KR102020529B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

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

Description

COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2015-0161370 filed with the Korea Intellectual Property Office on November 17, 2015, the entire contents of which are incorporated herein.

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

Representative examples of the organic electronic device include an organic light emitting device. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

International Patent Application Publication No. 2003-012890

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

The present specification provides a compound represented by the following Formula 1.

[Formula 1]

In Chemical 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; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar and R ₁ to R ₁₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In addition, the present specification is a first electrode; A second electrode provided to face 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 compound described above.

The compound according to one embodiment of the present specification is used in an organic electric device including an organic light emitting device to lower the driving voltage of the organic electric device, improve the light efficiency, and improve the life characteristics of the device by the thermal stability of the compound. have.

1 illustrates an organic electronic device 10 according to an exemplary embodiment of the present specification.
2 shows an organic electronic device 11 according to another embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a compound represented by Chemical Formula 1.

는 연결되는 부위를 의미한다.In the present specification,

Means a site to be connected.

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; An alkyl group; Cycloalkyl group; Alkenyl groups; Amine group; Phosphine oxide groups; Aryl group; Silyl groups; And one or two or more substituents selected from the group consisting of heteroaryl groups including one or more of N, O, S, Se, and Si atoms, or two or more substituents among the substituents exemplified above are substituted with a substituent, or any It means that it does not have a substituent.

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

In this specification, although carbon number of a carbonyl group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In this specification, although carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. 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 carbon number 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-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, 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 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR ₁₀₄ R ₁₀₅ R ₁₀₆ , R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

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,

,

,

,

,

,

Etc., but is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heteroaryl group are thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl Groups, oxadiazolyl groups, thiadiazolyl groups, dibenzofuranyl groups and the like, but are not limited thereto.

,

,

,

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

,

,

,

Etc., but is not limited thereto.

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

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

The hydrocarbon ring or heterocycle herein may be selected from the examples of the cycloalkyl group, aryl group or heteroaryl group described above, except that the hydrocarbon ring or heterocycle is monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic or condensed form thereof. But. It is not limited only to these.

In the present specification, the amine group refers to 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 hydrogen; heavy hydrogen; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And a substituent consisting of at least one of a heterocyclic group, provided that at least one of R ₁₀₀ and R ₁₀₁ is not hydrogen. For example, -NH ₂ ; Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group and a diheteroarylamine group, and the carbon number is not particularly limited, but is preferably 1 to 40. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrylamine group; N-biphenyl phenanthrylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthryl fluorenyl amine group; N-biphenyl fluorenyl amine group and the like, but is not limited thereto.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. 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 including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

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

In the present specification, the divalent to tetravalent aromatic ring group may be monocyclic or polycyclic, meaning that the aryl group has 2 to 4 bonding positions, that is, 2 to 4 valent groups. The description of the aforementioned aryl groups can be applied except that they are each 2 to 4 valent groups.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group. The description of the aforementioned heterocyclic groups can be applied except that they are each divalent.

According to an exemplary embodiment of the present disclosure, R ₁ and R ₂ or R ₃ and R ₄ are bonded to each other to form a ring.

According to an exemplary embodiment of the present disclosure, R ₁ and R ₂ or R ₃ and R ₄ are bonded to each other to form a hydrocarbon ring.

According to an exemplary embodiment of the present disclosure, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

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

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

According to an exemplary embodiment of the present specification, Ar and R ₁ to R ₁₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R _{One To} R _{14 They} 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 an exemplary embodiment of the present disclosure, R ₁ to R ₁₄ is hydrogen.

According to an exemplary embodiment of the present disclosure, R ₃ to R ₁₄ is hydrogen.

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

According to an exemplary embodiment of the present specification, Ar is hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group , Substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted perylenyl group, substituted or unsubstituted chrysenyl group, or substituted or unsubstituted Fluorenyl group.

According to an exemplary embodiment of the present specification, Ar is a phenyl group substituted or unsubstituted with hydrogen, deuterium, cyano group, halogen group or silyl group.

According to an exemplary embodiment of the present specification, Ar is a phenyl group.

According to an exemplary embodiment of the present specification, Ar is a biphenyl group unsubstituted or substituted with hydrogen, deuterium, cyano group, halogen group or silyl group.

According to an exemplary embodiment of the present specification, Ar is a biphenyl group.

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

According to an exemplary embodiment of the present specification, Ar is a naphthyl group.

According to an exemplary embodiment of the present specification, Ar is a terphenyl group substituted or unsubstituted with hydrogen, deuterium, cyano group, halogen group or silyl group.

According to an exemplary embodiment of the present specification, Ar is a terphenyl group.

According to an exemplary embodiment of the present specification, Ar is a phenanthryl group substituted or unsubstituted with hydrogen, deuterium, cyano group, halogen group or silyl group.

According to an exemplary embodiment of the present specification, Ar is a phenanthryl group.

According to an exemplary embodiment of the present specification, Ar is a fluorenyl group in which hydrogen, deuterium, cyano group, halogen group or silyl group is unsubstituted or substituted.

According to an exemplary embodiment of the present specification, Ar is a fluorenyl group.

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

According to an exemplary embodiment of the present specification, 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 Thiazole group, substituted or unsubstituted oxazole group, substituted or unsubstituted oxadiazole group, substituted or unsubstituted triazole group, substituted or unsubstituted pyridyl group, substituted or unsubstituted bipyridyl group, substituted or unsubstituted Pyrimidyl groups, substituted or unsubstituted triazine groups, substituted or unsubstituted acridil groups, substituted or unsubstituted pyridazine groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted quinolinyl groups, substituted or Unsubstituted quinazoline group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted pyrido pyrimidinyl group, substituted or unsubstituted pyrido pyrazinyl group, substituted or Unsubstituted pyrazinopyrazinyl groups, substituted or unsubstituted isoquinoline groups, substituted or unsubstituted indole groups, substituted or unsubstituted carbazole groups, substituted or unsubstituted benzoxazole groups, substituted or unsubstituted benziimi A doazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzocarbazole group, Substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted phenanthroline group (phenanthroline ), A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isooxazolyl group, a substituted or unsubstituted oxadiazolyl group, or a substituted or unsubstituted thiadiazolyl group.

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

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

According to an exemplary embodiment of the present specification, Ar is a pyridine group.

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

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

According to an exemplary embodiment of the present specification, Ar is a pyrimidine group.

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

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

According to an exemplary embodiment of the present specification, Ar is a triazine group.

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

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

According to an exemplary embodiment of the present specification, Ar is a quinolinyl group.

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

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

According to an exemplary embodiment of the present specification, Ar is a quinazoline group.

According to an exemplary embodiment of the present specification, Ar is a carbazole group unsubstituted or substituted with an aryl group.

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

According to an exemplary embodiment of the present specification, Ar is a carbazole group.

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

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

According to an exemplary embodiment of the present specification, Ar is a dibenzocarbazole group.

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

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

According to an exemplary embodiment of the present specification, Ar is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar is a dibenzofuran group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, Ar is a dibenzofuran group unsubstituted or substituted with a phenyl group, biphenyl group, naphthyl group, terphenyl group, triphenyl group or fluorenyl group.

According to an exemplary embodiment of the present specification, Ar is a dibenzofuran group.

, 치환 또는 비치환된

이다.According to an exemplary embodiment of the present specification, Ar is unsubstituted or substituted with an aryl group

, Substituted or unsubstituted

to be.

, 치환 또는 비치환된

이다.According to an exemplary embodiment of the present specification, Ar is unsubstituted or substituted with a phenyl group, biphenyl group, naphthyl group, terphenyl group, triphenyl group or fluorenyl group

, Substituted or unsubstituted

to be.

, 치환 또는 비치환된

이다.According to an exemplary embodiment of the present specification, Ar is unsubstituted or substituted with a dibenzothiophene group or a dibenzofuran group

, Substituted or unsubstituted

to be.

기, 치환 또는 비치환된

기, 치환 또는 비치환된

기, 또는 치환 또는 비치환된

기이다.According to an exemplary embodiment of the present specification, Ar is substituted or unsubstituted

Groups, substituted or unsubstituted

Groups, substituted or unsubstituted

Or substituted or unsubstituted groups

It is.

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

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted arylamine group.

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

According to an exemplary embodiment of the present specification, Ar is an amine group.

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

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

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

According to an exemplary embodiment of the present specification, Ar is a phosphine oxide group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

L, Ar, and R ₁ to R ₁₄ are the same 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; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; 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, a plurality of R ₁₅ are the same as or different from each other,

When q is 2 or more, a plurality of R _{16 s} are the same or different from each other.

According to an exemplary embodiment of the present disclosure, R ₁₅ and R ₁₆ 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 an exemplary embodiment of the present disclosure, R ₁₅ to R ₁₆ is hydrogen.

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

[A-1]

[A-2]

[A-3]

[A-4]

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

Compounds according to one embodiment of the present specification may be prepared by the production method described below. In the following production examples, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change the starting materials, reactants, reaction conditions and the like.

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art. Specific manufacturing method will be described later.

Scheme 1

The compound of Formula 1 shows electrons evenly distributed in the molecule relative to the compound of Comparative Example 1 and Comparative Example 2 as shown in the experimental example (device example) to be described later exhibits low voltage and high efficiency in the organic light emitting device.

In addition, the compound of Formula 1 has a high glass transition temperature (Tg) is excellent in thermal stability. For example, it can be seen that the compound of Formula 1-1 of Example 1 of the present specification has a glass transition temperature of 131 ° C., which is significantly higher than that of NPB (Tg: 98 ° C.). This increase in thermal stability is an important factor in increasing the lifetime by providing drive stability to the device.

In addition, the compounds of the Examples herein exhibit stable redox properties. Redox stability can be confirmed using CV (cyclovoltammetry) method. As a specific example, the compound of Formula 1-1 of Example 1 of the present specification was found to be oxidized at the same voltage and show the same amount of current when multiple repeated oxidation voltages were applied. It shows excellent stability.

In addition, the present specification provides an organic electronic device comprising the compound described above.

In one embodiment of the present specification, the first electrode; A second electrode provided to face 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 compound.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

The organic material layer of the organic electronic device of the present specification may have a single layer structure, but may have a multi-layered structure in which two or more organic material layers are stacked. For example, as a representative 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, a hole blocking layer as an organic material layer. Can be. However, the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.

According to an exemplary embodiment of the present specification, the organic electronic device may be 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.

Hereinafter, an organic light emitting diode will be described.

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

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

In one embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further comprises one or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer and an electron blocking layer.

In one embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers comprises the compound. In an exemplary embodiment of the present specification, the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electron injection, and a hole blocking layer.

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

In addition, in one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except for the compound may be the same or different from each other.

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

In one embodiment of the present specification, the light emitting layer includes a compound of Formula 1 and further includes a light emitting dopant.

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

In one embodiment of the present specification, the light emitting layer includes a compound of Formula 1 and includes an iridium-based phosphorescent dopant as the phosphorescent dopant.

In one embodiment of the present specification, the light emitting layer includes a compound of Formula 1, and Ir (ppy) ₃ as the iridium-based phosphorescent dopant It includes.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

When the organic material layer including the compound of Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may use those known in the art, for example, a metal or a metal complex. According to one example, the electron transport layer including the compound of Formula 1 may further include LiQ.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

1 illustrates a structure of an organic light emitting device 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 device according to an exemplary embodiment of the present specification, and may further include another organic material layer.

2, the first electrode 30, the hole injection layer 60, the hole transport layer 70, the electron blocking layer 80, the light emitting layer 40, the electron transport layer 90, and the electron injection layer The structure of the organic light emitting device in which the 100 and the second electrode 50 are sequentially stacked is illustrated. 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1-A.

[Formula 1-A]

In Chemical Formula 1-A,

n1 is an integer of 1 or more,

Ar ₇ is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

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

Ar ₈ and Ar ₉ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted germanium group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,

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

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-A as a dopant of the light emitting layer.

According to an exemplary embodiment of the present specification, L ₄ is a direct bond.

According to an exemplary embodiment of the present specification, n ₁ is 2.

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

According to an exemplary embodiment of the present specification, Ar ₈ and Ar ₉ are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar ₈ and Ar ₉ are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a germanium group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar ₈ and Ar ₉ are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a trimethylgermanium group.

According to an exemplary embodiment of the present specification, Ar ₈ and Ar ₉ are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, Ar ₈ and Ar ₉ is a phenyl group unsubstituted or substituted with a trimethylgermanium group.

According to an exemplary embodiment of the present specification, Chemical Formula 1-A is represented by the following compound.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 2-A.

[Formula 2-A]

In Chemical Formula 2-A,

이고,G ₁₁ is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9 -Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl -1-naphthyl group, or

ego,

G ₁₂ is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group , 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl Aryl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, Or 3-fluoranthenyl group,

G ₁₃ and G ₁₄ are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; 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 g ₁₂ to g ₁₄ are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

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

According to an exemplary embodiment of the present specification, G ₁₁ is a 1-naphthyl group.

According to an exemplary embodiment of the present specification, G ₁₂ is a 2-naphthyl group.

According to an exemplary embodiment of the present specification, the G ₁₃ And G ₁₄ Is hydrogen.

According to an exemplary embodiment of the present specification, Formula 2-A is represented by the following compound.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound.

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

 The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

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

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

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

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode 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), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, 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 thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The electron blocking layer is a layer that can prevent the holes injected from the hole injection layer to enter the electron injection layer through the light emitting layer to improve the life and efficiency of the device, if necessary, using a known material using a known material and the electron It may be formed in a suitable portion between the injection layers.

The light emitting material of the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; 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 containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, 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-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.

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

The compound according to the present specification may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic phosphors, organic solar cells, organic photoconductors, organic transistors, and the like.

Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present disclosure is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

< Example >

<Production Example 1> Synthesis of Compound 1-1

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 bottom flask in a nitrogen atmosphere. Sodium-tert-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 300ml of ethyl acetate to prepare the compound 1-1 (13.12g, yield: 79%).

MS [M + H] ⁺ = 609

<Preparation Example 2> Synthesis of compound 1-2

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 bottom flask in a nitrogen atmosphere. Sodium-tert-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 4 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 300ml of ethyl acetate to prepare the compound 1-2 (11.81g, yield: 71%).

MS [M + H] ⁺ = 609

<Preparation Example 3> Synthesis of Compound 1-3

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 bottom flask in a nitrogen atmosphere. Then sodium-tert-butoxide (3.41g, 35.43mol) was added, bis (tri-tert-butylphosphine) palladium (0.14g, 0.27mmol) was added thereto, and the mixture was heated and stirred for 4 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 300ml of ethyl acetate to prepare the compound 1-3 (10.63g, yield: 63%).

MS [M + H] ⁺ = 609

<Production Example 4> Synthesis of Compound 1-4

Compound A (10.0 g, 27.25 mmol) and 4-bromo-N, N-diphenylaniline (9.64 g, 29.97 mmol) were completely dissolved in 280 ml of xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. -tert-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 300ml of ethyl acetate to give the compound 1-4 (13.95g, yield: 83%).

MS [M + H] ⁺ = 611

<Production Example 5> Synthesis of Compound 1-5

Compound A (10.0 g, 27.25 mmol), N- (4-bromophenyl) -N-phenyl- [1,1'-biphenyl] -4-amine (11.99 g, in a 500 ml round bottom flask in nitrogen atmosphere 29.97 mmol) was completely dissolved in 250 ml of xylene, followed by addition of sodium-tert-butoxide (3.41 g, 35.43 mol) and bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol). After stirring, the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 280ml of ethyl acetate to give the compound 1-5 (15.91g, yield: 85%).

MS [M + H] ⁺ = 687

<Production Example 6> Synthesis of compound 1-6

Compound A (10.0 g, 27.25 mmol), N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1, in a 500 ml round bottom flask in nitrogen atmosphere 1'-biphenyl] -4-amine (14.25 g, 29.97 mmol) was completely dissolved in 250 ml of xylene, followed by addition of sodium-tert-butoxide (3.41 g, 35.43 mol), and bis (tri-tert Butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 7 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 320ml of ethyl acetate to give the compound 1-6 (18.54g, yield: 89%).

MS [M + H] ⁺ = 763

<Production Example 7> Synthesis of Compound 1-7

Compound A (10.0 g, 27.25 mmol), N- (4-bromophenyl) -9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (13.21 g) in a 500 ml round bottom flask in nitrogen atmosphere , 29.97 mmol) was dissolved completely in 230 ml of xylene, followed by addition of sodium-tert-butoxide (3.41 g, 35.43 mol), and bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) After stirring, the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 280ml of ethyl acetate to give the compound 1-7 (15.91g, yield: 85%).

MS [M + H] ⁺ = 727

<Production Example 8> Synthesis of compound 1-8

Compound A (10.0 g, 27.25 mmol), N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9 in a 500 ml round bottom flask in nitrogen atmosphere -Dimethyl-9H-fluorene-2-amine (15.45 g, 29.97 mmol) was completely dissolved in 330 ml of xylene, followed by addition of sodium-tert-butoxide (3.41 g, 35.43 mol), and bis (tri- tert-butylphosphine) palladium (0.14g, 0.27mmol) was added thereto, followed by heating and stirring for 8 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 280ml of ethyl acetate to give the compound 1-8 (18.72g, yield: 86%).

MS [M + H] ⁺ = 803

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

In a 500 ml round bottom flask in nitrogen atmosphere, 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 xylene. After dissolving completely in 220ml), sodium-tert-butoxide (3.41g, 35.43mol) was added, and bis (tri-tert-butylphosphine) palladium (0.14g, 0.27mmol) was added thereto, followed by heating and stirring for 5 hours. . After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 300 ml of ethyl acetate to prepare the compound 1-9 (13.44g, yield: 83%).

MS [M + H] ⁺ = 599

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

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-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 330ml of ethyl acetate to give the compound 1-10 (12.11g, yield: 74%).

MS [M + H] ⁺ = 598

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

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-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 330ml of ethyl acetate to give the compound 1-11 (10.91g, yield: 66%).

MS [M + H] ⁺ = 598

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

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-butoxide (3.41g, 35.43mol) was added, bis (tri-tert-butylphosphine) palladium (0.14g, 0.27mmol) was added thereto, and the mixture was heated and stirred for 10 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 360 ml of ethyl acetate to prepare the compound 1-12 (9.88g, yield: 59%).

MS [M + H] ⁺ = 597

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

Compound A (10.0 g, 27.25 mmol) and 2-chloro-4-phenylquinazoline (7.21 g, 29.97 mmol) were completely dissolved in 240 ml of xylene in a 500 ml round bottom flask in nitrogen atmosphere, followed by sodium-tert- Butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 7 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 336ml of ethyl acetate to give the compound 1-13 (13.26g, yield: 85%).

MS [M + H] ⁺ = 572

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

In a 500 ml round bottom flask in nitrogen atmosphere, Compound A (10.0 g, 27.25 mmol) and 2-chloro-4- (naphthalen-2-yl) quinazolin (8.71 g, 29.97 mmol) were completely added to 220 ml of xylene. After dissolving, sodium-tert-butoxide (3.41g, 35.43mol) was added, and bis (tri-tert-butylphosphine) palladium (0.14g, 0.27mmol) was added thereto, followed by stirring for 4 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 336ml of ethyl acetate to give the compound 1-14 (14.77g, yield: 87%).

MS [M + H] ⁺ = 622

<Preparation Example 15> synthesis of the compound 15

Compound A (10.0 g, 27.25 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (10.29 g, 29.97 mmol) in a 500 ml round bottom flask in nitrogen atmosphere Was dissolved completely in 290ml of xylene, and sodium-tert-butoxide (3.41g, 35.43mol) was added, and bis (tri-tert-butylphosphine) palladium (0.14g, 0.27mmol) was added thereto. Heat stirring for hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 370ml of ethyl acetate to give the compound 1-15 (13.44g, yield: 83%).

MS [M + H] ⁺ = 675

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

Compound A (10.0 g, 27.25 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (10.29 g, 29.97 mmol) in a 500 ml round bottom flask under nitrogen atmosphere Was dissolved completely in 290 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) was added. Heat stirring for hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 340ml of ethyl acetate to give the compound 1-16 (12.11g, yield: 74%).

MS [M + H] ⁺ = 675

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

290 ml of Xylene in Compound A (10.0 g, 27.25 mmol) and 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (10.29 g, 29.97 mmol) in a 500 ml round bottom flask under nitrogen atmosphere After completely dissolved in sodium-tert-butoxide (3.41g, 35.43mol) was added, bis (tri-tert- butylphosphine) palladium (0.14g, 0.27mmol) was added and stirred for 8 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 280ml of ethyl acetate to give the compound 1-17 (9.75g, yield: 62%).

MS [M + H] ⁺ = 674

<Example 18> Synthesis of compound 1-18

Compound A (10.0 g, 27.25 mmol) and (4-bromophenyl) diphenylphosphine oxide (10.68 g, 29.97 mmol) were completely dissolved in 280 ml of xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. -tert-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 300ml of ethyl acetate to give the compound 1-18 (14.92g, yield: 85%).

MS [M + H] ⁺ = 644

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

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 in a nitrogen atmosphere. tert-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 180 ml of ethyl acetate to prepare the compound 1-19 (10.74g, yield: 74%).

MS [M + H] ⁺ = 534

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

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-butoxide (3.41 g, 35.43 mol) was added, bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 4 hours. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 190ml of ethyl acetate to give the compound 1-20 (9.08g, yield: 66%).

MS [M + H] ⁺ = 550

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

Xyl-A compound (10.0 g, 27.25 mmol), 2- (4-bromophenyl) -1-phenyl-1H-benz [d] imidazole (10.44 g, 29.97 mmol) in a 500 ml round bottom flask under nitrogen atmosphere After completely dissolved in 290 ml of xylene, sodium-tert-butoxide (3.41 g, 35.43 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.14 g, 0.27 mmol) was added for 8 hours. It stirred by heating. After cooling to room temperature to remove the salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 280ml of ethyl acetate to give the compound 1-21 (9.75g, yield: 62%).

MS [M + H] ⁺ = 636

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

Compounds 1-22 to 1-42 were prepared by the same method as the method for preparing Compound 1-1 to 1-21, except that Compound B was used instead of Compound A in Preparation Examples 1 to 21. MS [M = H] ⁺ of the compound 1-22 to 1-42 are shown in Table 1 below.

[Compound B]

Compound number MS [M = H] ⁺ Compound number MS [M = H] ⁺ 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>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After completion of the distilled water washing, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

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

[HAT]

A hole transport layer was formed by vacuum evaporation of the following compound (4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 Pa)), which is a material for transporting holes on the hole injection layer. Formed.

[NPB]

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

[Compound 1-1]

Subsequently, the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the electron blocking layer with a film thickness of 300 GPa.

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 kPa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order 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 The organic light emitting device was manufactured by maintaining the ratio of 5 to 10 ⁻⁶ torr.

<Experimental Example 1-2>

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-3 was used instead of compound 1-1 in Experimental Example 1-1.

<Experimental Example 1-4>

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-29 was used instead of compound 1-1 in Experimental Example 1-1.

<Comparative Example 1-1>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 1 (TCTA) instead of the compound 1-1 in Experimental Example 1-1.

[EB 1]

<Comparative Example 1-2>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB 2 instead of compound 1-1 in Experimental Example 1-1.

[EB 2]

When current was applied to the organic light emitting diodes manufactured by Experimental Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-2, the results of Table 2 were obtained.

division compound
(Electronic blocking layer) Voltage
(V @ 10mA / 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 Example 1-4 Compound 1-4 3.48 5.77 (0.137, 0.125) Experimental Example 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 Example 1-8 Compound 1-8 3.44 5.75 (0.137, 0.125) Experimental Example 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 specification are used as the electron blocking layer in the organic light emitting device, the characteristics of lower voltage, higher efficiency than Comparative Examples 1-1 to 1-2 It can be seen that represents.

Therefore, the compound derivative of the formula according to the present specification was excellent in the electron suppression ability, it was confirmed that the low voltage and high efficiency and can be applied to the organic light emitting device.

< Experimental Example  2>

Experimental Example 2-1

After the high purity sublimation purification of the compounds synthesized in the synthesis example by a commonly known method, a green organic light emitting device was manufactured by the following method.

A glass substrate coated with a thickness of 1,000 kPa of ITO (indium tin oxide) was put in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

Using the compound 1-9 as a host on the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / compound 1-9 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) A light emitting device was constructed in the order of) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) to prepare an organic EL device.

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

Experimental Example 2-2

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 1-30 was used instead of compound 1-9 in Experimental Example 2-1.

Experimental Example 2-9

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as 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>

The organic light emitting device was manufactured by the same method as 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

The organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 1-38 was used instead of compound 1-9 in Experimental Example 2-1.

<Comparative Example 2-1>

An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 1 (CBP) instead of the compound 1-9 in Experimental Example 2-1.

[GH 1]

<Comparative Example 2-2>

An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following GH 2 instead of the compound 1-9 in Experimental Example 2-1.

[GH 1]

When the electric current was applied to the organic light emitting element produced by Experimental Example 2-1 to 2-14 and Comparative Examples 2-1 to 2-2, the result of Table 3 was obtained.

division compound
(Host) Voltage
(V @ 10mA / 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 Example 2-6 Compound 1-16 5.13 45.63 516 Experimental Example 2-7 Compound 1-17 5.29 45.42 516 Experimental Example 2-8 Compound 1-30 5.27 46.54 517 Experimental Example 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 Example 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 device of Experimental Examples 2-1 to 2-14 using the compound represented by Formula 1 as a host material of the green light emitting layer according to the present specification is a comparative example using a conventional CBP It can be seen that the green organic EL device of 2-1 and Comparative Example 2-2 has superior performance in terms of current efficiency and driving voltage.

< Experimental Example  3>

<Experimental Examples 3-1 to 3-4>

After the compounds synthesized in the above preparation was subjected to high purity sublimation purification by a commonly known method, a red organic light emitting device was manufactured by the following method.

The light emitting area of the ITO glass was patterned to have a size of 2 mm × 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), α-NPB (300 kPa), Compound 1-13 prepared by the present specification , 1-14, 1-34, and 1-35 were used as hosts (90 wt%), and the following (piq) ₂ Ir (acac) (10 wt%) was vacuum deposited (300 kPa) as dopant, Films were formed in the order of ₃ (350 Hz), LiF (5 Hz) and Al (1,000 Hz), and were measured at 0.4 mA.

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

<Comparative Example 3-1>

The organic light emitting device for Comparative Example 3-1 uses CBP which is widely used as a general phosphorescent host material instead of the organic light emitting compound prepared by the present invention as a host of the light emitting layer in the device structure of Experimental Examples 3-1 to 3-4. The same production was made except for the point.

For the organic electroluminescent devices manufactured according to Experimental Examples 3-1 to 3-4 and Comparative Example 3-1, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results of Table 4 were obtained. At this time, T95 means the time required for the luminance to be reduced to 95% from the initial luminance (5000nit).

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 in Formula 1 is a substituted or unsubstituted quinazoline group according to the present specification, are used as the host material of the emission layer. It can be seen that the red organic EL devices of Experimental Examples 3-1 to 3-4 exhibited superior performance in terms of current efficiency, driving voltage, and lifespan than the red organic EL devices of Comparative Example 3-1 using conventional CBP.

Although preferred embodiments of the present specification (electron blocking layer, green light emitting layer, and red light emitting layer) have been described above, the present specification is not limited thereto, and various modifications are made within the scope of the claims and the detailed description of the invention. It is possible to do this and this also belongs to the scope of the invention.

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

Claims (19)

Compound represented by the following formula (2) or
[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
L is a direct bond; Or an arylene group having 6 to 12 carbon atoms,
Ar is a phosphine oxide group unsubstituted or substituted with an aryl group having 6 to 12 carbon atoms; An amine group substituted with an aryl group having 6 to 20 carbon atoms; An amine group substituted with a dimethyl fluorenyl group or a diphenyl fluorenyl group; Or a heterocyclic group having 2 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms,
R ₁ to R ₁₆ are hydrogen,
p and q are integers of 0 or 1, respectively. delete The method according to claim 1,
L is a direct bond; Phenylene group; Biphenylene group; Or a naphthylene group. delete The method according to claim 1,
Ar is a pyridine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Pyrimidine groups unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Triazine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A quinolinyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A quinazoline group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Carbazole groups unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzocarbazole group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a dibenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms. The compound according to claim 1, wherein -L-Ar is any one of the following [A-2] to [A-4]:
[A-2]

[A-3]

[A-4]

The compound of claim 1, wherein the compound represented by Chemical Formula 2 or 3 is any one selected from the following structural formulas:

A first electrode; A second electrode provided to face 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 comprises a compound according to any one of claims 1, 3, and 5 to 7. An organic electronic device comprising. The method according to claim 8,
The organic material layer includes an emission layer, and the emission layer comprises the compound. The method according to claim 8,
The organic material layer comprises a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer is an organic electronic device comprising the compound. The method according to claim 8,
The organic material layer includes an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer is an organic electronic device containing the compound. The method according to claim 8,
The organic material layer includes an electron blocking layer, and the electron blocking layer comprises the compound. The method according to claim 8,
The organic electronic device further comprises one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer and an electron blocking layer. The organic electronic device of claim 8, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphor device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor. The organic electronic device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-A:
[Formula 1-A]

In Chemical Formula 1-A,
n ₁ is 2,
Ar ₇ is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl or tert-butyl group,
L ₄ is a direct bond,
Ar ₈ and Ar ₉ are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with a trimethylgermanium group,
When n ₁ is 2, the structures in two or more parentheses are the same as or different from each other. delete The organic electronic device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 2-A:
[Formula 2-A]

In Chemical Formula 2-A,
G ₁₁ is 1-naphthyl group or 2-naphthyl group,
G ₁₂ is a phenyl group, 1-naphthyl group or 2-naphthyl group,
G ₁₃ and G ₁₄ are hydrogen,
g ₁₂ is 1,
g ₁₃ and g ₁₄ are each an integer of 1 to 4; The organic electronic device of claim 17, wherein G ₁₁ is a 1-naphthyl group and G ₁₂ is a 2-naphthyl group. The organic electronic device of claim 15, wherein the emission layer includes a compound represented by Chemical Formula 2-A:
[Formula 2-A]

In Chemical Formula 2-A,
G ₁₁ is 1-naphthyl group or 2-naphthyl group,
G ₁₂ is a phenyl group, 1-naphthyl group or 2-naphthyl group,
G ₁₃ and G ₁₄ are hydrogen,
g ₁₂ is 1,
g ₁₃ and g ₁₄ are each an integer of 1 to 4;

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