KR101941176B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present disclosure relates to compounds and organic electronic devices comprising them.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic electronic device including the compound.

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0089371 filed with the Korean Intellectual Property Office on Jul. 14, 2016, the entire contents of which are incorporated herein by reference.

The present disclosure relates to compounds and organic electronic devices comprising them.

A representative example of the organic electronic device is an organic light emitting device. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

The present specification intends to provide a compound and an organic electronic device including the same.

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

[Chemical Formula 1]

In Formula 1,

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 to R15 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; 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 alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The R1 to R4 may combine with adjacent groups to form a ring.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

The compound according to one embodiment of the present invention can be used in an organic electronic device including an organic light emitting device to lower the driving voltage of the organic electronic device.

In addition, the compound according to one embodiment of the present invention can be used in an organic electronic device including an organic light emitting device, thereby improving light efficiency.

In addition, the compound according to one embodiment of the present invention can be used in an organic electronic device including an organic light emitting device, so that the lifetime characteristics of the device can be improved by the thermal stability of the compound.

1 shows an organic light emitting device 10 according to an embodiment of the present invention.
2 shows an organic light emitting element 11 according to another embodiment of the present invention.

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

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

Examples of substituents herein are described below, but are not limited thereto.

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; Amide group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; An alkenyl group; Silyl group; Boron group; Phosphine oxide groups; An amine group; An arylamine group; An aryl group; And a heterocyclic group containing at least one of N, O, S, Se and Si atoms, or wherein at least two of the substituents exemplified above are substituted with a substituent to which they are connected, Quot; means < / RTI >

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50 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 in the imide group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the silyl group is a substituent group containing Si and the Si atom is directly connected as a radical and is represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , R ₂₀₁ to R ₂₀₃ are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. But is not limited thereto.

In the present specification, the boron group may be -BR ₂₀₄ R ₂₀₅ , wherein R ₂₀₄ and R ₂₀₅ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 50 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

,

,

,

,

,

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

,

,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heterocyclic group is a hetero atom and includes at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazine group, a pyrazine group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, , A benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthroline group, a pteridine group, a thiazolyl group , An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a dibenzofurane group, but the present invention is not limited thereto.

In the present specification, the heteroaryl group may be selected from the examples of the heterocyclic group except that it is aromatic, but is not limited thereto.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the adjacent groups bonded to each other to form a ring means that adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above , Monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

In the present specification, the amine group is represented by -NR ₂₀₆ R ₂₀₇ , R ₂₀₆ and R ₂₀₇ are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, A heterocyclic group, a heterocyclic group, and a heterocyclic group. Examples of the substituent include -NH ₂ , monoalkylamine group, dialkylamine group, N-alkylarylamine group, monoarylamine group, diarylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, A heteroarylamine group and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N- Naphthylphenylenediamine amine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenyltriphenylamine group, An o-phenylamine group, an oleylamine group, and an N-biphenylfluorenylamine group, but are not limited thereto.

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

In the present specification, the alkyl group in the alkylamine group, the N-alkylarylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group and the N-arylheteroarylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenyloxy group, 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group. Examples of the arylthioxy group include phenylthio group, 2 -Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzenesulfoxy group and a p-toluenesulfoxy group, but the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present disclosure, L is a direct bond.

In one embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, Lt; / RTI > is a substituted fluorenylene group.

In one embodiment of the present disclosure, L is a phenylene group.

In one embodiment of the present disclosure, L is a biphenylene group.

In one embodiment of the present disclosure, L is a terphenylene group.

In one embodiment of the present disclosure, L is a naphthylene group

In one embodiment of the present specification, L is a substituted or unsubstituted divalent heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, L represents a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted divalent quinine A substituted or unsubstituted divalent pyridopyrimidine group, a substituted or unsubstituted divalent pteridine group, a substituted or unsubstituted divalent pyridine ring, a substituted or unsubstituted divalent heterocyclic ring, A pyrazine group, or a substituted or unsubstituted divalent pyrazino pyrazine group.

In one embodiment of the present specification, L is an aryl group, or a divalent pyridine group substituted or unsubstituted with a heterocyclic group.

In one embodiment of the present specification, L is a divalent pyridine group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a divalent pyridine group.

In one embodiment of the present specification, L is a divalent pyrimidine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present invention, L is a divalent pyrimidine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a divalent pyrimidine group.

In one embodiment of the present specification, L is a divalent triazine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present invention, L is a divalent triazine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a bivalent triazine group.

In one embodiment of the present specification, L is a divalent quinazoline group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, L is a divalent quinazoline group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present disclosure, L is a divalent quinazoline group.

In one embodiment of the present specification, L is a divalent benzoquinazoline group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, L is a divalent benzoquinazoline group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present disclosure, L is a divalent benzoquinazoline group.

In one embodiment of the present specification, L is a divalent pyridopyrimidine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present invention, L is a divalent pyridopyrimidine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a divalent pyridopyrimidine group.

In one embodiment of the present specification, L is a divalent pyridine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, L is a divalent pyridine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a bivalent pyridyl group.

In one embodiment of the present specification, L is a divalent pyridopyrazine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present invention, L is a divalent pyridopyrazine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a divalent pyrido-pyrazine group.

In one embodiment of the present specification, L is a divalent pyrazino pyrazine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, L is a divalent pyrazino pyrazine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, L is a divalent pyrazino pyrazine group.

, 또는 치환 또는 비치환된 2가의

이다. In one embodiment of the present disclosure, L is a substituted or unsubstituted divalent , A substituted or unsubstituted divalent

, Or a substituted or unsubstituted divalent

to be.

이다.In one embodiment of the present disclosure, L is a divalent group wherein the aryl group is substituted or unsubstituted

to be.

이다.In one embodiment of the present specification, L represents a divalent group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted

to be.

이다.In one embodiment of the present disclosure, L is a divalent

to be.

이다.In one embodiment of the present disclosure, L is a divalent group wherein the aryl group is substituted or unsubstituted

to be.

이다.In one embodiment of the present specification, L represents a divalent group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted

to be.

이다.In one embodiment of the present disclosure, L is a divalent

to be.

이다.In one embodiment of the present disclosure, L is a divalent group wherein the aryl group is substituted or unsubstituted

to be.

이다.In one embodiment of the present specification, L represents a divalent group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted

to be.

이다.In one embodiment of the present disclosure, L is a divalent

to be.

In one embodiment of the present disclosure, Ar is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, Ar is hydrogen or deuterium.

In one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorene Nylon.

In one embodiment of the present specification, Ar is a phenyl group.

In one embodiment of the present specification, Ar is a biphenyl group.

In one embodiment of the present disclosure, Ar is a terphenyl group.

In one embodiment of the present specification, Ar is a naphthyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms.

In one embodiment of the present specification, Ar represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted di A substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted pyridopyrimidine group, Pteridine, a substituted or unsubstituted pyridopyrazine group, or a substituted or unsubstituted pyrazinopyrazine group.

In one embodiment of the present specification, Ar is a pyridine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a pyridine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyridine group.

In one embodiment of the present specification, Ar is a pyrimidine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a pyrimidine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyrimidine group.

In one embodiment of the present specification, Ar is a triazine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a triazine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a triazine group.

In one embodiment of the present specification, Ar is a carbazole group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a carbazole group.

In one embodiment of the present specification, Ar is a dibenzofurane group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a dibenzofurane group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a dibenzofurane group.

In one embodiment of the present specification, Ar is a dibenzothiophene group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a dibenzothiophene group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a dibenzothiophene group.

In one embodiment of the present specification, Ar is an alkyl group, an aryl group, or a quinazoline group substituted or unsubstituted with a heterocyclic group.

In one embodiment of the present specification, Ar is a quinazoline group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a quinazoline group.

In one embodiment of the present specification, Ar is a benzoquinazoline group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a benzoquinazoline group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a benzoquinazoline group.

In one embodiment of the present specification, Ar is a pyridopyrimidine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present invention, Ar is a pyridopyrimidine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyridopyrimidine group.

In one embodiment of the present specification, Ar is a pyridyl group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a pyridyl group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyridyl group.

In one embodiment of the present specification, Ar is a pyridopyrazine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a pyridopyrazine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyridopyrazine group.

In one embodiment of the present specification, Ar is a pyrazinopyrazine group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar is a pyrazinopyrazine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, or a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyrazinopyrazine group.

, 치환 또는 비치환된

, 또는 치환 또는 비치환된

이다. In one embodiment of the present disclosure, Ar is substituted or unsubstituted

, Substituted or unsubstituted

, Or a substituted or unsubstituted

to be.

이다.In one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group

to be.

이다.In one embodiment of the present specification, Ar represents a phenyl group, a biphenyl group, or a substituted or unsubstituted naphthyl group

to be.

이다.In one embodiment of the present disclosure, Ar < RTI ID = 0.0 >

to be.

이다.In one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group

to be.

이다.In one embodiment of the present specification, Ar represents a phenyl group, a biphenyl group, or a substituted or unsubstituted naphthyl group

to be.

이다.In one embodiment of the present disclosure, Ar < RTI ID = 0.0 >

to be.

이다.In one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group

to be.

이다.In one embodiment of the present specification, Ar represents a phenyl group, a biphenyl group, or a substituted or unsubstituted naphthyl group

to be.

이다.In one embodiment of the present disclosure, Ar < RTI ID = 0.0 >

to be.

In one embodiment of the present disclosure, R 1 to R 15 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; 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 alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, and R 1 to R 4 may bond to adjacent groups to form a ring.

In one embodiment of the present disclosure, R 1 to R 15 are each hydrogen.

In one embodiment of the present specification, R 1 and R 2 may combine with each other to form a ring.

In one embodiment of the present disclosure, R 2 and R 3 may combine with each other to form a ring.

In one embodiment of the present disclosure, R3 and R4 may combine with each other to form a ring.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4, L, Ar, and R 1 to R 15 are the same as defined in Chemical Formula 1 above.

In one embodiment of the present disclosure, R16 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; 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 alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, a is an integer of 1 to 4, and when a is 2 or more, two or more R16 are the same or different from each other.

In one embodiment of the present disclosure, R16 is hydrogen.

In one embodiment of the present invention, Formula 1 may be selected from the following compounds.

The compound according to one embodiment of the present specification can be produced by a production method described below. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

The compound represented by the formula (1) in the present specification can be prepared by Suzuki coupling, Buckwald-Hartwig coupling, Heck coupling or the like, but is not limited thereto.

For example, the compound represented by Formula 1 may have a core structure as shown in Formula 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art. A substituent may be connected as shown in the following general formula (1), but it is not limited thereto.

≪ General Formula 1 > - Preparation of Chemical Formula 1

The following general formula 2 can be prepared in the same manner as in the general formula 1, except that 1-bromo-2-chloronaphthalene is used instead of 1-bromo-2-chlorobenzene in the general formula 1. [

(2)

The following general formula 3 can be prepared in the same manner as in the general formula 1, except that 2,3-dibromonaphthalene is used instead of 1-bromo-2-chlorobenzene in the general formula 1. [

(3)

The following general formula 4 can be prepared in the same manner as in the general formula 1, except that 2-bromo-1-chloronaphthalene is used instead of 1-bromo-2-chlorobenzene in the general formula 1. [

[Chemical Formula 4]

Further, the present invention provides an organic electronic device comprising the above-mentioned compounds.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is understood that it may include other components as well, without departing from the other components unless specifically stated otherwise.

The organic material layer of the organic electronic device in this 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, as a typical example of the organic electronic device in this specification, an organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, have. However, the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.

According to one embodiment of the present invention, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphor device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, the organic light emitting device will be described.

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

In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 1 as a host of the light-emitting layer.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a phosphorescent host or a fluorescent host of the light emitting layer.

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

In one embodiment of the present invention, the organic material layer contains the compound represented by Formula 1 as a host in the light emitting layer, and includes an iridium complex as a dopant.

According to one embodiment of the present disclosure, the dopant may be selected from the following structures, but is not limited thereto.

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer or a hole injecting and transporting layer, and the hole injecting layer, the hole transporting layer, or the hole injecting and transporting layer includes the compound represented by Formula 1 .

In one embodiment of the present invention, the organic layer may include a plurality of hole transporting layers.

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously injecting and transporting electrons, and the electron transporting layer, the electron injecting layer, Include the above compounds.

In one embodiment of the present invention, the organic material layer may include a plurality of electron transporting layers.

In one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by the above formula (1).

In one embodiment of the present invention, the organic material layer includes a light emitting layer, a hole injecting layer, and a hole transporting layer. A hole injecting and transporting layer, an electron injecting layer, an electron transporting layer, an electron injecting and transporting layer, an electron blocking layer and a hole blocking layer.

In one embodiment of the present invention, the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. In one embodiment of the present invention, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the above compound. Specifically, in one embodiment of the present specification, the compound may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In addition, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

In one embodiment of the present invention, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to an organic material layer containing the compound.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

When the organic compound layer containing the compound of Formula 1 is an electron transporting layer, the electron transporting layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. According to an example, the electron transport layer containing the compound of Formula 1 may further include LiQ (Lithium Quinolate).

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

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

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

2 shows a structure in which a first electrode 30, a hole injecting layer 60, a hole transporting layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transporting layer 90, 100 and a second electrode 50 are sequentially laminated on a transparent substrate 100. In this case, 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compound.

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

 The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound, i.e., the compound represented by the above formula (1).

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the organic material layer, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

In another embodiment, the first electrode is a cathode and the second electrode is a cathode.

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

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

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder furan compounds , Pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and ferriflantene having an arylamine group. Examples of the styrylamine compound include substituted or unsubstituted Substituted arylamine in which at least one aryl vinyl group is substituted, wherein at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

In the present specification, when the compound represented by Chemical Formula 1 is included in an organic material layer other than the light emitting layer, or a further light emitting layer is provided, the light emitting material of the light emitting layer may be formed by transporting holes and electrons from the hole transporting layer and the electron transporting layer, As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

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

The electron blocking layer is a layer which can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material 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 a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

In one embodiment of the present invention, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The compound according to the present invention can act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors and the like. For example, the organic solar cell may include a cathode, an anode, and a photoactive layer disposed between the anode and the cathode, and the photoactive layer may include the compound.

Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples. However, the examples and comparative examples according to the present specification can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments and comparative examples. The examples and comparative examples provided herein are provided to more fully describe the present specification to those skilled in the art.

The compound represented by the formula (1) in the present specification can be prepared by Suzuki coupling, Buckwald-Hartwig coupling, Heck coupling or the like, but is not limited thereto.

< Manufacturing example >

< Manufacturing example  1 > - Preparation of Compound 1-1

1) Synthesis of Compound 1-d

5-bromo-11H-benzo [ a] carbazole 300.0 g (1.00 eq), (2-nitrophenyl) boronic acid 186.85 g (1.1 eq) and tetrakis (triphenyl phosphino) palladium _{(Pd (PPh 3) 4)} 11.75 (0.01 eq) were dissolved in 4.0 L of tetrahydrofuran (THF) and stirred. Then, 281.09 g (2.0 eq) of potassium carbonate (K ₂ CO ₃ ) was dissolved in 1.0 L of water and the mixture was refluxed and stirred. After 2 hours, when the reaction was completed, the organic layer was separated, and the solvent was removed by decompression. The product was completely dissolved in chloroform (CHCl ₃ ) and washed with water. The solution was concentrated under reduced pressure to about 50%, ethanol was added thereto, and crystals were dropped and filtered. Thereafter, purification was carried out using column chromatography to obtain 278.51 g (yield: 81%) of the compound 1-d.

MS: [M + H] &lt; ⁺ &gt; = 339

2) Synthesis of compound 1-c

A mixture of 30.0 g (1.0 eq) of compound 1-d, 26.06 g (1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine, bis (tri- tert- butylphosphine) palladium -Bu ₃ P) ₂ ) and 37.66 g (2.0 eq) of tripotassium phosphate (K ₃ PO ₄ ) were added to 300 mL of xylene and the mixture was refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. The xylene was removed by decompression, and the reaction mixture was completely dissolved in CHCl ₃ and washed with water. The reaction mixture was reduced in pressure to remove the solvent and purified by column chromatography to obtain 36.86 g Yield: 73%).

MS: [M + H] &lt; ⁺ &gt; = 570

3) Preparation of compound 1-b

36.86 g (1.0 eq) of the compound 1-c was dissolved in 200 mL of triethyl phosphite (P (OEt) ₃ ), refluxed and stirred. After 3 hours, when the reaction was completed, the solvent was removed by vacuum decompression to remove about 50% of the solvent and the crystals were dropped. After filtration, the solution was completely dissolved in ethyl acetate and washed with water. The solution was concentrated under reduced pressure at 70%, cooled, cooled, and filtered to obtain 26.43 g (yield 76%) of compound 1-b.

MS: [M + H] &lt; ⁺ &gt; = 538

4) Preparation of compound 1-a

Compound 1-b 26.43 g (1.0 eq ), 1-bromo-2-chlorobenzene 10.27 g (1.1 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) and sodium -tert- butoxide (NaOtBu) 9.45 g (2.0 eq)) were placed in 200 mL of xylene, refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. After removing the xylene by decompression, the reaction mixture was completely dissolved in CHCl ₃ and washed with water. The reaction mixture was reduced in pressure to remove the solvent and purified by column chromatography to obtain 22.60 g Yield: 71%).

MS: [M + H] &lt; ⁺ &gt; = 648

4) Preparation of Compound 1-1

22.08 g (1.0 eq) of formula (1-a), Pd (t-Bu ₃ P) ₂ 0.17 g (0.01 eq) of K ₃ PO _{4 and} 14.48 g (2.0 eq) of K ₃ PO ₄ were added to 200 mL of dimethylacetamide (DMAC), and the mixture was refluxed and stirred. After 3 hours, the reaction mixture was cooled to room temperature, poured into water, and crystals were dropped and filtered. The filtered crystals were completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent, which was purified by column chromatography to obtain 14.17 g (yield 68%) of Compound 1-1.

MS: [M + H] &lt; ⁺ &gt; = 612

< Manufacturing example  2 > - Preparation of Compound 1-2

Except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 1 , Compound 1-2 was prepared in the same manner as in Preparation Example 1,

MS: [M + H] &lt; ⁺ &gt; = 688

< Manufacturing example  3 > - Preparation of Compound 1-3

Except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine was used in place of 2-chloro-4,6-diphenyl-1,3,5- , Compound 1-3 was prepared in the same manner as in Preparation Example 1,

MS: [M + H] &lt; ⁺ &gt; = 641

< Manufacturing example  4> - Preparation of compounds 1-4

Preparation Example 1 was repeated except that 2-chloro-4-phenylbenzofuro [3,2-d] pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5- Compounds 1-4 were prepared in the same manner.

MS: [M + H] &lt; ⁺ &gt; = 625

< Manufacturing example  5> - Preparation of compounds 1-5

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline was used in place of 2-chloro-4,6-diphenyl-1,3,5- Compound 1-5 was prepared in the same manner as in Preparation Example 1,

MS: [M + H] &lt; ⁺ &gt; = 661

< Manufacturing example  6> - Preparation of Compound 1-6

Except that 3- (2-chloroquinazolin-4-yl) -9-phenyl-9H-carbazole was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 1 Compound 1-6 was prepared in the same manner as in Preparation Example 1.

MS: [M + H] &lt; ⁺ &gt; = 750

< Manufacturing example  7> - Preparation of Compound 2-1

1) Synthesis of compound 2-c

Compound 1-d 30.0 g (1.0 eq ), 2-chloro-3- (naphthalen-2-yl) quinoxaline 28.31 g (1.1 eq), Pd (t-Bu 3 P) 2 0.23 g (0.005 eq) of K ₃ PO _{4 and} 37.66 g (2.0 eq) of K ₃ PO _{4 were} placed in 300 mL of xylene, refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. The xylene was removed by decompression, and the reaction mixture was completely dissolved in CHCl _{3. The} reaction mixture was washed with water and then decompressed to remove the solvent. The residue was purified by column chromatography to obtain 36.78 g Yield: 70%).

MS: [M + H] &lt; ⁺ &gt; = 593

2) Preparation of compound 2-b

36.78 g (1.0 eq) of the compound 2-c was dissolved in 200 mL of triethyl phosphite (P (OEt) ₃ ), refluxed and stirred. After 3 hours, when the reaction was completed, the solvent was removed by vacuum decompression to remove about 50% of the solvent and the crystals were dropped. After filtration, the solution was completely dissolved in ethyl acetate and washed with water. The solution was concentrated under reduced pressure at 70%, cooled, cooled, and filtered to obtain 25.05 g (yield 72%) of the compound 2-b.

MS: [M + H] &lt; ⁺ &gt; = 561

3) Preparation of compound 2-a

Compound 2-b 25.05 g (1.0 eq ), 1-bromo-2-chloronaphthalene 11.80 g (1.1 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) of NaOtBu and 8.59 g (2.0 eq) of NaOtBu were placed in 200 mL of xylene and refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. Xylene was removed by decompression, and the reaction mixture was completely dissolved in CHCl ₃ and washed with water. The reaction mixture was reduced in pressure to remove the solvent. Yield: 67%).

MS: [M + H] &lt; ⁺ &gt; = 721

4) Preparation of Compound 2-1

21.57 g (1.0 eq) of compound 2-a, Pd (t-Bu ₃ P) ₂ 0.17 g (0.01 eq) of K ₃ PO _{4 and} 12.71 g (2.0 eq) of K ₃ PO ₄ were added to 200 mL of DMAC, and the mixture was refluxed and stirred. After 3 hours, the reaction mixture was cooled to room temperature, poured into water, and crystals were dropped and filtered. The filtered crystals were completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent, which was purified by column chromatography to obtain 12.50 g (yield: 61%) of Compound 2-1.

MS: [M + H] &lt; ⁺ &gt; = 689

< Manufacturing example  8 > - Preparation of compound 2-2

Except that 2-chloro-4-phenylpyrido [2,3-d] pyrimidine was used in place of 2-chloro-3- (naphthalen-2-yl) quinoxaline in Preparation Example 7 Compound 2-2 was prepared.

MS: [M + H] &lt; ⁺ &gt; = 636

< Manufacturing example  9> - Preparation of Compound 3-1

1) Synthesis of compound 3-c

Compound 1-d 30.0 g (1.0 eq ), 4-chloro-2-phenylquinazoline 23.42 g (1.1 eq), Pd (t-Bu 3 P) 2 0.23 g (0.005 eq) of K ₃ PO _{4 and} 37.66 g (2.0 eq) of K ₃ PO _{4 were} placed in 300 mL of xylene, refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. The xylene was removed by decompression, and the reaction mixture was completely dissolved in CHCl _{3. The} reaction mixture was washed with water and then decompressed to remove the solvent. The residue was purified by column chromatography to obtain 34.63 g Yield: 72%).

MS: [M + H] &lt; ⁺ &gt; = 543

2) Preparation of compound 3-b

34.63 g (1.0 eq) of the compound 3-c was dissolved in 200 mL of triethyl phosphite (P (OEt) ₃ ), refluxed and stirred. After 3 hours, when the reaction was completed, the solvent was removed by vacuum decompression to remove about 50% of the solvent and the crystals were dropped. After filtration, the solution was completely dissolved in ethyl acetate and washed with water. The solution was concentrated under reduced pressure at 70%, cooled, cooled, and filtered to obtain 22.48 g of compound 3-b (yield 69%).

MS: [M + H] &lt; ⁺ &gt; = 511

3) Preparation of compound 3-a

Compound 3-b 22.48 g (1.0 eq ), 2,3-dibromonaphthalene 13.75 g (1.1 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) and NaOtBu 8.46 g (2.0 eq) 200 mL of Xylene And the mixture was refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. After removing the xylene by decompression, the reaction mixture was completely dissolved in CHCl ₃ and washed with water. The solvent was removed under reduced pressure to obtain 23.28 g Yield: 74%).

MS: [M + H] &lt; ⁺ &gt; = 715

4) Preparation of Compound 3-1

23.28 g (1.0 eq) of the compound 3-a, Pd (t-Bu ₃ P) ₂ 0.17 g (0.01 eq) of K ₃ PO _{4 and} 13.83 g (2.0 eq) of K ₃ PO ₄ were added to 200 mL of DMAC, and the mixture was refluxed and stirred. After 3 hours, the reaction mixture was cooled to room temperature, poured into water, and crystals were dropped and filtered. The obtained crystals were completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. This was purified by column chromatography to obtain 13.43 g (yield 65%) of Compound 3-1.

MS: [M + H] &lt; ⁺ &gt; = 635

< Manufacturing example  10> - Preparation of Compound 3-2

Compound 3-2 was prepared in the same manner as in PREPARATION 9, except that 2-chloro-4-phenylpyrido [3,2-d] pyrimidine was used in place of 4-chloro-2-phenylquinazoline .

MS: [M + H] &lt; ⁺ &gt; = 636

< Manufacturing example  11> - Preparation of Compound 4-1

1) Synthesis of compound 4-c

Compound 1-d 30.0 g (1.0 eq ), 2-chloro-4- (naphthalen-2-yl) quinazoline 28.31 g (1.1 eq), Pd (t-Bu 3 P) 2 0.23 g (0.005 eq) of K ₃ PO _{4 and} 37.66 g (2.0 eq) of K ₃ PO _{4 were} placed in 300 mL of xylene, refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature. After the reaction was completed, the reaction mixture was cooled to room temperature, and the xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure to obtain 39.40 g Yield: 75%).

MS: [M + H] &lt; ⁺ &gt; = 593

2) Preparation of compound 4-b

39.40 g (1.0 eq) of the compound 4-c was dissolved in 200 mL of triethyl phosphite (P (OEt) ₃ ), refluxed and stirred. After 3 hours, when the reaction was completed, the solvent was removed by vacuum decompression to remove about 50% of the solvent and the crystals were dropped. After filtration, the solution was completely dissolved in ethyl acetate and then washed with water. The solution was concentrated under reduced pressure at 70%, cooled, cooled, and filtered to obtain 26.09 g (yield 70%) of compound 4-b.

MS: [M + H] &lt; ⁺ &gt; = 561

3) Preparation of compound 4-a

Compound 4-b 26.09 g (1.0 eq ), 2-bromo-1-chloronaphthalene 12.29 g (1.1 eq), Pd (t-Bu 3 P) 2 0.13 g (0.005 eq) of NaOtBu and 8.95 g (2.0 eq) of NaOtBu were placed in 200 mL of xylene, refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was cooled to room temperature. The xylene was removed by decompression, and the reaction mixture was completely dissolved in CHCl _{3. The} reaction mixture was washed with water and then decompressed to remove the solvent. The product was purified by column chromatography to obtain 21.46 g Yield: 64%).

MS: [M + H] &lt; ⁺ &gt; = 721

4) Preparation of compound 4-1

Compound 4-a 21.46 g (1.0 eq ), Pd (t-Bu 3 P) 2 0.17 g (0.01 eq) of K ₃ PO _{4 and} 12.64 g (2.0 eq) of K ₃ PO ₄ were added to 200 mL of DMAC, and the mixture was refluxed and stirred. After 3 hours, the reaction mixture was cooled to room temperature, poured into water, and crystals were dropped and filtered. The filtered crystals were completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent, which was purified by column chromatography to obtain 13.25 g (yield 65%) of Compound 4-1.

MS: [M + H] &lt; ⁺ &gt; = 685

< Manufacturing example  12> - Preparation of compound 4-2

Except that 4- (4-chloronaphthalen-1-yl) -2- (naphthalen-2-yl) quinazoline was used in place of 2-chloro-4- (naphthalen- Compound 4-2 was prepared in the same manner as in Production Example 11.

MS: [M + H] &lt; ⁺ &gt; = 711

< Manufacturing example  13> - Preparation of compound 4-3

Except that 2-chloro-4-phenylbenzo [h] quinazoline was used in place of 2-chloro-4- (naphthalen-2-yl) quinazoline in Preparation Example 11, .

MS: [M + H] &lt; ⁺ &gt; = 685

< Example >

< Example 1 >

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HAT-CN compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 500 Å to form a hole injection layer. The HT1 compound shown below was thermally vacuum deposited to a thickness of 800 Å on the hole injection layer, and the HT2 compound was sequentially vacuum deposited to a thickness of 500 Å to form a hole transport layer. The compound 1-1 prepared in Preparation Example 1 and the following dopant Dp-7 compound were vacuum-deposited as a host in the light emitting layer to a thickness of 300 Å. The amount of the dopant was 3 wt% based on the total amount of the host and the dopant. An ET-1 material was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer. An ET-2 material and LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron transporting layer of 250 ANGSTROM . Lithium fulleride (LiF) was sequentially deposited on the electron transporting layer to a thickness of 10 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode. The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 X 10 &lt; ^-8 &gt; torr.

< Example  2>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-2 was used instead of Compound 1-1 in Example 1.

< Example  3>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-3 was used instead of Compound 1-1 in Example 1.

< Example  4>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-4 was used instead of Compound 1-1 in Example 1.

< Example  5>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 1-5 was used instead of Compound 1-1 in Example 1.

< Example  6>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound 1-6 was used in place of the compound 1-1 in Example 1.

< Example  7>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 2-1 was used instead of Compound 1-1 in Example 1.

< Example  8>

An organic light emitting device was prepared in the same manner as in Example 1 except that the compound 2-2 was used instead of the compound 1-1 in Example 1.

< Example  9>

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 3-1 was used instead of Compound 1-1 in Example 1.

< Example  10>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 3-2 was used instead of Compound 1-1 in Example 1.

< Example  11>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 4-1 was used instead of Compound 1-1 in Example 1.

< Example  12>

An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 4-2 was used instead of Compound 1-1 in Example 1.

< Example  13>

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 4-3 was used instead of Compound 1-1 in Example 1.

< Comparative Example  1>

An organic light emitting device was fabricated in the same manner as in Example 1, except that H-1 was used instead of Compound 1-1 in Example 1.

< Comparative Example  2>

An organic light emitting device was fabricated in the same manner as in Example 1, except that H-2 was used instead of Compound 1-1 in Example 1.

< Comparative Example  3>

An organic light emitting device was fabricated in the same manner as in Example 1, except that H-3 was used instead of Compound 1-1 in Example 1.

The Examples 1 to 13 and Comparative Example 1 was an organic light emitting device produced by the 1-3 measurement of driving voltage and luminous efficiency at a current density of 10 mA / cm ^2, the initial luminance compared to 98 at a current density of 20mA / cm ² % (T98) was measured. Further, the luminescent color was measured at a luminance of 5000 nit. The results are shown in Table 1 below.

division matter Driving voltage
(V) efficiency
(cd / A) Lifetime T98
(hr) Luminous color Example 1 Compound 1-1 3.9 38.8 97 Red Example 2 Compound 1-2 3.9 37.6 91 Red Example 3 Compound 1-3 3.8 36.5 105 Red Example 4 Compound 1-4 3.8 38.0 120 Red Example 5 Compound 1-5 4.2 33.2 108 Red Example 6 Compound 1-6 4.2 34.7 113 Red Example 7 Compound 2-1 4.1 33.8 103 Red Example 8 Compound 2-2 3.9 39.6 93 Red Example 9 Compound 3-1 4.0 39.1 110 Red Example 10 Compound 3-2 3.8 38.0 103 Red Example 11 Compound 4-1 4.1 33.5 117 Red Example 12 Compound 4-2 3.9 37.3 61 Red Example 13 Compound 4-3 3.8 39.7 61 Red Comparative Example 1 H-1 4.7 32.3 71 Red Comparative Example 2 H-2 4.3 35.6 49 Red Comparative Example 3 H-3 4.4 34.3 40 Red

The organic light emitting device manufactured using the compound represented by Chemical Formula 1 as the light emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Specifically, the compound represented by the formula (1) of the present invention is more stable than the H-1 to H-3 of the comparative examples 1 to 3 by condensing the benzene ring bonded to N, Can be widely spread. This has the advantage that the hole transport can be well transferred to the host material since the energy level can be adjusted to a level similar to that of the hole transport layer.

Therefore, as can be seen from the results of Table 1, the organic light emitting device using the compound represented by Formula 1 of the present invention as the light emitting layer improved the light emitting efficiency while lowering the driving voltage, and all emitted red light. In addition, it was confirmed that the life span increased more than twice as compared with Comparative Examples 1 to 3.

While the present invention has been described with reference to the preferred embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. Category.

10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer

Claims (10)

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

In Formula 1,
L is a direct bond; An unsubstituted arylene group having 6 to 30 carbon atoms; Or an N-containing bivalent heterocyclic group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms and having 2 to 40 carbon atoms,
Ar is an unsubstituted aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 50 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms,
R1 to R4 are hydrogen or combine with adjacent groups to form a benzene ring,
R5 to R15 are hydrogen. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2 to 4:
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
L, Ar, and R1 to R15 are the same as defined in Formula 1,
R16 is hydrogen.
a is an integer of 1 to 4; The compound according to claim 1, wherein the compound of formula (1) is selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 3. 4. The organic electronic device according to claim 1, Electronic device. 5. The organic electronic device according to claim 4, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. [4] The organic electronic device according to claim 4, wherein the organic compound layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, the hole transport layer or the hole injection and transport layer comprises the compound. 5. The organic electronic device according to claim 4, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer comprises the compound. 5. The organic electronic device according to claim 4, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound. 5. The organic electroluminescent device according to claim 4, wherein the organic electronic device is a light emitting layer, a hole injecting layer, and a hole transporting layer. A hole injection and transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron blocking layer and a hole blocking layer. 5. The organic electronic device according to claim 4, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphor device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.

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