KR101896174B1 - 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. 10-2016-0015701 filed on Feb. 11, 2016, filed with 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,

R1 to R14 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a ring.

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

The compound according to one embodiment of the present invention 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.

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; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; An alkyl group; A cycloalkyl group; An amine group; Phosphine oxide groups; An aryl group; Silyl group; And a heterocyclic group containing at least one of N, O, S, Se and Si atoms, or wherein at least two of the substituents exemplified above are substituted with a substituent to which they are connected, Quot; means < / RTI >

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

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

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

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

In the present specification, the 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, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

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

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

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

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

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

,

,

,

,

,

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

,

,

,

,

,

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

In the present specification, the heterocyclic group is a hetero atom and includes at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heteroaryl group include a thiophene group, a furane group, a furyl 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.

As used herein, the term "adjacent group" means a group in which the substituent is substituted with an atom directly bonded to the atom to which the substituted atom is substituted, a substituent having the closest stereostructure to the substituent, It can mean. 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 ".

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

As used herein, the hydrocarbon ring or heterocycle may be selected from the examples of cycloalkyl, aryl or heteroaryl groups described above, except monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic, or a condensed form thereof Yes. But is not limited thereto.

), 하이드로나프탈렌(예컨대,

,

), 하이드로페난트렌(예컨대,

), 하이드로안트라센(예컨대,

), 하이드로벤조테트라센(예컨대,

)등이 있으나, 이에만 한정되는 것은 아니다.In the present specification, the aromatic and aliphatic condensation rings are hydrobenzoanthracene (for example,

), Hydro naphthalene (e.g.,

,

), Hydroperanthene (e.g.,

), Hydroanthracene (e.g.,

), Hydrobenzotetracene (e.g.,

), But the present invention is not limited thereto.

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

In the present specification, the 2- to 4-valent aromatic ring group may be monocyclic or polycyclic, meaning that the aryl group has 2 to 4 bonding positions, that is, 2 to 4 bonds. The description of the aryl group described above can be applied, except that these are each 2 to 4 groups.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent and is represented by -NR ₂₀₆ R ₂₀₇ , and R ₂₀₆ and R ₂₀₇ are the same or different from each other Each independently selected from the group consisting of 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 (provided that at least one of R ₂₀₆ and R ₂₀₇ is not hydrogen). For example, -NH ₂ ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. 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; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; An N-biphenylfluorenylamine group, and the like, 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, 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. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

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.

According to one embodiment of the present disclosure, R 1 to R 14 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a ring.

According to one embodiment of the present invention, R 1 to R 14 are the same or different and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, R1 to R14 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.

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently is a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

According to one embodiment of the present invention, R 1 to R 14 are the same or different and each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, R 1 to R 14 are the same or different and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted A substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently a phenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, A phenyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R 1 to R 14 are the same or different and each independently a biphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, A biphenyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R1 to R14 are the same or different and are each independently a terphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, Is a terphenyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present disclosure, R1 to R14 are the same or different and are each independently a triphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, A triphenyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R1 to R14 are the same or different and are each independently a naphthyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, A naphthyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R 1 to R 14 are the same or different and each independently a phenanthryl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, A phenanthryl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently an anthracenyl group substituted or unsubstituted with cyano group, alkyl group, aryl group, or heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, Anthracenyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently a fluorenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a phenyl group substituted with deuterium, cyano group, methyl group, ethyl group, phenyl group, cyano group, biphenyl group, naphthyl group, A fluorenyl group substituted or unsubstituted with a carbazole group, a dibenzocarbazole group, a dibenzothiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, R 1 to R 14 are the same or different and are each independently a substituted or unsubstituted heterocyclic group having 3 to 50 carbon atoms.

According to one embodiment of the present invention, R 1 to R 14 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, A substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted benzoimidazole group. The substituted or unsubstituted dibenzothiophene group may be substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently represents a pyridine group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different from each other and each independently represents a pyridine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group .

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently is a pyrimidine group in which an alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a pyrimidine group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group to be.

According to one embodiment of the present disclosure, R 1 to R 14 are the same or different and are each independently a triazine group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different and are each independently a triazine group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted .

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently a carbazol group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently a carbazolyl group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group .

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently is a dibenzocarbazole group in which an alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represents a dibenzocarb which is substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group, It is sleepiness.

According to one embodiment of the present invention, R 1 to R 14 are the same or different from each other and each independently is a dibenzofurane group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R 1 to R 14 are the same or different and each independently represents a dibenzofuranyl group substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group, .

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently is a substituted or unsubstituted dibenzothiophene group in which the alkyl group or aryl group is substituted.

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently represents a substituted or unsubstituted dibenzothi (methyl, ethyl, phenyl, biphenyl, terphenyl, naphthyl, or fluorenyl group) Lt; / RTI >

According to one embodiment of the present invention, R1 to R14 are the same or different from each other, and each independently is a benzoimidazole group in which an alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R1 to R14 are the same or different from each other and each independently represents a benzoimide substituted or unsubstituted with a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group It is sleepiness.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represent a substituted or unsubstituted amine group having 1 to 50 carbon atoms.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently an amine group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different and are each independently an aryl group substituted or unsubstituted with a phenyl group, a phenyl group substituted with a methyl group, a biphenyl group, a naphthyl group, or a fluorenyl group.

 According to one embodiment of the present invention, R1 to R14 are the same or different and each independently represent a substituted or unsubstituted phosphine oxide group having 1 to 20 carbon atoms.

According to one embodiment of the present invention, R1 to R14 are the same or different and each independently a phosphine oxide group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, R1 to R14 are the same or different from each other and each independently a phosphine oxide group in which a phenyl group, a biphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R 1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, R 1 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.

According to one embodiment of the present disclosure, R1 is a methyl group.

According to one embodiment of the present disclosure, R1 is an ethyl group.

According to one embodiment of the present disclosure, R1 is an isopropyl group.

According to one embodiment of the present disclosure, R 1 is a tert-butyl group.

According to one embodiment of the present disclosure, R 1 is an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, R 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to one embodiment of the present disclosure, R1 is a phenyl group.

According to one embodiment of the present disclosure, at least one of R 2 to R 7 may be represented by -L 1 -Ar 1.

According to one embodiment of the present disclosure, R5 may be designated as -L1-Ar1.

According to one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

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

According to one embodiment of the present disclosure, L1 is a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, or a substituted or unsubstituted fluorenylene group.

According to one embodiment of the present invention, L1 is a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrylene group, a triphenylene group, a pyrenylene group, or a fluorenylene group.

According to one embodiment of the present disclosure, L1 is a phenylene group.

According to one embodiment of the present disclosure, L1 is a biphenylene group.

According to one embodiment of the present disclosure, L1 is an anthracenylene group.

According to one embodiment of the present disclosure, L1 is a substituted or unsubstituted heteroarylene group.

According to one embodiment of the present invention, L 1 is a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent dibenzocarbazole group, a substituted or unsubstituted divalent dibenzofurane group, A substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, or a substituted or unsubstituted divalent triazine group.

According to one embodiment of the present invention, L1 is a divalent carbazole group.

According to one embodiment of the present disclosure, L1 is a divalent dibenzocarbazole group.

According to one embodiment of the present disclosure, L1 is a divalent dibenzofurane group.

According to one embodiment of the present disclosure, L1 is a divalent dibenzothiophene group.

According to one embodiment of the present disclosure, L1 is a divalent pyridine group.

According to one embodiment of the present disclosure, L1 is a divalent pyrimidine group.

According to one embodiment of the present invention, L1 is a bivalent triazine group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.

According to one embodiment of the present invention, Ar1 is a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group , A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar1 is a phenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A phenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a biphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A biphenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a terphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo Is a terphenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a triphenyl group substituted or unsubstituted with cyano group, alkyl group, aryl group, or heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A triphenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a naphthyl group substituted or unsubstituted with cyano group, alkyl group, aryl group, or heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a phenanthryl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A phenanthryl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is an anthracenyl group substituted or unsubstituted with cyano group, alkyl group, aryl group, or heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a fluorenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar1 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A fluorenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted heterocyclic group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted A dibenzocarbazole group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted benzoimidazole group.

According to one embodiment of the present invention, Ar1 is a pyridine group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a pyridine group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a pyrimidine group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a pyrimidine group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a triazine group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a triazine group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar 1 is a carbazole group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a carbazol group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a dibenzocarbazole group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a dibenzocarbazole group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar 1 is a dibenzofurane group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a dibenzofurane group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a dibenzothiophene group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a dibenzothiophene group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a benzoimidazole group in which the alkyl group or aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a benzoimidazole group in which a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted C6 to C50 amine group.

According to one embodiment of the present invention, Ar1 is an amine group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar1 is an amine group substituted or unsubstituted with a phenyl group, a phenyl group substituted with a methyl group, a biphenyl group, a naphthyl group, or a fluorenyl group.

 According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted phosphine oxide group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, Ar1 is a phosphine oxide group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar1 is a phosphine oxide group in which a phenyl group, a biphenyl group, a naphthyl group, or a fluorenyl group is substituted or unsubstituted.

, 또는 치환 또는 비치환된

이다. According to one embodiment of the present disclosure, Ar < 1 > is a substituted or unsubstituted

, Or a substituted or unsubstituted

to be.

이다.According to one embodiment of the present disclosure,

to be.

이다.According to one embodiment of the present disclosure,

to be.

According to one embodiment of the present disclosure, R2 and R3, R3 and R4, R4 and R5, R5 and R6, or R6 and R7 may be bonded to each other to form a ring.

According to one embodiment of the present invention, two or more adjacent of R1 to R14 may be bonded to each other to form a substituted or unsubstituted aliphatic ring; A substituted or unsubstituted aromatic ring; Or a substituted or unsubstituted aromatic or aliphatic condensed ring.

,

,

,

,

, 또는

를 형성할 수 있다. According to one embodiment of the present invention, two or more adjacent of R2 to R14 are bonded to each other to form a benzene ring, a naphthalene ring, an indene ring,

,

,

,

,

, or

Can be formed.

According to one embodiment of the present invention, -L 1 -Ar 1 may be any one selected from the following structural formulas of Groups 1 to 4.

 [Group 1]

[Group 2]

[Group 3]

[Group 4]

According to one embodiment of the present invention, Ar1 may be represented by any one of the following formulas (a) to (e).

"는 상기 L1에 결합되는 부분을 의미한다.In the following formulas (a) to (e)

"Means a portion coupled to L1.

(A)

[Formula b]

(C)

[Chemical formula d]

(E)

In the above formulas (a) to (e)

Ar11 represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

X1 to X3 are the same or different from each other and each independently N or CR,

Ar12 to Ar15, Ar21 and Ar22 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

X4 is NR ', S or O,

Ar16 to Ar19 are the same or different and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a ring,

R, R 'and Ar20 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n is an integer of 0 to 4, and when n is 2 or more, a plurality of Ar 20 s are the same or different from each other.

According to one embodiment of the present invention, Ar11 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, Ar11 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.

According to one embodiment of the present invention, Ar11 is a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

According to one embodiment of the present invention, Ar11 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, Ar 11 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group , A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar11 is a phenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A phenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is a biphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A biphenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is a terphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo Is a terphenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is a triphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A triphenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is a naphthyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is a phenanthryl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A phenanthryl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is an anthracenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, Ar11 is a fluorenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

According to one embodiment of the present invention, Ar11 is a group selected from the group consisting of deuterium, cyano, methyl, ethyl, phenyl, cyano, phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl, dibenzocarbazolyl, dibenzo A fluorenyl group substituted or unsubstituted with a thiophene group, a dibenzofurane group, a pyridine group, a pyrimidine group, a triazine group, or a benzoimidazole group.

According to one embodiment of the present invention, X1 to X3 are the same or different from each other and each independently N or CR.

According to one embodiment of the present invention, Ar12 to Ar15, Ar21 and Ar22 are the same or different and each independently substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, Ar12 to Ar15, Ar21 and Ar22 are the same or different from each other and are each independently a phenyl group, a phenyl group substituted with a methyl group, a biphenyl group, a naphthyl group or a fluorenyl group.

According to one embodiment of the present disclosure, X4 is NR ', S or O.

According to one embodiment of the present disclosure, X4 is NR '.

According to one embodiment of the present disclosure, X4 is S.

According to one embodiment of the present disclosure, X4 is O.

According to one embodiment of the present invention, Ar16 to Ar19 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a ring.

According to one embodiment of the present specification, Ar16 and Ar17, Ar17 and Ar18, or Ar18 and Ar19 may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring of 6 members.

According to one embodiment of the present invention, Ar16 to Ar19 are the same or different from each other, and each independently combine with adjacent groups to form a benzene ring or a naphthalene ring.

According to one embodiment of the present invention, Ar16 to Ar19 are the same or different from each other and each independently hydrogen.

According to one embodiment of the present disclosure, R, R 'and Ar20 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, R, R ', and Ar 20 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, R, R 'and Ar 20 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 naphthyl group, Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, R is a phenyl group, a biphenyl group, a naphthyl group, or a fluorenyl group.

According to one embodiment of the present invention, R is a phenyl group.

According to one embodiment of the present disclosure, R is a biphenyl group.

According to one embodiment of the present disclosure, R is a naphthyl group.

According to one embodiment of the present disclosure, R is a fluorenyl group.

According to one embodiment of the present disclosure, R 'and Ar20 are hydrogen.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (6).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 2 to 6,

R1 to R14 are the same as defined in Formula 1,

R15 is hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a ring,

m is an integer of 1 to 4,

When m is 2 or more, a plurality of R 15 s are the same or different from each other.

According to one embodiment of the present disclosure, R15 is hydrogen or may combine with adjacent groups to form a ring.

According to one embodiment of the present invention, the compound represented by Formula 1 may be any one selected from the following structural formulas.

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.

For example, the compound of Formula 1 may be prepared as a core structure as shown in Formula 1 or 2 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art. Substituents may be connected as shown in the following general formulas (1) and (2), but the present invention is not limited thereto.

[Formula 1]

[Formula 2]

Ar12 and Ar13 in the general formula (1) are the same as defined in the above formula (b).

The dashed line in the general formula 2 indicates that any boronic acid containing a 1-naphthyl group can synthesize a core structure. For example, all of the following materials are capable of synthesizing a material having a core structure.

The above general formulas (1) and (2) describe an example of a method for synthesizing the core of the above formula (1), but are not limited thereto.

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

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

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

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

The organic material layer of the organic electronic device in this specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic electronic device of the present invention, the 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.

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 cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, 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 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.

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 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.

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 with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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

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

The 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, BCP, aluminum complexes and the like.

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.

< Example >

< Manufacturing example  1>

After completely dissolving the compound A (30.0 g, 146 mmol) and B (34.4 g, 133 mmol) in tetrahydrofuran (300 ml), 3M aqueous potassium carbonate solution (150 ml) was added and tetrakistriphenylphosphinopalladium , 1.33 mmol), and the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the organic layer was separated and treated with magnesium sulfate. After filtration and concentration, Compound C (39.8 g, yield 88%) was prepared.

The compound C (15.0 g, 44.2 mmol) was completely dissolved in tetrahydrofuran (200 ml), 1M PhMgBr tetrahydrofuran solution (88 ml) was added at 0 ° C, and the mixture was stirred at room temperature for 5 hours. A saturated aqueous ammonium chloride solution (200 mL) was added to the reaction, and the organic layer was separated and washed with brine (200 mL). The organic layer was separated again, treated with magnesium sulfate, and then filtered / concentrated to prepare Compound D1. The compound D1 was dissolved in acetic acid (100 mL) without further purification, and concentrated sulfuric acid (0.2 mL) was added and the mixture was heated and stirred at 90 ° C for 2 hours. Water (100 mL) and ethanol (100 mL) were added to the reaction mixture to precipitate a solid, which was then cooled to room temperature and filtered to give 14.1 g (yield 80%) of compound E1.

MS [M + H] &lt; ⁺ &gt; = 401

< Manufacturing example  2>

Compound E2 was prepared in the same manner as in the preparation of Compound E1 except that MeMgBr was used instead of PhMgBr in Preparation Example 1.

MS [M + H] &lt; ⁺ &gt; = 339

< Manufacturing example  3>

After completely dissolving Compound A2 (11.0 g, 90.9 mmol) and E1 (28.0 g, 82.7 mmol) in 1,4-dioxane (300 ml), 3M aqueous potassium carbonate solution (150 ml) was added, tetrakis Pin) palladium (0) (1.0 g, 0.83 mmol) were added thereto, and the mixture was heated and stirred for 8 hours. The dioxane (300 mL) was removed under reduced pressure and the temperature was lowered to room temperature. At this time, the resulting solid was filtered to obtain Compound 2 (28.9 g, yield 79%).

MS [M + H] &lt; ⁺ &gt; = 443

< Manufacturing example  4>

Compound 8 was prepared in the same manner as in the preparation of Compound 2, except that Compound P was used in place of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 619

< Manufacturing example  5>

The compound Q (9.0 g, 53.9 mmol) and E1 (18.2 g, 53.9 mmol) were dissolved in xylene (150 mL) and sodium-tert-butoxide (5.7 g, 59.3 mmol) Respectively. Bis (dibenzylidineacetone) palladium (632 mg, 1.1 mmol) and tricyclohexylphosphine (616 mg, 2.2 mmol) were added under reflux and stirred at reflux for 12 hours. After completion of the reaction, the temperature was lowered to room temperature, and the precipitated solid was filtered. The obtained solid was washed with water and ethanol to prepare Compound 12 (23.5 g, yield 82%).

MS [M + H] &lt; ⁺ &gt; = 532

< Manufacturing example  6>

Compound 16 was prepared in the same manner as Compound 2, except that Compound R was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 608

< Manufacturing example  7>

Compound 27 was prepared in the same manner as Compound 2 except that Compound S was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 559

< Manufacturing example  8>

Compound 33 was prepared in the same manner as Compound 2, except that Compound T was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 549

< Manufacturing example  9>

Compound 40 was prepared in the same manner as Compound 2, except that Compound U was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 671

< Manufacturing example  10>

Compound 48 was prepared in the same manner as in the preparation of Compound 2, except that Compound V was used instead of Compound A2 of Preparation Example 3, and E2 was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 547

< Manufacturing example  11>

Compound 53 was prepared in the same manner as in the preparation of Compound 2, except that Compound W was used instead of Compound A2 of Preparation Example 3, and E2 was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 546

< Manufacturing example  12>

Compound 64 was prepared in the same manner as in the preparation of Compound 2, except that Compound X was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 608

< Manufacturing example  13>

Compound 75 was prepared in the same manner as Compound 12, except that Compound Y was used instead of Compound Q of Preparation Example 5.

MS [M + H] &lt; ⁺ &gt; = 686

< Manufacturing example  14>

Compound 81 was prepared in the same manner as Compound 12, except that Compound Z was used instead of Compound Q of Preparation Example 5.

MS [M + H] &lt; ⁺ &gt; = 650

< Manufacturing example  15>

Compound 111 was prepared in the same manner as Compound 2, except that Compound AA was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 598

< Manufacturing example  16>

Compound 119 was prepared in the same manner as in the preparation of Compound 2, except that Compound BB was used instead of Compound A2 of Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 674

< Manufacturing example  17>

Compound 135 was prepared in the same manner as Compound 2 above, except that Compound CC was used instead of Compound A2 of Preparation Example 3 and E2 was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 612

< Manufacturing example  18>

Compound 140 was prepared in the same manner as Compound 2 above, except that Compound DD was used instead of Compound A2 of Preparation Example 3, and E2 was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 610

< Manufacturing example  19>

The compound EE (37.4 g, 168.6 mmol) and the compound B (39.6 g, 153.3 mmol) were completely dissolved in 320 ml of tetrahydrofuran, followed by addition of 3M aqueous potassium carbonate solution (160 ml), tetrakis (triphenylphosphine) Palladium (0) (1.8 g, 1.53 mmol) was added thereto, followed by heating and stirring for 8 hours. The pressure was reduced to remove tetrahydrofuran (320 mL) and the temperature was lowered to room temperature. The resulting solid was filtered to obtain compound FF (51.8 g, yield 95%).

The compound FF (32 g, 55.9 mmol) was completely dissolved in chloroform (250 ml), NBS (10.9 g, 61.5 mmol) was added thereto, and the mixture was stirred at room temperature for 12 hours. Distilled water (200 mL) was added to the reaction mixture, and the resulting solid was completely dissolved in tetrahydrofuran (300 ml) without further purification. 1M PhMgBr and tetrahydrofuran solution (112 ml) were added at 0 ° C and stirred at room temperature for 5 hours . Saturated ammonium chloride aqueous solution (250 mL) was added to the reaction, and the organic layer was separated and washed with brine (250 mL). The organic layer was separated again, treated with magnesium sulfate, filtered and concentrated to prepare a compound GG. Compound GG was dissolved in acetic acid (150 mL) without further purification, and concentrated sulfuric acid (0.3 mL) was added thereto, followed by heating and stirring at 90 ° C for 2 hours. Water (130 mL) and ethanol (130 mL) were added to the reaction mixture to precipitate a solid, which was then cooled to room temperature and filtered to give HH (24.6 g, yield 89%).

MS [M + H] &lt; ⁺ &gt; = 495

< Manufacturing example  20>

Compound 147 was prepared in the same manner as Compound 2 except that Compound HH was used instead of Compound E1 in Preparation Example 3.

MS [M + H] &lt; ⁺ &gt; = 493

< Manufacturing example  21>

Compound 155 was prepared in the same manner as in the preparation of Compound 2, except that Compound II was used instead of Compound A2 of Preparation Example 3, and Compound HH was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 660

< Manufacturing example  22>

Compound 175 was prepared in the same manner as Compound 2 above, except that Compound T was used instead of Compound A2 of Preparation Example 3 and HH was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 599

< Manufacturing example  23>

Compound 176 was prepared in the same manner as Compound 2 was prepared, except that Compound JJ was used instead of Compound A2 of Preparation Example 3 and HH was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 693

< Manufacturing example  24>

Compound 181 was prepared in the same manner as in the preparation of Compound 2, except that Compound KK was used instead of Compound A2 of Preparation Example 3, and HH was used instead of E1.

MS [M + H] &lt; ⁺ &gt; = 685

< Manufacturing example  25>

After the compound LL (20.0 g, 81.3 mmol) and the compound B (19.1 g, 73.9 mmol) were completely dissolved in 160 ml of tetrahydrofuran, 3M aqueous potassium carbonate solution (80 ml) was added, tetrakis (triphenylphosphine) Palladium (0) (1.8 g, 1.53 mmol) was added thereto, followed by heating and stirring for 8 hours. The pressure was reduced to remove tetrahydrofuran (160 mL) and the temperature was lowered to room temperature. The resulting solid was filtered to obtain Compound MM (22.5 g, yield 80%).

The compound MM (22.5 g, 59.3 mmol) was completely dissolved in tetrahydrofuran (120 ml), and 1M PhMgBr tetrahydrofuran solution (120 ml) was added at 0 ° C and stirred at room temperature for 5 hours. A saturated aqueous ammonium chloride solution (200 mL) was added to the reaction, and the organic layer was separated and washed with brine (200 mL). The organic layer was separated again, treated with magnesium sulfate, filtered and concentrated to prepare a compound NN. The compound NN was dissolved in acetic acid (120 mL) without further purification, and concentrated sulfuric acid (0.2 mL) was added and the mixture was heated and stirred at 90 ° C for 2 hours. Water (100 mL) and ethanol (100 mL) were added to the reaction mixture to precipitate a solid. The mixture was cooled to room temperature and filtered to obtain Compound 200 (9.1 g, yield 77%).

MS [M + H] &lt; ⁺ &gt; = 441

< Example >

&Lt; Comparative Example 1 &

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a product of Fischer Co. was used as a detergent, and distilled water, which was secondly filtered by a filter manufactured by 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. A hole injection layer was formed by thermal vacuum deposition of hexanitrile hexaazatriphenylene (HAT) to a thickness of 100 Å by using the oxygen plasma for 5 minutes.

(NPB) (700 angstroms), hexanitrile hexaazatriphenylene (HAT) (50 angstroms), and 4,4'-bis [N- (1-naphthyl) N-phenylamino] biphenyl (NPB) (600 angstroms) were sequentially deposited by vacuum deposition to form the hole transport layer 1.

NPB (100 Å) was vacuum deposited on the hole transport layer 1 to form a hole transport layer 2.

Subsequently, the following H1 and D1 were vacuum deposited on the hole transport layer 2 to a thickness of 200 Å at a weight ratio of 25: 1 to form a light emitting layer. On the light emitting layer, an electron transport layer 1 was formed to a thickness of 100 Å by the following E1.

E1 and E2 were vacuum deposited on the electron transport layer 1 at a weight ratio of 1: 1 to form an electron transporting and injecting layer having a thickness of 200 ANGSTROM. Aluminum was sequentially deposited on the electron transporting and injecting layer to form a 15 Å thick lithium fluoride (LiF) film and a 2,000 Å thick aluminum film.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of the lithium fluoride of the cathode was 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. by keeping the ^-7 to 5 X 10 ^-8 torr, an organic light emitting device was produced.

&Lt; Example 1-1 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 16 was used instead of NPB in the hole transport layer 2 in Comparative Example 1.

&Lt; Example 1-2 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 64 was used instead of NPB in the hole transport layer 2 in Comparative Example 1.

&Lt; Example 1-3 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 81 was used instead of NPB in the hole transport layer 2 in Comparative Example 1.

&Lt; Example 2-1 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 147 was used instead of H1 in the light emitting layer in Comparative Example 1.

&Lt; Example 3-1 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 111 was used instead of E1 in the electron transport layer 1 in Comparative Example 1.

&Lt; Example 3-2 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 119 was used instead of E1 in the electron transport layer 1 in Comparative Example 1.

<Example 3-3>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1 except that Compound 140 was used instead of E1 in the electron transport layer 1 in Comparative Example 1.

When current was applied to the organic light-emitting device manufactured by Comparative Example 1, Examples 1-1 to 1-3, Examples 2-1 and 3-1 to 3-3, the results shown in Table 1 were obtained.

division HTL 2 EML ETL 1 Voltage
(V @ 10 mA / cm ² ) Current efficiency
(cd / A @ 10mA / cm 2) Comparative Example 1 NPB H1: D1 E1 4.1 4.6 Example 1-1 Compound 16 H1: D1 E1 4.3 4.9 Examples 1-2 Compound 64 H1: D1 E1 4.3 5.0 Example 1-3 Compound 81 H1: D1 E1 4.4 4.8 Example 2-1 NPB Compound 147: D1 E1 4.3 4.9 Example 3-1 NPB H1: D1 Compound 111 4.0 4.7 Example 3-2 NPB H1: D1 Compound 119 4.1 5.1 Example 3-3 NPB H1: D1 Compound 140 4.2 4.9

As shown in Table 1, when the compound represented by Formula 1 according to the present invention is used as a hole transporting layer, a light emitting layer, or an electron transporting layer, a compound exhibiting characteristics of low voltage and high efficiency as compared with Comparative Example 1 using conventional materials Able to know.

In addition, the compound according to the present invention can be used as a material for an organic material layer of an organic light emitting device including an organic light emitting device, and an organic electronic device including the organic light emitting device exhibits excellent characteristics in terms of efficiency and driving voltage.

Although the preferred embodiments (the hole transporting layer, the electron transporting layer, and the light emitting layer) of the present invention have been described above, the present invention is not limited thereto, but various variations and modifications may be made within the scope of the claims and the detailed description of the invention And is also within the scope of the specification.

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,
R1 is a phenyl group or a methyl group
R2 and R8 to R14 are hydrogen,
R 3 to R 7 are the same or different from each other and each independently hydrogen or -L 1 -Ar 1 or form an aromatic ring which is directly condensed to the core by bonding with adjacent substituents,
L1 is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a divalent anthracene group, a divalent phenanthrene group, or a divalent carbazole group,
Ar1 represents a methyl group; A phenyl group substituted or unsubstituted with a deuterium, a nitrile group or a methyl group; Biphenyl group; A terphenyl group; Naphthyl group; Anthracene group; Phenanthrene; Triphenylene group; A phenyl group, or a carbazolyl group substituted or unsubstituted with a naphthyl group; A benzocarbazolyl group substituted or unsubstituted with a phenyl group or a naphthyl group; A fluorene group substituted or unsubstituted with a methyl group or a phenyl group; A dibenzothiophene group; A dibenzofurane group; An amino group substituted or unsubstituted with a phenyl group, a phenyl group substituted with a methyl group, a naphthyl group, a biphenyl group, or a dimethylfluorene group; A triazine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a dimethylfluorene group; A phenyl group, a biphenyl group, or a dimethylfluorene group substituted or unsubstituted pyrimidine group; A phenyl group, a biphenyl group, or a pyridine group substituted or unsubstituted with a dimethylfluorene group; A phosphine oxide group substituted or unsubstituted with a phenyl group; Or a benzimidazole group substituted or unsubstituted with a phenyl group. delete 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,
R1 to R14 are the same as defined in Formula 1,
R15 is hydrogen,
m is an integer of 1 to 4; delete The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formulas:

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 comprises a compound according to any one of claims 1, 3, and 5 Lt; / RTI &gt; The method of claim 6,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The method of claim 6,
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. The method of claim 6,
Wherein the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously injecting and transporting electrons, wherein the electron transporting layer, the electron injecting layer, Electronic device. The method of claim 6,
Wherein the organic material layer further comprises one or more layers selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, an electron injecting and transporting layer, an electron blocking layer, and a hole blocking layer Organic electronic device.

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