KR101996512B1 - 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.

The present invention claims the benefit of Korean Patent Application No. 10-2015-0169403, filed on November 30, 2015, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not yet been sufficiently developed. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

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,

X is N or CR,

L is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R and R ₁ to R ₉ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or may combine with adjacent groups to form a ring,

R ₁₀ to R ₁₇ are the same or different 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; A substituted or unsubstituted phosphine oxide 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.

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 electronic device 10 according to an embodiment of the present invention.
2 shows an organic electronic device 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).

According to one embodiment of the present invention, the compound represented by Formula 1 has a large energy band gap. Compounds having various energy bandgaps can be synthesized by introducing various substituents to a core having a large energy bandgap. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. Therefore, in this specification, introduction of various substituent groups into the core structure having the above structure has an excellent effect of controlling the HOMO and LUMO energy levels of the compound. In this specification, the energy band gap was calculated using a general method calculated by the UV-VIS spectrum.

Further, according to one embodiment of the present invention, the compounds of the following examples exhibit stable redox properties. The stability against oxidation and reduction can be confirmed by CV (cyclovoltammetry) method. As a specific example, when the compound of formula (1-1) of Example 1 was oxidized at the same voltage and applied with the same voltage repeatedly, the same amount of current was exhibited. This indicates that the compound has excellent stability against oxidation .

Meanwhile, according to another embodiment of the present invention, the compound of Chemical Formula 1 has a high glass transition temperature (Tg) and thus is excellent in thermal stability. For example, the compound of Formula 1-1 of Example 1 of the present invention has a glass transition temperature of 133 占 폚, which is significantly higher than that of NPB (Tg: 96 占 폚) which has been generally used. This increase in thermal stability is an important factor in providing drive stability to the device.

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

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

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the 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; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a heterocyclic group containing at least one of N, O, S, Se, and Si atoms, or wherein at least two of the above-exemplified substituents are substituted with a substituent to which they are connected, or Quot; means having no substituent.

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 20 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 20 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

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

In this specification, the silyl group is a substituent including Si and a direct connection as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R ₁₀₆ are the same as 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 trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group and phenylsilyl group. But is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; 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 heteroaryl group having 2 to 30 carbon atoms.

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 30. 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 is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

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

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

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 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, phenanthryl, triphenyl, pyrenyl, perylenyl, klychenyl and fluorenyl groups. no.

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 heterocyclic group and is a heterocyclic group containing 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, But are not limited to, benzothiophene group, dibenzothiophene group, benzofurane group, phenanthroline, isoxazolyl group, thiadiazolyl group, and dibenzofurane group.

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

In the present specification, the condensed structure may be a structure in which an aromatic carbon-hydrogen ring is condensed with the substituent.

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.For example, as a condensation ring of benzimidazole

,

,

,

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

(spiro[fluorene-9,8'-indolo[3,2,1-de]acridine]) 등이 될 수 있으나, 이에 한정되는 것은 아니다.For example, as a condensation ring of acridine

(spiro [fluorene-9,8'-indolo [3,2,1-de] acridine]), but the present invention is not limited thereto.

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

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

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent, represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same or different 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 ₁₀₇ and R ₁₀₈ 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 methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , 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 aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

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

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

In the present specification, the aromatic ring group 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, an alkylene group means that the alkyl group has two bonding positions, i.e., divalent. The description of the above-mentioned alkyl groups can be applied, except that they are each 2 groups.

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, X is N or CR.

According to one embodiment of the present disclosure, X is N.

According to one embodiment of the present disclosure, X is CR.

According to one embodiment of the present disclosure, X is CH.

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

According to one embodiment of the present disclosure, R is hydrogen.

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

According to one embodiment of the present invention, L is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, 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, L is a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a triphenylene group, a pyrenylene group, or a fluorenylene group.

According to one embodiment of the present disclosure, R ₁ to R ₉ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or may combine with adjacent groups to form a ring.

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different and each independently a substituted or unsubstituted alkyl group.

According to one embodiment of the present disclosure, R ₁ and R ₂ are the same or different 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 disclosure, R ₁ and R ₂ are methyl groups.

According to one embodiment of the present disclosure, R ₃ and R ₉ are hydrogen.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, or a substituted or unsubstituted fluorenyl group, or may form a ring by bonding with adjacent groups to form a cyclic naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, can do.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ 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 heterocyclic group, Can be formed.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a cyano group or a phenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different from each other and are each independently a phenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a naphthyl group substituted or unsubstituted with cyano group, alkyl group, aryl group, or heterocyclic group, A ring can be formed.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a cyano group or a naphthyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a naphthyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ 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 heterocyclic group, A ring can be formed.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a cyano group or a biphenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and are each independently a biphenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ 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 heterocyclic group, A ring can be formed.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a cyano group or a terphenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present specification, R ₁₀ to R ₁₇ are the same or different from each other, and each independently is a terphenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently an anthracenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heterocyclic group, To form a ring.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently anthracenyl substituted or unsubstituted with cyano group or phenyl group.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and each independently an anthracenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ 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 heterocyclic group, A ring can be formed.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a cyano group or a triphenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different from each other, and each independently is a triphenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ 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 heterocyclic group, To form a ring.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each is a phenanthryl group substituted or unsubstituted with a cyano group or a phenyl group.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and each independently a phenanthryl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a fluorenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heterocyclic group, To form a ring.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a cyano group or a fluorenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different from each other, and each independently is a fluorenyl group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently represent a substituted or unsubstituted amine group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different, and each independently represents an amine group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different from each other and each independently represents an amine group in which a phenyl group, biphenyl group, terphenyl group, naphthyl group, or fluorenyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and each independently an amine group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently represents a substituted or unsubstituted heterocyclic group having 3 to 50 carbon atoms.

According to one embodiment of the present specification, R ₁₀ to R ₁₇ are the same or different and each independently represents a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted dibenzocarbazole group , A substituted or unsubstituted furan group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted thiophene group, , Or a substituted or unsubstituted benzimidazole group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different, and each independently is a substituted or unsubstituted carbazol group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each is a carbazol group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a carbazole group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzocarbazolyl group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different, and each independently is a benzocarbazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and are each independently a benzocarbazole group.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different, and each independently is a dibenzocarbazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a dibenzocarbazole group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and are each independently a dibenzocarbazole group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently is a dibenzofurane group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a dibenzofurane group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a dibenzofurane group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently is a dibenzothiophene group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different, and each independently is a dibenzothiophene group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and are each independently a dibenzothiophene group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a substituted or unsubstituted pyridine group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different from each other and each independently represents a pyridine group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a pyridine group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a pyrimidine group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different from each other, and each independently is a pyrimidine group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a pyrimidine group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different, and each independently is a triazine group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a triazine group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a triazine group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzothiazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzothiazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a benzothiazole group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzoxazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzoxazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different from each other, and each independently is a benzoxazole group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzimidazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a benzimidazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and each independently a benzimidazole group.

,

,

, 또는

이다.According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and each independently

,

,

, or

to be.

,

,

, 또는

이다.According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and each independently

,

,

, or

to be.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and each independently a substituted or unsubstituted phosphine oxide group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different and are each independently a substituted or unsubstituted phosphine oxide group.

According to one embodiment of the present invention, R ₁₀ to R ₁₇ are the same or different, and each independently represents a phosphine oxide group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₇ are the same or different and are each independently a phosphine oxide group.

According to one embodiment of the present disclosure, R ₁₀ to R ₁₃ are the same or different from each other and each independently hydrogen.

According to one embodiment of the present disclosure, R ₁₄ to R ₁₇ are the same or different from each other and each independently hydrogen.

According to one embodiment of the present invention, the formula 1 may be represented by the following formula 1-A or 1-B.

[Chemical Formula 1-A]

[Chemical Formula 1-B]

In the above formulas (1-A) and (1-B)

L, and R ₁ to R ₁₇ are as defined in the above formula (1).

According to one embodiment of the present invention, at least one of R ₁₀ to R ₁₇ is -L ₁ -Ar ₁ , and the rest of R ₁₀ to R ₁₇ may be the same as defined in Formula 1, or may be bonded to adjacent groups to form a ring,

L &_lt; ₁ > is a direct bond; Or a substituted or unsubstituted arylene group,

Ar ₁ is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted phosphine oxide group.

According to one embodiment of the present disclosure, at least one of R ₁₀ to R ₁₃ is -L ₁ -Ar ₁ and the others are the same as defined in Formula 1; The adjacent groups may be bonded to each other to form a ring,

At least one of R ₁₄ to R ₁₇ is -L ₂ -Ar ₂ , and the others are the same as defined in Formula 1; The adjacent groups may be bonded to each other to form a ring,

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

The Ar ₁ And Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted phosphine oxide group.

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

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

X, L and R ₁ to R ₁₇ are as defined in the above formula (1)

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

The Ar ₁ And Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted phosphine oxide group.

According to one embodiment of the present disclosure, any one of R ₁₀ to R ₁₇ is -L ₁ -Ar ₁ .

According to one embodiment of the present disclosure, any one of R ₁₀ to R ₁₃ is -L ₁ -Ar _1, and one of R ₁₄ to R ₁₇ is -L ₂ -Ar ₂ .

According to one embodiment of the present disclosure, any one of R ₁₀ to R ₁₇ is -L ₁ -Ar ₁ , and the remainder is hydrogen.

According to one embodiment of the present disclosure, any one of R ₁₀ to R ₁₇ is -L ₁ -Ar ₁ , and the other is -L ₂ -Ar ₂ , and the remainder is hydrogen.

According to one embodiment of the present disclosure, R ₁₁ or R ₁₂ is -L ₁ -Ar ₁ .

According to one embodiment of the present disclosure, R ₁₁ is -L ₁ -Ar ₁ and R ₁₆ is -L ₂ -Ar ₂ .

According to one embodiment of the present disclosure, R ₁₂ is -L ₁ -Ar ₁ and R ₁₅ is -L ₂ -Ar ₂ .

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

According to one embodiment of the present invention, L ₁ and L ₂ are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

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

According to one embodiment of the present invention, L ₁ and L ₂ are the same or different and each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group , A substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene 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, L ₁ and L ₂ are the same or different from each other and each independently represent a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a triphenylene group, Or a fluorenylene group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ 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 naphthyl group, a substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, or a substituted or unsubstituted fluorenyl group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a phenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heterocyclic group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a cyano group or a phenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different from each other and are each independently a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ may be the same or different and each independently a naphthyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heterocyclic group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a cyano group or a naphthyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a naphthyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ may be 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 heterocyclic group, or may combine with adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a cyano group or a biphenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a biphenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ may be the same or different and each independently a terphenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heterocyclic group, or may form a ring by bonding to adjacent groups.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a cyano group or a terphenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a terphenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently an anthracenyl group substituted or unsubstituted with a cyano group, an alkyl group, an aryl group, or a heterocyclic group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently anthracenyl substituted or unsubstituted with a cyano group or a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently an anthracenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a cyano group, an alkyl group, an aryl group, or a substituted or unsubstituted triphenyl group with a heterocyclic group, or may form a ring by bonding with adjacent groups.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a cyano group or a triphenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a triphenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ may be 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 heterocyclic group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a cyano group or a phenanthryl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and are each independently a phenanthryl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ may be 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 heterocyclic group, or may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different from each other, and each independently is a cyano group or a fluorenyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a fluorenyl group.

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

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and each independently represents an amine group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently represents an amine group in which 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 disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and each independently an amine group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ 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 disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently represents a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted dibenzocarbazole group, a substituted or unsubstituted furan group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted benzothiophene group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzoxazole group, or a substituted or unsubstituted benzimidazole group to be.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different, and each independently is a substituted or unsubstituted carbazol group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different from each other and each independently is a substituted or unsubstituted carbazol group with a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a carbazole group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently represents a benzocarbazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different from each other, and each independently is a benzocarbazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a benzocarbazole group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a dibenzocarbazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently is a dibenzocarbazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and are each independently a dibenzocarbazole group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a dibenzofurane group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a dibenzofurane group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a dibenzofurane group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different, and each independently is a dibenzothiophene group in which an aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently is a dibenzothiophene group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently dibenzothiophene group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and each independently represents a pyridine group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and each independently represents a pyridine group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and are each independently a pyridine group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and each independently represents a pyrimidine group in which an aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a pyrimidine group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a pyrimidine group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a triazine group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a triazine group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a triazine group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a benzothiazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different from each other, and each independently is a benzothiazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and each independently is a benzothiazole group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a benzoxazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a benzoxazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different, and each independently is a benzoxazole group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently a benzimidazole group in which the aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different from each other and each independently a benzimidazole group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different, and each independently is a benzimidazole group.

,

,

, 또는

이다.According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different from each other,

,

,

, or

to be.

,

,

, 또는

이다.According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different from each other,

,

,

, or

to be.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and are each independently a substituted or unsubstituted phosphine oxide group.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different and each independently represents a phosphine oxide group in which an aryl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar ₂ are the same or different from each other, and each independently is a phosphine oxide group in which a phenyl group, biphenyl group or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, the Ar ₁ Or Ar < _{2 &gt}; are the same or different and are each independently a phosphine oxide group.

According to an exemplary embodiment of the present disclosure, R ₁₀ and R _11, R ₁₁ and R _12, R ₁₂ and R _13, R ₁₄ and R _15, R ₁₅ and R ₁₆ and R ₁₆ and R ₁₇ at least one pair of of the They can be combined with each other to form a ring.

According to an exemplary embodiment of the present disclosure, R ₁₀ and R _11, R ₁₁ and R _12, R ₁₂ and R _13, R ₁₄ and R _15, R ₁₅ and R ₁₆ and R ₁₆ and R ₁₇ at least one pair of of the Bonded to each other to form a hydrocarbon ring, and the formed hydrocarbon ring may be a bicyclic or tricyclic ring.

According to an exemplary embodiment of the present disclosure, R ₁₀ and R _11, R ₁₁ and R _12, R ₁₂ and R _13, R ₁₄ and R _15, R ₁₅ and R ₁₆ and R ₁₆ and R ₁₇ at least one pair of of the May be represented by the following formulas (6) to (9).

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the general formulas (6) to (9)

R ₁₈ to R ₂₉ are independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

p is an integer of 0 to 4,

q, r, and s are an integer of 0 to 6;

In the above formulas (6) to (9), * and ** mean a bonding moiety, and * and ** bond at different positions.

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

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 and 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 the following Formulas 1 to 4. 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.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

The above general formula 1 is merely one example of the method for synthesizing the cores of the above formulas 2 to 5, but is not limited thereto.

In the general formulas 1 to 4, L ₁ , L ₂ , R ₁ to R ₁₇ , Ar ₁ and Ar ₂ are as defined above, Ar ₃ and Ar ₄ connected to N are substituted or unsubstituted aryl groups; Or a substituted or unsubstituted heterocyclic group, Ar ₅ and Ar ₆ are substituted or unsubstituted aryl groups; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted phosphine oxide group. A concrete manufacturing method will be described later.

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 disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

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

Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer 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 an embodiment of the present invention, the organic light emitting diode may be selected from the group consisting of an organic phosphor element, an organic solar battery, an organic photoconductor (OPC), and an organic transistor.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound.

In one embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, A light emitting layer, an electron transporting layer, an electron injecting 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, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and 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 light emitting material of the light emitting layer is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having high quantum efficiency for fluorescence or phosphorescence. 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 having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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

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

The 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.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Example  1>

<Reaction Scheme 1>

<Reaction Scheme 2>

< Manufacturing example  1>

Compound A (8.44 g, 17.26 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (5.45 g, 18.99 mmol) were completely dissolved in 260 ml of tetrahydrofuran in a 500 ml round- 2M aqueous potassium carbonate solution (130 ml) was added, tetrakis- (triphenylphosphine) palladium (0.60 g, 0.52 mmol) was added, and the mixture was heated with stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (200 ml) to give Compound 1 (7.69 g, 68%).

MS [M + H] &lt; ⁺ &gt; = 653

< Manufacturing example  2>

Compound A (7.29 g, 14.91 mmol) and (4- (9H-carbazol-9-yl) phenyl) boronic acid (4.71 g, 16.40 mmol) were completely dissolved in 220 ml of tetrahydrofuran in a 500 ml round- Then, 2M aqueous potassium carbonate solution (110 ml) was added, tetrakis- (triphenylphosphine) palladium (0.52 g, 0.45 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to obtain Compound 2 (8.16 g, 84%).

MS [M + H] &lt; ⁺ &gt; = 653

< Manufacturing example  3>

Compound A-1 (8.15 g, 15.18 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (5.34 g, 13.80 mmol) was completely dissolved in 320 ml of tetrahydrofuran, and 2M potassium carbonate aqueous solution (160 ml) was added thereto. Tetrakis- (triphenylphosphine) palladium (0.58 g, 0.52 mmol) was added and the mixture was heated with stirring for 8 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 180 ml of tetrahydrofuran to obtain Compound 3 (6.08 g, 61%).

MS [M + H] &lt; ⁺ &gt; = 719

< Manufacturing example  4>

Compound A-1 (8.15 g, 15.18 mmol) and 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (5.34 g, 13.80 mmol) was completely dissolved in 360 ml of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (180 ml) was added thereto. Tetrakis- (triphenylphosphine) palladium (0.75 g, 0.69 mmol) was added and the mixture was stirred for 11 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 280 ml of tetrahydrofuran to obtain Compound 4 (7.61 g, 77%).

MS [M + H] &lt; ⁺ &gt; = 719

< Manufacturing example  5>

(8.15 g, 15.18 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (5.34 g, 13.80 mmol) in a 500 ml round- (160 ml) was added to the solution, and tetrakis- (triphenylphosphine) palladium (0.71 g, 0.67 mmol) was added thereto. The mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 180 ml of tetrahydrofuran to obtain Compound 5 (5.27 g, 53%).

MS [M + H] &lt; ⁺ &gt; = 718

< Manufacturing example  6>

(7.87 g, 14.66 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (3-bromophenyl) -6- Phenyl-1,3,5-triazine (4.85 g, 13.32 mmol) was completely dissolved in 300 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (150 ml) was added, and tetrakis- (triphenylphosphine) palladium , 0.61 mmol), and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 280 ml of tetrahydrofuran to obtain Compound 6 (7.16 g, 61%).

MS [M + H] &lt; ⁺ &gt; = 795

< Manufacturing example  7>

Compound A-1 (9.14 g, 17.03 mmol) and (4-bromophenyl) diphenylphosphine oxide (5.51 g, 13.80 mmol) were completely dissolved in 360 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, Potassium aqueous solution (180 ml) was added, tetrakis- (triphenylphosphine) palladium (0.54 g, 0.46 mmol) was added, and the mixture was heated and stirred for 11 hours. The mixture was cooled to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 450 ml of acetone to obtain Compound 7 (8.29 g, 78%).

MS [M + H] &lt; ⁺ &gt; = 688

< Manufacturing example  8>

Compound A (7.86 g, 16.04 mmol) and (4- (diphenylamino) phenyl) boronic acid (5.10 g, 17.64 mmol) were completely dissolved in 220 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, (110 ml), tetrakis- (triphenylphosphine) palladium (0.45 g, 0.41 mmol) was added, and the mixture was heated with stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (200 ml) to prepare Compound 8 (7.69 g, 68%).

MS [M + H] &lt; ⁺ &gt; = 655

< Manufacturing example  9>

Compound A (5.58 g, 11.39 mmol), (4- (di ([1,1'-biphenyl] -4- yl) amino) phenyl) boronic acid (5.52 g, 12.53 mmol ) Was completely dissolved in 240 ml of tetrahydrofuran. To the mixture was added 2M potassium carbonate aqueous solution (120 ml), tetrakis- (triphenylphosphine) palladium (0.39 g, 0.34 mmol) was added and the mixture was heated with stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (200 ml) to obtain Compound 9 (7.76 g, 84%).

MS [M + H] &lt; ⁺ &gt; = 808

< Manufacturing example  10>

Compound A (5.03 g, 10.28 mmol), (4 - ([1,1'-biphenyl] -2-yl ([1,1'- biphenyl] -4- yl) amino ) Phenyl) boronic acid (4.97 g, 11.28 mmol) was completely dissolved in 220 ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (110 ml) was added, and tetrakis- (triphenylphosphine) palladium (0.35 g, 0.31 mmol) And the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (200 ml) to prepare Compound 10 (7.76 g, 84%).

MS [M + H] &lt; ⁺ &gt; = 808

< Manufacturing example  11>

In a nitrogen atmosphere, Compound A (6.13 g, 12.51 mmol), (4 - ([1,1'-biphenyl] -4-yl (9,9- (Triphenylphosphine) palladium (0.43 g, 0.38 mmol) was dissolved in 280 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (140 ml) Followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to obtain Compound 11 (7.69 g, 73%).

MS [M + H] &lt; ⁺ &gt; = 847

< Experimental Example  1>

&Lt; Comparative Example 1-1 >

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

[LINE]

The following compound N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9- 3-yl) phenyl) -9H-furan-2-amine (HTL) (300 Å) was vacuum deposited thereon to form a hole transport layer.

[HTL]

Subsequently, the following compound N, N-di ([1,1'-biphenyl] -4- yl) -4'- (9H-carbazol-9- Apos; -biphenyl] -4-amine was vacuum-deposited to form an electron blocking layer.

[EBL]

Subsequently, the following BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

The compound ETL and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at a vapor deposition rate of 0.4 to 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

<Experimental Example 1-1>

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

<Experimental Example 1-2>

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

<Experimental Example 1-3>

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

<Experimental Example 1-4>

An organic light emitting device was prepared in the same manner as in Comparative Example 1-1, except that Compound 6 was used instead of ETL in Comparative Example 1-1.

<Experimental Example 1-5>

An organic light emitting device was prepared in the same manner as in Comparative Example 1-1, except that Compound 7 was used instead of ETL in Comparative Example 1-1.

&Lt; Comparative Example 1-2 >

An organic light emitting device was prepared in the same manner as in Comparative Example 1-1, except that the compound of ET1 was used in place of the ETL in Comparative Example 1-1.

[ET1]

&Lt; Comparative Example 1-3 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 1-1, except that the compound of ET2 was used in place of the ETL in Comparative Example 1-1.

[ET2]

When current was applied to the organic luminescent devices fabricated by Examples 1-1 to 1-5 and Comparative Examples 1-1 and 1-3, the results shown in Table 1 were obtained.

compound
(Electron transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Comparative Example 1-1 ETL 4.05 5.72 (0.137, 0.126) Experimental Example 1-1 Compound 3 3.51 6.44 (0.137, 0.126) Experimental Example 1-2 Compound 4 3.53 6.33 (0.136, 0.127) Experimental Example 1-3 Compound 5 3.67 6.35 (0.137, 0.127) Experimental Examples 1-4 Compound 6 3.75 6.29 (0.136, 0.127) Experimental Examples 1-5 Compound 7 3.76 6.27 (0.137, 0.126) Comparative Example 1-2 ET1 3.99 5.72 (0.136, 0.121) Comparative Example 1-3 ET2 3.86 5.90 (0.135, 0.122)

As shown in Table 1, in the case of an organic light emitting device manufactured using the compound represented by Chemical Formula 1 as an electron transport layer, the organic light emitting device exhibits excellent characteristics in terms of efficiency, driving voltage and / Able to know.

Specifically, the compound of Comparative Example 1-3 having a 4-phenylquinazoline structure different from the core structure (7,7-dimethylbenzoperimidine) of the compound represented by Chemical Formula 1 of the present invention was used as an electron transport layer, The voltage is reduced by 8 to 10% and the efficiency is improved by more than 10%. In addition, the organic EL device of the present invention exhibits lower voltage and higher efficiency than the organic light emitting device of Comparative Example 1-1 manufactured using the conventional ETL material as the electron transport layer.

Therefore, as can be seen from the results of Table 1, it was confirmed that the compound represented by Chemical Formula (1) of the present invention is excellent in electron transporting ability and applicable to organic light emitting devices.

< Experimental Example  2>

&Lt; Comparative Example 2-1 >

The compounds synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and then a green organic light emitting device was prepared in the following manner.

The glass substrate coated with ITO (ndium tin oxide) with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

(60 nm) / TCTA (80 nm) / GH + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ 30 nm) / LiF (1 nm) / Al (200 nm) were fabricated in this order to produce an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , GH and BCP are as follows.

<Experimental Example 2-1>

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

<Experimental Example 2-2>

An organic light emitting device was prepared in the same manner as in Comparative Example 2-1, except that Compound 4 was used instead of Compound GH in Comparative Example 2-1.

<Experimental Example 2-3>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 5 was used instead of Compound GH in Comparative Example 2-1.

<Experimental Example 2-4>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 6 was used instead of Compound GH in Comparative Example 2-1.

<Experimental Example 2-5>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 7 was used instead of Compound GH in Comparative Example 2-1.

When an electric current was applied to the organic light-emitting device manufactured in Experimental Examples 2-1 to 2-5 and Comparative Example 2-1, the results shown in Table 2 were obtained. Voltage, efficiency, EL peak and lifetime were measured, and the results are shown in Table 2 below. T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

compound
(Host) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) EL peak
(nm) T95
(hr) Comparative Example 2-1 GH 7.46 39.55 516 280 Experimental Example 2-1 Compound 3 6.98 43.06 517 335 EXPERIMENTAL EXAMPLE 2-2 Compound 4 7.16 41.75 516 320 Experimental Example 2-3 Compound 5 7.02 42.46 517 335 Experimental Example 2-4 Compound 6 6.95 43.65 517 340 Experimental Example 2-5 Compound 7 6.84 43.55 517 345

As a result of the experiment, the green organic EL devices of Experimental Examples 2-1 to 2-5 using the compound represented by Chemical Formula 1 as the host material of the light emitting layer used Comparative Example 2-1 using the conventional GH as the host material It was confirmed that the organic light emitting device according to the present invention exhibits higher current efficiency and better driving voltage.

While the present invention has been described with reference to the preferred embodiments thereof (the electron transport layer and the green light emitting layer), the present invention is not limited thereto and can be variously modified and embodied within the scope of the claims and the detailed description of the invention This also falls within the scope of the invention.

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 (14)

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

In Formula 1,
X is N or CR,
L is a direct bond,
R ₁ and R ₂ are methyl groups,
R, R ₃ to R ₁₁ and R ₁₃ to R ₁₇ are hydrogen,
R ₁₂ is an amine group substituted with an aryl group; A phosphine oxide group substituted with an aryl group; A triazine group substituted with an aryl group; A pyrimidine group substituted with an aryl group; A pyridine group substituted with an aryl group; Or an aryl group, a phosphine oxide group substituted with an aryl group, a triazine group substituted with an aryl group, a pyrimidine group substituted with an aryl group, or a phenyl group substituted with a pyridine group substituted with an aryl group. delete The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-A or Formula 1-B:
[Chemical Formula 1-A]

[Chemical Formula 1-B]

In the above formulas (1-A) and (1-B)
L, and R ₁ to R ₁₇ are as defined in the above formula (1). delete delete 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 includes a compound according to any one of claims 1, 3, and 7 Organic electronic device. The organic electronic device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The organic electronic device according to claim 8, 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 organic electronic device according to claim 8, wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer comprises the compound. The organic electronic device according to claim 8, wherein the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound. 10. The organic electroluminescent device according to claim 8, 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 injecting layer, an electron transporting layer, Electronic device. The organic electronic device according to claim 8, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

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