KR101917953B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present invention relates to compounds of formula (I) or (II) and organic electronic devices comprising them.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic electronic device including the compound.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0069087 filed with the Korean Intellectual Property Office on June 02, 2016, the entire contents of which are incorporated herein by reference.

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

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

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

International Patent Application Publication No. 2003-012890

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

The present invention provides a compound represented by the following general formula (1) or (2).

[Chemical Formula 1]

(2)

In the above formula (1) or (2)

Q is a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n1 is an integer of 1 to 5,

n2 is an integer of 1 to 5,

n3 is an integer of 1 to 4,

n4 is an integer of 1 to 3,

n5 is an integer of 1 to 3,

n6 is an integer of 1 to 4,

When n1 to n6 are two or more, the structures in parentheses of two or more are the same or different from each other.

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

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

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

Hereinafter, the present invention will be described in more detail.

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

The compounds represented by the formulas (1) and (2) have an effect of enhancing the device performance by enhancing the triplet energy and facilitating the hole transporting ability by Q having a monocyclic or polycyclic aliphatic hydrocarbon ring.

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

또는

는 연결되는 부위를 의미한다.In the present specification,

or

Refers to the connected area.

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; An alkenyl group; Silyl group; Boron group; Phosphine oxide groups; An amine group; An arylamine group; An aryl group; And a heteroaryl group containing at least one of N, O, S, Se and Si atoms, or wherein at least two of the substituents exemplified above are substituted with a substituent to which they are connected, Quot; means < / RTI >

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

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 40 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In this specification, the silyl group is a substituent including Si and a direct connection as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. But is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

,

,

,

,

,

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

,

,

,

,

,

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

In the present specification, the heteroaryl group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms. Examples of the heteroaryl group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, A benzothiophene group, a benzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, But are not limited to these.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent, represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same or different Each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group (provided that at least one of R ₁₀₇ and R ₁₀₈ is not hydrogen). -NH ₂ ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; An N-biphenylfluorenylamine group, and the like, but are not limited thereto.

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

In the present specification, the aryl group in the aryloxy group and arylthioxy group is the same as the above-mentioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

In one embodiment of the present specification, Q is a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring.

In one embodiment of the present disclosure, Q is selected from substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctane, substituted or unsubstituted bicyclo Heptane, substituted or unsubstituted tricycloheptane, or substituted or unsubstituted decahydronaphthalene.

In one embodiment of the present disclosure, Q is a cyclopentane that is substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is a cyclopentane substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In one embodiment of the present disclosure, Q is cyclopentane.

In one embodiment of the present disclosure, Q is cyclohexane substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is cyclohexane substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In one embodiment of the present disclosure, Q is cyclohexane.

In one embodiment of the present disclosure, Q is cycloheptane substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is cycloheptane substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In one embodiment of the present disclosure, Q is cycloheptane.

In one embodiment of the present disclosure, Q is cyclooctane substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a cyclooctane substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, Q is cyclooctane.

In one embodiment of the present disclosure, Q is bicycloheptane substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is bicycloheptane substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In one embodiment of the present disclosure, Q is bicycloheptane.

In one embodiment of the present disclosure, Q is tricycloheptane substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is tricycloheptane substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In one embodiment of the present disclosure, Q is tricycloheptane.

In one embodiment of the present disclosure, Q is a decahydronaphthalene substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a decahydronaphthalene substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, Q is decahydronaphthalene.

In one embodiment of the present specification, Q may be any one selected from the following structural formulas.

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

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

In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted terphenylene group, Lt; / RTI > is a substituted fluorenylene group.

In one embodiment of the present specification, L 1 is a divalent fluorenylene group in which a methyl group, an ethyl group, or a tert-butyl group is substituted or unsubstituted.

In one embodiment of the present invention, L 1 is a phenylene group, a biphenylene group, a naphthylene group, a terphenylene group, or a fluorenylene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted divalent dibenzofurane group, a substituted or unsubstituted divalent dibenzothiophene group, or a substituted or unsubstituted divalent carbazole group.

In one embodiment of the present specification, L < 1 > is a divalent carbazole group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, L < 1 > is a divalent dibenzofurane group, a divalent dibenzothiophene group, or a divalent carbazole group.

In one embodiment of the present specification, L1 may be any one selected from the following formulas.

In one embodiment of the present disclosure, Arl is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

In one embodiment of the present specification, Ar 1 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, Or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Ar1 represents a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, Orrenyl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted dibenzofurane group or a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Ar1 is a dibenzofurane group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar1 is a dibenzothiophene group in which the phenyl group is substituted or unsubstituted.

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

In one embodiment of the present specification, Ar1 may be any one selected from the following structural formulas.

In one embodiment of the present invention, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group A substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, An amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present disclosure, R 1 to R 6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present disclosure, R 1 to R 6 are the same or different from each other and each independently hydrogen.

In one embodiment of the present invention, the formula (1) may be represented by the following formulas (3) to (6).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,

Q, L1, Ar1, R1 to R6, and n1 to n6 are the same as defined in the above formula (1).

In one embodiment of the present invention, the formula (2) may be represented by the following formulas (7) to (10).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above formulas (7) to (10)

Q, L1, Ar1, R1 to R6, and n1 to n6 are the same as defined in Formula 2 above.

In one embodiment of the present invention, the formula (1) may be any one selected from the following compounds.

In one embodiment of the present invention, the formula (2) may be any one selected from the following compounds.

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

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

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

The present invention also provides an organic light emitting device comprising the above-described compound.

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

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

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

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

According to an embodiment of the present invention, the organic light emitting diode may be selected from the group consisting of an organic phosphor element, an organic solar battery, an organic photoconductor (OPC), and an organic transistor.

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

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

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

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

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, A light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and an electron blocking layer.

In one embodiment of the present invention, the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. In one embodiment of the present invention, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.

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

In addition, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

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

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

When the organic compound layer containing the compound of Formula 1 is an electron transporting layer, the electron transporting layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. According to an example, the electron transport layer containing the compound of Formula 1 may further include LiQ.

In one embodiment of the present invention, the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. In one embodiment of the present invention, the two or more organic layers may be selected from the group consisting of a hole transport layer, a hole injection layer, a layer that simultaneously transports holes and electrons, and a hole blocking layer.

In one embodiment of the present disclosure, the organic layer may include a laminated structure of a p-type doped layer.

In this specification, the p-doped layer means a layer doped with p-dopant. p dopant refers to a material that has a p semiconducting property of the host material. p semiconductor property means a property of injecting or transporting holes at a highest occupied molecular orbital (HOMO) energy level, that is, a material having a high conductivity of holes.

In one embodiment of the present invention, when the organic compound layer containing the compound of Formula 1 is a hole injection layer, the hole injection layer may be doped with a p dopant.

In one embodiment of the present invention, the p-type dopant may be those known in the art, and the concentration of the doping layer may be 0.01 wt% to 50 wt%.

In one embodiment of the present specification, a hole transporting layer doped with a p-type dopant may be included between the light emitting layer and the anode. According to one example, a hole transporting layer containing Compound 1 doped with a dopant may be included between the light emitting layer and the anode. More specifically, a hole transporting layer containing Compound 1 doped with a dopant may be included between the hole adjusting layer and the hole injecting layer.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

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

1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.

2 shows a structure in which a first electrode 30, a hole injecting layer 60, a hole transporting layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transporting layer 90, 100 and a second electrode 50 are sequentially laminated on a transparent substrate 100. In this case, 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compound.

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

 The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound, i.e., the compound represented by the above formula (1).

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

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

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

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The electron blocking layer is a layer which can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The light emitting material of the light emitting layer is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder furan compounds , Pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

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

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

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

The hole-adjusting layer effectively receives holes from the hole-transporting layer and regulates the hole mobility to control the amount of holes transferred to the light-emitting layer. In addition, it can simultaneously serve as an electron barrier to prevent electrons supplied from the light emitting layer from migrating to the hole transporting layer. This can increase the luminous efficiency by maximizing the balance of holes and electrons in the light emitting layer, improve the lifetime of the device through the electron stability of the hole controlling layer, and materials known in the art can be used.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

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

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

Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples. However, the examples and comparative examples according to the present specification can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments and comparative examples. The examples and comparative examples provided herein are provided to more fully describe the present specification to those skilled in the art.

<Production Example>

PREPARATION EXAMPLE 1 Synthesis of A1 to A4, B1 and B2

(1) Synthesis of A1

2-Bromo--9 H - fluorene (100g, 407.96mmol) and 50wt% sodium hydroxide aqueous solution (70g, 897.51mmol) in 1,4-Val 160 ℃ was added to a dimethyl sulfoxide (1000ml) Mobutane (88.09 g, 407.96 mmol) was added dropwise thereto, followed by heating and stirring for 3 hours. The reaction mixture was cooled to room temperature and the reaction was terminated. The reaction mixture was extracted with toluene and water, and then subjected to column refinement to prepare an i-bivalent liquid A1 (120 g, yield 98%).

MS [M + H] &lt; ⁺ &gt; = 299.14

(2) Synthesis of A2

(11.29 g, 33.89 mmol) and sodium-tert-butoxide (4.5 g, 46.97 mol) were dissolved in toluene, , And the mixture was stirred under heating, refluxed, and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (490 mg, 2 mmol%) was added. After the temperature was lowered to room temperature, the reaction was terminated and recrystallized using chloroform and ethyl acetate to prepare A2.

MS [M + H] &lt; + &gt; = 552.26

(3) Synthesis of A3

(13.87 g, 41.61 mmol) and sodium-t-butoxide (4.5 g, 46.97 mol) were dissolved in toluene ), And the mixture was heated with stirring, refluxed, and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (490 mg, 2 mmol%) was added. After the temperature was lowered to room temperature and the reaction was terminated, recrystallization was performed using chloroform and ethyl acetate to prepare A3.

MS [M + H] &lt; + &gt; = 498.64

(4) Synthesis of A4

(5.92 g, 25.17 mmol) and sodium-t-butoxide (4.5 g, 46.97 mol) were dissolved in toluene ), And the mixture was heated with stirring, refluxed, and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (490 mg, 2 mmol%) was added. After lowering the temperature to room temperature, the reaction was terminated, and recrystallized using ethyl acetate and hexane to prepare A4.

MS [M + H] &lt; + &gt; = 552.73

(5) Synthesis of B1

B1 was synthesized by the same method except for using 1,5-dibromopentane instead of 1,4-dibromobutane in the synthesis of A1

MS [M + H] &lt; + &gt; = 313.05

(6) Synthesis of B2

B1 was synthesized in the same manner except that B1 was used instead of A1 in the synthesis of A2.

MS [M + H] &lt; + &gt; = 566.28

PREPARATION EXAMPLE 2 Synthesis of Compound 1

      [A2] [Compound 1]

(7.75 g, 27.7 mmol) and sodium-tert-butoxide (3.57 g, 38.02 mmol) were added to toluene and the mixture was heated under reflux. -tert-butylphosphine) palladium (277 mg, 2 mmol%). After the temperature was lowered to room temperature and the reaction was terminated, compound 1 was prepared by recrystallization using tetrahydrofuran and ethyl acetate.

MS [M + H] &lt; ⁺ &gt; = 713.32

PREPARATION EXAMPLE 3 Synthesis of Compound 2

          [A2] [Compound 2]

Compound 2 was prepared by the same method except for using 2-bromo-9,9-dimethyl-9H-fluorene instead of 4-iodobiphenyl in the synthesis of Compound 1

MS [M + H] &lt; ⁺ &gt; = 744.36

&Lt; Preparation Example 4 > - Synthesis of Compound 3

       [A2] [Compound 3]

Compound 3 was synthesized in the same manner as Compound 1 except that 2-bromo-9,9-diphenyl-9H-fluorene was used instead of 4-iodobiphenyl.

MS [M + H] &lt; ⁺ &gt; = 868.39

PREPARATION EXAMPLE 5 Synthesis of Compound 4

         [A2] [Compound 4]

Compound 4 was synthesized in the same manner as in the synthesis of Compound 1, except that 4- (4-chlorophenyl) dibenzo [ b, d ] furan was used instead of 4-iodobiphenyl.

MS [M + H] &lt; ⁺ &gt; = 794.33

PREPARATION EXAMPLE 6 Synthesis of Compound 5

         [B2] [Compound 5]

Compound 5 was prepared by the same method as Compound 1 except that B2 was used instead of A2 and 4-bromophenyl was used instead of 4-iodobiphenyl.

MS [M + H] &lt; ⁺ &gt; = 794.37

&Lt; Preparation Example 7 > - Synthesis of Compound 6

         [B2] [Compound 6]

Compound 6 was prepared by the same method as Compound 1 except that B2 was used instead of A2 and 4-chloro-1,1: 2,1 " -terphenyl was used instead of 4-iodobiphenyl.

MS [M + H] &lt; ⁺ &gt; = 794.37

PREPARATION EXAMPLE 8 Synthesis of Compound 7

         [B2] [Compound 7]

Compound 7 was prepared by the same method except that B2 was used in place of A2 in the synthesis of Compound 3 above.

MS [M + H] &lt; ⁺ &gt; = 882.40

PREPARATION EXAMPLE 9 Synthesis of Compound 8

[B2] [Compound 8]

Compound 8 was prepared by the same method as Compound 1 except that B2 was used instead of A2 and 4- (4-chlorophenyl) dibenzo [ b, d ] thiophene was used instead of 4-iodobiphenyl .

MS [M + H] &lt; ⁺ &gt; = 824.33

PREPARATION EXAMPLE 10 Synthesis of Compound 9

       [A2] [Compound 9]

T-butoxide (3.57 g, 38.02 mmol) was dissolved in toluene in the same manner as in Example 1, , And the mixture was heated with stirring, refluxed, and [bis (tri-t-butylphosphine)] palladium (277 mg, 2 mmol%) was added. After the temperature was lowered to room temperature and the reaction was terminated, compound 9 was prepared by recrystallization using tetrahydrofuran and ethyl acetate.

MS [M + H] &lt; + &gt; = 870.12

PREPARATION EXAMPLE 11 Synthesis of Compound 10

      [A3] [Compound 10]

(10.26 g, 30.77 mmol) and sodium-t-butoxide (3.57 g, 38.02 mmol) were added to toluene and the mixture was heated under reflux. (Tri-t-butylphosphine)] palladium (277 mg, 2 mmol%). After the temperature was lowered to room temperature and the reaction was terminated, compound 10 was prepared by recrystallization using tetrahydrofuran and ethyl acetate.

MS [M + H] &lt; + &gt; = 650.84

PREPARATION EXAMPLE 12 Synthesis of Compound 11

   [A4] [Compound 11]

4-iodobiphenyl (7.76 g, 27.73 mmol) and sodium-t-butoxide (3.57 g, 38.02 mmol) were added to toluene and the mixture was heated under reflux. (Tri-t-butylphosphine)] palladium (277 mg, 2 mmol%). After the temperature was lowered to room temperature and the reaction was terminated, compound 11 was prepared by recrystallization using tetrahydrofuran and ethyl acetate.

MS [M + H] &lt; + &gt; = 704.93

<Examples>

&Lt; Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

X1 (hexanitrile hexaazatriphenylene) was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. The compound 1 synthesized in the above Preparation Example 2, which is a hole transport material, was vacuum deposited (1100 Å) on the hole transport layer, and HT2 was vacuum deposited thereon to a thickness of 600 Å on the hole transport layer to form a hole control layer. As a compound emitting layer, a host H1 and a dopant D1 compound (H1 having 98% volume ratio of the layer and D1 having 2% volume ratio of the layer) were vacuum deposited to a thickness of 300 ANGSTROM. Next, an E1 compound was formed as an electron transport layer with LiQ at a volume ratio (350 ANGSTROM) of 1: 1 with LiQ, followed by sequentially depositing lithium fluoride (LiF) having a thickness of 10 A and aluminum having a thickness of 1000 ANGSTROM to form a cathode. .

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

    [X1] [X2]

   [HT1] [HT2]

   [HT3] [HT4]

     [H1] [D1]

      [E1]

&Lt; Example 2 >

The same experiment was conducted as in Example 1 except that Compound 3 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

&Lt; Example 3 >

The same experiment was conducted as in Example 1 except that Compound 6 was used instead of Compound 1 synthesized in Production Example 2 as the hole transport layer.

<Example 4>

The same experiment was conducted as in Example 1 except that Compound 9 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

&Lt; Example 5 >

In the same manner as Example 1, HT1 was used instead of Compound 1 synthesized in Preparation Example 2, and Compound 5 was used in place of HT2 as a hole transport layer.

&Lt; Example 6 >

The same experiment was conducted as in Example 5 except that Compound 7 was used instead of Compound 5 synthesized in Preparation Example 6 as the hole control layer.

&Lt; Example 7 >

The same experiment was conducted as in Example 5 except that Compound 11 was used instead of Compound 5 synthesized in Preparation Example 6 as the hole control layer.

&Lt; Example 8 >

The same experiment was carried out as in Example 5 except that Compound 10 was used instead of Compound 5 synthesized in Preparation Example 6 as the hole control layer.

&Lt; Example 9 >

Compound 3 was thermally vacuum deposited to a thickness of 50 Å on a ITO transparent electrode prepared as in Example 1 to form a hole injection layer (100 Å), wherein X2 was doped at a doping concentration of 5% (compound 3 was present in a volume ratio of 95% X2 is present in the layer at a volume ratio of 5%). On top of this, the above compound 3 (1100 Å), which is a hole transporting material, is vacuum deposited and then HT2 is vacuum deposited on the HTL to a thickness of 600 Å, To form a control layer. A host H1 and a dopant D1 compound (H1 present in a volume ratio of 98% and D1 in a 2% volume ratio) to the compound light emitting layer were vacuum deposited to a thickness of 300 Å. Next, an E1 compound was formed as an electron transport layer with LiQ at a volume ratio of 1: 1 (350 ANGSTROM), followed by sequentially depositing lithium fluoride (LiF) having a thickness of 10 A and aluminum having a thickness of 1000 ANGSTROM to form a cathode. .

&Lt; Example 10 >

The same experiment was conducted as in Example 9 except that Compound 4 was used instead of Compound 3 synthesized in Production Example 4 as the hole injecting layer and the hole transporting layer.

&Lt; Example 11 >

In Example 9, the same experiment was conducted except that HT1 was used instead of Compound 3 as the hole injecting layer and the hole transporting layer, and Compound 3 was used instead of HT2 as the hole adjusting layer

&Lt; Example 12 >

The same experiment was conducted as in Example 10 except that Compound 7 was used instead of Compound 3 synthesized in Preparation Example 4 as the hole control layer.

&Lt; Comparative Example 1 &

The same experiment was conducted as in Example 1 except that HT1 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

&Lt; Comparative Example 2 &

The same experiment was performed except that HT3 was used instead of HT2 as the hole-adjusting layer in Comparative Example 1.

&Lt; Comparative Example 3 &

The same experiment was performed except that HT4 was used instead of HT1 as the hole transport layer in Comparative Example 1.

&Lt; Comparative Example 4 &

In the same manner as in Example 11 except that HT2 was used instead of the compound 3 synthesized in Preparation Example 4 as the hole control layer.

&Lt; Comparative Example 5 &

The same experiment was conducted as in Example 1 except that Compound 10 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

&Lt; Comparative Example 6 >

The same experiment was conducted as in Example 9 except that Compound 10 was used instead of Compound 3 synthesized in Production Example 4 as the hole control layer.

Experimental Example
(10 mA / cm ² ) Hole
Injection layer Hole
Transport layer Hole
Regulating layer Voltage
(V) efficiency
(cd / A) CIE-x CIE-y Example 1 X1 Compound 1 HT2 4.01 25.95 0.658 0.340 Example 2 X1 Compound 3 HT2 4.04 25.53 0.658 0.340 Example 3 X1 Compound 6 HT2 3.99 25.99 0.658 0.340 Example 4 X1 Compound 9 HT2 3.99 26.01 0.658 0.340 Example 5 X1 HT1 Compound 5 3.84 26.32 0.658 0.341 Example 6 X1 HT1 Compound 7 3.95 28.66 0.657 0.340 Example 7 X1 HT1 Compound 11 3.95 28.66 0.657 0.340 Example 8 X1 HT1 Compound 10 4.01 29.99 0.657 0.340 Example 9 X2 + Compound 3 Compound 3 HT2 3.82 27.01 0.658 0.340 Example 10 X2 + compound 4 Compound 4 HT2 3.93 28.21 0.658 0.340 Example 11 X2 + HT1 HT1 Compound 3 3.86 27.88 0.657 0.341 Example 12 X2 + HT1 HT1 Compound 7 3.88 28.12 0.658 0.340 Comparative Example 1 X1 HT1 HT2 4.32 23.55 0.658 0.340 Comparative Example 2 X1 HT1 HT3 4.42 24.21 0.658 0.340 Comparative Example 3 X1 HT4 HT2 4.33 23.98 0.658 0.340 Comparative Example 4 X2 + HT1 HT1 HT2 4.21 23.88 0.658 0.340 Comparative Example 5 X1 Compound 10 HT2 3.99 22.31 0.658 0.340 Comparative Example 6 X2 + compound 10 Compound 10 HT2 3.92 27.39 0.658 0.341

&Lt; Example 13 >

The above-described X1 was thermally vacuum-deposited to a thickness of 50 Å on the ITO transparent electrode thus prepared to form a hole injection layer. Compound 1 (800 Å), which is a hole transport material, was vacuum deposited to form a hole transport layer. HT2 (100 Å) was formed as a hole adjusting layer, and host H2 and dopant D2 (4 wt%) 300 &lt; RTI ID = 0.0 &gt; A. &lt; / RTI &gt; Next, the E1 compound was formed as an electron transport layer with a volume ratio (300 ANGSTROM) of LiQ and 1: 1, followed by sequentially depositing lithium fluoride (LiF) having a thickness of 10 ANGSTROM and aluminum having a thickness of 800 ANGSTROM to form a cathode. .

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

[X1] [X2]

   [HT1] [HT2]

[H2] [D2]

[E1]

&Lt; Example 14 >

The same experiment was conducted as in Example 13 except that Compound 3 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

&Lt; Example 15 >

The same experiment was conducted as in Example 13 except that Compound 8 was used instead of Compound 1 synthesized in Production Example 2 as the hole transport layer.

&Lt; Example 16 >

Compound 2 was thermally vacuum deposited on ITO transparent electrode prepared in Example 1 to a thickness of 50 Å to form a hole injection layer. Compound X2 was doped at a doping concentration of 10% (Compound 2 exists in a volume ratio of 90% and X2 10% by volume), and a hole transport layer was formed by vacuum evaporation of compound (2) to a thickness of 800 ANGSTROM, Compound (5) (100 ANGSTROM) was formed thereon as a hole control layer, D2 (4% by weight) was vacuum-deposited to a thickness of 300 Å. Next, the E1 compound was formed as an electron transport layer with a volume ratio (300 ANGSTROM) of LiQ and 1: 1, followed by sequentially depositing lithium fluoride (LiF) having a thickness of 10 ANGSTROM and aluminum having a thickness of 800 ANGSTROM to form a cathode. .

&Lt; Example 17 >

The same experiment was conducted except that Compound 5 was used instead of Compound 2 as the hole injecting layer and the hole transporting layer in Example 16 and Compound 7 was used in place of Compound 5 as the hole controlling layer.

&Lt; Example 18 >

The same experiment was conducted except that Compound 9 was used instead of Compound 2 as the hole injecting layer and the hole transporting layer in Example 16, and Compound 7 was used in place of Compound 5 as the hole controlling layer.

&Lt; Example 19 >

In Example 16, HT1 was used instead of Compound 2 as the hole injecting layer and the hole transporting layer, and Compound 6 was used instead of Compound 5 as the hole controlling layer.

&Lt; Comparative Example 5 &

In the same manner as in Example 13 except that HT1 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

&Lt; Comparative Example 6 >

The same experiment was carried out as in Example 16 except that HT1 was used instead of Compound 2 as the hole injecting layer and the hole transporting layer, and HT2 was used instead of Compound 5 as the hole controlling layer.

&Lt; Comparative Example 7 &

The same experiment was conducted as in Example 13 except that Compound 10 was used instead of Compound 1 synthesized in Production Example 2 as a hole transport layer.

Experimental Example
(10 mA / cm ² ) Hole
Injection layer Hole
Transport layer Hole
Regulating layer Voltage
(V) efficiency
(cd / A) CIE-x CIE-y Example 13 X1 Compound 1 HT2 3.65 7.79 0.135 0.093 Example 14 X1 Compound 3 HT2 3.56 7.82 0.135 0.093 Example 15 X1 Compound 8 HT2 3.68 8.12 0.135 0.093 Example 16 X2 + Compound 2 Compound 2 Compound 5 3.61 8.05 0.135 0.094 Example 17 X2 + Compound 5 Compound 5 Compound 7 3.71 7.99 0.135 0.093 Example 18 X2 + Compound 9 Compound 9 Compound 7 3.71 7.99 0.135 0.093 Example 19 X2 + HT1 HT1 Compound 6 3.69 8.01 0.135 0.093 Comparative Example 5 X1 HT1 HT2 3.91 7.12 0.135 0.093 Comparative Example 6 X2 + HT1 HT1 HT2 3.98 7.22 0.135 0.093 Comparative Example 7 X1 Compound 10 HT2 3.88 7.02 0.135 0.093

As shown in Table 1 and Table 2, the compounds used in Examples 1 to 19 were used as a hole injecting layer, a hole transporting layer, and a hole controlling layer in an organic light emitting device. Based on the hole transporting ability superior to other materials, Quot ;. &lt; / RTI &gt;

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

Claims (15)

A compound represented by the following formula (1) or (2):
[Chemical Formula 1]

(2)

In the above formula (1) or (2)
Q is a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 5 to 10 carbon atoms, and when the aliphatic hydrocarbon ring is substituted, the substituent is an alkyl group having 1 to 3 carbon atoms substituted with an aryl group having 6 to 12 carbon atoms, An alkyl group having 6 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms,
L1 is a direct bond; An arylene group having 6 to 25 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 12 carbon atoms; Or a heteroarylene group having 2 to 12 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms,
Ar1 is hydrogen; A substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a heteroaryl group having 2 to 12 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms, and when Ar1 is an aryl group having 6 to 25 carbon atoms substituted, the substituent of the aryl group is an alkyl group having 1 to 3 carbon atoms; A heteroaryl group having 2 to 12 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms; Or an aryl group having 6 to 12 carbon atoms,
Gt; to R &lt; 6 &gt; are each independently hydrogen,
n1 is an integer of 1 to 5,
n2 is an integer of 1 to 5,
n3 is an integer of 1 to 4,
n4 is an integer of 1 to 3,
n5 is an integer of 1 to 3,
n6 is an integer of 1 to 4,
When n1 to n6 are two or more, the structures in parentheses of two or more are the same or different from each other. 2. The compound according to claim 1, wherein Q is selected from the following structures:

. 2. The compound according to claim 1, wherein L &lt; 1 &gt; is selected from the following structures:

. 2. The compound according to claim 1, wherein Ar &lt; 1 &gt; is selected from the following structures:

R 'is hydrogen; Or a phenyl group,
Rm and Rn are the same or different from each other, and each independently hydrogen; An alkyl group having 1 to 3 carbon atoms; An aryl group having 2 to 12 carbon atoms; Or a heteroaryl group having 2 to 12 carbon atoms. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Chemical Formulas 3 to 6:
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,
Q, L1, Ar1, R1 to R6, and n1 to n6 are the same as defined in the above formula (1). The compound of claim 1, wherein the compound of formula (2) is represented by any one of the following formulas (7) to (10):
(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above formulas (7) to (10)
Q, L1, Ar1, R1 to R6, and n1 to n6 are the same as defined in Formula 2 above. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

2. The compound according to claim 1, wherein the formula (2) is any one selected from the following compounds:

. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 8. 2. The organic electronic device according to claim 1, Electronic device. The organic electronic device according to claim 9, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The organic electronic device according to claim 9, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The organic electronic device according to claim 9, wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer comprises the compound. The organic electronic device according to claim 9, wherein the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound. 10. The organic electroluminescent device according to claim 9, wherein the organic electronic device is a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. The organic electronic device according to claim 9, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphor device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

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