KR20170057850A - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present invention relates to a compound which is represented by chemical formula 1, and an organic electronic device including the same. According to an embodiment of the present invention, the compound can lower driving voltage of organic electronic devices and increases light efficiency.

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. 10-2015-0161370, filed on November 17, 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.

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

International Patent Application Publication No. 2003-012890

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

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

[Chemical Formula 1]

In Formula 1,

R ₁ and R ₂ or R ₃ and R ₄ may combine with each other to form a ring,

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

Ar and R ₁ to R ₁₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

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).

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

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

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

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

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

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

In 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 a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. But is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

,

,

,

,

,

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

,

,

,

,

,

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

In the present specification, the heterocyclic group is a 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 quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, An oxadiazolyl group, a thiadiazolyl group, a dibenzofuranyl group, and the like, but are not limited thereto.

,

,

,

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

,

,

,

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

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

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

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

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 ₁₀₀ R ₁₀₁ , and R ₁₀₀ and R ₁₀₁ are the same as or different from each other Each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group (provided that at least one of R ₁₀₀ and R ₁₀₁ 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 40. 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-phenylphenanthrylamine group; An N-biphenyl phenanthryl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthryl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

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

In the present specification, 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 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 heterocyclic group can be applied except that each of these is 2 groups.

According to one embodiment of the present disclosure, R ₁ and R ₂ or R ₃ and R ₄ combine with each other to form a ring.

According to one embodiment of the present disclosure, R ₁ and R ₂ or R ₃ and R ₄ combine with each other to form a hydrocarbon ring.

According to one embodiment of the present disclosure, L is a direct bond; 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 invention, L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

According to one embodiment of the present disclosure, L is a direct bond or a phenylene group, a biphenylene group, or a naphthylene group.

According to one embodiment of the present disclosure, Ar and R ₁ to R ₁₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, R ₁ to R ₁₄ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group.

According to one embodiment of the present disclosure, R ₁ to R ₁₄ are hydrogen.

According to one embodiment of the present disclosure, R ₃ to R ₁₄ are hydrogen.

According to one embodiment of the present disclosure, R ₁ , R ₂ and R ₅ to R ₁₄ are hydrogen.

According to one embodiment of the present disclosure, Ar is hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

According to one embodiment of the present invention, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group , A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted creicenyl group, or a substituted or unsubstituted pyrenyl group, Lt; / RTI >

According to one embodiment of the present invention, Ar is a phenyl group in which hydrogen, deuterium, a cyano group, a halogen group or a silyl group is substituted or unsubstituted.

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

According to one embodiment of the present invention, Ar is hydrogen, deuterium, cyano, halogen or a biphenyl group in which the silyl group is substituted or unsubstituted.

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

According to one embodiment of the present invention, Ar is hydrogen, deuterium, cyano, halogen or a naphthyl group in which the silyl group is substituted or unsubstituted.

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

According to one embodiment of the present invention, Ar is hydrogen, deuterium, cyano, halogen or a terphenyl group in which the silyl group is substituted or unsubstituted.

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

According to one embodiment of the present invention, Ar is a phenanthryl group in which hydrogen, deuterium, cyano group, halogen group or silyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, Ar is a phenanthryl group.

According to one embodiment of the present invention, Ar is hydrogen, deuterium, cyano, halogen or substituted or unsubstituted fluorenyl group.

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

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

According to one embodiment of the present invention, Ar is a substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted imidazole group, a substituted or unsubstituted Substituted or unsubstituted thiazoles, substituted or unsubstituted oxazole groups, substituted or unsubstituted oxadiazole groups, substituted or unsubstituted triazole groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted bipyridyl groups, substituted or unsubstituted Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted pyrazinyl groups, Substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted phthalazinyl groups, substituted or unsubstituted pyridopyrimidinyl groups, substituted or unsubstituted pyridopyrimidinyl groups, substituted or unsubstituted quinoxalinyl groups, A substituted or unsubstituted pyrazinyl group, an unsubstituted pyrazinopyranyl group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted indole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoxazole group, A substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzocarbazole group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted phenanthroline group ), A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, or a substituted or unsubstituted thiadiazolyl group.

According to one embodiment of the present disclosure, Ar is a pyridine group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a pyridine group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group, or a fluorenyl group.

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

According to one embodiment of the present invention, Ar is a pyrimidine group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group, or a fluorenyl group.

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

According to one embodiment of the present invention, Ar is a triazine group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a triazine group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group or a fluorenyl group.

According to one embodiment of the present disclosure, Ar is a triazine group.

According to one embodiment of the present invention, Ar is a quinolinyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a quinolinyl group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group or a fluorenyl group.

According to one embodiment of the present disclosure, Ar is a quinolinyl group.

According to one embodiment of the present disclosure, Ar is a quinazoline group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a quinazoline group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group, or a fluorenyl group.

According to one embodiment of the present disclosure, Ar is a quinazoline group.

According to one embodiment of the present invention, Ar is a carbazolyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a carbazole group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group or a fluorenyl group.

According to one embodiment of the present disclosure, Ar is a carbazole group.

According to one embodiment of the present disclosure, Ar is a dibenzocarbazole group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a dibenzocarbazole group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group or a fluorenyl group.

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

According to one embodiment of the present disclosure, Ar is a dibenzothiophene group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a dibenzothiophene group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group or a fluorenyl group.

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

According to one embodiment of the present invention, Ar is a dibenzofurane group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar is a dibenzofurane group substituted or unsubstituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a triphenyl group, or a fluorenyl group.

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

, 치환 또는 비치환된

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

, Substituted or unsubstituted

to be.

, 치환 또는 비치환된

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

, Substituted or unsubstituted

to be.

, 치환 또는 비치환된

이다.According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted dibenzothiophene group or a dibenzofurane group,

, Substituted or unsubstituted

to be.

기, 치환 또는 비치환된

기, 치환 또는 비치환된

기, 또는 치환 또는 비치환된

기이다.According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted

Group, a substituted or unsubstituted

Group, a substituted or unsubstituted

Group, or a substituted or unsubstituted

.

According to one embodiment of the present invention, Ar is a substituted or unsubstituted amine group having 1 to 40 carbon atoms.

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

According to one embodiment of the present invention, Ar is an amine group substituted or unsubstituted with phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenyl or fluorenyl.

According to one embodiment of the present disclosure, Ar is an amine group.

According to one embodiment of the present disclosure, Ar is a phosphine oxide group substituted or unsubstituted with a cyano group or a silyl group.

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

According to one embodiment of the present invention, Ar is a phosphine oxide group substituted or unsubstituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group or a fluorenyl group.

According to one embodiment of the present disclosure, Ar is a phosphine oxide group.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

L, Ar, and R ₁ to R ₁₄ are as defined in Formula 1,

R ₁₅ and R ₁₆ are the same as 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; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p and q are each an integer of 0 to 4,

when p is 2 or more, plural R < ₁₅ > are the same or different from each other,

When q is 2 or more, the plural R < ₁₆ > s are the same or different from each other.

According to one embodiment of the present disclosure, R ₁₅ and R ₁₆ are the same or different from each other and each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group.

According to one embodiment of the present disclosure, R ₁₅ to R ₁₆ are hydrogen.

According to one embodiment of the present specification, -L-Ar may be any of substituents of the following [A-1] to [A-4].

[A-1]

[A-2]

[A-3]

[A-4]

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

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

For example, the compound of Formula 1 can be prepared as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position, or number of substituent groups may be varied according to techniques known in the art. A concrete manufacturing method will be described later.

[Reaction Scheme 1]

As shown in the experimental example (device example) to be described later, the compound of the formula (1) exhibits low voltage and high efficiency in an organic light emitting device because electrons are evenly distributed in a molecule relative to the compounds of Comparative Examples 1 and 2.

In addition, the compound of 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 131 ° C, which is significantly higher than that of NPB (Tg: 98 ° C) which has been generally used. Such an increase in thermal stability is an important factor for increasing lifetime by providing driving stability to the device.

In addition, the compounds of the examples herein exhibit stable redox properties. The stability against oxidation and reduction can be confirmed by CV (cyclovoltammetry) method. As a specific example, the compound of formula (1-1) of Example 1 of the present invention was oxidized at the same voltage and exhibited the same current amount when a plurality of repetitive oxidation voltages were applied, Indicating excellent stability.

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

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

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

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

The organic material layer of the organic electronic device in this specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic electronic device of the present invention, the organic light emitting device has a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, . However, the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.

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

Hereinafter, the organic light emitting device will be described.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes 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, and the electron 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 one embodiment of the present invention, the light emitting layer comprises a compound of the general formula (1), and further comprises a luminescent dopant.

In one embodiment of the present invention, the light emitting layer comprises a compound of Formula 1, and the light emitting dopant includes a phosphorescent dopant.

In one embodiment of the present invention, the light emitting layer comprises a compound of Formula 1, and the phosphorescent dopant includes an iridium phosphorescent dopant.

In one embodiment of the present invention, the light emitting layer comprises a compound represented by Chemical Formula 1, and the iridium phosphorescent dopant is Ir (ppy) ₃ .

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.

According to one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following formula 1-A.

[Chemical Formula 1-A]

In the above formula (1-A)

n1 is an integer of 1 or more,

Ar ₇ is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,

L ₄ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar ₈ and Ar ₉ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted germanium group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group or may be bonded to each other to form a substituted or unsubstituted ring,

When n ₁ is 2 or more, the structures in parentheses two or more are the same or different from each other.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by the formula 1-A as a dopant in the light emitting layer.

According to one embodiment of the present disclosure, L < ₄ > is a direct bond.

According to one embodiment of the present disclosure, n ₁ is 2.

In one embodiment of the present specification, Ar ₇ is a divalent pyylene group substituted or unsubstituted with a deuterium, a methyl group, an ethyl group or a tert-butyl group.

According to one embodiment of the present invention, Ar ₈ and Ar ₉ are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, Ar ₈ and Ar ₉ are the same or different and each independently represents an aryl group substituted or unsubstituted with a germanium group substituted with an alkyl group.

According to one embodiment of the present invention, Ar ₈ and Ar ₉ are the same or different and each independently an aryl group substituted or unsubstituted with a trimethyl germanium group.

According to one embodiment of the present invention, Ar ₈ and Ar ₉ are the same or different and are each independently a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, Ar ₈ and Ar ₉ are phenyl groups substituted or unsubstituted with trimethylgermanium groups.

According to one embodiment of the present invention, the above formula (1-A) is represented by the following compounds.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following formula (2-A).

[Chemical Formula 2-A]

In the above formula (2-A)

이고,G ₁₁ represents a group selected from the group consisting of a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacene group, 1-naphthacene group, 1-naphthacene group, 1-pyrene group, 2-pyrene group, 4-pyrene group, 3- -1-naphthyl group, or a group represented by the formula

ego,

G ₁₂ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacenylene group, 1-naphthacenylene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl group, P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl group, 4 " Or a 3-fluorantheny group,

G ₁₃ and G ₁₄ are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g ₁₂ is an integer of 1 to 5,

g ₁₃ and g ₁₄ are each an integer of 1 to 4,

When each of g ₁₂ to g ₁₄ is 2 or more, the structures in parentheses of 2 or more are the same or different.

According to one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 2-A as a host of the light-emitting layer.

According to one embodiment of the present invention, G ₁₁ is a 1-naphthyl group.

According to one embodiment of the present invention, G ₁₂ is a 2-naphthyl group.

According to an exemplary embodiment of the present disclosure, wherein G ₁₃ and G ₁₄ is hydrogen.

According to one embodiment of the present invention, the formula (2-A) is represented by the following compound.

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, perylene tetracarboxylic 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 >

<Production Example 1> Synthesis of Compound 1-1

The compound A (10.0 g, 27.25 mmol) and 3-bromo-9-phenyl-9H-carbazole (9.62 g, 29.97 mmol) were completely dissolved in 240 ml of xylene in a 500 ml round- (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain Compound 1-1 (13.12 g, yield: 79%).

MS [M + H] &lt; ⁺ &gt; = 609

<Preparation Example 2> Synthesis of compound 1-2

The compound A (10.0 g, 27.25 mmol) and 2-bromo-9-phenyl-9H-carbazole (9.62 g, 29.97 mmol) were completely dissolved in 210 ml of xylene in a 500 ml round- (Tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain Compound 1-2 (11.81 g, yield: 71%).

MS [M + H] &lt; ⁺ &gt; = 609

<Preparation Example 3> Synthesis of Compound 1-3

The compound A (10.0 g, 27.25 mmol) and 9- (4-bromophenyl) -9H-carbazole (9.62 g, 29.97 mmol) were completely dissolved in 210 ml of xylene in a 500 ml round- (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from 300 ml of ethyl acetate to obtain Compound 1-3 (10.63 g, yield: 63%).

MS [M + H] &lt; ⁺ &gt; = 609

<Production Example 4> Synthesis of Compound 1-4

The compound A (10.0 g, 27.25 mmol) and 4-bromo-N, N-diphenyl aniline (9.64 g, 29.97 mmol) were completely dissolved in 280 ml of xylene in a 500 ml round bottom flask under nitrogen atmosphere, (tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating with stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain the compound 1-4 (13.95 g, yield: 83%).

MS [M + H] &lt; ⁺ &gt; = 611

<Production Example 5> Synthesis of Compound 1-5

(10.0 g, 27.25 mmol) and N- (4-bromophenyl) -N-phenyl- [1,1'-biphenyl] -4-amine (11.99 g, (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added to the reaction mixture, followed by addition of sodium tert-butoxide (3.41 g, 35.43 mol) And the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain the compound 1-5 (15.91 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 687

& Lt; Preparation Example 6 > - Synthesis of Compound 1-6

(10.0 g, 27.25 mmol) and N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ Biphenyl] -4-amine (14.25 g, 29.97 mmol) was completely dissolved in 250 ml of xylene and sodium tert-butoxide (3.41 g, 35.43 mol) -Butylphosphine) palladium (0.14 g, 0.27 mmol) were added thereto, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (320 ml) to obtain the compound 1-6 (18.54 g, yield: 89%).

MS [M + H] &lt; ⁺ &gt; = 763

& Lt; Preparation Example 7 > - Synthesis of Compound 1-7

(10.0 g, 27.25 mmol) and N- (4-bromophenyl) -9,9-dimethyl-N-phenyl-9H-fluoren- , Triethylphosphine) palladium (0.14 g, 0.27 mmol) was added to the solution in the same manner as in Example 1, except that sodium tert-butoxide (3.41 g, 35.43 mol) Followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain the compound 1-7 (15.91 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 727

& Lt; Preparation Example 8 > - Synthesis of Compound 1-8

(10.0 g, 27.25 mmol), N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9 (15.45 g, 29.97 mmol) was dissolved in 330 ml of xylene and sodium tert-butoxide (3.41 g, 35.43 mol) was added, and bis (tri- tert-butylphosphine) palladium (0.14 g, 0.27 mmol) were added thereto, followed by heating and stirring for 8 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain the compound 1-8 (18.72 g, yield: 86%).

MS [M + H] &lt; ⁺ &gt; = 803

<Production Example 9> synthesis of the compound 1-9

Compound A (10.0 g, 27.25 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.01 g, 29.97 mmol) were dissolved in a 500 ml round bottom flask in a nitrogen atmosphere, (Tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 5 hours . The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from 300 ml of ethyl acetate to obtain 13.44 g (yield: 83%) of the compound 1-9.

MS [M + H] &lt; ⁺ &gt; = 599

<Preparation Example 10> synthesis of the compound 1-10

The compound A (10.0 g, 27.25 mmol) and 2-chloro-4,6-diphenylpyrimidine (8.01 g, 29.97 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round bottom flask in a nitrogen atmosphere, (tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating with stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (330 ml) to obtain the compound 1-10 (12.11 g, yield: 74%).

MS [M + H] &lt; ⁺ &gt; = 598

<Preparation Example 11> synthesis of the compound 1-11

The compound A (10.0 g, 27.25 mmol) and 4-chloro-2,6-diphenylpyrimidine (8.01 g, 29.97 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round bottom flask in a nitrogen atmosphere, (tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating with stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (330 ml) to obtain the compound 1-11 (10.91 g, yield 66%).

MS [M + H] &lt; ⁺ &gt; = 598

<Preparation Example 12> synthesis of the compound 1 - 12

The compound A (10.0 g, 27.25 mmol) and 2-chloro-4,6-diphenylpyrimidine (8.01 g, 29.97 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round bottom flask in a nitrogen atmosphere, (tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating with stirring for 10 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure, and recrystallized from 360 ml of ethyl acetate to obtain Compound 1-12 (9.88 g, yield: 59%).

MS [M + H] &lt; ⁺ &gt; = 597

<Preparation Example 13> synthesis of the compound 1-13

The compound A (10.0 g, 27.25 mmol) and 2-chloro-4-phenylquinazoline (7.21 g, 29.97 mmol) were dissolved in 240 ml of xylene in a 500 ml round-bottomed flask under a nitrogen atmosphere, (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (336 ml) to obtain Compound 1-13 (13.26 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 572

<Preparation Example 14> synthesis of the compound 1-14

(10.0 g, 27.25 mmol) and 2-chloro-4- (naphthalen-2-yl) quinazoline (8.71 g, 29.97 mmol) were dissolved in 220 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added and the mixture was heated with stirring for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (336 ml) to obtain the compound 1-14 (14.77 g, yield: 87%).

MS [M + H] &lt; ⁺ &gt; = 622

<Preparation Example 15> synthesis of the compound 15

(10.0 g, 27.25 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (10.29 g, 29.97 mmol) were added to a 500 ml round bottom flask in a nitrogen atmosphere. (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by addition of sodium tri-tert-butoxide (3.41 g, 35.43 mol) Lt; / RTI &gt; The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (370 ml) to obtain the compound 1-15 (13.44 g, yield: 83%).

MS [M + H] &lt; ⁺ &gt; = 675

<Preparation Example 16> synthesis of the compound 1-16

(10.0 g, 27.25 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (10.29 g, 29.97 mmol) were added to a 500 ml round bottom flask in a nitrogen atmosphere. (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by addition of sodium tert-butoxide (3.41 g, 35.43 mol) Lt; / RTI &gt; The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (340 ml) to obtain the compound 1-16 (12.11 g, yield: 74%).

MS [M + H] &lt; ⁺ &gt; = 675

<Preparation Example 17> synthesis of the compound 1-17

In a nitrogen atmosphere, Compound A (10.0 g, 27.25 mmol) and 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (10.29 g, 29.97 mmol) were dissolved in 290 ml (Tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 8 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain the compound 1-17 (9.75 g, yield: 62%).

MS [M + H] &lt; ⁺ &gt; = 674

& Lt; Production Example 18 > - Synthesis of Compound 1-18

The compound A (10.0 g, 27.25 mmol) and (4-bromophenyl) diphenylphosphine oxide (10.68 g, 29.97 mmol) were dissolved in 280 ml of xylene in a 500 ml round bottom flask under nitrogen atmosphere, (tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating with stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain the compound 1-18 (14.92 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 644

<Preparation Example 19> synthesis of the compound 1-19

The compound A (10.0 g, 27.25 mmol) and 2-bromodibenzo [b, d] furan (7.38 g, 29.97 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round bottom flask under nitrogen atmosphere, (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (180 ml) to obtain the compound 1-19 (10.74 g, yield: 74%).

MS [M + H] &lt; ⁺ &gt; = 534

<Preparation Example 20> synthesis of the compound 1-20

The compound A (10.0 g, 27.25 mmol) and 2-bromodibenzo [b, d] thiophene (7.38 g, 29.97 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round bottom flask in a nitrogen atmosphere, (tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating with stirring for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (190 ml) to obtain the compound 1-20 (9.08 g, yield 66%).

MS [M + H] &lt; ⁺ &gt; = 550

<Preparation Example 21> synthesis of the compound 1-21

The compound A (10.0 g, 27.25 mmol) and 2- (4-bromophenyl) -1-phenyl-1H-benz [d] imidazole (10.44 g, 29.97 mmol) were dissolved in a 500- (Tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added to the solution, and sodium borohydride was added thereto for 8 hours Followed by heating and stirring. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to give the above compound 1-21 (9.75 g, yield: 62%).

MS [M + H] &lt; ⁺ &gt; = 636

<Preparation Example 22> synthesis of the compounds 1-22 to 1-42

Compounds 1-22 to 1-42 were prepared in the same manner as in the preparation of Compounds 1-1 to 1-21 except for using Compound B instead of Compound A in Preparative Examples 1-21. MS [M = H] ⁺ of each of the above compounds 1-22 to 1-42 is shown in Table 1 below.

[Compound B]

Compound No. MS [M = H] &lt; ⁺ &gt; Compound No. MS [M = H] &lt; ⁺ &gt; 1-22 609 1-33 597 1-23 609 1-34 572 1-24 609 1-35 622 1-25 611 1-36 675 1-26 687 1-37 675 1-27 763 1-38 674 1-28 727 1-39 644 1-29 804 1-40 534 1-30 599 1-41 550 1-31 598 1-42 636 1-32 598 - -

< Experimental Example  1>

<Experimental 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

(4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 angstroms), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer .

[NPB]

Subsequently, the following compound 1-1 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form an electron blocking layer.

[Compound 1-1]

Subsequently, 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 ET1 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 1-2>

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

<Experimental Example 1-3>

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

<Experimental Example 1-4>

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

<Experimental Example 1-5>

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

<Experimental Example 1-6>

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

<Experimental Example 1-7>

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

 <Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-8 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-22 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-23 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-24 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-25 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-26 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-27 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-28 was used instead of Compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 1-29 was used instead of Compound 1-1 in Experimental Example 1-1.

&Lt; Comparative Example 1-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that EB 1 (TCTA) was used in place of Compound 1-1 in Experimental Example 1-1.

[EB 1]

&Lt; Comparative Example 1-2 >

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

[EB 2]

When current was applied to the organic light-emitting devices fabricated in Experimental Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-2, the results shown in Table 2 were obtained.

division compound
(Electron blocking layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1-1 Compound 1-1 3.75 5.30 (0.139, 0.125) Experimental Example 1-2 Compound 1-2 3.62 5.45 (0.138, 0.126) Experimental Example 1-3 Compound 1-3 3.47 5.89 (0.138, 0.127) Experimental Examples 1-4 Compound 1-4 3.48 5.77 (0.137, 0.125) Experimental Examples 1-5 Compound 1-5 3.49 5.88 (0.136, 0.125) Experimental Example 1-6 Compound 1-6 3.44 5.71 (0.136, 0.127) Experimental Example 1-7 Compound 1-7 3.43 5.83 (0.136, 0.125) Experimental Examples 1-8 Compound 1-8 3.44 5.75 (0.137, 0.125) Experimental Examples 1-9 Compound 1-22 3.53 5.64 (0.138, 0.125) Experimental Example 1-10 Compound 1-23 3.58 5.53 (0.136, 0.125) Experimental Example 1-11 Compound 1-24 3.53 5.61 (0.137, 0.125) Experimental Example 1-12 Compound 1-25 3.55 5.51 (0.136, 0.125) Experimental Example 1-13 Compound 1-26 3.62 5.65 (0.138, 0.126) Experimental Example 1-14 Compound 1-27 3.67 5.64 (0.137, 0.125) Experimental Example 1-15 Compound 1-28 3.60 5.56 (0.136, 0.127) Experimental Example 1-16 Compound 1-29 3.61 5.68 (0.135, 0.127) Comparative Example 1-1 EB 1 4.16 4.72 (0.138, 0.127) Comparative Example 1-2 EB 2 4.35 4.58 (0.139, 0.125)

As shown in Table 2, when the compounds of Experimental Examples 1-1 to 1-16 of the present invention were used as an electron blocking layer in an organic light emitting device, the characteristics of low voltage and high efficiency . &Lt; / RTI &gt;

Accordingly, it has been confirmed that the compound represented by the chemical formula according to the present invention has excellent electron suppression ability, exhibits low voltage and high efficiency, and is applicable to organic light emitting devices.

< Experimental Example  2>

<Experimental Example 2-1>

The compounds synthesized in the above 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.

The compound 1-9 was used as a host on the ITO transparent electrode thus prepared, and m-MTDATA (60 nm) / TCTA (80 nm) / Compound 1-9 + 10% Ir (ppy) ₃ (300 nm) / BCP ) / 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 and BCP are as follows.

<Experimental Example 2-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-10 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-11 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-12 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-15 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 1-16 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-17 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-30 was used in place of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-31 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-32 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-11>

An organic light emitting device was prepared in the same manner as in Experimental Example 2-1, except that Compound 1-33 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that Compound 1-36 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-37 was used instead of Compound 1-9 in Experimental Example 2-1.

<Experimental Example 2-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 1-38 was used instead of Compound 1-9 in Experimental Example 2-1.

&Lt; Comparative Example 2-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the following GH 1 (CBP) was used instead of the compound 1-9 in Experimental Example 2-1.

[GH 1]

&Lt; Comparative Example 2-2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that the following GH 2 was used instead of the compound 1-9 in Experimental Example 2-1.

[GH 1]

The results shown in Table 3 were obtained when current was applied to the organic light-emitting devices manufactured in Experimental Examples 2-1 to 2-14 and Comparative Examples 2-1 to 2-2.

division compound
(Host) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) EL peak
(nm) Experimental Example 2-1 Compound 1-9 5.18 43.93 517 EXPERIMENTAL EXAMPLE 2-2 Compound 1-10 5.26 45.24 516 Experimental Example 2-3 Compound 1-11 5.15 44.99 518 Experimental Example 2-4 Compound 1-12 5.29 46.15 517 Experimental Example 2-5 Compound 1-15 5.28 44.31 515 Experimental Examples 2-6 Compound 1-16 5.13 45.63 516 Experimental Example 2-7 Compound 1-17 5.29 45.42 516 Experimental Examples 2-8 Compound 1-30 5.27 46.54 517 Experimental Examples 2-9 Compound 1-31 5.23 46.68 518 Experimental Example 2-10 Compound 1-32 5.30 45.23 517 Experimental Example 2-11 Compound 1-33 5.37 45.33 517 Experimental Examples 2-12 Compound 1-36 5.29 45.73 517 Experimental Example 2-13 Compound 1-37 5.35 45.63 517 Experimental Example 2-14 Compound 1-38 5.21 46.13 517 Comparative Example 2-1 GH 1 (CBP) 7.81 35.72 517 Comparative Example 2-2 GH 2 6.51 39.72 517

As shown in Table 3, the green organic EL devices of Experimental Examples 2-1 to 2-14 using the compound represented by Formula 1 according to the present invention as a host material of the green light emitting layer were compared with Comparative Example using conventional CBP It is confirmed that the organic EL device of the present invention exhibits better current efficiency and better driving voltage than the green organic EL devices of Examples 2-1 and 2-2.

< Experimental Example  3>

<Experimental Examples 3-1 to 3-4>

The compounds synthesized in the above Production Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared as follows.

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was pressurized to have a pressure of 1 × 10 ^-6 torr. Then, organic substances were injected onto the ITO using DNTPD (700 Å), α-NPB (300 Å) (Alq), 1-14, 1-34, and 1-35 were used as a host (90 wt%) and the following (piq) ₂ Ir (acac) ₃ (350 Å), LiF (5 Å), and Al (1,000 Å) in this order and measured at 0.4 mA.

The DNTPD, α-NPB, (piq ) 2 Ir (acac), The structure of Alq ₃ is as follows.

&Lt; Comparative Example 3-1 >

The organic luminescent device for Comparative Example 3-1 was the host of the luminescent layer in the device structures of Experimental Examples 3-1 to 3-4, and CBP which is widely used as a general phosphorescent host material instead of the organic luminescent compound prepared by the present invention was used Except for the point.

The voltage, the current density, the luminance, the color coordinate, and the life span of the organic electroluminescent device manufactured according to the following Experimental Examples 3-1 to 3-4 and Comparative Example 3-1 were measured and the results shown in Table 4 were obtained. At this time, T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

division compound
(Host) Dopant Voltage
(V) Luminance
(cd / m ² ) CIEx
CIEy
T95
(hr) Experimental Example 3-1 Compound 1-13 [(piq) ₂ Ir (acac)] 4.4 1860 0.670 0.329 465 Experimental Example 3-2 Compound 1-14 [(piq) ₂ Ir (acac)] 4.2 1850 0.674 0.325 445 Experimental Example 3-3 Compound 1-34 [(piq) ₂ Ir (acac)] 4.1 1900 0.672 0.327 440 Experimental Example 3-4 Compound 1-35 [(piq) ₂ Ir (acac)] 4.3 1840 0.673 0.335 435 Comparative Example 3-1 CBP [(piq) ₂ Ir (acac)] 7.5 920 0.679 0.339 160

As shown in Table 4, compounds 1-13, 1-14, 1-34, and 1-35 in which Ar of Formula 1 is a substituted or unsubstituted quinazoline group are used as a host material in the light emitting layer The red organic EL devices of Experimental Examples 3-1 to 3-4 exhibited superior performance in terms of current efficiency, driving voltage and lifetime than the red organic EL device of Comparative Example 3-1 using conventional CBP.

Although the preferred embodiments of the present invention (the electron blocking layer, the green luminescent layer, and the red luminescent layer) have been described above, the present invention is not limited thereto and various modifications may be made within the scope of the claims and the detailed description of the invention. It is also 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 (19)

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

In Formula 1,
R ₁ and R ₂ or R ₃ and R ₄ may combine with each other to form a ring,
L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar and R ₁ to R ₁₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In the general formulas (2) and (3)
L, Ar, and R ₁ to R ₁₄ are as defined in Formula 1,
R ₁₅ and R ₁₆ are the same as 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; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
p and q are each an integer of 0 to 4,
when p is 2 or more, plural R &lt; ₁₅ &gt; are the same or different from each other,
When q is 2 or more, the plural R &lt; ₁₆ &gt; s are the same or different from each other. The method according to claim 1,
L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group. The method according to claim 1,
Ar 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 fluorenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted phosphine oxide group. The method according to claim 1,
Ar represents a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzocarbazole group; A substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted dibenzofurane group. The compound according to claim 1, wherein -L-Ar is any one of the following [A-1] to [A-4].
[A-1]

[A-2]

[A-3]

[A-4]

The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 7 Organic electronic device. The method of claim 8,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The method of 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 method of claim 8,
Wherein the organic material layer comprises an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound. The method of claim 8,
Wherein the organic layer comprises an electron blocking layer, and the electron blocking layer comprises the compound. The method of claim 8,
Wherein the organic electronic device further comprises one or more layers selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer and an electron blocking layer. 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. The organic electronic device according to claim 8, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (1-A):
[Chemical Formula 1-A]

In the above formula (1-A)
n ₁ is an integer of 1 or more,
Ar ₇ is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,
L ₄ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar ₈ and Ar ₉ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted germanium group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group or may be bonded to each other to form a substituted or unsubstituted ring,
When n ₁ is 2 or more, the structures in parentheses two or more are the same or different from each other. The compound according to claim 15, wherein L ₄ is a direct bond, Ar ₇ is a bivalent phenylene group, Ar ₈ and Ar ₉ are the same or different and each is an aryl group substituted or unsubstituted with a germanium group substituted with an alkyl group , and n &lt; ₁ &gt; The organic electronic device according to claim 8, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (2-A):
[Chemical Formula 2-A]

In the above formula (2-A)
G ₁₁ represents a group selected from the group consisting of a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacene group, 1-naphthacene group, 1-naphthacene group, 1-pyrene group, 2-pyrene group, 4-pyrene group, 3- -1-naphthyl group, or a group represented by the formula

ego,
G ₁₂ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacenylene group, 1-naphthacenylene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl group, P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl group, 4 " Or a 3-fluorantheny group,
G ₁₃ and G ₁₄ are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
g ₁₂ is an integer of 1 to 5,
g ₁₃ and g ₁₄ are each an integer of 1 to 4,
When each of g ₁₂ to g ₁₄ is 2 or more, the structures in parentheses of 2 or more are the same or different. The organic electronic device according to claim 17, wherein G ₁₁ is a 1-naphthyl group and G ₁₂ is a 2-naphthyl group. The organic electronic device according to claim 15, wherein the light-emitting layer comprises a compound represented by the following formula (2-A):
[Chemical Formula 2-A]

In the above formula (2-A)
G ₁₁ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacene group, a 9-naphthacene group, a 1-pyrene group, a 2-pyrene group, a 4-pyrene group, a 3-methyl-2-naphthyl group, a 4-phenanthryl group, Methyl-1-naphthyl group,

ego,
G ₁₂ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacenylene group, 1-naphthacenylene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl group, P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl group, 4 " Or a 3-fluorantheny group,
G ₁₃ and G ₁₄ are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
g ₁₂ is an integer of 1 to 5,
g ₁₃ and g ₁₄ are each an integer of 1 to 4,
When each of g ₁₂ to g ₁₄ is 2 or more, the structures in parentheses of 2 or more are the same or different.

Images