KR101837896B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by Chemical Formula 1 and an organic electronic device including the same.

Description

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

The present application claims the benefit of Korean Patent Application No. 10-2016-0045032 filed on April 12, 2016, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

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

International Patent Application Publication No. 2003-012890

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

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

[Chemical Formula 1]

In Formula 1,

Q is a substituted or unsubstituted naphthyl group,

Ar ₁ and _one of R ₁ to R ₁₂ may be represented by - [L ₁ ] m-Ar ₂ or the following formula (2)

n is an integer of 1 to 6,

When n is 2 or more, a plurality of Ar < ₁ > s are the same or different from each other,

L ₁ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

m is an integer of 0 to 2,

When m is 2 or more, plural L < _{1 > s} are the same or different from each other,

Ar ₂ is a nitrile group; A phenyl group substituted with a nitrile group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted phosphine oxide group, a group represented by the following formula (6) or (7)

(2)

In Formula 2,

L ₁ and m are the same as defined in Formula 1,

At least two of X ₁ to X ₃ are N and the others are N or CR,

R is hydrogen, R ₁₃ and R ₁₄ are the same or different and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

[Chemical Formula 6]

In Formula 6,

X < ₄ > is N or CR < ₁₅ &

R ₁₅ and G ₁ to G ₆ are the moieties bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1), and the rest are the same or different and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

(7)

In Formula 7,

X ₅ is N or CR ₁₆ , X ₆ is N or CR ₁₇ , X ₇ is N or CR ₁₈ , X ₈ is N or CR ₁₉ ,

At least one of X ₅ to X ₈ is N,

Any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ in the formula 1 and the others are the same or different and are independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. 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 electronic 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 compound represented by the formula (1) of the present invention cyclizes a naphthyl group to a spiro compound, and electron clouds are not so abundant at the HOMO energy level in the molecule, so that the electron transporting ability is appropriately adjusted in the organic electronic device, And the lifetime characteristics of the device can be improved.

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

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. Preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. Specific examples include methyl, ethyl, propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- Pentyl, neopentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2- But are not limited to, 1-ethylpropyl, 1,1-dimethylpropyl, 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, preferably 3 to 20 carbon atoms, and more preferably 3 to 10 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms. More preferably from 6 to 20. 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.

In the present specification, 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. More preferably from 6 to 20. 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 2 to 50 carbon atoms. More preferably 2 to 20 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, But are not limited to, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, and dibenzofuranyl groups. It is not.

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.

The compound represented by Chemical Formula 1 according to one embodiment of the present invention has excellent thermal stability and hole stability because the HOMO energy level is at least 6.0 eV. Accordingly, the compound represented by the formula (1) has a low driving voltage and / or a high efficiency, and the stability of the device can be improved by the hole stability of the compound.

In one embodiment of the present specification, Q is a substituted or unsubstituted naphthylene group.

In one embodiment of the present disclosure, Q is a naphthylene group.

In one embodiment of the present disclosure, L &_lt; ₁ > is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L ₁ is a direct bond or a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present disclosure, L < ₁ > is a phenylene group.

In one embodiment of the present specification, L < ₁ > is a biphenylene group.

In one embodiment of the present disclosure, L < ₁ > is a naphthylene group.

In one embodiment of the present specification, m is an integer of 0 to 2, and when m is 2 or more, a plurality of L ₁ are the same or different from each other.

In one embodiment of the present invention, the compound in which the heteroaryl substituent group is substituted with the spirofluorene core structure in the formula (1) is applied to an organic electronic device as compared to a compound in which the heteroaryl substituent group is substituted in the spirofluorene core structure The device efficiency is high.

Specifically, the compound of Formula 1 according to one embodiment of the present disclosure has a triplet energy of 2.1 eV or greater, while a compound in which the heteroaryl substituent is two substituted in the spirofluorene core structure has a triplet energy of less than 2.1 eV, As a result, compounds having two heteroaryl substituents substituted in the spirofluorene core structure have low device efficiency when applied to organic electronic devices because the effect of triplet-triplet annihilation (TTA) is attenuated.

In one embodiment of the present specification, one of Ar ₁ and R ₁ to R ₁₂ may be represented by - [L ₁ ] m-Ar ₂ or the following formula 2, and the remainder is hydrogen.

(2)

In Formula 2,

L ₁ and m are the same as defined in Formula 1,

At least two of X ₁ to X ₃ are N and the others are N or CR,

R is hydrogen, R ₁₃ and R ₁₄ are the same or different and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R ₁₃ and R ₁₄ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

In one embodiment of the present specification, R ₁₃ and R ₁₄ are the same or different and are each independently 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 fluorene group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted pyridyl group.

In one embodiment of the present specification, R ₁₃ and R ₁₄ are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A fluorene group substituted or unsubstituted with an alkyl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted pyridyl group.

In one embodiment of the present specification, R ₁₃ and R ₁₄ are the same or different from each other, and each independently represents a phenyl group, a naphthyl group, a carbazole group, a substituted or unsubstituted fluorene group, a dibenzothiophene group, A phenyl group substituted or unsubstituted with a pyridyl group, a benzocarbazole group or phenoxathiin; A biphenyl group; A terphenyl group; A 1-naphthyl group substituted or unsubstituted with a phenyl group; A 2-naphthyl group substituted or unsubstituted with a phenyl group; A fluorene group substituted or unsubstituted with a methyl group; Phenylene; Carbazole group; A dibenzothiophene group; A dibenzofurane group; Or a pyridyl group.

According to one embodiment of the present disclosure, X ₁ to X ₃ are each N.

According to one embodiment of the present disclosure, X ₁ and X ₂ are each N, X ₃ is CR, and R is hydrogen.

According to one embodiment of the present disclosure, Ar ₂ is a nitrile group; A phenyl group substituted with a nitrile group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted phosphine oxide group, or a group represented by the following formula (6) or (7).

[Chemical Formula 6]

In Formula 6,

X < ₄ > is N or CR < ₁₅ &

R ₁₅ and G ₁ to G ₆ are the moieties bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1), and the rest are the same or different and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

(7)

In Formula 7,

X ₅ is N or CR ₁₆ , X ₆ is N or CR ₁₇ , X ₇ is N or CR ₁₈ , X ₈ is N or CR ₁₉ ,

At least one of X ₅ to X ₈ is N,

Any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ in the formula 1 and the others are the same or different and are independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present disclosure, Ar ₂ is a nitrile group; A phenyl group substituted with a nitrile group; A pyrazinyl group substituted or unsubstituted with an aryl group; Or a phosphine oxide group substituted or unsubstituted with an aryl group, or represented by the above formula (6) or (7).

In one embodiment of the present disclosure, Ar ₂ is a nitrile group; A phenyl group substituted with a nitrile group; A pyridazinyl group substituted or unsubstituted with a phenyl group or a naphthyl group; A phosphine oxide group substituted or unsubstituted with a phenyl group, or represented by the above formula (6) or (7).

In one embodiment of the present disclosure, X ₄ is N.

In one embodiment of the present disclosure, X < ₄ > is CH.

In one embodiment of the present invention, any one of R ₁₅ and G ₁ to G ₆ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of Formula 1, A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present invention, any one of R ₁₅ and G ₁ to G ₆ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of Formula 1, A substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

In one embodiment of the present invention, any one of R ₁₅ and G ₁ to G ₆ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of Formula 1, A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, any one of R ₁₅ and G ₁ to G ₆ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of Formula 1, A phenyl group; A biphenyl group; Or a naphthyl group.

In one embodiment of the present disclosure, at least two of X ₅ to X ₈ are N.

In one embodiment of the present disclosure, X ₆ and X ₇ are each N, X ₅ is CR ₁₆ , and X ₈ is CR ₁₉ .

In one embodiment of the present invention, any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1) And each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present invention, any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1) And each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

In one embodiment of the present invention, any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1) And each independently hydrogen; Or a substituted or unsubstituted aryl group.

Any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ in the formula 1 and the others are the same or different and are independently hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1) And each independently hydrogen; A phenyl group; Or a naphthyl group.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (3) to (5).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas (3) to (5)

Ar ₁ , n, and R ₁ to R ₁₂ are the same as defined in Formula 1 above.

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

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

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

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 do.

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

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

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

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

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 layer includes a layer that simultaneously transports electrons and electron, and the layer that simultaneously transports electrons and electron includes a compound represented by the above formula (1).

In one embodiment of the present invention, the organic layer includes an electron control layer, and the electron control layer includes a compound represented by the general formula (1).

In one embodiment of the present invention, the organic electronic device 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 electronic 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 electronic device may be a normal type organic electronic 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 this case, the weight ratio of the compound of Formula 1 to the n-type dopant may be 10: 1 to 1:10.

When the organic compound layer containing the compound of Formula 1 is a layer which simultaneously transports electrons and injects electrons, the layer which simultaneously transports electrons and electrons 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 one example, the layer that simultaneously includes electron transport and electron injection including the compound of Formula 1 may further include LiQ. In this case, the weight ratio of the compound of Formula 1 to the n-type dopant may be 10: 1 to 1:10.

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

For example, the structure of the organic electronic device in this specification may have a structure as shown in Figs. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic electronic 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 electronic device 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 substrate 100. The structure of the organic electronic device 11 is shown in Fig. 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

The organic electronic 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 electronic device includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

 The organic electronic device in this specification can be produced by materials and methods known in the art, except that at least one of the organic layers includes the compound, that is, the compound represented by the above formula (1).

For example, the organic electronic device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a 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 electronic device can be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode 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 electronic 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 electronic 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 hole blocking layer prevents the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

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

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

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

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

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

The organic electronic device according to the present invention may be a top emission type, a back emission type, or a both-sided 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 light emitting device, an organic solar cell, or an organic transistor in addition to an organic electronic device.

The compound according to the present invention can act on a principle similar to that applied to an organic electronic device in an organic electronic device including an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), an organic transistor and the like.

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

< Example >

Manufacturing example  1. Synthesis of Compound E1

The compound 4,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-fluorene] -2'- yl) -1,3,2-dioxaboro 4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 21.8 mmol) and 2 - ([ (8.4 g, 60.9 mmol) was dissolved in 50 ml of water, followed by addition of tetrakistriphenylphosphinopalladium (704 mg, 0.61 mmol), and the mixture was stirred for 8 hours Lt; / RTI &gt; After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to give the above compound E1 (12.3 g, yield 90%).

MS [M + H] &lt; ⁺ &gt; = 674

Manufacturing example  2. Synthesis of Compound E2

In the same manner as in Preparation Example 1, except for using 2- (3-chlorophenyl) -1,3,5-triazine in place of the compound 2 - ([1,1'-biphenyl] -4,6-diphenyl-1,3,5-triazine, the compound E2 was prepared in the same manner as in Preparation Example 1,

MS [M + H] &lt; ⁺ &gt; = 674

Manufacturing example  3. Synthesis of Compound E3

The compound 4,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-fluorene] -2'-yl) -1,3,2 - spiro [benzo [b] fluorene-11,9'-fluorene] -2'-yl) -1,3,2-dioxabororane instead of 4,4,5,5-tetramethyl- -Dioxaborolane was used in place of the compound 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5- -9-phenyl-1,10-phenanthroline, the compound E3 was prepared in the same manner as in Preparation Example 1,

MS [M + H] &lt; ⁺ &gt; = 621

Manufacturing example  4. Synthesis of Compound E4

The compound 4,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-fluorene] -2'-yl) -1,3,2 - spiro [benzo [c] fluorene-7,9'-fluorene] -4'-yl) -1,3,2-dioxabororane instead of 4,4,5,5- -Dioxaborolane was used in place of the compound 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5- -6- (4-chlorophenyl) -2-phenylpyrimidine, the compound E4-1 was prepared.

MS [M + H] &lt; ⁺ &gt; = 63

The compound E4-1 (10.0 g, 15.8 mmol) and dibenzo [b, d] furan-4-ylboronic acid (3.35 g, 15.8 mmol) were completely dissolved in tetrahydrofuran (100 ml) 6.6 g, 47.5 mmol) was dissolved in 50 ml of water and tetraquistriphenylphosphinopalladium (549 mg, 0.48 mmol) was added thereto, followed by heating with stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to give the above compound E4 (10.8 g, yield 89%).

MS [M + H] &lt; ⁺ &gt; = 763

Manufacturing example  5. Synthesis of Compound E5

In the same manner as in Production Example 4 except that 2-chloro-4- (3-chlorophenyl) -6-phenyl-1,3,5-tri Compound E5-1 was prepared in the same manner as Compound E4-1 of Preparation Example 4, except that azine was used.

MS [M + H] &lt; ⁺ &gt; = 632

After the compound E5-1 (10.0 g, 15.8 mmol) and carbazole (2.6 g, 15.8 mmol) were completely dissolved in xylene (100 ml), sodium-t-butoxide (1.4 eq) was dissolved in xylene and added , And the mixture was heated and stirred. Then, 2 mmol% of [bis (tri-t-butylphosphine)] palladium was added thereto at 80 ^° C. After the temperature was lowered to room temperature and the reaction was terminated, water was added and the white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to obtain the above compound E5 (9.8 g, yield 81%).

MS [M + H] &lt; ⁺ &gt; = 763

Manufacturing example  6. Synthesis of Compound E6

The compound 4,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-fluorene] -2'-yl) -1,3,2 -Spiro [benzo [c] fluorene-7,9'-fluorene] -5-yl) -1,3,2- Dioxaborolane was used in place of the compound 2 - (4-chloro-phenyl) -1,3,5-triazine in place of the compound 2 - ([ (Dibenzo [b, d] thiophen-3-yl) -phenylpyrimidine, the compound E6 was prepared in the same manner as in Preparation Example 1,

MS [M + H] &lt; ⁺ &gt; = 779

Manufacturing example  7. Synthesis of Compound E7

4 - ([1,1 '-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was obtained in the same manner as in Preparation Example 1, -Biphenyl] -4-yl) -2-chloroquinazoline, the compound E7 was prepared in the same manner as in Preparation Example 1,

MS [M + H] &lt; ⁺ &gt; = 647

Manufacturing example  8. Synthesis of Compound E8

Compound E8 was prepared in the same manner as in Preparation Example 1, except that the starting materials were the same as in the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 621

Manufacturing example  9. Synthesis of Compound E9

The above compound E9 was prepared in the same manner as in Production Example 1, except that each starting material was changed to the above reaction formula.

MS [M + H] &lt; ⁺ &gt; = 545

Manufacturing example  10. Synthesis of Compound E10

The above compound E10 was prepared in the same manner as in Preparation Example 1, except that each starting material was changed to the above reaction formula.

MS [M + H] &lt; ⁺ &gt; = 621

Manufacturing example  11. Synthesis of Compound E11

The above compound E11 was prepared in the same manner as in Production Example 1, except that each starting material was changed to the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 621

Manufacturing example  12. Synthesis of Compound E12

The compound E12 was prepared in the same manner as in Preparation Example 1, except that the starting materials were the same as in the above reaction scheme.

MS [M + H] &lt; ⁺ &gt; = 597

< Experimental Example  1-1>

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

The following compound [HI-A] was thermally vacuum-deposited on the thus-prepared ITO transparent electrode to a thickness of 600 Å to form a hole injection layer. A hole transport layer was formed on the hole injection layer by sequentially vacuum-depositing hexa-nitrile hexaazatriphenylene (HAT) of the following formula and 50 Å of the following compound [HT-A] (600 Å).

Subsequently, the following compounds [BH] and [BD] were vapor-deposited at a weight ratio of 25: 1 on the hole transport layer to a thickness of 200 ANGSTROM to form a light emitting layer.

The compound [E1] and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 1000 Å on the electron injecting and transporting layer sequentially to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec, the deposition rate of lithium fluoride at 0.3 A / sec for aluminum and 2 A / sec at aluminum was maintained, ^-7 to 5 × 10 ^- to maintain the ⁸ torr, it was produced in the organic electronic device.

< Experimental Example  1-2>

An organic electronic device was prepared in the same manner as in Experimental Example 1-1, except that Compound E2 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-3>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E3 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-4>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E4 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-5>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E5 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-6>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E6 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-7>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E7 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-8>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E8 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-9>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E9 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-10>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E10 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-11>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E11 was used instead of Compound E1 in Experimental Example 1-1.

< Experimental Example  1-12>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound E12 was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-1>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-A was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-2>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-B was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-3>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that the compound ET-1-C was used instead of the compound E1 in Experimental Example 1-1.

< Comparative Example  1-4>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-D was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-5>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-E was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-6>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-F was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-7>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-G was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-8>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-H was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-9>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-I was used instead of Compound E1 in Experimental Example 1-1.

< Comparative Example  1-10>

An organic electronic device was fabricated in the same manner as in Experimental Example 1-1, except that Compound ET-1-J was used instead of Compound E1 in Experimental Example 1-1.

The organic electronic device manufactured by the methods of Experimental Examples 1-1 to 1-12 and Comparative Examples 1-1 to 1-10 was measured for driving voltage and luminous efficiency at a current density of 10 mA / cm ² , / Cm &lt; ² &gt; was measured to be 90% of the initial luminance ( _T90 ). The results are shown in Table 1 below.

compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Life span (h)
T ₉₀ at 20 mA / cm ² Experimental Example 1-1 E1 4.20 5.67 (0.142, 0.097) 160 Experimental Example 1-2 E2 4.31 5.41 (0.142, 0.095) 170 Experimental Example 1-3 E3 4.43 5.37 (0.142, 0.096) 141 Experimental Examples 1-4 E4 4.26 5.30 (0.142, 0.096) 149 Experimental Examples 1-5 E5 4.34 5.39 (0.142, 0.096) 174 Experimental Example 1-6 E6 4.37 5.23 (0.142, 0.097) 153 Experimental Example 1-7 E7 4.39 5.02 (0.142, 0.096) 148 Experimental Examples 1-8 E8 4.24 5.39 (0.142, 0.096) 166 Experimental Examples 1-9 E9 4.34 5.69 (0.142, 0.096) 175 Experimental Example 1-10 E10 4.30 5.53 (0.142, 0.097) 172 Experimental Example 1-11 E11 4.39 5.28 (0.142, 0.096) 167 Experimental Example 1-12 E12 4.40 5.22 (0.142, 0.096) 147 Comparative Example 1-1 ET-1-A 4.74 3.87 (0.142, 0.098) 88 Comparative Example 1-2 ET-1-B 4.84 4.01 (0.142, 0.102) 85 Comparative Example 1-3 ET-1-C 4.97 3.96 (0.142, 0.096) 97 Comparative Example 1-4 ET-1-D 4.75 4.11 (0.142, 0.096) 64 Comparative Example 1-5 ET-1-E 5.21 3.67 (0.142, 0.096) 76 Comparative Example 1-6 ET-1-F 4.74 3.55 (0.142, 0.098) 20 Comparative Example 1-7 ET-1-G 4.89 4.01 (0.142, 0.102) 82 Comparative Example 1-8 ET-1-H 4.97 3.54 (0.142, 0.096) 40 Comparative Example 1-9 ET-1-I 4.75 4.00 (0.142, 0.096) 55 Comparative Example 1-10 ET-1-J 5.22 3.60 (0.142, 0.096) 60

From the results shown in Table 1, it was confirmed that the compound represented by Chemical Formula 1 according to one embodiment of the present invention can be used for an organic material layer capable of simultaneously performing electron injection and electron transport of organic electronic devices.

Specifically, comparing Experimental Examples 1-1 to 1-12 according to Formula 1 with Comparative Examples 1-1, 1-2, 1-3, 1-5, and 1-7, Compounds in which the heteroaryl group is substituted on the thiospirofluorene skeleton are more effective than the compound having heteroaryl group substituent on the skeleton of the phenanthrene spirofluorene, spirofluorene, and diben irradiated iophenyl spirofluorene, / RTI &gt; and / or &lt; RTI ID = 0.0 &gt; life. &Lt; / RTI &gt;

Further, in comparison with Experimental Examples 1-4, 1-5 and 1-6 and Comparative Examples 1-5, it was found that the structure of the above formula (1) containing at least two heteroaryl substituents in naphthyl spirofluorene is a spirofluorene group It is confirmed that the organic electroluminescent device exhibits excellent characteristics in the organic electronic device.

Comparing the examples 1-1 to 1-12 with the comparative examples 1-4, the structure of the above formula (1) containing a heteroaryl substituent on the naphthyl spirofluorene has a structure similar to the structure comprising a diphenylfluorene group And it was confirmed that it exhibits excellent characteristics in an electronic device.

Comparing Experimental Examples 1-4, 1-6 and 1-12 with Comparative Example 1-6, it can be seen that the structure of Formula 1 containing a heteroaryl substituent on naphthyl spirofluorene is substituted with hydrogen only in the six-membered heterocyclic group It is confirmed that the organic electroluminescent device exhibits excellent characteristics in the organic electronic device.

Further, in Experimental Examples 1-3, 1-8, 1-9, 1-10 and 1-11 and Comparative Examples 1-9. 1-10, the structure of the above formula (1) containing a heteroaryl substituent in naphthyl spirofluorene has superior properties in organic electronic devices compared to a structure in which phenanthroline is substituted with two substituents and a structure in which two naphthyl spiro groups are substituted .

Comparing the examples 1-1 to 1-12 and the comparative example 1-8, it was found that the structure of the above formula (1) containing a heteroaryl substituent on naphthyl spirofluorene is a structure in which a five-membered heterocyclic group is substituted with a naphthyl spiro group The organic electroluminescent device of the present invention exhibits excellent characteristics in the organic electronic device.

Accordingly, the compound represented by Formula 1 according to one embodiment of the present invention has excellent thermal stability, has a deep HOMO level equal to or higher than 6.0 eV, and has hole stability, and thus exhibits excellent properties.

In one embodiment of the present invention, when the compound represented by Formula 1 is used for an organic layer capable of electron injection and electron transport at the same time, n-type dopant used in the art can be mixed and used .

Accordingly, the compound represented by Formula 1 according to one embodiment of the present invention has low driving voltage and high efficiency, and it can be understood that the stability of the device can be improved by the hole stability of the compound.

< Experimental Example  2-1>

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

The following compound [HI-A] was thermally vacuum-deposited on the thus-prepared ITO transparent electrode to a thickness of 600 Å to form a hole injection layer. A hole transport layer was formed on the hole injection layer by sequentially vacuum-depositing 50 Å of hexanitrile hexaazatriphenylene (HAT) having the following formula and the following compound [HT-A] (600 Å).

Subsequently, the following compounds [BH] and [BD] were vapor-deposited at a weight ratio of 25: 1 on the hole transport layer to a thickness of 200 ANGSTROM to form a light emitting layer.

[Formula E1] was vacuum deposited on the light emitting layer to form an electron control layer having a thickness of 200 ANGSTROM. The following compounds [ET-1-K] and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited on the electron control layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 150 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 1000 Å on the electron injecting and transporting layer sequentially to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec, the deposition rate of lithium fluoride at 0.3 A / sec for aluminum and 2 A / sec at aluminum was maintained, ^-7 to 5 × 10 ^- to maintain the ⁸ torr, it was produced in the organic electronic device.

< Experimental Example  2-2>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E2 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-3>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E3 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-4>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that Compound E4 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-5>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that Compound E5 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-6>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E6 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-7>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E7 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-8>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E8 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-9>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E9 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-10>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E10 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-11>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound E11 was used instead of Compound E1 in Experimental Example 2-1.

< Experimental Example  2-12>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that Compound E12 was used instead of Compound E1 in Experimental Example 2-1.

< Comparative Example  2-1>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that the compound ET-1-A was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-2>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that the compound ET-1-B was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-3>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that the compound ET-1-C was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-4>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that the compound ET-1-D was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-5>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that the compound ET-1-E was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-6>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that the compound ET-1-F was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-7>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1 except that the compound ET-1-G was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-8>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that the compound ET-1-H was used instead of the compound E1 in Experimental Example 2-1.

< Comparative Example  2-9>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that Compound ET-1-I was used instead of Compound E1 in Experimental Example 2-1.

< Comparative Example  2-10>

An organic electronic device was fabricated in the same manner as in Experimental Example 2-1, except that the compound ET-1-J was used instead of the compound E1 in Experimental Example 2-1.

The organic electronic device manufactured by the methods of Experimental Examples 2-1 to 2-12 and Comparative Examples 2-1 to 2-10 was measured for driving voltage and luminous efficiency at a current density of 10 mA / cm ² , / Cm &lt; ² &gt; was measured to be 90% of the initial luminance ( _T90 ). The results are shown in Table 2 below.

compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Life span (h)
T ₉₀ at 20 mA / cm ² Experimental Example 2-1 E1 4.10 5.77 (0.142, 0.097) 180 EXPERIMENTAL EXAMPLE 2-2 E2 4.21 5.80 (0.142, 0.096) 179 Experimental Example 2-3 E3 4.23 5.57 (0.142, 0.096) 160 Experimental Example 2-4 E4 4.16 5.70 (0.142, 0.096) 184 Experimental Example 2-5 E5 4.20 5.69 (0.142, 0.096) 194 Experimental Examples 2-6 E6 4.22 5.73 (0.142, 0.097) 175 Experimental Example 2-7 E7 4.40 5.10 (0.142, 0.096) 150 Experimental Examples 2-8 E8 4.21 5.56 (0.142, 0.096) 162 Experimental Examples 2-9 E9 4.30 5.48 (0.142, 0.096) 161 Experimental Example 2-10 E10 4.28 5.53 (0.142, 0.097) 158 Experimental Example 2-11 E11 4.39 5.28 (0.142, 0.096) 160 Experimental Examples 2-12 E12 4.37 5.46 (0.142, 0.096) 150 Comparative Example 2-1 ET-1-A 4.75 3.88 (0.142, 0.097) 78 Comparative Example 2-2 ET-1-B 4.84 3.55 (0.142, 0.096) 55 Comparative Example 2-3 ET-1-C 4.97 3.77 (0.142, 0.097) 60 Comparative Example 2-4 ET-1-D 4.66 4.12 (0.142, 0.096) 80 Comparative Example 2-5 ET-1-E 5.31 3.77 (0.142, 0.096) 46 Comparative Example 2-6 ET-1-F 5.55 3.01 (0.142, 0.098) 15 Comparative Example 2-7 ET-1-G 4.92 4.00 (0.142, 0.102) 68 Comparative Example 2-8 ET-1-H 4.99 3.14 (0.142, 0.096) 20 Comparative Example 2-9 ET-1-I 4.88 4.01 (0.142, 0.096) 59 Comparative Example 2-10 ET-1-J 5.31 4.08 (0.142, 0.096) 67

From the results shown in Table 2, it was confirmed that the compound represented by Chemical Formula 1 according to one embodiment of the present invention can be used for an electron control layer of an organic electronic device.

Specifically, comparing Experimental Examples 2-1 to 2-12 according to Formula 1 with Comparative Examples 2-1, 2-2, 2-3, 2-5, and 2-7, Compounds in which the heteroaryl group is substituted on the thiospirofluorene skeleton are more effective than the compound having heteroaryl group substituent on the skeleton of the phenanthrene spirofluorene, spirofluorene, and diben irradiated iophenyl spirofluorene, / RTI &gt; and / or &lt; RTI ID = 0.0 &gt; life. &Lt; / RTI &gt;

Comparing the examples 2-4, 2-5 and 2-6 with those of the comparative example 2-5, the structure of the above formula (1) containing at least two heteroaryl substituents in the naphthyl spirofluorene is a spirofluorene group It is confirmed that the organic electroluminescent device exhibits excellent characteristics in the organic electronic device.

Comparing the experimental examples 2-1 to 2-12 and the comparative example 2-4, it was found that the structure of the above formula (1) containing a heteroaryl substituent on the naphthyl spirofluorene is more stable than the structure containing the diphenylfluorene group And it was confirmed that it exhibits excellent characteristics in an electronic device.

Further, in comparison of Experimental Examples 2-4, 2-6 and 2-12 and Comparative Example 2-6, it was found that the structure of the above formula (1) containing a heteroaryl substituent on naphthyl spirofluorene is substituted with hydrogen only in the six-membered heterocyclic group It is confirmed that the organic electroluminescent device exhibits excellent characteristics in the organic electronic device.

Further, in Experimental Examples 2-3, 2-8, 2-9, 2-10 and 2-11 and Comparative Examples 2-9. 2-10, the structure of the above formula (1) containing a heteroaryl substituent in naphthyl spirofluorene has superior properties to organic electronic devices compared to a structure in which two phenanthrolines are substituted and a structure in which two naphthyl spiro groups are substituted .

Further, in comparison between Experimental Examples 2-1 to 2-12 and Comparative Example 2-8, it was found that the structure of the above-mentioned formula (1) containing a heteroaryl substituent on naphthyl spirofluorene was a structure in which a pentagonal heterocyclic group was substituted with a naphthyl spiro group The organic electroluminescent device of the present invention exhibits excellent characteristics in the organic electronic device.

Accordingly, the compound represented by Formula 1 according to one embodiment of the present invention has excellent thermal stability, has a deep HOMO level equal to or higher than 6.0 eV, and has hole stability, and thus exhibits excellent properties.

Accordingly, the compound represented by Formula 1 according to one embodiment of the present invention has low driving voltage and high efficiency, and it can be understood that the stability of the device can be improved by the hole stability of the compound.

< Experimental Example  3>

The triplet energy value (E _T) of the represented by the general formula (1) according to one embodiment of the disclosure to the compound E1, E3, E8 and E9 compound represented by the compound ET-1-I and ET-1-J Table 3 shows the results.

The triplet energies (E _T ) were performed using a quantum chemistry calculation program Gaussian 03, manufactured by Gaussian, USA, using the Density Functional Theory (DFT) and the B3LYP (Becke, three-parameter , Lee-Yang-Parr) and 6-31G * as a basis function, the triplet energies were calculated by TD-DFT.

The E _T (eV) E1 2.29 E3 2.25 E8 2.24 E9 2.25 ET-1-I 2.01 ET-1-J 1.98

As a result of Table 3, it was confirmed that all of the compounds represented by the above formulas [ET-1-I] and [ET-1-J] had triplet energies of less than 2.1 eV, As a result of the comparative example, it is confirmed that the compound having a low triplet energy of less than 2.1 eV has low device efficiency. This is because, when a compound having a low triplet energy is used, the effect of triplet-triplet annihilation (TTA) is attenuated.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

10, 11: organic electronic 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 (12)

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

In Formula 1,
Q is a naphthyl group,
Ar ₁ and _one of R ₁ to R ₁₂ may be represented by - [L ₁ ] m-Ar ₂ or the following formula (2)
n is an integer of 1 to 6,
When n is 2 or more, a plurality of Ar &lt; ₁ &gt; s are the same or different from each other,
L ₁ is a direct bond; An arylene group; Or a heteroarylene group,
m is an integer of 0 to 2,
When m is 2 or more, plural L &lt; _{1 &gt; s} are the same or different from each other,
Ar ₂ is a nitrile group; A phenyl group substituted with a nitrile group; A pyrazinyl group substituted or unsubstituted with an aryl group; A phosphine oxide group substituted or unsubstituted with an aryl group, or a group represented by the following formula (6) or (7)
(2)

In Formula 2,
L ₁ and m are the same as defined in Formula 1,
At least two of X ₁ to X ₃ are N and the others are N or CR,
R is hydrogen, R ₁₃ and R ₁₄ are the same or different and are each independently an alkyl group, an aryl group, or an aryl group substituted or unsubstituted with a heteroaryl group; Or a heteroaryl group,
[Chemical Formula 6]

In Formula 6,
X &lt; ₄ &gt; is N or CR &lt; ₁₅ &
R ₁₅ and G ₁ to G ₆ are the moieties bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1), and the rest are the same or different and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; An alkenyl group; Silyl group; Boron group; An amine group; Arylphosphine groups; Phosphine oxide groups; An aryl group; Or a heteroaryl group,
(7)

In Formula 7,
X ₅ is N or CR ₁₆ , X ₆ is N or CR ₁₇ , X ₇ is N or CR ₁₈ , X ₈ is N or CR ₁₉ ,
At least one of X ₅ to X ₈ is N,
Any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ in the formula 1 and the others are the same or different and are independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; An alkenyl group; Silyl group; Boron group; An amine group; Arylphosphine groups; Phosphine oxide groups; An aryl group; Or a heteroaryl group. The compound according to claim 1, wherein R ₁₃ and R ₁₄ are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A biphenyl group; A terphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; A fluorene group substituted or unsubstituted with an alkyl group; Phenylene; Carbazole group; A dibenzothiophene group; A dibenzofurane group; Or a pyridyl group. The compound according to claim 1, wherein any one of R ₁₅ and G ₁ to G ₆ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ in the formula (1), and the remaining moieties are the same or different, ; A biphenyl group; Or a naphthyl group. The compound according to claim 1, wherein any one of G ₇ to G ₁₂ and R ₁₆ to R ₁₉ is a moiety bonded to L ₁ of Ar ₁ and R ₁ to R ₁₂ of the formula (1) Independently hydrogen; A phenyl group; Or a naphthyl group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 3 to 5:
(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas (3) to (5)
Ar ₁ , n, and R ₁ to R ₁₂ are the same as defined in Formula 1 above. The compound according to claim 1, wherein the compound of formula (1) 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 6. The organic electronic device according to any one of claims 1 to 6, Electronic device. [7] The organic EL device according to claim 7, wherein the organic material layer includes an electron injection layer, an electron transport layer, or a layer simultaneously performing electron injection and electron transport, wherein the electron injection layer, Organic electronic device. The organic electronic device according to claim 7, wherein the organic layer includes an electron control layer, and the electron control layer includes the compound. The organic electronic device according to claim 7, 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. The organic electroluminescent device according to claim 7, 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, an electron control layer, and a hole blocking layer. The organic electronic device according to claim 7, 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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