 1, wherein the formula 1 is represented by the following formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
Definitions of A1 to A5, R1 to R8, and R11 to R18 are the same as defined in Formula 1,
A11 to A15 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl group; Haloalkoxy group; Or a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a phenyl group unsubstituted or substituted with a haloalkoxy group. The method according to claim 1, wherein R1 to R8 and R11 to R18 are the same as or different from each other, and each independently hydrogen; Or an alkyl group. The compound according to claim 1, wherein adjacent groups among R5 to R8 and R15 to R18 are bonded to each other to form an indene ring substituted with an alkyl group. The compound of claim 1, wherein Formula 1 is selected from the following compounds:

The compound of claim 1, wherein the compound represented by Formula 1 is a delayed fluorescent compound. A first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of any one of claims 1 to 6. The organic light-emitting device of claim 7, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 7, wherein the organic material layer includes an emission layer, and the emission layer includes the compound as a dopant of the emission layer. The organic light-emitting device of claim 9, wherein the dopant has a maximum emission wavelength of 450 nm to 570 nm. The organic light-emitting device of claim 7, wherein the organic material layer includes an emission layer, and the emission layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic-containing compound as a host of the emission layer. The organic light-emitting device of claim 11, wherein the host comprises any one or more selected from the following compounds:

8. Organic light emitting device. The organic light-emitting device of claim 13, wherein the emission layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.

Images