KR102123745B1 - 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

A compound and an organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING THE SAME}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2017-0160337, 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 the organic light emitting device, it is necessary to improve the efficiency of the light emitting material, and for this, studies on phosphorescent and delayed fluorescent materials have been 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 necessary for realizing phosphorescence is high and the life is short.

In the case of delayed fluorescent materials, recently, the concept of thermally activated delayed fluorescence (TADF) was introduced to introduce high-efficiency green fluorescent materials that are fluorescent materials and have high external quantum efficiency. The concept of thermally activated delayed fluorescence (TADF) represents the phenomenon that the reverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission. This is called delayed fluorescence in that long luminescence occurs. Since the delayed fluorescent material can use both fluorescence and phosphorescence, it can solve the problem of external quantum efficiency of the existing fluorescent material and can solve the price problem of the phosphorescent material in that it does not need to include 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, to provide a compound represented by the formula (1).

[Formula 1]

In Chemical 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 groups; Alkenyl group; Haloalkoxy groups; 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 combine with each other to form an aromatic ring,

R1 to R8 and R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

n is 1 or 2,

When n is 2, structures in a 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 rest 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 an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.

The organic light emitting diode including the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can improve the efficiency, improve the low driving voltage and / or life characteristics.

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

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

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

Since the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification combines two cyano groups in an ortho position around a benzene core, the light emitting of a specific wavelength region emits light, and the organic light emitting device including the same emits high efficiency. Has the characteristics of

In addition, since two carbazole derivatives and one or two aryl groups are combined based on the benzene core of Chemical Formula 1 herein, the charge balance injected into the light emitting layer is controlled so that the organic light emitting device including the low driving voltage, efficiency and life It is possible to improve.

In the present specification, when a part is to “include” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substitution" 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 to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Cyano group; Nitro group; Imide group; Amide group; Carbonyl group; Ester groups; 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 alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy 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 substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group consisting of substituted or unsubstituted substituents, or having no substituents. For example, "a substituent having two or more substituents" 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 this specification, the number of carbon atoms of 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 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 this specification, the number of carbon atoms 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 oxygen of the ester group may be substituted with a straight chain, branched 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 straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specific examples are 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 is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, 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, and the like. It is not.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but 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. It is not limited.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 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 is not limited thereto.

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

In the present specification, the N-aryl heteroarylamine group means 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, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the above-described 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, etc., and an alkyl sulfoxy group is methyl sulfoxy group, ethyl sulfoxyl group, propyl sulfoxyl group, and butyl There is a drinking time, but is not limited thereto.

In the present specification, the alkenyl group may be straight chain or branched chain, and carbon number 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 linear or branched alkyl group having 1 to 30 carbon atoms; 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 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, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 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. 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, phenenyl group, perylene 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 combine with each other to form a ring.

,

,

,

,

및

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

,

,

,

,

And

It can be back. However, it is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring 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 aryl sulfoxy group, the N-aryl alkylamine group, the N-aryl heteroarylamine group, and the arylphosphine group are the same as those of the above-described aryl group. Specifically, aryloxy groups include phenoxy group, p-toryloxy group, m-toryloxy 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, 9-phenanthryloxy group, and the like, and arylthioxy groups are phenylthioxy groups, 2- Methylphenyl thioxy group, 4-tert-butylphenyl thioxy group, and the like, but aryl sulfoxy group includes benzene sulfoxy group, 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 including 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 can be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more non-carbon atoms and heteroatoms, and specifically, the heteroatoms 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, and 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, pyrrol group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Sleepy group, acridil group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyridopyrimidyl 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, pe Nanthrolyl group (phenanthroline), isooxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group, 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 simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl groups described above.

In the present specification, examples of the heteroaryl group in the N-aryl heteroarylamine 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 a substituted or unsubstituted hetero ring.

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

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 is a non-carbon atom, and contains one or more heteroatoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocyclic ring may be monocyclic or polycyclic, aromatic, aliphatic or aromatic and aliphatic condensed ring, 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, the formula 1 is represented by the following formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

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

A11 to A15 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl groups; Alkenyl group; Haloalkoxy groups; 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 combine with each other to form an aromatic ring.

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

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

According to one embodiment of the present specification, in Chemical 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 the general 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 the general 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 the formula 1, any one of R2 and R3 is a substituted or unsubstituted aryl group, the rest is a substituted or unsubstituted alkyl group, R2 and R3 are bonded to each other or substituted or To form an unsubstituted hydrocarbon ring.

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

According to the exemplary embodiment of the present specification, in Chemical 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 the formula 1, R3 is a phenyl group, R2 is an isopropyl group, 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 the 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 the formula 1, R6 and R7 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 the 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 the 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 the 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 the formula 1, any one of R6 and R7 is a substituted or unsubstituted aryl group, the rest is a substituted or unsubstituted alkyl group, R6 and R7 are bonded to each other or substituted To form an unsubstituted hydrocarbon ring.

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

According to the exemplary embodiment of the present specification, in Chemical 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 the formula 1, R6 is a phenyl group, R7 is an isopropyl group, 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 the formula 1, R12 and R13 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present specification, in Chemical 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 the formula 1, R12 and R13 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 the formula 1, R12 and R13 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 the 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 the general formula 1, any one of R12 and R13 is a substituted or unsubstituted aryl group, the rest is a substituted or unsubstituted alkyl group, R12 and R13 are bonded to each other or substituted or To form an unsubstituted hydrocarbon ring.

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

According to the exemplary embodiment of the present specification, in Chemical 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 the formula 1, R13 is a phenyl group, R12 is an isopropyl group, 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 specification, in Chemical 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 the 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 the formula 1, R16 and R17 are bonded to each other to form an aromatic ring substituted with one or more alkyl groups.

According to one embodiment of the present specification, in Chemical 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 the 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 the general formula 1, any one of R16 and R17 is a substituted or unsubstituted aryl group, the rest is a substituted or unsubstituted alkyl group, R16 and R17 are bonded to each other or substituted To form an unsubstituted hydrocarbon ring.

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

According to the exemplary embodiment of the present specification, in Chemical 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 the formula 1, R16 is a phenyl group, R17 is an isopropyl group, 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 groups; Alkenyl group; Haloalkoxy groups; 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; A phenyl group unsubstituted or substituted with a fluorine, cyano group, trifluoromethyl group, methyl group, or trifluoromethoxy group; Or a carbazolyl group.

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

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

According to one embodiment of the present specification, adjacent groups among A11 to A15 combine with each other to form an aromatic ring.

According to one embodiment of the present specification, adjacent groups among A11 to A15 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 are bonded to 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with 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 combine with each other to form a benzene ring.

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

According to one 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 rest is hydrogen.

According to an exemplary embodiment of the present specification, the 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 a typical organic light emitting device, the number of excitons generated in singlet and triplet is generated at a ratio of 25:75 (single term: triplet), and fluorescent emission, phosphorescence emission and thermal activation delayed fluorescence depending on the light emission type according to exciton movement It can be divided into luminescence. In the case of the phosphorescence emission, it means that the exciton of the triplet excited state moves to the ground state to emit light, and in the case of the fluorescent emission, the exciton of the singlet excited state is the ground state ( It means that it moves to the ground state to emit light, and the thermally activated delayed fluorescence emission reverses the transition from the triplet excited state to the singlet excited state, and the singlet excited state. It means that the exciton moves to the ground state and causes 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 _{1 It} is different from phosphorescence in that it differs as much as the difference in 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 an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.

According to the exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer 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 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 device 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, may further include another organic material layer.

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

According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant in the light emitting layer.

According to an exemplary embodiment of the present specification, the maximum emission wavelength of the dopant is 450nm to 495nm.

According to an 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 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 receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, wherein the light-emitting layer is a light emitting layer It contains as a dopant, and at least one of the excitation singlet energy and the triplet excitation energy has a higher value than the light emitting material of the compound, has hole transport ability, electron transport ability, and also prevents long wavelength emission of light emission, An organic compound having a high glass transition temperature may be included as a host.

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

According to an exemplary embodiment of the present specification, the organic material 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 an exemplary embodiment of the present specification, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluorene derivatives, fluoranthene compounds, etc., as heterocyclic compounds Is a carbazole derivative, dibenzofuran derivative, ladder-type furan compound, pyrimidine derivative, and the like, but is not limited thereto.

According to an 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 a light emitting layer, the light emitting layer includes a compound represented by the formula (1) as a dopant of the light emitting layer, any one or more selected from condensed aromatic ring derivatives and heterocyclic compounds It contains as a host of a light emitting layer.

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

According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes at least one selected from a dopant containing the compound represented by Chemical Formula 1 and the condensed aromatic ring derivative and a heterocyclic compound. The containing host 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 that the compound of the present specification, that is, the compound represented by Formula 1, is used as a dopant in the light emitting 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 can 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: Physical Vapor Deposition), such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), by depositing a metal or conductive metal oxide or alloys thereof on the substrate It can be produced by forming a first electrode, and then forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, and then depositing a material that can be used as a second electrode thereon. In addition to this method, an organic light emitting device may be formed 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 Chemical Formula 1 may be formed into 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

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.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode 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; A multilayer structure material such as LiF/Al or LiO ₂ /Al, Mg/Ag, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based , Organic anthraquinone and 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 light emitting layer. As the hole transport material, the hole is transported from the anode or the hole injection layer to the hole and is transported 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, 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 light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including 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 followed by an aluminum layer or a silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or silver layer.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, 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-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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

[Example]

[Production Example 1]

end. Preparation of compound P2

Under nitrogen conditions, 27.2 g of 1,6-dibromo-3,4-difluorobenzene (P1) and 24 g of trimethylsilylchloride (TMSCl) were mixed with 200 ml of tetrahydrofuran (THF) and cooled to -78°C. . Next, 220 ml 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, the mixture was extracted with 3% dilute hydrochloric acid and dichloromethane, dried over anhydrous sodium sulfate, and filtered. Dichloromethane was distilled 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 reaction was mixed in 1320 ml of chloroform, stirred for 30 minutes under nitrogen, and the temperature of the reactant 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, then raised 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. Recrystallization was carried out with ethanol and dried to obtain 32.2 g of solid compound P2.

I. Preparation of compound P3

Compound 2 (1,6-dibromo-3,4-difluoro-2,5-diiodobenzene) (26.18 g, 50 mmol), phenyl boronic acid (12.2 g, 100 mmol) tetrahydrofuran (THF) Dissolved in 800 ml. Sodium carbonate (Na ₂ CO ₃ ) 2M solution (500 mL), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ , 4.6g, 4mmol) was added thereto and refluxed for 12 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. After separating the toluene layer and drying with magnesium sulfate, the filtered filtrate was distilled under reduced pressure. The concentrated compound was separated by column chromatography with a solution of hexane and ethyl acetate mixed in a volume ratio of 8:1 to obtain 22.6 g of compound P3. After drying in a vacuum oven for 24 hours, the obtained solid had a peak at M/Z=422 by mass spectrum measurement.

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, copper cyanide (CuCN, 6 g, 67 mmol) was added and refluxed under nitrogen. After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted with water and ethyl acetate. After separating the ethyl acetate layer, the compound was concentrated by distillation under reduced pressure. Next, recrystallization with tetrahydrofuran yielded 12.2 g of compound P4. The peak was confirmed at M/Z=316 by mass spectrum measurement of the obtained solid.

la. Preparation of compound 1

9H-carbazole (2.8 g, 17 mmol), potassium carbonate (2.4 g, 17 mmol) and 40 ml of dimethyl sulfoxide were mixed and stirred at room temperature and nitrogen for 1 hour. Compound P4 (2.6 g, 8.3 mmol) was added to the reaction mixture and stirred at 50° C. for 12 hours. After cooling to room temperature, distilled water was added dropwise and filtered. After washing with distilled water, the obtained solid was dissolved in dichloromethane, and the organic layer was separated, dried over magnesium sulfate, filtered through silica gel, and concentrated. Recrystallization with dichloromethane and ethanol produced 1.8 g of Compound 1. The peak was confirmed by M/Z=610 by mass spectrum measurement of the obtained solid.

[Production Example 2]

Preparation of compound 2

3,6-dimethyl-9H-carbazole instead of 9H-carbazole was prepared in the same manner as in compound 1, except that 3.3 g and 17 mmol were used, to prepare 1.6 g of compound 2. The peak was confirmed at M/Z=666 by mass spectrum measurement of the obtained solid.

[Production Example 3]

Preparation of compound 3

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

[Production Example 4]

end. Preparation of compound P5

It was prepared in the same manner as in the synthesis of Compound P3, except that [1,1'-biphenyl]-2-yl boronic acid (19.8g, 100mmol) was used instead of phenyl boronic acid to prepare 19.4g of Compound P5. The obtained solid was confirmed to have a peak at M/Z=574 by mass spectrum measurement.

I. Preparation of compound P6

It was prepared by the same method as the synthesis of compound P4, except that P5 (19.1 g, 33.1 mmol) was used instead of P3 to obtain 10.0 g of compound P6. The peak was confirmed by M/Z=468 by mass spectrum measurement of the obtained solid.

All. Preparation of compound 4

It was prepared 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, and 1.0 g of Compound 4 was obtained. The peak was confirmed by M/Z=762 by mass spectrum measurement of the obtained solid.

[Production Example 5]

Preparation of compound 5

3,6-dimethyl-9H-carbazole instead of 9H-carbazole was prepared in the same manner as in compound 4, except that 3.3 g and 17 mmol were used, to prepare 1.6 g of compound 5. The peak was confirmed by M/Z=818 by mass spectrum measurement of the obtained solid.

[Production Example 6]

Preparation of compound 6

Prepared in the same manner as in Compound 4, except that 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole 4.8g, 17mmol was used instead of 9H-carbazole, and 1.4g. Compound 6 was prepared. The peak was confirmed by M/Z=994 by mass spectrum measurement of the obtained solid.

[Production Example 7]

end. Preparation of compound P7

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

I. Preparation of compound P8

It was prepared by the same method as the synthesis of compound P4, except that P7 (15.2 g, 33.1 mmol) was used instead of P3 to obtain 7.0 g of compound P8. The peak was confirmed by M/Z=352 by mass spectrum measurement of the obtained solid.

All. Preparation of compound 7

It was prepared by the same method as the synthesis of Compound 1, except that P8 (2.9 g, 8.3 mmol) was used instead of P4, to obtain 1.4 g of Compound 7. The peak was confirmed by M/Z=646 by mass spectrum measurement of the obtained solid.

[Production Example 8]

Preparation of compound 8

3,6-dimethyl-9H-carbazole instead of 9H-carbazole was prepared in the same manner as in the synthesis of compound 7, except that 3.3 g and 17 mmol were used to obtain 1.4 g of compound 8.

The peak was confirmed at M/Z=702 by mass spectrum measurement of the obtained solid.

[Production Example 9]

Preparation of compound 9

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

[Production Example 10]

end. Preparation of compound P9

Phenyl boronic acid was prepared in the same manner as compound P3 synthesis, except that (4-cyanophenyl)boronic acid (14.7 g, 100 mmol) was used instead, to prepare 17.4 g of compound P9. The obtained solid had a peak at M/Z=472 by mass spectrum measurement.

I. Preparation of compound P10

It was manufactured by the same method as the synthesis of compound P4, except that P9 (15.7 g, 33.1 mmol) was used instead of P3 to obtain 8.8 g of compound P10. The peak was confirmed by M/Z=366 by mass spectrum measurement of the obtained solid.

All. Preparation of compound 10

It was prepared 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 to obtain 1.4 g of Compound 10. The peak was confirmed by M/Z=660 by mass spectrum measurement of the obtained solid.

[Production Example 11]

Preparation of compound 11

3,6-dimethyl-9H-carbazole instead of 9H-carbazole was prepared in the same manner as in Compound 10, except that 3.3 g and 17 mmol were used, to prepare 1.6 g of Compound 11. The peak was confirmed at M/Z=716 by mass spectrum measurement of the obtained solid.

[Production Example 12]

Preparation of compound 12

Prepared in the same manner as Compound 10, except that 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole 4.8g, 17mmol was used instead of 9H-carbazole, 1.8g Compound 12 was prepared. The peak was confirmed at M/Z=892 by mass spectrum measurement of the obtained solid.

[Production Example 13]

end. Preparation of compound P11

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

I. Preparation of compound P12

It was manufactured by the same method as the synthesis of compound P4, except that P11 (15.7 g, 33.1 mmol) was used instead of P3 to obtain 8.6 g of compound P12. The peak was confirmed by M/Z=428 by mass spectrum measurement of the obtained solid.

All. Preparation of compound 13

It was prepared by the same method as the synthesis of Compound 1, except that P12 (3.6 g, 8.3 mmol) was used instead of P4 to obtain 1.4 g of Compound 13. The peak was confirmed by M/Z=722 by mass spectrum measurement of the obtained solid.

[Production Example 14]

Preparation of compound 14

3,6-dimethyl-9H-carbazole instead of 9H-carbazole was prepared in the same manner as in compound 13, except that 3.3 g and 17 mmol were used, to prepare 1.6 g of compound 14. The peak was confirmed by M/Z=778 by mass spectrum measurement of the obtained solid.

[Example 1]

Organic light emitting device manufacturing

First, a 40 mm × 40 mm × 0.5 mm thick glass substrate with an ITO electrode was subjected to ultrasonic cleaning for 5 minutes with isopropyl alcohol, acetone, or DI water, and then dried in an oven at 100°C. After the substrate was cleaned, the plasma was treated with O ₂ in a vacuum for 2 minutes and transferred to a deposition chamber to deposit other layers on top. The organic layer was deposited on the ITO of the 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 10nm/s.

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

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

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

4. Light 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 forming a CPL (capping layer), it was encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a drying box and subsequently encapsulated using UV cured epoxy and a moisture getter.

[Example 2]

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

[Example 3]

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

[Example 4]

An organic light-emitting device was manufactured using Compound 4 as the dopant for the emission layer.

[Example 5]

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

[Example 6]

An organic light-emitting device was manufactured using Compound 6 as the dopant for the emission layer.

[Example 7]

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

[Example 8]

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

[Example 9]

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

[Example 10]

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

[Example 11]

An organic light-emitting device was manufactured using Compound 14 as the dopant for the emission layer.

[Comparative Example 1]

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

[Comparative Example 2]

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

[Comparative Example 3]

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

[Comparative Example 4]

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

[Comparative Example 5]

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

[Comparative Example 6]

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

[Comparative Example 7]

An organic light emitting device was manufactured by using Compound D7 below instead of Compound 1 as a dopant in the light emitting layer.

[Comparative Example 8]

An organic light emitting device was manufactured by using Compound D8 below instead of Compound 1 as a dopant in the light emitting layer.

[Comparative Example 9]

An organic light-emitting device was manufactured using Compound D9 below instead of Compound 1 as a dopant in the emission layer.

[Comparative Example 10]

An organic light emitting device was manufactured by using Compound D10 below instead of Compound 1 as a dopant in the light emitting layer.

[Comparative Example 11]

An organic light emitting device was manufactured by using Compound D11 below instead of Compound 1 as a dopant in the light emitting layer.

[Comparative Example 12]

An organic light-emitting device was manufactured using Compound D12 below instead of Compound 1 as a dopant in the emission layer.

Physical properties were measured for the organic light emitting devices manufactured in Examples 1 to 11 and Comparative Examples 1 to 12, respectively, prepared by setting the thickness of the light-emitting layer doped with 10 wt% of the delayed fluorescent dopant to 35 nm. Device characteristics were evaluated at room temperature using a current source (KEITHLEY) and a photometer (PR 650). For each organic light emitting device, at a driving voltage (V), current efficiency (cd/A), power efficiency (lm/W), luminance (cd/m ² ), and luminance (cd/m ² ) measured at a current density of 10 μs/cm ² at 3000 nit The time until the brightness was reduced 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 3.8 54.4 45.0 5440 400 Example 2 2 4 50.8 39.9 5080 480 Example 3 3 4.4 53 37.9 5300 280 Example 4 4 4.6 62.6 42.8 6260 280 Example 5 5 4.2 55.8 41.8 5580 240 Example 6 6 4.6 55 37.6 5500 260 Example 7 8 4.8 59.4 38.9 5940 260 Example 8 9 4.2 58.8 44.0 5880 280 Example 9 10 4.4 60.4 43.1 6040 300 Example 10 13 4 56.4 44.3 5640 300 Example 11 14 4.2 56 41.9 5600 420 Comparative Example 1 D1 6.8 47 21.7 4700 110 Comparative Example 2 D2 6.2 42 21.3 4200 120 Comparative Example 3 D3 6 42.8 22.4 4280 120 Comparative Example 4 D4 8 32 12.6 3200 80 Comparative Example 5 D5 5.4 44.6 26.0 4460 120 Comparative Example 6 D6 5.6 45.2 25.4 4520 120 Comparative Example 7 D7 6.6 48.8 23.2 4880 160 Comparative Example 8 D8 6.4 48.6 23.9 4860 160 Comparative Example 9 D9 8 33.2 13.0 3320 100 Comparative Example 10 D10 8 33.6 13.2 3360 100 Comparative Example 11 D11 5.2 49.8 30.1 4980 140 Comparative Example 12 D12 5.2 49.6 30.0 4960 160

The devices of Examples 1 to 11 using the heterocyclic compound of the present invention have lower driving voltages, higher current efficiency, higher power efficiency, higher luminance, and higher life characteristics compared to those of Comparative Examples 1 to 12. .

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

Claims (14)

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

In Chemical 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 groups; Alkenyl group; Haloalkoxy groups; 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 combine with each other to form an aromatic ring,
R1 to R8 and R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
n is 1 or 2,
When n is 2, structures in a 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 rest is hydrogen. The method according to claim 1, wherein Formula 1 is a compound represented by the following Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,
The definitions of A1 to A5, R1 to R8 and R11 to R18 are the same as defined in Formula 1 above,
A11 to A15 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Haloalkyl group; Alkyl groups; Alkenyl group; Haloalkoxy groups; 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 combine with each other to form an aromatic ring. 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 a compound that is an alkyl group. The method according to claim 1, wherein R1 to R8 and R11 to R18 adjacent groups are bonded to each other to form a hydrocarbon ring substituted with an alkyl group. The method according to claim 1, wherein Formula 1 is a compound selected from the following compounds:

The method according to 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 layer of the organic material layer comprises the compound of any one of claims 1 to 6. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer contains the compound as a dopant in the light emitting layer. The organic light emitting diode of claim 9, wherein the maximum emission wavelength of the dopant is 450 nm to 495 nm. The organic light emitting device of claim 7, wherein the organic material 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. The method according to claim 11, The host is an organic light emitting device comprising any one or more selected from the following compounds:

The method according to claim 7, wherein the organic material layer includes a light emitting layer, the light emitting layer comprises the compound as a dopant in the light emitting layer, and one or more selected from condensed aromatic ring derivatives and heterocyclic compounds containing as a host of the light emitting layer Organic light emitting device. The method according to claim 13, The light emitting layer is an organic light emitting device comprising the dopant and the host in a weight ratio of 1: 99 to 50: 50.

Images