KR102234191B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of Formula 1 and an organic light-emitting device including the same.

Description

A novel compound and an organic light emitting device including the same TECHNICAL FIELD [NOVEL COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to a novel compound and an organic light emitting device including the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by 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 multilayer 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. When it falls back to the ground, it glows.

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

US Patent Application Publication No. 2004-0251816

The present specification provides a novel compound and an organic light emitting device including the same.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

At least one of X1 to X3 is N, and the rest are CH,

G1 and G2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,

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

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 heteroaryl group,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r1, r2 and r4 are each an integer of 1 to 3,

r3 is an integer from 1 to 4,

When r1 is 2 or more, the 2 or more R1s are the same as or different from each other,

When r2 is 2 or more, the two or more R2s are the same as or different from each other,

When r3 is 2 or more, the 2 or more R3s are the same as or different from each other,

When r4 is 2 or more, the two or more R4s are the same as or different from each other.

In addition, an exemplary embodiment of the present specification is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .

The compound according to the exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device.

1 illustrates an organic light-emitting device 10 according to an exemplary embodiment of the present specification.
2 illustrates an organic light-emitting device 11 according to another exemplary embodiment of the present specification.

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

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

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 deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxy 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 alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl 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 does not have any substituents.

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 connected to two phenyl groups.

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

Means a site bonded to another substituent or a bonding portion.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, oxygen of the ester group may be substituted with a C 1 to C 25 linear, branched or cyclic chain alkyl group or a C 6 to C 30 aryl group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. 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 30 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, etc., but are limited thereto. It is not.

In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, 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., but It is not limited.

In the present specification, the amine group is -NH ₂ ; Monoalkylamine group; Dialkylamine group; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N- Naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylflu Orenylamine group, N-biphenylfluorenylamine group, and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a linear or branched alkyl group. The alkylamine group containing two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched-chain alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.

In the present specification, the alkyl group in the N-alkylarylamine group, the alkylthioxy group, the alkylsulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group is a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, and butyl. There is a sulfoxy group and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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, a stilbenyl group, and a styrenyl group, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

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

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

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 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 preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc., but limited thereto. It does not become.

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

,

,

,

,

및

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

,

,

,

,

And

Can be, etc. However, it is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the corresponding substituent is substituted, a substituent located 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 aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group is a phenylthioxy group, 2- There are a methylphenyl thioxy group, a 4-tert-butylphenyl thioxy group, and the like, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuran group, and the like, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

The definitions of X1 to X3, G1, G2, L1, Ar1, Ar2, R1 to R4, and r1 to r4 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, in Formula 1, any one of X1 to X3 is N, and the rest is CH.

According to an exemplary embodiment of the present specification, in Formula 1, X1 is N, and X2 and X3 are CH.

According to an exemplary embodiment of the present specification, in Formula 1, X2 is N, and X1 and X3 are CH.

According to an exemplary embodiment of the present specification, in Formula 1, X3 is N, and X1 and X2 are CH.

According to an exemplary embodiment of the present specification, in Formula 1, any two of X1 to X3 are N, and the rest are CH.

According to an exemplary embodiment of the present specification, in Formula 1, X1 and X2 are N, and X3 is CH.

According to an exemplary embodiment of the present specification, in Formula 1, X2 and X3 are N, and X1 is CH.

According to an exemplary embodiment of the present specification, in Formula 1, X1 and X3 are N, and X2 is CH.

According to an exemplary embodiment of the present specification, in Formula 1, X1 to X3 are N.

According to an exemplary embodiment of the present specification, in Formula 1, G1 and G2 are the same as or different from each other, and each independently an alkyl group.

According to an exemplary embodiment of the present specification, in Formula 1, G1 and G2 are methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, L1 is a direct bond; An arylene group unsubstituted or substituted with an alkyl group; Or a heteroarylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; A fluorenylene group unsubstituted or substituted with an alkyl group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; A fluorenylene group unsubstituted or substituted with a methyl group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a nitrile group, an alkyl group, or an aryl group; Or a heteroaryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with a nitrile group; Naphthyl group; A fluorenyl group unsubstituted or substituted with an alkyl group; Phenanthrenyl group; Triphenylenyl group; Pyridyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group; A biphenyl group unsubstituted or substituted with a nitrile group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Phenanthrenyl group; Triphenylenyl group; Pyridyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the core of the compound represented by Chemical Formula 1 may be prepared by the method of the following General Formulas 1 to 6, but is not limited thereto.

[General Formula 1]

[General Formula 2]

[General Formula 3]

[General Formula 4]

[General Formula 5]

[General Formula 6]

In the general formulas 1 to 6, the definitions of G1, G2, X1 to X3, L1, Ar1 and Ar2 are the same as those defined in Chemical Formula 1.

According to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.

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

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

According to an exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may be formed in a single-layer structure, but may be formed in 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, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron 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 fewer or more organic layers.

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

1 illustrates a structure of an organic light-emitting device 10 in which an anode 30, an emission layer 40, and a cathode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.

2, the anode 30, the hole injection layer 60, the hole transport layer 70, the light emitting layer 40, the hole blocking layer 80, the electron transport layer 90, the electron injection layer 100 on the substrate 20. ) And the cathode 50 are sequentially stacked, and the structure of the organic light-emitting device is illustrated. 2 is an exemplary structure according to the exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above. The emission layer is a green emission layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons is It includes the above compound.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, and the electro-injection layer includes a compound represented by Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer, and the electron transport layer includes a compound represented by Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. .

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

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.

For example, the organic light emitting device of the present specification may 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 physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be manufactured by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the compound represented by 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, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment of the present specification, 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 anode 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 metal and 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 a multilayered material such as LiF/Al, LiO ₂ /Al, and Mg/Ag, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode as a hole injection material, and has an ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. , A compound that prevents the movement of excitons generated in the light-emitting layer to 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.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 electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. It may be formed in an appropriate portion between the injection layer.

When the organic light-emitting device of the present specification includes an additional light-emitting layer in addition to the light-emitting layer including the compound represented by Formula 1, the light-emitting material of the light-emitting layer is As a material capable of emitting light in the visible region, 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-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The hole blocking layer is a layer capable of improving the life and efficiency of the device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer, and the organic light emitting device of the present specification is represented by Formula 1 above. In the case of including an additional hole blocking layer in addition to the hole blocking layer including the compound to be formed, it may be formed in an appropriate portion between the light emitting layer and the electron injection layer using a known material, if necessary.

The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. In the case of including a transport layer, the electron transport material is a material capable of transferring electrons to the light emitting layer by receiving electrons from the cathode, and a material having high mobility for electrons is suitable. Specific examples include 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, and when the organic light emitting device of the present specification includes an additional electron injection layer in addition to the electron injection layer including the compound represented by Formula 1, it transports electrons. A compound that has the ability, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, prevents the movement of excitons generated from the light emitting layer to the hole injection layer, and has excellent thin film formation ability. Do. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

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

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

[Scheme 1]

The compounds A-1 to C-1 used in the preparation of Chemical Formula 1 of the present specification may be prepared by Scheme 1, but are not limited thereto.

Although Preparation Examples 1 to 14 are described below, the compound of Formula 1 may be prepared by changing the substituents of Compounds A to C and A-1 to C-1 of Scheme 1 above.

Preparation Example 1. Preparation of Compound 1

Compound A (6.50 g, 14.98 mmol) and compound a1 (5.82 g, 16.47 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate to prepare compound 1 (7.11 g, 71%).

MS[M+H] ⁺ = 664

Preparation Example 2. Preparation of Compound 2

Compound A (6.0 g, 13.82 mmol) and compound a2 (5.37 g, 15.21 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After tetrakis-(triphenylphosphine)palladium (0.48 g, 0.41 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 mL of ethyl acetate to prepare compound 2 (5.27 g, 57%).

MS[M+H] ⁺ = 664

Preparation Example 3. Preparation of compound 3

Compound A (5.50 g, 12.67 mmol) and compound a3 (4.91 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 3 (5.73 g, 68%).

MS[M+H] ⁺ = 663

Preparation Example 4. Preparation of compound 4

Compound A (5.50 g, 12.67 mmol) and compound a4 (5.98 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto. After tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 340 mL of tetrahydrofuran to prepare compound 4 (6.95 g, 74%).

MS[M+H] ⁺ = 740

Preparation Example 5. Preparation of compound 5

Compound A-1 (8.50 g, 17.64 mmol) and compound a5 (5.50 g, 16.03 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.56 g, 0.48 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 5 (7.12 g, 67%).

MS[M+H] ⁺ = 664

Preparation Example 6. Preparation of compound 6

Compound A-1 (5.50 g, 12.67 mmol) and compound a6 (7.92 g, 16.44 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 6 (8.11 g, 79%).

MS[M+H] ⁺ = 689

Preparation Example 7. Preparation of compound 7

Compound B-1 (8.23 g, 17.06 mmol) and compound a7 (6.50 g, 15.51 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 7 (8.13 g, 85%).

MS[M+H] ⁺ = 740

Preparation Example 8. Preparation of compound 8

Compound B-1 (8.23 g, 17.06 mmol) and compound a5 (6.50 g, 15.51 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 8 (7.22 g, 57%).

MS[M+H] ⁺ = 664

Preparation Example 9. Preparation of compound 9

Compound B (6.50 g, 14.98 mmol) and compound a1 (5.82 g, 16.47 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto. After tetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare compound 9 (7.77 g, 78%).

MS[M+H] ⁺ = 664

Preparation Example 10 Preparation of Compound 10

Compound B (5.50 g, 12.67 mmol) and compound a9 (4.89 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto. After tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare compound 10 (4.78 g, 57%).

MS[M+H] ⁺ = 662

Preparation Example 11. Preparation of compound 11

Compound B (5.50 g, 12.67 mmol) and compound a10 (4.95 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added. After tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 11 (6.23 g, 74%).

MS[M+H] ⁺ = 666

Preparation Example 12. Preparation of compound 12

Compound C (5.50 g, 12.67 mmol) and compound a1 (4.92 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto. After tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 12 (5.95 g, 71%).

MS[M+H] ⁺ = 664

Preparation Example 13. Preparation of compound 13

Compound C-1 (5.50 g, 12.67 mmol) and compound a11 (6.15 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 13 (8.13 g, 85%).

MS[M+H] ⁺ = 638

Preparation Example 14 Preparation of Compound 14

Compound C-1 (5.50 g, 12.67 mmol) and compound a5 (6.15 g, 13.94 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After addition, tetrakis-(triphenylphosphine)palladium (0.44 g, 0.38 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 14 (8.13 g, 85%).

MS[M+H] ⁺ = 664

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å 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 washing 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.

The following compound HI1 and the following compound HI2 were thermally vacuum deposited to a thickness of 100 Å to a ratio of 98:2 (molar ratio) on the ITO transparent electrode, which is the anode thus prepared, to form a hole injection layer. The following compound HT1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1150 Å. Subsequently, the following compound EB1 was vacuum deposited on the hole transport layer with a film thickness of 50 Å to form an electron blocking layer. Subsequently, a light emitting layer was formed by vacuum depositing the following compound BH and the following compound BD at a weight ratio of 25:1 to a film thickness of 200 Å on the electron blocking layer. A hole blocking layer was formed by vacuum depositing Compound 1 prepared in Preparation Example 1 with a film thickness of 50 Å on the emission layer. Subsequently, the following compound ET1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 310 Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of organic material was maintained at 0.4 to 0.7 Å/sec, lithium fluoride at the cathode was maintained at 0.3 Å/sec, and the deposition rate for aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10 ^-7 to An organic light emitting device was manufactured by maintaining ^{5x10 -6 torr.}

Examples 1-1 to 1-14

In Example 1-1, an organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of the compound 1 prepared in Preparation Example 1.

Comparative Example 1-1

In Example 1-1, an organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound HB1 was used instead of Compound 1 prepared in Preparation Example 1.

Comparative Example 1-2

In Example 1-1, an organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound HB2 was used instead of Compound 1 prepared in Preparation Example 1.

^{When a current of 20 mA/cm 2} was applied to the organic light emitting devices manufactured according to Examples 1-1 to 1-14, Comparative Example 1-1 and Comparative Example 1-2, voltage, efficiency, color coordinates, and lifetime were measured. And the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nits) to 95%.

compound
(Hole Blocking Layer) Voltage
(V@20mA
/cm ² ) efficiency
(cd/A@20mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1-1 Manufacturing Example 1 3.51 6.31 (0.140, 0.047) 275 Example 1-2 Manufacturing Example 2 3.53 6.26 (0.141, 0.047) 280 Example 1-3 Manufacturing Example 3 3.46 6.58 (0.143, 0.047) 260 Example 1-4 Manufacturing Example 4 3.52 6.28 (0.139, 0.046) 280 Example 1-5 Manufacturing Example 5 3.50 6.39 (0.140, 0.047) 285 Example 1-6 Manufacturing Example 6 3.53 6.24 (0.141, 0.047) 275 Example 1-7 Manufacturing Example 7 3.54 6.25 (0.140, 0.046) 280 Example 1-8 Manufacturing Example 8 3.58 6.43 (0.139, 0.045) 290 Example 1-9 Manufacturing Example 9 3.53 6.42 (0.141, 0.046) 295 Example 1-10 Manufacturing Example 10 3.43 6.59 (0.142, 0.046) 255 Example 1-11 Manufacturing Example 11 3.59 6.47 (0.140, 0.047) 295 Example 1-12 Manufacturing Example 12 3.58 6.46 (0.141, 0.045) 280 Example 1-13 Manufacturing Example 13 3.63 6.43 (0.140, 0.046) 275 Example 1-14 Manufacturing Example 14 3.63 6.42 (0.141, 0.045) 290 Comparative Example 1-1 EB1 4.17 5.72 (0.139, 0.041) 145 Comparative Example 1-2 EB2 3.95 6.03 (0.141, 0.042) 220

As shown in Table 1, in the case of an organic light-emitting device manufactured by using the compound of Formula 1 as a hole blocking layer according to an exemplary embodiment of the present specification, it is excellent in terms of efficiency, driving voltage and/or stability of the organic light-emitting device. Characteristics.

Specifically, the organic light-emitting device of Examples 1-1 to 1-14 is Comparative Example 1-1 and spirobifluorene in which a compound in which G1 and G2 in Formula 1 of the present specification is a phenyl group is used as a hole blocking layer of the organic light-emitting device Compared to Comparative Example 1-2 in which a compound having a triazine group bonded to the core was used as a hole blocking layer of an organic light-emitting device, characteristics of lower voltage, high efficiency, and long life were shown.

As shown in the results of Table 1, it was confirmed that the compound of Formula 1 of the present specification has excellent hole blocking ability, and thus can be applied to an organic light-emitting device.

Although the preferred embodiment (hole blocking layer) of the present invention has been described above, the present invention is not limited thereto, and it is possible to implement various modifications within the scope of the claims and the detailed description of the invention. It belongs to the scope of the invention.

10, 11: organic light emitting device
20: substrate
30: anode
40: light-emitting layer
50: cathode
60: hole injection layer
70: hole transport layer
80: hole blocking layer
90: electron transport layer
100: electron injection layer

Claims (10)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
At least one of X1 to X3 is N, and the rest are CH,
G1 and G2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,
L1 is a direct bond; An arylene group unsubstituted or substituted with an alkyl group; Or a heteroarylene group,
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 heteroaryl group,
R1 to R4 are the same as or different from each other, and each independently hydrogen; Or deuterium,
r1, r2 and r4 are each an integer of 1 to 3,
r3 is an integer from 1 to 4,
When r1 is 2 or more, the 2 or more R1s are the same as or different from each other,
When r2 is 2 or more, the two or more R2s are the same as or different from each other,
When r3 is 2 or more, the two or more R3s are the same as or different from each other,
When r4 is 2 or more, the two or more R4s are the same as or different from each other. The compound of claim 1, wherein the formula 1 is represented by the following formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
The definitions of X1 to X3, G1, G2, L1, Ar1, Ar2, R1 to R4, and r1 to r4 are the same as defined in Formula 1 above. The compound according to claim 1, wherein G1 and G2 are the same as or different from each other, and each independently an alkyl group. delete The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a nitrile group, an alkyl group, or an aryl group; Or a compound that is a heteroaryl group. The compound of claim 1, wherein Formula 1 is selected from the following compounds:

A first electrode;
A second electrode provided opposite to the first electrode; And
An organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound of any one of claims 1 to 3, 5, and 6. Light-emitting element. The organic light-emitting device of claim 7, wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound. The method according to claim 7, wherein the organic material layer comprises an electron injection layer, an electron transport layer, or a layer for simultaneously injecting and transporting electrons, and the layer for simultaneously injecting and transporting electrons, the electron injection layer, the electron transport layer, or the layer containing the compound The organic light emitting device. The organic light-emitting device of claim 7, wherein the organic material layer includes an emission layer, and the emission layer includes the compound.

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