KR102179708B1 - Organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides an organic light-emitting device including the compounds of Formulas 1 and 2.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2018-0045681 filed with the Korean Intellectual Property Office on April 19, 2018, the entire contents of which are incorporated herein.

The present application relates to an organic light emitting device.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2014-0124530

It is to provide the compound of the present application and an organic light emitting device including the same.

The present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode,

The organic material layer includes a host and a dopant,

The host includes a compound represented by the following formula (1),

The dopant provides an organic light-emitting device comprising a compound represented by Formula 2 below.

[Formula 1]

In Formula 1,

R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

At least one of R1 to R10 is the following formula A,

[Formula A]

In formula A,

A is O or S,

Any one of R'1 to R'8 is a linking group represented by Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or groups adjacent to each other may be bonded to each other to form a ring,

[Formula 2]

In Formula 2,

Any one of X1 and Y1 is a direct bond, and the other is NAr1,

Any one of X2 and Y2 is a direct bond, and the other is NAr2,

Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It is a cyclic heterocyclic group,

R”1 to R”14 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, It is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

R”7 and R”14 are not isopropyl groups.

The organic light-emitting device using the compound according to the exemplary embodiment of the present application may obtain a low driving voltage, high luminous efficiency, or high color purity.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device in which the cathode 4 is sequentially stacked.

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

The present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode,

The organic material layer includes a host and a dopant,

The host includes the compound represented by Formula 1,

The dopant provides an organic light-emitting device including the compound represented by Chemical Formula 2.

According to an exemplary embodiment of the present application, the compound represented by Formulas 1 and 2 has the advantage of controlling triplet energy by having the core structure as described above, and when used as a compound of a host and a dopant, respectively, It can exhibit long life and high efficiency characteristics.

Examples of the substituent in the present specification are described below, but are not limited thereto.

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

In the present specification, the term "substituted or unsubstituted" refers to hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

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

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

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

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

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

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

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, 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 it is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

,

,

및

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

,

,

And

And the like, but is not limited thereto.

In the present specification, the heterocyclic group includes at least one atom or hetero atom other than carbon, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto. In the present specification, the heterocyclic group includes at least one atom or hetero atom other than carbon, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Or it means to form a substituted or unsubstituted aromatic heterocycle.

In the present specification, the aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring containing at least one heteroatom.

In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom.

In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

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

In addition, in the exemplary embodiment of the present application, the R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C3 to C60 heterocyclic group.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In addition, in the exemplary embodiment of the present application, the R1 to R10 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In the exemplary embodiment of the present application, R9 and R10 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In the exemplary embodiment of the present application, R9 and R10 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In the exemplary embodiment of the present application, R9 and R10 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group; Or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms N, O or S.

In the exemplary embodiment of the present application, R9 and R10 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a naphthyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Phenanthrene group; Dibenzofuran group; Dibenzothiophene group; Benzonaphtho furan group; Benzonaphthothiophene group; Or it is a polycyclic heteroaryl group containing O.

In the exemplary embodiment of the present application, R4, R5, and R9 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In the exemplary embodiment of the present application, R4, R5, and R9 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group; Or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms N, O or S.

In the exemplary embodiment of the present application, R4, R5, and R9 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a naphthyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Phenanthrene group; Dibenzofuran group; Dibenzothiophene group; Benzonaphtho furan group; Benzonaphthothiophene group; Or it is a polycyclic heteroaryl group containing O.

In addition, in the exemplary embodiment of the present application, any one of R'1 to R'8 is a linking group with Formula 2, and the other is hydrogen.

In addition, in the exemplary embodiment of the present application, Formula 1 is selected from the following structural formulas.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, according to the exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms. It is a ring group.

In addition, according to the exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms. It is a ring group.

In addition, according to the exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group, an alkylsilyl group, or a heteroaryl group; Or an alkyl group, an alkylsilyl group, an aryl group, or a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with a heteroaryl group.

According to an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a methyl group, a terbutyl group, or a phenyl group unsubstituted or substituted with a trimethylsilyl group; A biphenyl group unsubstituted or substituted with a methyl group, terbutyl group, or trimethylsilyl group; Dibenzothiophene group unsubstituted or substituted with a methyl group, terbutyl group, or trimethylsilyl group; Or a methyl group, a terbutyl group, or a dibenzofuran group unsubstituted or substituted with a trimethylsilyl group.

In addition, according to the exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a methyl group, a terbutyl group, or a phenyl group unsubstituted or substituted with a trimethylsilyl group; Biphenyl group; Or a dibenzofuran group.

According to an exemplary embodiment of the present application, the R"1 to R"14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted silyl group.

In addition, according to an exemplary embodiment of the present application, the R"1 to R"14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C1-C60 alkyl group; Or a substituted or unsubstituted C1-C60 silyl group.

In addition, according to an exemplary embodiment of the present application, the R"1 to R"14 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted C 1 to C 30 silyl group.

In addition, according to an exemplary embodiment of the present application, the R"1 to R"14 are the same as or different from each other, and each independently hydrogen; It is a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C1-C10 silyl group.

Further, according to an exemplary embodiment of the present application, the isobutyl group in R"7 and R"14 is excluded.

According to an exemplary embodiment of the present application, the R"7 and R"14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a substituted or unsubstituted silyl group.

According to an exemplary embodiment of the present application, the R"7 and R"14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a substituted or unsubstituted C 1 to C 10 silyl group.

According to an exemplary embodiment of the present application, the R"7 and R"14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a trimethylsilyl group.

According to an exemplary embodiment of the present application, the R"2 and R"9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a substituted or unsubstituted silyl group.

According to an exemplary embodiment of the present application, the R"2 and R"9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a substituted or unsubstituted C 1 to C 10 silyl group.

According to an exemplary embodiment of the present application, the R"2 and R"9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a trimethylsilyl group.

According to an exemplary embodiment of the present application, the R"3 and R"10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a substituted or unsubstituted silyl group.

According to an exemplary embodiment of the present application, the R"3 and R"10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a substituted or unsubstituted C 1 to C 10 silyl group.

According to an exemplary embodiment of the present application, the R"3 and R"10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Terbutyl group; Or a trimethylsilyl group.

According to an exemplary embodiment of the present application, Formula 2 is selected from the following structural formulas.

In the present application, when a member is positioned "on" another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In the present application, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise specified.

The organic material layer of the organic light emitting device of the present application 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 injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like 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 the exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound 1 or 2.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound 1 or 2.

In the exemplary embodiment of the present application, the compounds of Formulas 1 and 2 are included in the emission layer.

In the exemplary embodiment of the present application, the compound of Formula 1 is included as a host of the emission layer, and the compound of Formula 2 is included as a dopant.

In the exemplary embodiment of the present application, the emission layer includes a host and a dopant in a mass ratio of 1:99 to 99:1.

In the exemplary embodiment of the present application, the emission layer includes a host and a dopant in a mass ratio of 50:50 to 99:1.

In the exemplary embodiment of the present application, the emission layer may include an additional host material.

In the exemplary embodiment of the present application, the emission layer may include an additional dopant material.

In the exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound 1 or 2.

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

In the exemplary embodiment of the present application, the thickness of the organic material layer including the compounds of Formulas 1 and 2 is 10 Å to 500 Å.

In the exemplary embodiment of the present application, the organic light-emitting device includes: a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. It includes two or more organic material layers provided between the emission layer and the first electrode, or between the emission layer and the second electrode, and at least one of the organic material layers of the two or more layers includes the compound. In the exemplary embodiment of the present application, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.

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

In addition, in the exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, materials other than the compound may be the same or different from each other.

In the exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazole group, or benzocarbazole group in addition to the organic material layer including the compound.

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

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the compound may be included in the light emitting layer 3.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And a structure of an organic light-emitting device in which the cathode 4 is sequentially stacked is illustrated. In such a structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light-emitting layer 3, the electron transport layer 8, and the electron injection layer 9.

In such a structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

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

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

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

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

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

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

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

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

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected 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); A combination of a metal and an oxide such as ZnO:Al or SNO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

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

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The electron transport material is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can transfer electrons from the cathode to the emission layer and transfers them to the emission layer. This is suitable. Specific examples include the 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 transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered cyclic derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

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

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

[Production Example]

<Production Example 1> Synthesis of Compound 1-1

(Production Example 1-a) Synthesis of Compound 1-1-a

In a three-neck flask, 9-bromoanthracene (20.0g, 77.8mmol) and naphthalen-2-ylboronic acid (14.7g, 85.6mmol) were dissolved in 300ml of THF and K ₂ CO ₃ (43.0g, 311.1mmol) is dissolved in 150ml of H ₂ O. Here Pd(PPh ₃ ) ₄ (3.6g, 3.1mmol) was added and stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 18.5 g of compound 1-1-a. (Yield 78%, MS[M+H] ⁺ = 304)

(Production Example 1-b) Synthesis of Compound 1-1-b

Compound 1-1-a (15.0g, 49.3mmol), NBS (9.2g, 51.7mmol), and 300mL of DMF were added to a two-necked flask, and stirred at room temperature for 8 hours under an argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 16.6 g of compound 1-1-b. (Yield 88%, MS[M+H] ⁺ = 383)

(Production Example 1-c) Synthesis of Compound 1-1

Compound 1-1-b (15.0g, 39.1mmol), 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3, in a three necked flask 2-dioxaborolane (12.7g, 43.0mmol) was dissolved in THF 225ml and K ₂ CO ₃ (21.6g, 156.5mmol) is dissolved in 113ml of H ₂ O. Here Pd(PPh ₃ ) ₄ (1.8g, 1.6mmol) was added and stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography, and then 6.4 g of compound 1-1 was obtained through sublimation purification. (Yield 35%, MS[M+H] ⁺ = 471)

<Production Example 2> Synthesis of Compound 1-2

(Production Example 2-a) Synthesis of Compound 1-2-a

Same as the synthesis of compound 1-1-a, except that naphthalen-2-yl boronic acid was changed to [1,1'-biphenyl]-2-yl boronic acid in Preparation Example 1-a). 19.3g of compound 1-2-a was synthesized using the method. (Yield 75%, MS[M+H] ⁺ = 330)

(Production Example 2-b) Synthesis of Compound 1-2-b

Compound 1-2-b using the same method as the synthesis of compound 1-1-b, except that compound 1-1-a was changed to compound 1-2-a in (Preparation Example 1-b) Was synthesized 16.9g. (Yield 91%, MS[M+H] ⁺ = 409)

(Production Example 2-c) Synthesis of Compound 1-2

In (Preparation Example 1-c), compound 1-1-b to compound 1-2-b, 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl Compound 1- using the same method as the synthesis of Compound 1-1, except that -1,3,2-dioxaborolein was changed to dibenzo[b,d]furan-3-yl boronic acid. 2 was synthesized in 5.8g. (Yield 32%, MS[M+H] ⁺ = 497)

<Production Example 3> Synthesis of Compound 1-3

(Production Example 3-a) Synthesis of Compound 1-3-a

The same method as the synthesis of compound 1-1-a was used, except that naphthalen-2-yl boronic acid was changed to (4-phenylnaphthalen-1-yl) boronic acid in (Preparation Example 1-a). Thus, 20.1g of compound 1-3-a was synthesized. (Yield 68%, MS[M+H] ⁺ = 380)

(Preparation Example 3-b) Synthesis of Compound 1-3-b

Compound 1-3-b using the same method as the synthesis of compound 1-1-b, except that compound 1-1-a was changed to compound 1-3-a in (Preparation Example 1-b). Was synthesized 15.4g. (Yield 85%, MS[M+H] ⁺ = 459)

(Production Example 3-c) Synthesis of Compound 1-3

In (Preparation Example 1-c), compound 1-1-b to compound 1-3-b, 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl Compound 1 using the same method as the synthesis of Compound 1-1, except that -1,3,2-dioxaborolein was changed to dibenzo[b,d]thiophen-4-ylboronic acid and used. 5.1g of -3 was synthesized. (Yield 28%, MS[M+H] ⁺ = 563)

<Production Example 4> Synthesis of Compound 2-1

(Production Example 4-1) Synthesis of Compound 2-1-a

In a three-necked flask, 1,6-dibromopyrene (20.0g, 55.5mmol), (2-nitrophenyl) boronic acid (19.5g, 116.7mmol) was dissolved in 300ml of THF and K ₂ CO ₃ (30.7g, 222.2mmol) is dissolved in 150ml of H ₂ O. Here Pd(PPh ₃ ) ₄ (1.9g, 1.7mmol) was added and stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 21.0 g of compound 2-1-a. (Yield 85%, MS[M+H] ⁺ = 444)

(Production Example 4-2) Synthesis of Compound 2-1-b

Compound 2-1-a (20.0g, 45.0mmol), triphenylphosphine (15.5g, 112.5mmol), and 200ml of o-dichlorobenzene were added to a two-necked flask and stirred for 12 hours under reflux conditions. When the reaction was completed, the mixture was cooled to room temperature, distilled under reduced pressure to remove the solvent, and extracted with water and CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered, and concentrated, and the sample was purified by silica gel column chromatography to obtain 12.2 g (71% yield) of compound 2-1-b. (MS[M+H] ⁺ = 380)

(Production Example 4-3) Synthesis of Compound 2-1

In a three-necked flask, compound 2-1-b (12.0g, 31.5mmol), 1-bromo-4-(terbutyl)benzene (14.1g, 66.2mmol) was dissolved in xylene 300ml, and sodium terbutoxide (9.1g , 94.6mmol), bis(tri-terbutylphosphine)palladium(0) (0.6g, 1.3mmol) was added, followed by stirring for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, and 200 ml of H ₂ O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography, and then 8.5 g of compound 2-1 was obtained through sublimation purification. (Yield 42%, MS[M+H] ⁺ = 644)

<Production Example 5> Synthesis of Compound 2-2

In <Production Example 4>, 1,6-dibromopyrene was replaced with 1,6-dibromo-4,9-di-terbutylpyrene, and 1-bromo-4-(terbutyl)benzene was replaced with bromobenzene. Compound 2-2 was synthesized using the same method as that of synthesizing Compound 2-1, except that it was changed to and used. (MS[M+H] ⁺ = 644)

<Production Example 6> Synthesis of Compound 2-3

In <Production Example 4>, (2-nitrophenyl) boronic acid was used as (4-(terbutyl)-2-nitrophenyl) boronic acid, and 1-bromo-4-(terbutyl) benzene was used as (4-bromo). Compound 2-3 was synthesized using the same method as that for synthesizing Compound 2-1, except that it was changed to phenyl) trimethylsilane. (MS[M+H] ⁺ = 789)

<Production Example 7> Synthesis of Compound 2-4

In <Production Example 4>, (2-nitrophenyl) boronic acid was used as (4-(terbutyl)-2-nitrophenyl) boronic acid, and 1-bromo-4-(terbutyl) benzene was used as 4-bromodibenzo. Compound 2-4 was synthesized using the same method as that of synthesizing Compound 2-1, except that it was changed to [b,d] furan. (MS[M+H] ⁺ = 825)

<Production Example 8> Synthesis of Compound 2-5

(Production Example 8-1) Synthesis of Compound 2-5-a

Dissolve 1,6-dibromopyrene (20.0g, 55.5mmol) and 2-chloroaniline (14.9g, 116.7mmol) in 500ml of toluene in a three-necked flask, and sodium terbutoxide (16.0g, 166.6mmol), bis( Tri-terbutylphosphine) palladium (0) (1.1 g, 2.2 mmol) was added, followed by stirring for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, and 200 ml of H ₂ O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 17.9 g of compound 2-5-a. (Yield 71%, MS[M+H] ⁺ = 453)

(Production Example 8-2) Synthesis of Compound 2-5-b

In a three-necked flask, compound 2-5-a (15.0g, 33.1mmol), palladium (II) acetate (0.4g, 1.7mmol), tricyclohexylphosphine tetrafluoroborate (1.2g, 3.3mmol), K ₂ CO ₃ (18.3 g, 132.3 mmol) was dissolved in 375 ml of toluene and stirred for 18 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the mixture was cooled to room temperature, and 200 ml of H ₂ O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 8.7 g of compound 2-5-b. (Yield 69%, MS[M+H] ⁺ = 380)

(Production Example 8-3) Synthesis of Compound 2-5

In a three-necked flask, compound 2-5-b (8.0g, 21.0mmol) and bromobenzene (6.9g, 44.2mmol) were dissolved in xylene 300ml, sodium terbutoxide (6.1g, 63.1mmol), bis(tri- After terbutylphosphine) palladium (0) (0.4 g, 0.8 mmol) was added, the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, after cooling to room temperature, 150 ml of H ₂ O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO ₄ , filtered and concentrated, the sample was purified by silica gel column chromatography, and then 4.6 g of Compound 2-5 was obtained through sublimation purification. (Yield 41%, MS[M+H] ⁺ = 532)

<Production Example 9> Synthesis of Compound 2-6

Compound 2-6 was synthesized using the same method as that of synthesizing Compound 2-5, except that bromobenzene was changed to 1-bromo-4-(terbutyl)benzene in <Preparation Example 8>. . (MS[M+H] ⁺ = 644)

<Production Example 10> Synthesis of Compound 2-7

Compound 2 except that 2-chloroaniline was changed to (5-(terbutyl)-2-chloroaniline and bromobenzene was changed to 4-bromodibenzo[b,d]furan in Preparation Example 8> Compound 2-7 was synthesized using the same method as synthesized in -5 (MS[M+H] ⁺ = 825).

[Example 1]

Example 1-1

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, a compound represented by HI-A and a compound represented by the following HAT were sequentially thermally vacuum deposited to a thickness of 650 Å and 50 Å, respectively, to form a hole injection layer. A compound represented by HT-A below was vacuum-deposited as a hole transport layer to a thickness of 600 Å, and then a compound represented by HT-B as an electron blocking layer was thermally vacuum deposited to a thickness of 50 Å. Subsequently, the compound 1-1 prepared in Preparation Example 1-1 and the compound 2-1 prepared in Preparation Example 2-1 with a dopant were vacuum-deposited to a thickness of 200Å at a weight ratio of 96:4 as a host on the emission layer. Subsequently, as the electron transport layer and the electron injection layer, the compound represented by ET-A and the compound represented by Liq were thermally vacuum deposited to a thickness of 360Å at a weight ratio of 1:1, and then the compound represented by the following Liq was deposited to a thickness of 5Å. It was vacuum deposited. An organic light-emitting device was manufactured by sequentially depositing magnesium and silver on the electron injection layer to a thickness of 220 Å at a weight ratio of 10:1 and aluminum to a thickness of 1000 Å to form a cathode.

Examples 1-2 to 1-14

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 below were used as host materials and dopant materials in Example 1-1.

Comparative Examples 1-1 to 1-11

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 below were used as host materials and dopant layer materials in Example 1-1. In Table 1 below, BH-A and BD-A are as follows.

The device performance was measured when a current density of 10 mA/cm ² was applied to the organic light emitting device prepared in the above Examples and Comparative Examples, and the initial luminance decreased to 90% at a current density of 20 mA/cm ² . The results obtained by measuring the time of each are shown in Table 1.

Example Host Dopant @ 10mA / cm ² @ 20mA / cm ² V cd/A FWHM(nm) Life (hr) Example 1-1 Compound 1-1 Compound 2-1 3.89 5.21 32 131 Example 1-2 Compound 1-1 Compound 2-2 3.81 5.28 31 128 Example 1-3 Compound 1-1 Compound 2-3 3.85 5.26 33 131 Example 1-4 Compound 1-1 Compound 2-4 3.88 5.21 32 127 Example 1-5 Compound 1-1 Compound 2-5 3.92 5.20 32 130 Example 1-6 Compound 1-1 Compound 2-6 3.95 5.24 32 132 Example 1-7 Compound 1-1 Compound 2-7 3.98 5.21 33 141 Example 1-8 Compound 1-2 Compound 2-1 3.97 5.23 31 138 Example 1-9 Compound 1-2 Compound 2-3 3.89 5.27 32 126 Example 1-10 Compound 1-2 Compound 2-5 3.90 5.21 32 132 Example 1-11 Compound 1-2 Compound 2-7 3.88 5.26 33 136 Example 1-12 Compound 1-3 Compound 2-2 3.87 5.13 33 141 Example 1-13 Compound 1-3 Compound 2-4 3.98 5.15 33 127 Example 1-14 Compound 1-3 Compound 2-6 3.94 5.12 32 128 Comparative Example 1-1 BH-A BD-A 4.38 4.46 55 75 Comparative Example 1-2 BH-A Compound 2-1 4.34 4.87 34 100 Comparative Example 1-3 BH-A Compound 2-2 4.40 4.98 33 80 Comparative Example 1-4 BH-A Compound 2-3 4.35 4.99 32 76 Comparative Example 1-5 BH-A Compound 2-4 4.30 4.80 31 91 Comparative Example 1-6 BH-A Compound 2-5 4.42 4.89 33 75 Comparative Example 1-7 BH-A Compound 2-6 4.41 4.90 31 80 Comparative Example 1-8 BH-A Compound 2-7 4.33 4.88 32 83 Comparative Example 1-9 Compound 1-1 BD-A 3.91 4.23 55 57 Comparative Example 1-10 Compound 1-2 BD-A 3.94 4.10 55 50 Comparative Example 1-11 Compound 1-3 BD-A 4.00 3.99 56 62

As can be seen in Table 1, the compound represented by Formula 1 of the present invention is advantageous for injecting holes and electrons into the light emitting layer, and thus exhibits low voltage characteristics when a host material is used. In the structure in which two amines are substituted, as in the BD-A applied in Comparative Example 1 of Table 1, all the bonds connected to the amine are bonds capable of rotation, so the vibration of the material is easy. When this structure is used as a light emitting dopant in an organic electroluminescent device, a broad spectrum having an FWHM of 50 nm or more is obtained. The compound represented by the formula (2) is a structure obtained by condensing a phenyl group on one of the amine substituents. In this case, it has a more rigid structure than BD-A, which reduces the FWHM of the emission spectrum, thereby obtaining an organic electroluminescent device having a higher color purity than BD-A. In particular, when the compound of Formula 1 is used as the host of the light emitting layer and the compound of Formula 2 is used as the dopant of the light emitting layer, energy transfer from the host to the dopant becomes easier than that of BH-A, resulting in high efficiency, as well as characteristics of low voltage and high color purity. Long life characteristics can also be obtained.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: e-low layer
8: electron transport layer
9: electron injection layer

Claims (13)

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode,
The organic material layer includes a host and a dopant,
The host includes a compound represented by the following formula (1),
The dopant is an organic light emitting device comprising a compound represented by the following formula (2):
[Formula 1]

In Formula 1,
R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms N, O or S,
At least one of R1 to R10 is the following formula A,
[Formula A]

In formula A,
A is O or S,
Any one of R'1 to R'8 is a linking group represented by Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted C 3 to C 10 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing N, O or S having 3 to 30 carbon atoms, or groups adjacent to each other may be bonded to each other to form an unsubstituted benzene ring,
[Formula 2]

In Formula 2,
Any one of X1 and Y1 is a direct bond, and the other is NAr1,
Any one of X2 and Y2 is a direct bond, and the other is NAr2,
Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or It is an unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heterocyclic group containing N, O, or S,
R”1 to R”14 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or 6 to 30 carbon atoms A substituted or unsubstituted silyl group with an aryl group of, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N having 3 to 30 carbon atoms, It is a heterocyclic group containing O or S,
R”7 and R”14 are not isopropyl groups. The method according to claim 1,
R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms N, O, or S. Organic light-emitting device. The method according to claim 1,
R9 and R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms N, O, or S. Organic light-emitting device. The method according to claim 1,
R4, R5, and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An organic light-emitting device that is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group containing N, O or S having 3 to 30 carbon atoms. The method according to claim 1,
Any one of R'1 to R'8 is a linking group with Formula 1, and the remainder is hydrogen, or an organic light-emitting device capable of forming an unsubstituted benzene ring by bonding adjacent groups to each other. The method according to claim 1,
Formula 1 is an organic light-emitting device selected from the following structural formulas:

The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing 3 to 30 carbon atoms N, O, or S. Organic light-emitting device. The method according to claim 1,
R”1 to R”14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or an organic light-emitting device that is a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms. The method according to claim 1,
R”7 and R”14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; t-butyl group; Or an organic light-emitting device that is a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms. The method according to claim 1,
Formula 2 is an organic light-emitting device selected from the following structural formulas:

The method according to claim 1,
The organic material layer includes an emission layer, and the emission layer includes a compound represented by Chemical Formulas 1 and 2 above. The method according to claim 1,
The organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer each independently contain a compound represented by Formula 1 or 2 Organic light emitting device. The method according to claim 1,
The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer each independently contain a compound represented by Formula 1 or 2 Organic light emitting device.

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