KR20170126812A - Carbazole based compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a carbazole-based compound represented by chemical formula 1, and an organic light-emitting device comprising the same. According to one embodiment of the present specification, the compound may be used as a material for an organic material layer in an organic light-emitting device to improve efficiency, lower driving voltage, and/or improve lifetime characteristics of the device. Additionally, another embodiment of the present specification provides an organic light-emitting device which comprises: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic layer materials comprises a compound represented by the chemical formula 1.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a carbazole-based compound and an organic light-

This application claims the benefit of Korean Patent Application No. 10-2016-0057148 filed on May 10, 2016, the entire contents of which are incorporated herein by reference.

The present invention relates to a carbazole-based compound and an organic light emitting device including the same.

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.

Korean Patent Publication No. 2000-0051826

In this specification, a carbazole-based compound and an organic light emitting device including the same are disclosed.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Ar ₁ to Ar ₃ are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

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

r and t are each an integer of 0 to 2, r + t is 1 or more,

when r is 2, L < _{1 >} are the same or different from each other,

when t is 2, L ₂ are the same or different from each other,

X is a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or -O-,

s is an integer of 1 to 3, and when s is 2 or 3, X is the same or different,

R ₁ to R ₄ are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine 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 heterocyclic group,

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

m and p are each an integer of 0 to 3,

when n is 2 or more, R1 is the same or different, and when m is 2 or more, R2 is the same or different,

When p is 2 or more, R3 is the same or different, and when q is 2 or more, R4 is the same or different from each other.

In addition, one embodiment of the present disclosure includes a 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 of Formula 1.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, light emitting, electron transporting, or electron injecting materials. In addition, the compounds described in the present specification can be preferably used as a light emitting layer, an electron transporting or electron injecting material. More preferably, the compounds described in this specification exhibit low voltage, high efficiency, and / or long life characteristics when used as a material for a light emitting layer.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
3 is a graph showing the result of LC / MS measurement of Compound 1. Fig.
4 is a graph showing the result of LC / MS measurement of Compound 2. Fig.
5 is a graph showing the results of LC / MS measurement of Compound 3. Fig.
Fig. 6 is a graph showing the results of LC / MS measurement of Compound 5. Fig.
7 is a graph showing the results of LC / MS measurement of Compound 6. Fig.
8 is a graph showing the result of LC / MS measurement of Compound 7. Fig.

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

An embodiment of the present invention provides a compound represented by the above formula (1).

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

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 amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; A silyl group substituted or unsubstituted with an alkyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. 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 of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BR _d R _e , wherein R _d and R _e are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or 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. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

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. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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 cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 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, the alkoxy group is not particularly limited, but preferably has 1 to 40 carbon atoms. According to one embodiment, the number of carbon atoms in the alkoxy group is from 1 to 10. According to another embodiment, the number of carbon atoms of the alkoxy group is from 1 to 6. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group and a hexyloxy group.

In the present specification, the number of carbon atoms of the amine group 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- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine 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 containing two or more 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.

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, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group containing at least two heterocyclic groups may contain a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, the arylheteroarylamine group means an aryl group and an amine group substituted with a heterocyclic group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine 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.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, a fluorenyl group and a triphenylene group.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

,

,

,

,

,

및

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

,

,

,

,

,

,

And

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

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic 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, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, A benzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group , A phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylheteroarylamine group, The description of one aryl group may be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group can be applied to the alkyl group described above.

In the present specification, the heteroaryl group in the heteroaryl group, the heteroarylamine group and the arylheteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.

In the present specification, the description of the aryl group described above can be applied, except that the arylene group is a divalent group.

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

In the present specification, the cycloalkylene group means a cycloalkylene group having two bonding positions, i.e., divalent. The description of the above-mentioned cycloalkyl group can be applied except that each of them is 2 groups.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the divalent heterocyclic group is divalent.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (10).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In formulas (2) to (10)

Ar ₁ to Ar ₃ , L ₁ , L ₂ , r, t, X, s, R ₁ to R ₄ , n, q, m and p are as defined in formula (1).

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

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

According to one embodiment of the present invention, L ₁ and L ₂ are the same or different and are each independently an alkylene group substituted with an alkyl group.

According to one embodiment of the present invention, L ₁ and L ₂ are the same or different and each independently is a straight or branched alkylene group having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, L ₁ and L ₂ are phenylene.

According to one embodiment of the present disclosure, L ₁ and L ₂ are biphenylene

According to one embodiment of the present disclosure, L ₁ and L ₂ are substituted or unsubstituted bivalent fluorenyl groups.

According to one embodiment of the present disclosure, L ₁ and L ₂ are direct bonds.

According to one embodiment of the present invention, X is a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group or -O-.

According to one embodiment of the present invention, X is a linear or branched alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 30 carbon atoms, or -O-.

According to one embodiment of the present disclosure, X is selected from methylene, ethylene, propylene, butylene, pentylene, heptylene, heptylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclopentylene, phenyl Or -O-.

According to one embodiment of the present disclosure, s is one.

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

According to one embodiment of the present disclosure, r is zero.

According to one embodiment of the present disclosure, r is one.

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

According to one embodiment of the present disclosure, t is zero.

According to one embodiment of the present disclosure, t is one.

According to one embodiment of the present disclosure, t is two.

According to one embodiment of the present invention, Ar ₂ and Ar ₃ are the same or different and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar ₂ and Ar ₃ are the same or different and each independently represents an aryl group substituted or unsubstituted with at least one of an alkyl group, an aryl group and a heterocyclic group; Or a heterocyclic group substituted or unsubstituted with at least one of an alkyl group, an aryl group and a heterocyclic group.

According to one embodiment of the present invention, Ar ₂ and Ar ₃ are the same or different and each independently an aryl group substituted or unsubstituted with at least one of an alkyl group, an aryl group and a heterocyclic group.

According to one embodiment of the present invention, Ar ₂ and Ar ₃ are the same or different and each independently a phenyl group substituted or unsubstituted with at least one of an aryl group and a heterocyclic group.

According to one embodiment of the present disclosure, Ar ₂ and Ar ₃ are substituted or unsubstituted fluorenyl groups.

According to one embodiment of the present invention, Ar ₂ and Ar ₃ are the same or different from each other and are each independently a heterocyclic group.

According to one embodiment of the present disclosure, Ar ₂ and Ar ₃ are the same or different and are each independently dibenzothiophene.

According to one embodiment of the present disclosure, Ar ₂ and Ar ₃ are the same or different and are each independently dibenzofuran.

According to one embodiment of the present disclosure, Ar ₁ is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Ar < ₁ > is a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, Ar < ₁ > is a phenyl group.

According to one embodiment of the present disclosure, R ₁ to R ₄ are hydrogen.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 1 are selected from the following Table 1.

[Table 1]

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 2 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 3 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 4 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 5 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 6 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 7 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 8 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 9 are selected in Table 1 above.

According to one embodiment of the present invention, L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in Formula 10 are selected in Table 1 above.

In the present specification, the numbers of the compounds having substituents in Table 1 can be indicated by attaching the symbols denoted by # in Table 1 after the above-mentioned Formulas 2 to 10. For example, 2-1A has a compound of the following structural formula.

[Compound 2-1A]

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1.

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 of Formula 1.

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, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a host material, and further includes another host material.

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

In one embodiment of the present disclosure, the dopant compound is a phosphorescent dopant.

In one embodiment of the present disclosure, the dopant compound is an iodide based complex.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the compound and the dopant compound in a ratio of 100: 1 to 5: 5.

In the present specification, the following compounds Dp-1 to Dp-38 may be used as the dopant material, but the present invention is not limited thereto.

In one embodiment of the present invention, the organic material layer includes an electron transport layer, an electron injection layer, or a layer which simultaneously transports electrons and electrons, and the electron transport layer, the electron injection layer, The compound of formula (1).

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, The compound of formula (1).

In one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound of the above formula (1).

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; Wherein at least one of the two or more organic layers includes the compound of Formula 1, wherein the organic layer comprises at least two organic layers including at least two 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, the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, 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 compound of the above formula (1). Specifically, in one embodiment of the present invention, the compound of Formula 1 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 one embodiment of the present invention, when the compound of Formula 1 is contained in each of the two or more electron transporting layers, the materials other than the compound of Formula 1 may be the same or different from each other.

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.

 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 according to one embodiment of the present disclosure is illustrated in FIGS.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound may be included in the light emitting layer.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting 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 include the compound of the present invention, i.e., the compound of the above formula (1).

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.

 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 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 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 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 light emitting material 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 good 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 the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, 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 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 of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Preparation Example 1. Synthesis of Intermediates A, B, C, D, E, F, G, H and I

(1) Synthesis of intermediate A

20.0 g (1.0 eq) of compound 1a (9H-carbazol-2-yl) boronic acid and 33.6 g (1.1 eq) of compound 1b (2-bromo-9-phenyl-9H-carbazole) were dissolved in 200 ml of tetrahydrofuran after the mixture was stirred with 1.5M potassium carbonate solution (100ml) and refluxed back into the tetrakis (triphenylphosphine) palladium _{(0) (Pd (PPh 3} ) 4) 1.10g (0.01eq). After 10 hours, the temperature was lowered to room temperature, the water layer was separated off, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved completely in ethyl acetate and washed with water. The resulting solution was concentrated under reduced pressure, Recrystallization was performed using a mixture of furan and ethanol to obtain 30.1 g (yield: 78%) of intermediate A. MS: [M + H] < ⁺ > = 409

(2) Synthesis of intermediate B

Intermediate B was prepared in the same manner as Intermediate A except for using Compound 2b (3-bromo-9-phenyl-9H-carbazole) instead of Compound 1b.

(3) Synthesis of intermediate C

Intermediate C was prepared in the same manner as Intermediate A except for using Compound 3b (4-bromo-9-phenyl-9H-carbazole) instead of Compound 1b.

(4) Synthesis of intermediate D

Intermediate D was prepared in the same manner as Intermediate A except that Compound 2a ((9H-carbazol-3-yl) boronic acid) was used instead of Compound 1a.

(5) Synthesis of intermediate E

Intermediate E was prepared in the same manner as Intermediate A except for using Compound 2a and Compound 2b instead of Compound 1a and Compound 1b.

(6) Synthesis of intermediate F

Intermediate F was prepared in the same manner as Intermediate A except that Compound 2a and Compound 3b were used instead of Compound 1a and Compound 1b.

(7) Synthesis of intermediate G

The intermediate G was prepared in the same manner as the compound A except for using the compound 3a ((9H-carbazol-4-yl) boronic acid instead of the compound 1a).

(8) Synthesis of Intermediate H

Intermediate H was prepared in the same manner as Intermediate A except for using Compound 3a and Compound 2b instead of Compound 1a and Compound 1b.

(9) Synthesis of intermediate I

Intermediate I was prepared in the same manner as Intermediate A except that Compound 4a ((9H-carbazol-1-yl) boronic acid) and Compound 3b were used instead of Compound 1a and Compound 1b.

Production example 2. Synthesis of intermediates C1 to C6

(1) Synthesis of intermediate C-1

(4-chlorophenyl) magnesium bromide was dissolved in 300 ml of tetrahydrofuran at 0 ° C. After 30.0 g (1.0 eq) of propan-2-one was dissolved in 300 ml of tetrahydrofuran in a nitrogen atmosphere, (3.0 eq) was slowly added dropwise over 30 minutes, and the mixture was stirred at room temperature for about 1 hour. After quenched with NH ₄ Cl aqueous solution, the organic layer was separated by dissolving in ethyl acetate, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. This was purified by column chromatography to obtain 69.1 g (yield: 78%) of intermediate C-1. MS: [M + H] < ⁺ > = 171

(2) Synthesis of intermediate C-2

69.1 g (1.7 eq) of Intermediate C-1 was dissolved in 650 ml of acetonitrile, 92.2 g (1.5q) of calcium carbonate was dissolved in 400 ml of water, and then nonafluorobutanesulfonyl fluoride 80.0 ml (1.1 eq) is slowly added dropwise for 30 minutes. Thereafter, the mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, the reaction mixture was filtered and completely dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain 135.2 g (yield: 74%) of Intermediate C-2. MS: [M + H] < ⁺ > = 452

(3) Synthesis of intermediate C1

40.0 g (1.1 eq) of Pd (dppf) Cl _2, 1.0 g (0.1 mol%) of 4,4,5,5-tetramethyl- [1,3,2] , And 42.1 g (3.0 eq) of KOAc were placed in 600 mL of dioxane, and the mixture was stirred at reflux for 12 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 36.1 g (yield: 90%) of Intermediate C1 was prepared. MS: [M + H] < ⁺ > = 281

(4) Synthesis of intermediate C2

Intermediate C-3 was prepared in the same manner as Intermediate C-1 except for using Compound 3c ((3-chlorophenyl) magnesium bromide) instead of Intermediate 1c.

Intermediate C-4 was prepared in the same manner as Intermediate C-2 except for using Intermediate C-3 instead of Intermediate C-1.

Intermediate C2 was prepared in the same manner as Intermediate C1 except that Intermediate C-4 was used instead of Intermediate C-2.

(5) Synthesis of intermediate C3

2.47 g (0.02 eq) of Pd (PPh ₃ ) _{4 was} added to 20.0 g (1.0 eq) of Intermediate Compound C1 and 28.6 g (1.0 eq) of Compound 4c (2-chloro-4,6-diphenyl- 29.6 g (2.0 eq) of K ₂ CO ₃ dissolved in water was added to 250 ml of THF, and the mixture was refluxed and stirred. After 2 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and recrystallized from chloroform and ethanol to obtain 35.2 g (yield: 85%) of intermediate C3 as a white solid. MS: [M + H] < ⁺ > = 386

(6) Synthesis of intermediate C4

Intermediate C4 was prepared in the same manner as Intermediate C3 except that Intermediate C2 was used instead of Intermediate C1.

(7) Synthesis of intermediate C5

Compound 4c was prepared in the same manner as in Example 1 except that Compound 5c (3- (4 - ([1,1'-biphenyl] -4-yl) -6-chloro-1,3,5-triazin-2-yl) benzene- , The intermediate C5 was prepared in the same manner as in the preparation of intermediate C3.

(8) Synthesis of intermediate C6

Except that Intermediate C2 and Compound 6c (2,4-di ([1,1'-biphenyl] -4-yl) -6-chloro-1,3,5-triazine were used in place of Intermediate C1 and Intermediate 4c, The intermediate C6 was prepared in the same manner as in the preparation of C3.

Production Example 3. Synthesis of Intermediate D1 to D3

(1) Synthesis of intermediate D1

50.00 g (1.0 eq) of Compound 1d ((4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenol) and 35.3 g (0.2 eq) of CuI, 5.54 g (0.2 eq) of 1,10-phenanthroline and 25.0 g (3.0 eq) of KOH were added to 600 ml of xylene and the mixture was refluxed and stirred. After the reaction was completed, the reaction solution was cooled to room temperature and copper was removed by filtration. The solution in which the product was dissolved was decompressed to remove all of the solvent. The solution was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and recrystallization was performed using a mixed solution of tetrahydrofuran and ethanol to obtain 59.4 g Yield: 89%). MS: [M + H] < ⁺ > = 436

(2) Synthesis of intermediate D2

Intermediate D2 was prepared in the same manner as Intermediate D1 except that compound 3d (1-bromo-3-chlorobenzene) was used instead of compound 2d.

(3) Synthesis of intermediate D3

Except that the compound 4d (4- (4 - ([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin- The intermediate D3 was prepared in the same manner as in the preparation of D1.

Synthesis Example 1. Synthesis of Compound 1

After dissolving 8.0 g (1.0 eq) of intermediate A, 8.3 g (1.1 eq) of intermediate C3 and 2.45 g (1.3 eq) of sodium tert-butoxide (NaOt-Bu) in 80 ml of xylene, bis (tri- tert-butylphosphine) 0.30 g (0.03 eq) of palladium (0) was added thereto, and the mixture was refluxed and stirred. After 9 hours, the temperature is lowered to room temperature, and the filter is washed with water to remove the base. 10.3 g of Compound 1 (yield: 69%) was prepared using tetrahydrofuran and ethyl acetate. MS: [M + H] < ⁺ > = 758

3 is a graph showing the result of LC / MS measurement of Compound 1. Fig.

Synthesis Example 2. Synthesis of Compound 2

9.4 g of Compound 2 (yield: 70%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate B and Intermediate C4 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 758

4 is a graph showing the result of LC / MS measurement of Compound 2. Fig.

Synthesis Example 3. Synthesis of Compound 3

10.0 g of Compound 3 (yield: 71%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate C and Intermediate D1 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 808

5 is a graph showing the results of LC / MS measurement of Compound 3. Fig.

Synthesis Example 4. Synthesis of Compound 4

8.7 g of Compound 4 (yield: 65%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate D and Intermediate D2 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 808

Synthesis Example 5. Synthesis of Compound 5

10.1 g of Compound 5 (yield: 73%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate E and Intermediate C5 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 834

Fig. 6 is a graph showing the results of LC / MS measurement of Compound 5. Fig.

Synthesis Example 6. Synthesis of Compound 6

10.8 g of Compound 6 (yield: 77%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate F and Intermediate D3 were used instead of Intermediate F and Intermediate D3. MS: [M + H] < ⁺ > = 884

7 is a graph showing the results of LC / MS measurement of Compound 6. Fig.

Synthesis Example 7: Synthesis of Compound 7

8.8 g of Compound 7 (yield: 68%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate G and Intermediate C4 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 758

8 is a graph showing the result of LC / MS measurement of Compound 7. Fig.

Synthesis Example 8. Synthesis of Compound 8

10.4 g of Compound 8 (yield: 74%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate H and Intermediate D1 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 808

Synthesis Example 9 Synthesis of Compound 9

9.1 g of Compound 9 (yield: 67%) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate H and Intermediate C3 were used instead of Intermediate A and Intermediate C3. MS: [M + H] < ⁺ > = 758

Experimental Example 1

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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 HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer.

The HT-1 compound was thermally vacuum-deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and an HT-2 compound was vacuum deposited on the HT-1 deposition layer to a thickness of 50 Å to form an electron blocking layer.

Compound 1 and phosphorescent dopant Dp-25 were vacuum deposited on the HT-2 deposited film at a weight ratio of 12% to form a 400Å thick light emitting layer.

The ET-1 material was vacuum deposited on the light-emitting layer to a thickness of 250 ANGSTROM, and the ET-2 material was vacuum deposited on the EL material to a thickness of 100 ANGSTROM to a 2% weight ratio of Li to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

The deposition rate of the organic material in the above process, 0.4Å / sec to 0.7Å / sec was maintained, aluminum were deposited at speeds, degree of vacuum upon deposition of 2Å / sec is 1 × 10 ^-7 torr to 5 × 10 ^{- 8} torr.

Experimental Example 2

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

Experimental Example 3

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

Experimental Example 4

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

Experimental Example 5

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

Experimental Example 6

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

Comparative Example 1

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

Comparative Example 2

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound J1 was used instead of Compound 1 in Experimental Example 1

Experimental Example 7

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example 8

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example 9

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example 10

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound 4 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example 11

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 6 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example 12

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 7 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example 13

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 9 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Comparative Example 3

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that Compound H-1 and Compound H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

The results of the measurement of the performance of the organic light emitting devices manufactured in Experimental Examples 1 to 13 and Comparative Examples 1 to 3 are shown in Table 1 below.

compound Voltage V
(@ 10 mA / cm ² ) Efficiency cd / A
(@ 10 mA / cm ² ) Luminous color Experimental Example 1 One 2.75 65.0 green Experimental Example 2 3 2.77 71.0 green Experimental Example 3 4 2.79 69.5 green Experimental Example 4 5 2.78 67.3 green Experimental Example 5 7 2.76 65.4 green Experimental Example 6 8 2.80 70.1 green Experimental Example 7 1, H-2 3.25 69.1 green Experimental Example 8 2, H-2 3.23 70.7 green Experimental Example 9 3, H-2 3.24 73.9 green Experimental Example 10 4, H-2 3.30 75.0 green Experimental Example 11 6, H-2 3.27 74.9 green Experimental Example 12 7, H-2 3.24 74.7 green Experimental Example 13 9, H-2 3.26 75.0 green Comparative Example 1 H-1 3.01 60 green Comparative Example 2 J1 2.89 64 green Comparative Example 3 H-1, H-2 3.52 67 green

The results of Table 1 show that the compound of the present invention has higher efficiency than the compound H-1, which is a green luminescent host material that has been widely used in the past, and that the two-component host exhibits better performance in terms of efficiency .

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, but can be variously modified and embodied within the scope of the claims and the detailed description of the invention, and is also within the scope of the specification .

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7:
8: Electron transport layer

Claims (10)

A compound of formula
[Chemical Formula 1]

In Formula 1,
Ar ₁ to Ar ₃ are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 and L2 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
r and t are each an integer of 0 to 2, r + t is 1 or more,
when r is 2, L < _{1 >} are the same or different from each other,
when t is 2, L ₂ are the same or different from each other,
X is a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or -O-,
s is an integer of 1 to 3, and when s is 2 or 3, X is the same or different,
R ₁ to R ₄ are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine 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 heterocyclic group,
n and q are each an integer of 0 to 4,
m and p are each an integer of 0 to 3,
when n is 2 or more, R1 is the same or different, and when m is 2 or more, R2 is the same or different,
When p is 2 or more, R3 is the same or different, and when q is 2 or more, R4 is the same or different from each other. The method according to claim 1,
Wherein the formula (1) is represented by any one of the following formulas (2) to (10):
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In formulas (2) to (10)
Ar ₁ to Ar ₃ , L ₁ , L ₂ , r, t, X, s, R ₁ to R ₄ , n, q, m and p are as defined in formula (1). The method according to claim 1,
Lt; RTI ID = 0.0 > R4 < / RTI > is hydrogen. The method of claim 2,
Wherein L ₁ , X, L ₂ , Ar ₂ and Ar ₃ in the general formulas (2) to (10) are selected from the following Table 1:

A 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 according to any one of claims 1 to 4 Organic light emitting device. The method of claim 5,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The method of claim 5,
Wherein the organic layer includes a light emitting layer, the light emitting layer includes the compound as a host material, and further includes another host material. The method of claim 5,
Wherein the organic layer includes a light emitting layer, the light emitting layer includes the compound, and further comprises a dopant compound. The method of claim 5,
Wherein the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, device. The method of claim 5,
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes, wherein the hole transporting layer, the hole injecting layer, or the layer that simultaneously transports holes and holes injects the organic light emitting device.

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