KR101913504B1 - 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 Korean Patent Application No. 10-2016-0078245, filed on June 22, 2016, to the Korean Intellectual Property Office, 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 increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

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

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,

이고,At least one of R < 1 > to R < 8 > and R &

ego,

L, L 1, and L 2 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 and Ar2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

가 아닌 기, R9 내지 R12, R20 및 R21은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기고,Among said R1 to R8 and R13 to R19

, R9 to R12, R20 and R21 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; An amino 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 phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

는 연결되는 부위를 의미한다.

Refers to the connected area.

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 is used in an organic electronic device including an organic light emitting device to lower the driving voltage of the organic electronic device, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound. have.

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.
3 is an LC / MS spectrum of Compound 1. Fig.
4 is an LC / MS spectrum of Compound 4. FIG.
5 is an LC / MS spectrum of Compound 8. Fig.
6 is a graph showing an LC / MS spectrum of Compound 15. Fig.

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; An amino 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 heteroaryl 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 amino group of the amino group may be substituted with hydrogen, a straight chain, branched chain or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the 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. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, 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 30 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, 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, and 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 furan 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 pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, An oxadiazolyl group, a thiadiazolyl group, and a dibenzofuranyl 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.

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the condensation structure may be a structure in which an aromatic carbon-hydrogen bond is condensed with the substituent. For example, as a condensation ring of benzimidazole

,

,

,

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

As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted 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 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 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 the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

이다.In one embodiment of the present disclosure, at least one of Rl to R8 and R13 to R19 is

to be.

이다.In one embodiment of the present disclosure, R 2 and R 7 are

to be.

이다.In one embodiment of the present disclosure, R < 14 >

to be.

이다.In one embodiment of the present disclosure, R19 is

to be.

이다.In one embodiment of the present disclosure, R14 and R19 are

to be.

In one embodiment of the present specification, L, L 1 and L 2 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, 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 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted divalent fluorenyl group to be.

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

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

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

In one embodiment of the present invention, L is a divalent fluorenyl group.

In one embodiment of the present invention, L is a bivalent dimethylfluorenyl group.

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

In one embodiment of the present specification, L is a substituted or unsubstituted divalent dibenzofurane group, or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present invention, L is a divalent dibenzofurane group.

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

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present specification, L2 is a direct bond.

In one embodiment of the present invention, L1 and L2 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, Or a substituted or unsubstituted divalent fluorenyl group.

In one embodiment of the present invention, L1 is a phenylene group.

In one embodiment of the present invention, L1 is a biphenylene group.

In one embodiment of the present specification, L1 is a naphthylene group.

In one embodiment of the present invention, L1 is a divalent fluorenyl group.

In one embodiment of the present invention, L1 is a bivalent dimethylfluorenyl group.

In one embodiment of the present invention, L2 is a phenylene group.

In one embodiment of the present invention, L2 is a biphenylene group.

In one embodiment of the present specification, L2 is a naphthylene group.

In one embodiment of the present specification, L2 is a divalent fluorenyl group.

In one embodiment of the present invention, L2 is a divalent dimethylfluorenyl group

In one embodiment of the present invention, L 1 and L 2 are the same or different and each independently a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L 1 and L 2 are the same or different and are each independently a substituted or unsubstituted divalent dibenzofurane group, or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present invention, Ar1 and Ar2 are the same or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present invention, Ar1 and Ar2 are the same or different from each other and are each independently a halogen group.

In one embodiment of the present specification, Ar1 is boron.

In one embodiment of the present specification, Ar2 is boron.

In one embodiment of the present specification, Ar1 is a nitrile group.

In one embodiment of the present specification, Ar2 is a nitrile group.

In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present invention, Ar 1 and Ar 2 are the same or different from each other and each independently represents a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, Butyl group.

In one embodiment of the present invention, Ar1 is a methyl group.

In one embodiment of the present specification, Ar1 is an ethyl group.

In one embodiment of the present invention, Ar1 is an isopropyl group.

In one embodiment of the present specification, Ar1 is a tert-butyl group.

In one embodiment of the present specification, Ar2 is a methyl group.

In one embodiment of the present specification, Ar2 is an ethyl group.

In one embodiment of the present specification, Ar2 is an isopropyl group.

In one embodiment of the present specification, Ar2 is a tert-butyl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted alkoxy group.

In one embodiment of the present invention, Ar1 is an alkoxy group substituted or unsubstituted with a halogen group.

In one embodiment of the present specification, Ar1 is an alkoxy group substituted or unsubstituted with fluorine.

In one embodiment of the present specification, Ar1 is a methoxy group.

In one embodiment of the present specification, Ar1 is ethoxy group.

In one embodiment of the present specification, Ar2 is an alkoxy group substituted or unsubstituted with a halogen group.

In one embodiment of the present specification, Ar2 is an alkoxy group substituted or unsubstituted with fluorine.

In one embodiment of the present specification, Ar2 is a methoxy group.

In one embodiment of the present specification, Ar2 is ethoxy group.

In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted silyl group.

In one embodiment of the present specification, Ar1 is a silyl group substituted or unsubstituted with a methyl group.

In one embodiment of the present specification, Ar1 is a trimethylsilyl group.

In one embodiment of the present invention, Ar2 is a silyl group substituted or unsubstituted with a methyl group.

In one embodiment of the present specification, Ar2 is a trimethylsilyl group.

In one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In one embodiment of the present invention, Ar 1 and Ar 2 are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, A substituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar1 represents a hydrogen atom, a heavy hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a phenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar1 is a phenyl group.

In one embodiment of the present invention, Ar1 is a biphenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar1 represents a hydrogen atom, a heavy hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a biphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar1 is a biphenyl group.

In one embodiment of the present invention, Ar1 is a terphenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar1 represents a hydrogen atom, a heavy hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a terphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar1 is a terphenyl group.

In one embodiment of the present invention, Ar1 is a naphthyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar1 represents a hydrogen atom, a heavy hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a naphthyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar1 is a naphthyl group.

In one embodiment of the present invention, Ar1 is a fluorenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar1 represents a hydrogen atom, a heavy hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a fluorenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar1 is a fluorenyl group.

In one embodiment of the present specification, Ar1 is a dimethylfluorenyl group.

In one embodiment of the present invention, Ar1 is an indenofluorenyl group substituted with an alkyl group.

In one embodiment of the present invention, Ar2 is a phenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar2 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a phenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar2 is a phenyl group.

In one embodiment of the present invention, Ar2 is a biphenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar2 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a biphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar2 is a biphenyl group.

In one embodiment of the present invention, Ar2 is a terphenyl group substituted or unsubstituted with hydrogen, deuterium, halogen, nitrile, silyl, alkoxy, alkyl, aryl or heterocyclic.

In one embodiment of the present specification, Ar2 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a terphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar2 is a terphenyl group.

In one embodiment of the present invention, Ar2 is a naphthyl group substituted or unsubstituted with hydrogen, deuterium, halogen, nitrile, silyl, alkoxy, alkyl, aryl or heterocyclic group.

In one embodiment of the present specification, Ar2 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a naphthyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar2 is a naphthyl group.

In one embodiment of the present invention, Ar2 is a fluorenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar2 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a fluorenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar2 is a fluorenyl group.

In one embodiment of the present specification, Ar2 is a dimethylfluorenyl group.

In one embodiment of the present invention, Ar2 is an indenofluorenyl group substituted with an alkyl group.

In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted heterocyclic group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, An unsubstituted dibenzofurane group, a substituted or unsubstituted benzonaphthofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted benzonaphthothiophene group.

In one embodiment of the present specification, Ar1 is a pyridine group.

In one embodiment of the present specification, Ar1 is a dibenzofurane group.

In one embodiment of the present specification, Ar1 is a benzonaphthofuran group.

In one embodiment of the present specification, Ar1 is a dibenzothiophene group.

In one embodiment of the present specification, Ar1 is a benzonaphthothiophene group.

In one embodiment of the present specification, Ar2 is a pyridine group.

In one embodiment of the present specification, Ar2 is a dibenzofurane group.

In one embodiment of the present specification, Ar2 is a benzonaphthofuran group.

In one embodiment of the present specification, Ar2 is a dibenzothiophene group.

In one embodiment of the present specification, Ar2 is a benzonaphthothiophene group.

가 아닌 기 및 R7 내지 R21은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기다. In one embodiment of the present disclosure, any of R1 to R6

And R < 7 > to R < 21 > 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; An amino 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 phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocycle.

가 아닌 기 및 R7 내지 R21은 각각 수소이다. In one embodiment of the present disclosure, any of R1 to R6

And R < 7 > to R < 21 > are each hydrogen.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (5).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

L, L1, L2, and R1 to R21 are the same as defined in Formula 1,

L ', L3 and L4 are the same or different from each other, and each independently is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar3 and Ar4 are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, L ', L3 and L4 are the same or different from each other, and each independently is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, 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 invention, L 'is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted divalent fluorene Nylon.

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

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

In one embodiment of the present invention, L 'is a naphthylene group.

In one embodiment of the present invention, L 'is a bivalent fluorenyl group.

In one embodiment of the present invention, L 'is a divalent dimethylfluorenyl group.

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

In one embodiment of the present specification, L 'is a substituted or unsubstituted divalent dibenzofurane group, or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present invention, L 'is a divalent dibenzofurane group.

In one embodiment of the present specification, LL 'is a divalent dibenzothiophene group.

In one embodiment of the present specification, L3 is a direct bond.

In one embodiment of the present specification, L4 is a direct bond.

In one embodiment of the present invention, L3 and L4 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L3 and L4 are the same or different and each independently represent a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted divalent fluorenyl group.

In one embodiment of the present invention, L3 is a phenylene group.

In one embodiment of the present invention, L3 is a biphenylene group.

In one embodiment of the present invention, L3 is a naphthylene group.

In one embodiment of the present invention, L3 is a bivalent fluorenyl group.

In one embodiment of the present invention, L3 is a divalent dimethylfluorenyl group.

In one embodiment of the present invention, L4 is a phenylene group.

In one embodiment of the present invention, L4 is a biphenylene group.

In one embodiment of the present specification, L4 is a naphthylene group.

In one embodiment of the present invention, L4 is a bivalent fluorenyl group.

In one embodiment of the present invention, L4 is a divalent dimethylfluorenyl group

In one embodiment of the present invention, L3 and L4 are the same or different and each independently represent a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L3 and L4 are the same or different and each independently a substituted or unsubstituted divalent dibenzofurane group, or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile 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 silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present invention, Ar3 and Ar4 are the same or different and are each independently a halogen group.

In one embodiment of the present specification, Ar3 is boron.

In one embodiment of the present specification, Ar4 is boron.

In one embodiment of the present specification, Ar3 is a nitrile group.

In one embodiment of the present specification, Ar4 is a nitrile group.

In one embodiment of the present specification, Ar 3 and Ar 4 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present invention, Ar 3 and Ar 4 are the same or different from each other and each independently represents a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, Butyl group.

In one embodiment of the present specification, Ar3 is a methyl group.

In one embodiment of the present specification, Ar3 is an ethyl group.

In one embodiment of the present specification, Ar3 is an isopropyl group.

In one embodiment of the present specification, Ar3 is a tert-butyl group.

In one embodiment of the present specification, Ar4 is a methyl group.

In one embodiment of the present specification, Ar4 is an ethyl group.

In one embodiment of the present specification, Ar4 is an isopropyl group.

In one embodiment of the present specification, Ar4 is a tert-butyl group.

In one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently represents a substituted or unsubstituted alkoxy group.

In one embodiment of the present invention, Ar3 is an alkoxy group substituted or unsubstituted with a halogen group.

In one embodiment of the present invention, Ar3 is an alkoxy group substituted or unsubstituted with fluorine.

In one embodiment of the present specification, Ar3 is a methoxy group.

In one embodiment of the present specification, Ar3 is ethoxy group.

In one embodiment of the present invention, Ar4 is an alkoxy group substituted or unsubstituted with a halogen group.

In one embodiment of the present specification, Ar4 is an alkoxy group substituted or unsubstituted with fluorine.

In one embodiment of the present specification, Ar4 is a methoxy group.

In one embodiment of the present specification, Ar4 is ethoxy group.

In one embodiment of the present invention, Ar3 and Ar4 are the same or different and each independently a substituted or unsubstituted silyl group.

In one embodiment of the present specification, Ar3 is a silyl group substituted or unsubstituted with a methyl group.

In one embodiment of the present specification, Ar3 is a trimethylsilyl group.

In one embodiment of the present specification, Ar4 is a silyl group substituted or unsubstituted with a methyl group.

In one embodiment of the present invention, Ar4 is a trimethylsilyl group.

In one embodiment of the present invention, Ar 3 and Ar 4 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In one embodiment of the present invention, Ar 1 and Ar 2 are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, A substituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present invention, Ar3 is a phenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar3 is a group selected from the group consisting of hydrogen, deuterium, boron, nitrile group, trimethylsilyl group, methyl group, ethyl group, isopropyl group, tert- butyl group, trifluoromethyl group, A methoxy group, or a phenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar3 is a phenyl group.

In one embodiment of the present invention, Ar3 is a biphenyl group substituted or unsubstituted with hydrogen, deuterium, halogen, nitrile, silyl, alkoxy, alkyl, aryl or heterocyclic.

In one embodiment of the present specification, Ar3 is a group selected from the group consisting of hydrogen, deuterium, boron, nitrile group, trimethylsilyl group, methyl group, ethyl group, isopropyl group, tert- butyl group, trifluoromethyl group, A methoxy group, or a biphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar3 is a biphenyl group.

In one embodiment of the present invention, Ar3 is a terphenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar3 is a group selected from the group consisting of hydrogen, deuterium, boron, nitrile group, trimethylsilyl group, methyl group, ethyl group, isopropyl group, tert- butyl group, trifluoromethyl group, A methoxy group, or a terphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar3 is a terphenyl group.

In one embodiment of the present invention, Ar1 is a naphthyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar3 is a group selected from the group consisting of hydrogen, deuterium, boron, nitrile group, trimethylsilyl group, methyl group, ethyl group, isopropyl group, tert- butyl group, trifluoromethyl group, A methoxy group, or a naphthyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar3 is a naphthyl group.

In one embodiment of the present specification, Ar3 is a fluorenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar3 is a group selected from the group consisting of hydrogen, deuterium, boron, nitrile group, trimethylsilyl group, methyl group, ethyl group, isopropyl group, tert- butyl group, trifluoromethyl group, A methoxy group, or a fluorenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar3 is a fluorenyl group.

In one embodiment of the present invention, Ar3 is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar3 is an indenofluorenyl group substituted with an alkyl group.

In one embodiment of the present invention, Ar4 is a phenyl group substituted or unsubstituted with hydrogen, deuterium, halogen, nitrile, silyl, alkoxy, alkyl, aryl or heterocyclic.

In one embodiment of the present specification, Ar4 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a phenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar4 is a phenyl group.

In one embodiment of the present invention, Ar4 is a biphenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar4 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a biphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar4 is a biphenyl group.

In one embodiment of the present invention, Ar4 is a terphenyl group substituted or unsubstituted with hydrogen, deuterium, halogen, nitrile, silyl, alkoxy, alkyl, aryl or heterocyclic.

In one embodiment of the present specification, Ar4 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a terphenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar4 is a terphenyl group.

In one embodiment of the present invention, Ar4 is a naphthyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group or a heterocyclic group.

In one embodiment of the present specification, Ar4 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a naphthyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present specification, Ar4 is a naphthyl group.

In one embodiment of the present invention, Ar4 is a fluorenyl group substituted or unsubstituted with hydrogen, deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an alkyl group, an aryl group, or a heterocyclic group.

In one embodiment of the present specification, Ar4 represents a hydrogen atom, a hydrogen atom, a boron atom, a nitrile group, a trimethylsilyl group, a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a trifluoromethyl group, A methoxy group, or a fluorenyl group substituted or unsubstituted with an alkoxy group substituted with a trifluoromethyl group.

In one embodiment of the present invention, Ar4 is a fluorenyl group.

In one embodiment of the present invention, Ar4 is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar4 is an indenofluorenyl group substituted with an alkyl group.

In one embodiment of the present invention, Ar 3 and Ar 4 are the same or different and are each independently a substituted or unsubstituted heterocyclic group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar 3 and Ar 4 are the same or different from each other and each independently represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, An unsubstituted dibenzofurane group, a substituted or unsubstituted benzonaphthofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted benzonaphthothiophene group.

In one embodiment of the present specification, Ar3 is a pyridine group.

In one embodiment of the present specification, Ar3 is a dibenzofurane group.

In one embodiment of the present specification, Ar3 is a benzonaphthofuran group.

In one embodiment of the present specification, Ar3 is a dibenzothiophene group.

In one embodiment of the present specification, Ar3 is a benzonaphthothiophene group.

In one embodiment of the present specification, Ar4 is a pyridine group.

In one embodiment of the present specification, Ar4 is a dibenzofurane group.

In one embodiment of the present specification, Ar4 is a benzonaphthofuran group.

In one embodiment of the present specification, Ar4 is a dibenzothiophene group.

In one embodiment of the present specification, Ar4 is a benzonaphthothiophene group.

In one embodiment of the present specification, the compound may be any one 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.

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 to be understood that the component may include other components as well, without departing from the scope of the present invention.

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 representative example of the organic electronic device in this specification, an organic light emitting device has 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, . 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.

In one embodiment of the present invention, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound represented by the above 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 is a hole injection layer, a hole transport layer. A light emitting layer, an electron transporting layer, an electron injecting layer, an electron injecting and transporting layer, a hole blocking layer, and an electron 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 layer further includes a hole injection layer or a hole transport layer containing a compound having an arylamino group, a carbazolyl group or a benzocarbazolyl group in addition to the organic compound 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 arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

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 an 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.

May be prepared by using Suzuki coupling reaction, Buchwald-Hartwig coupling reaction, Heck coupling synthesis, etc., but the present invention is not limited thereto.

< Manufacturing example >

< Manufacturing example  a > - Preparation of compound a

1) Preparation of compound a-3

A mixture of 200.0 g (1.0 eq) of the starting material 4-iodo-9H-fluoren-9-one, 176.88 g (1.1 eq) of 1-bromo-9H- carbazole, and bis (tri-tert- butylphosphine) palladium 1.66 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ ) and 208.03 g (1.5 eq) of tripotassium phosphate (K ₃ PO ₄ ) were placed in 2000 mL of toluene and refluxed and stirred. After 7 hours, the reaction mixture was cooled to room temperature. Toluene was removed by reduced pressure, and the reaction mixture was completely dissolved in chloroform (CHCl ₃ ) and washed with water. The reaction mixture was reduced in pressure to remove the solvent and purified by column chromatography. 169.11 g (yield: 61%) was obtained.

MS: [M + H] &lt; ⁺ &gt; = 425

2) Preparation of compound a-2

169.11 g (1.0 eq) of a-3 and Pd (t-Bu ₃ P) ₂ 4.07 g (0.02 eq) of K ₂ CO _{3 and} 82.62 g (1.5 eq) of K ₂ CO ₃ were added to 2000 mL of DMAC, and the mixture was refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature. After the reaction was completed, DMAC 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 105.38 g Yield: 77%).

MS: [M + H] &lt; ⁺ &gt; = 344

3) Synthesis of compound a-1

90.0 g (1.0 eq) of 2-bromo-4,4'-dichloro-1,1'-biphenyl was dissolved in 700 mL of anhydrous tetrahydrofuran and then cooled to -78 ° C. 123.3 mL (1.0 eq) of n-butyllithium (2.5 M) was slowly added to the cooled solution and stirred at the same temperature for 30 minutes. 102.33 g (1.0 eq) of the compound a-2 was put into the above-mentioned mixture in a cooled state. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added and stirred. The mixture was extracted with ethyl acetate, which was treated with anhydrous magnesium sulfate, filtered and concentrated. An excessive amount of hexane and a small amount of ethyl acetate were added to the concentrated compound, which was stirred and filtered to obtain 136.74 g (yield: 81%) of the compound a-1.

2) Synthesis of compound a

136.74 g (1.0 eq) of the compound a-1 was diluted in 1000 mL of acetic acid, and then 3 mL of concentrated sulfuric acid was added and stirred for about 3 hours under reflux. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and purified by recrystallization with addition of ethyl acetate. The purified solid was filtered to obtain 116.58 g (yield 80%) of white compound a.

MS: [M + H] &lt; ⁺ &gt; = 549

< Manufacturing example  b > - Preparation of compound b

1) Preparation of compound b-1

4-iodo -9,9'- RY lobby [fluorene] 200.0 g (1.0 eq), 1- bromo-7-chloro -9H- carbazol 139.54 g (1.1 eq), Pd (t-Bu 3 P ) ₂ 1.15 g (0.005 eq) of K ₃ PO _{4 and} 143.97 g (1.5 eq) of K ₃ PO _{4 were} placed in 1200 mL of toluene, refluxed and stirred. After 7 hours, the reaction mixture was cooled to room temperature. Toluene was removed by decompression, and the reaction solution 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 180.24 g Yield: 67%).

MS: [M + H] &lt; ⁺ &gt; = 595

2) Preparation of compound b

Compound b-1 180.24 g (1.0 eq ), Pd (t-Bu 3 P) 2 3.09 g (0.02 eq) of K ₂ CO _{3 and} 62.80 g (1.5 eq) of K ₂ CO ₃ were added to 1500 mL of DMAC, and the mixture was refluxed and stirred. After 3 hours, the reaction mixture was cooled to room temperature, DMAC was removed by decompression, and the reaction mixture was completely dissolved in CHCl _{3. The} reaction mixture was washed with water and then reduced in pressure to remove the solvent. The product was purified by column chromatography to obtain 123.02 g (yield: 71% %).

MS: [M + H] &lt; ⁺ &gt; = 515

< Manufacturing example  c > - Preparation of compound c

Compound c was prepared in the same manner as in the above Production Example b, except that 1-bromo-2-chloro-9H-carbazole was used in place of 1-bromo-7-chloro-9H- .

< Manufacturing example  d > - Preparation of compound d

Bromo-2,7-dichloro-9H-carbazole was used in place of 1-bromo-7-chloro-9H-carbazole in the same manner as in the above Production Example b, d.

< Manufacturing example  1 > - Preparation of compound 1

Compound (c) (1.0 eq), 6,6,12,12-tetramethyl-N-phenyl-6,12-dihydroindeno [1,2- b] fluoren- ), Pd (t-Bu ₃ P) ₂ 0.05 g (0.005 eq) of NaOtBu and 2.80 g (1.5 eq) of NaOtBu were added to 100 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 reaction mixture was reduced in pressure to remove the solvent and purified by column chromatography to obtain 10.43 g %).

MS: [M + H] &lt; ⁺ &gt; = 880

< Manufacturing example  2 > - Preparation of compound 2

8.24 g (1.1 eq) of N, N'- (1,1'-biphenyl-4-yl) naphtho [2,3- b] benzofuran- t-Bu ₃ P) ₂ 0.05 g (0.005 eq) of NaOtBu and 2.80 g (1.5 eq) of NaOtBu were placed in 100 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 10.91 g %).

MS: [M + H] &lt; ⁺ &gt; = 864

< Manufacturing example  3> - Preparation of Compound 3

Compound b 10.0 g (1.0 eq), N- phenyl-naphtho [2,3-b] benzofuran-2-amine 6.62 g (1.1 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of NaOtBu and 2.80 g (1.5 eq) of NaOtBu were placed in 100 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. 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 9.64 g %).

MS: [M + H] &lt; ⁺ &gt; = 787

< Manufacturing example  4> - Preparation of compound 4

Compound b 10.0 g (1.0 eq), bis (9,9-dimethyl -9H- fluoren-2-yl) amine 8.59 g (1.1 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of NaOtBu and 2.80 g (1.5 eq) of NaOtBu were placed in 100 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 solvent was removed under reduced pressure to obtain 10.43 g %).

MS: [M + H] &lt; ⁺ &gt; = 880

< Manufacturing example  5> - Preparation of compound 5

Compound a 10.0 g (1.0 eq), bis (9,9-dimethyl -9H- fluoren-2-yl) amine 8.05 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 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 solvent was removed under reduced pressure to obtain 14.45 g %).

MS: [M + H] &lt; ⁺ &gt; = 1,279

< Manufacturing example  6> - Preparation of Compound 6

Compound a 10.0 g (1.0 eq), N- phenyl-naphtho [2,3-b] benzofuran-2-amine 6.20 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 mL of xylene, refluxed and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, and then 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 13.36 g %).

MS: [M + H] &lt; ⁺ &gt; = 1,095

< Manufacturing example  7> - Preparation of Compound 7

Compound d 10.0 g (1.0 eq), diphenylamine 6.78 g (2.2 eq), Pd (t-Bu ₃ P) ₂ 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 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 9.94 g %).

MS: [M + H] &lt; ⁺ &gt; = 815

< Manufacturing example  8> - Preparation of Compound 8

Compound d 10.0 g (1.0 eq), 4- (tert- butyl) -N- phenyl aniline 9.03 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) and NaOtBu 5.25 g (3.0 eq ) Was added to 100 mL of xylene, refluxed and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature, and then 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 11.82 g %).

MS: [M + H] &lt; ⁺ &gt; = 927

< Manufacturing example  9> - Preparation of Compound 9

Compound d 10.0 g (1.0 eq), bis (4- (tert- butyl) phenyl) amine 11.28 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) and NaOtBu 5.25 g (3.0 eq ) Was added to 100 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. 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 13.25 g %).

MS: [M + H] &lt; ⁺ &gt; = 1,039

< Manufacturing example  10> - Preparation of Compound 10

Compound d 10.0 g (1.0 eq), bis (4- (trimethylsilyl) phenyl) -amine 12.57 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 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 13.67 g %).

MS: [M + H] &lt; ⁺ &gt; = 1,103

< Manufacturing example  11> - Preparation of Compound 11

Compound d 10.0 g (1.0 eq), 9,9- dimethyl-phenyl -N- -9H- fluorene-2-amine 11.45 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 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 distilled off under reduced pressure to obtain 12.78 g %).

MS: [M + H] &lt; ⁺ &gt; = 977

< Manufacturing example  12> - Preparation of Compound 12

10.04 g (2.2 eq) of Pd (t-Bu ₃ P) ₂ (1.0 eq), N- (phenyl- 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 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. Xylene was removed by decompression, and the reaction mixture was completely dissolved in CHCl _{3. The} reaction mixture was washed with water and reduced in pressure to remove the solvent. The product was purified by column chromatography to obtain 12.28 g %).

MS: [M + H] &lt; ⁺ &gt; = 977

< Manufacturing example  13> - Preparation of Compound 13

14.49 g (2.2 eq) of Pd ((1 eq)), 10.0 g (1.0 eq) of compound d, t-Bu ₃ P) ₂ 0.05 g (0.005 eq) of NaOtBu and 5.25 g (3.0 eq) of NaOtBu were placed in 100 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 then the xylene was removed 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 13.54 g %).

MS: [M + H] &lt; ⁺ &gt; = 1,199

< Manufacturing example  14> - Preparation of Compound 14

Compound d 10.0 g (1.0 eq), di ([1,1'-biphenyl] -4-yl) -amine 12.89 g (2.2 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) and NaOtBu 5.25 g (3.0 eq) was added to 100 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 solvent was removed under reduced pressure to obtain 14.47 g (yield: 71% %).

MS: [M + H] &lt; ⁺ &gt; = 1,119

< Experimental Example 1 >

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 150 Å to form a hole injection layer. The following compound HT (1150 ANGSTROM), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the following compound EB was vacuum deposited on the hole transport layer to a thickness of 150 ANGSTROM to form an electron blocking layer. Subsequently, the following compounds BH and BD were vacuum deposited on the electron blocking layer at a weight ratio of 25: 1 at a thickness of 30 ANGSTROM to form a light emitting layer. The compound ET and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 360 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode. Was maintained at a vapor deposition rate of 0.4 to 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

<Experimental Example 1-1>

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

<Experimental Example 1-2>

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

<Experimental Example 1-3>

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

<Experimental Example 1-4>

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

<Experimental Example 1-5>

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

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 6 was used instead of Compound BD in Experimental Example 1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 7 was used instead of Compound BD in Experimental Example 1.

<Experimental Example 1-8>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 8 was used instead of the compound BD in Experimental Example 1.

<Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 9 was used instead of Compound BD in Experimental Example 1.

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 10 was used in place of Compound BD in Experimental Example 1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 11 was used instead of Compound BD in Experimental Example 1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 12 was used instead of Compound BD in Experimental Example 1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 13 was used instead of Compound BD in Experimental Example 1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 14 was used instead of Compound BD in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound B1 was used instead of the compound BD in Experimental Example 1.

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound B2 was used in place of the compound BD in Experimental Example 1.

&Lt; Comparative Example 3 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound B3 was used instead of Compound BD in Experimental Example 1.

&Lt; Comparative Example 4 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound B4 was used in place of Compound BD in Experimental Example 1.

The voltage, efficiency, color coordinate and lifetime of the organic light-emitting device fabricated according to Experimental Example 1, Experimental Examples 1-1 to 1-14 and Comparative Examples 1 to 4 were measured, and the results are shown in Table 1 ]. T95 means the time required for the luminance to be reduced to 95% of the initial luminance.

compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) T95
(hr) Experimental Example 1-1 BD 4.77 5.41 (0.144, 0.051) 205 Experimental Example 1-1 Compound 1 4.47 6.10 (0.141, 0.051) 250 Experimental Example 1-2 Compound 2 4.67 6.14 (0.140, 0.055) 275 Experimental Example 1-3 Compound 3 4.44 5.92 (0.142, 0.051) 253 Experimental Examples 1-4 Compound 4 4.43 6.45 (0.142, 0.051) 261 Experimental Examples 1-5 Compound 5 4.51 6.31 (0.143, 0.050) 255 Experimental Example 1-6 Compound 6 4.40 5.89 (0.140, 0.050) 255 Experimental Example 1-7 Compound 7 4.63 6.31 (0.143, 0.050) 267 Experimental Examples 1-8 Compound 8 4.59 6.38 (0.140, 0.051) 251 Experimental Examples 1-9 Compound 9 4.70 6.51 (0.142, 0.051) 230 Experimental Example 1-10 Compound 10 4.43 6.51 (0.142, 0.051) 260 Experimental Example 1-11 Compound 11 4.67 6.07 (0.140, 0.052) 251 Experimental Example 1-12 Compound 12 4.41 6.51 (0.140, 0.052) 254 Experimental Example 1-13 Compound 13 4.41 6.39 (0.141, 0.052) 251 Experimental Example 1-14 Compound 14 4.61 6.40 (0.142, 0.052) 253 Comparative Example 1 B1 5.35 4.21 (0.145, 0.051) 190 Comparative Example 2 B2 5.16 3.95 (0.146, 0.050) 184 Comparative Example 3 B3 5.27 4.27 (0.145, 0.051) 163 Comparative Example 4 B4 5.37 3.71 (0.146, 0.053) 177

As shown in Table 1, the organic light emitting device manufactured using the compound represented by Chemical Formula 1 as a blue dopant has characteristics of low voltage and high efficiency as compared with the compounds of Comparative Examples 1 to 4 have. In addition, it can be seen that the lifetime is increased by 10 to 50% or more as compared with the compounds of Comparative Examples 1 to 5.

Compared with the compounds represented by the general formula (1) of the present invention, the compounds of Comparative Examples 1 to 4 have low Tg and low luminous efficiency because the phenyl group bonded to the N of the core structure is inferior in structural flatness and rigidity. Therefore, it can be seen that the compound represented by the formula (1) is suitable as a blue light emitting material of an organic light emitting device.

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,
At least one of R &lt; 1 &gt; to R &lt; 8 &gt; and R &

ego,
L is independently a direct bond, L 1 and L 2 are the same or different and are each independently a direct bond; Or an arylene group,
Ar1 and Ar2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group; A cycloalkyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group; Silyl group; An aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, an alkyl group and a silyl group; Or a heterocyclic group,
Among said R1 to R8 and R13 to R19

, R9 to R12, R20 and R21 are the same or different from each other and each independently hydrogen; Or deuterium,

Refers to the connected area. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2 to 5:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
L, L 1, L 2, Ar 1, Ar 2, and R 1 to R 21 are the same as defined in Formula 1,
L 'is independently a direct bond, L3 and L4 are the same or different from each other, and each independently is a direct bond; Or an arylene group,
Ar3 and Ar4 are the same or different and are each independently hydrogen; heavy hydrogen; An alkyl group; A cycloalkyl group substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group; Silyl group; An aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, an alkyl group and a silyl group; Or a heterocyclic group. The compound according to claim 1, wherein the compound of formula (1) is any one 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. 5. The organic electronic device according to claim 4, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. 5. The organic electronic device according to claim 4, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection 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. An electron injection layer, an electron 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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