KR20200127961A - Organic light emitting device - Google Patents

Abstract

The present specification relates to an organic light-emitting device including: an anode; a cathode provided to face the anode; a light-emitting layer provided between the anode and the cathode; at least one first organic material layer provided between the anode and the light-emitting layer; and a second organic material layer provided between the cathode and the light-emitting layer, wherein the first organic material layer includes at least one of the compounds represented by chemical formula 1 and chemical formula 2, and the second organic material layer includes the compound represented by chemical formula 3, thereby improving the low voltage, lifespan characteristics and/or efficiency characteristics of the device.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2017-0160340 filed with the Korean Intellectual Property Office on November 28, 2017, the entire contents of which are incorporated herein.

The present specification 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. 2000-0051826

In the present specification, an organic light emitting device is provided.

The present specification is a positive electrode; A cathode provided to face the anode; A light emitting layer provided between the anode and the cathode; At least one first organic material layer provided between the anode and the emission layer; And a second organic material layer provided between the cathode and the emission layer, wherein the first organic material layer includes at least one of compounds represented by the following Chemical Formulas 1 and 2, and the second organic material layer includes the following Chemical Formulas: It provides an organic light-emitting device comprising the compound represented by 3.

[Formula 1]

In Formula 1,

Any one of Ar1 to Ar4 is a polycyclic aryl group, the others are the same as or different from each other, and each independently a monocyclic aryl group,

[Formula 2]

In Formula 2,

Ar5 and Ar6 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,

Y1 is a group represented by any one of the following structures,

,

,

In the above structure,

X is O or S,

R1 to R8 are hydrogen, or adjacent groups are bonded to each other to form an aromatic ring,

[Formula 3]

In Chemical Formula 3,

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

At least one of X4 to X6 is N, the rest are CH,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar7 to Ar10 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

The organic light-emitting device according to the exemplary embodiment of the present specification may improve low voltage, lifetime characteristics, and/or efficiency characteristics of the device.

1 illustrates an organic light-emitting device 10 according to an exemplary embodiment of the present specification.
2 shows 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 is a positive electrode; A cathode provided to face the anode; A light emitting layer provided between the anode and the cathode; At least one first organic material layer provided between the anode and the emission layer; And a second organic material layer provided between the cathode and the emission layer, wherein the first organic material layer includes at least one of the compounds represented by Chemical Formulas 1 and 2, and the second organic material layer includes the chemical formula It provides an organic light-emitting device comprising the compound represented by 3.

According to an exemplary embodiment of the present specification, the first organic material layer includes a hole transport layer and an electron blocking layer.

According to an exemplary embodiment of the present specification, the electron blocking layer is provided between the anode and the light emitting layer, and the hole transport layer is provided between the electron blocking layer and the anode.

According to an exemplary embodiment of the present specification, the first organic material layer is a hole transport layer or an electron blocking layer.

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

According to an exemplary embodiment of the present specification, the first organic material layer is a hole transport layer, and the hole transport layer includes the compound represented by Chemical Formula 1.

According to an exemplary embodiment of the present specification, Formula 1 is a structure in which amine groups are bonded to both sides of a biphenylylene core, and a non-shared electron pair of an amine group bonded to both sides of biphenylylene is conjugated to biphenylene. Excellent hole transport capability due to the dispersing structural features.

In addition, the compound in which any one of Ar1 to Ar4 is a polycyclic aryl group in Chemical Formula 1 of the present specification has a relatively high glass transition temperature (Tg) compared to the material used for the hole transport layer of a conventional material, and thus has excellent thermal stability. When applied to a light emitting device, there is an effect of reducing the driving voltage. However, when two or more of Ar1 to Ar4 in Formula 1 of the present specification are polycyclic aryl groups, the glass transition temperature (Tg) of the compound is low and thermal stability is low. When this is applied to an organic light-emitting device, the lifetime of the device and Efficiency decreases.

According to an exemplary embodiment of the present specification, the first organic material layer includes a hole transport layer and an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 2 above.

According to an exemplary embodiment of the present specification, the first organic material layer is an electron blocking layer, and the electron blocking layer includes a compound represented by Chemical Formula 2.

According to an exemplary embodiment of the present specification, Formula 2 is a structure in which an amine group and a tricyclic heteroaryl group are bonded to both sides of a biphenylylene core, and each amine group and 3 are bonded to both sides of the biphenylylene core. The structural feature of dispersing the non-shared electron pair of N, O, or S of the ring heteroaryl group by the conjugation of biphenylene has excellent electron blocking ability.

In addition, since Formula 2 has carbazole, dibenzofuran, and dibenzothiophene as substituents in the meta direction in the monoamine form, molecular symmetry is disrupted and amorphous properties are improved, so that organic light emission containing them The device has high device efficiency.

According to an exemplary embodiment of the present specification, the first organic material layer includes a hole transport layer and an electron blocking layer, the hole transport layer includes the compound represented by Formula 1, and the electron blocking layer is represented by Formula 2 Contains compounds.

According to an exemplary embodiment of the present specification, the second organic material layer is 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 a compound represented by Formula 3 above.

According to an exemplary embodiment of the present specification, the second organic material layer is an electron transport layer.

According to an exemplary embodiment of the present specification, the second organic material layer is an electron transport layer, and the electron transport layer includes a compound represented by Chemical Formula 3.

According to an exemplary embodiment of the present specification, the second organic material layer is a layer that simultaneously injects and transports electrons.

According to an exemplary embodiment of the present specification, the second organic material layer is a layer that simultaneously injects and transports electrons, and the electron transport layer includes the compound represented by Formula 3 above.

According to an exemplary embodiment of the present specification, in Formula 3, both monocyclic heteroaryl groups bonded around naphthalene have an appropriate twisting structure, and the electronic interaction due to conjugation is reduced, thereby maintaining the independent characteristics of the substituents. Conjugation, which is properly maintained, is suitable for use as an electron transport layer because of its structural feature that can prevent the lifespan of the organic light-emitting device from deteriorating due to excessive electron injection.

In addition, in Formula 3, naphthalene acts as an electron donor and substituents act as electron acceptors. When there is a certain distance between the two units, the orbital distribution of HOMO and LUMO is desired. In the case of including as the electron transport layer material, characteristics of the organic light emitting device are improved.

In addition, since Chemical Formula 3 includes a triazine-substituted naphthalene core having very excellent electron injection capability and thermal stability, an organic light-emitting device including the same may improve driving voltage, luminous efficiency, and lifetime characteristics of the device.

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 located "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.

Examples of the substituents 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; Ether 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; 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 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.

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 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 ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group 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 ether group may be substituted with an oxygen of the ether group with a straight, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, 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 preferably has 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 linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 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 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-phenanthrenylfluorenylamine 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 means 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 exemplary alkyl group described above. 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 mesyl, ethyl sulfoxy group, propyl sulfoxy group, butyl sulfoxy group And the like, but are 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 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, stilbenyl group, styrenyl group, and the like, 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 it may be selected from the group consisting of 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

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 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 aryl group among 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 includes 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 containing 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 and heteroatoms other than carbon, 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.

In the present specification, in a substituted or unsubstituted aromatic ring formed by bonding of adjacent groups to each other, the "aromatic ring" may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

The definition of Ar1 to Ar4 is the same as defined in Chemical Formula 1.

According to an exemplary embodiment of the present specification, in Formula 1, any one of Ar1 to Ar4 is a naphthyl group; Phenanthrenyl group; Or a triphenylenyl group, the rest are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or terphenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a naphthyl group; Phenanthrenyl group; Or a triphenylenyl group, Ar2 to Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or terphenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 is a naphthyl group; Phenanthrenyl group; Or a triphenylenyl group, Ar1, Ar3, and Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or terphenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar3 is a naphthyl group; Phenanthrenyl group; Or a triphenylenyl group, Ar1, Ar2, and Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or terphenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar4 is a naphthyl group; Phenanthrenyl group; Or a triphenylenyl group, Ar1 to Ar3 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or terphenyl 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, Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

The definitions of R1 to R8, X, Ar5, and Ar6 are the same as those defined in Chemical Formula 2.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, X is O.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, X is S.

According to an exemplary embodiment of the present specification, in Formula 2, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar5 and Ar6 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar5 and Ar6 are the same as or different from each other, and each independently an aryl group or a phenyl group unsubstituted or substituted with a heteroaryl group; A biphenyl group unsubstituted or substituted with an aryl group; Terphenyl group; Or a fluorenyl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar5 and Ar6 are the same as or different from each other, and each independently a phenyl group or a phenyl group unsubstituted or substituted with a biphenyl group; A phenyl group substituted with a dibenzofuran group; A phenyl group substituted with a dibenzothiophene group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group; Or a fluorenyl group substituted with a methyl group.

According to an exemplary embodiment of the present specification, adjacent groups of R1 to R8 combine with each other to form a benzene ring.

According to an exemplary embodiment of the present specification, R1 and R2 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, Formula 2 is selected from the following compounds.

According to an exemplary embodiment of the present specification, Formula 3 is represented by any one of the following Formulas 3-1 to 3-8.

[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

In Formulas 3-1 to 3-8,

The definitions of X1 to X6, L1, L2, and Ar7 to Ar10 are as defined in Chemical Formula 3.

According to an exemplary embodiment of the present specification, in Formula 3, any one of X1 to X3 is N, and the rest is CH.

According to an exemplary embodiment of the present specification, in Formula 3, X1 is N, and X2 and X3 are CH.

According to an exemplary embodiment of the present specification, in Chemical Formula 3, X2 is N, and X1 and X3 are CH.

According to an exemplary embodiment of the present specification, in Formula 3, X3 is N, and X1 and X2 are CH.

According to an exemplary embodiment of the present specification, in Formula 3, any two of X1 to X3 are N, and the rest are CH.

According to an exemplary embodiment of the present specification, in Formula 3, X1 and X2 are N, and X3 is CH.

According to an exemplary embodiment of the present specification, in Formula 3, X2 and X3 are N, and X1 is CH.

According to an exemplary embodiment of the present specification, in Chemical Formula 3, X1 and X3 are N, and X2 is CH.

According to an exemplary embodiment of the present specification, in Formula 3, X1 to X3 are N.

According to an exemplary embodiment of the present specification, in Formula 3, any one of X4 to X6 is N, and the rest is CH.

According to an exemplary embodiment of the present specification, in Formula 3, X4 is N, and X5 and X6 are CH.

According to an exemplary embodiment of the present specification, in Formula 3, X5 is N, and X4 and X6 are CH.

According to an exemplary embodiment of the present specification, in Chemical Formula 3, X6 is N, and X4 and X5 are CH.

According to an exemplary embodiment of the present specification, in Formula 3, any two of X4 to X6 are N, and the rest are CH.

According to an exemplary embodiment of the present specification, in Formula 3, X4 and X5 are N, and X6 is CH.

According to an exemplary embodiment of the present specification, in Formula 3, X5 and X6 are N, and X4 is CH.

According to an exemplary embodiment of the present specification, in Chemical Formula 3, X4 and X6 are N, and X5 is CH.

According to an exemplary embodiment of the present specification, in Formula 3, X4 to X6 are N.

According to an exemplary embodiment of the present specification, in Formula 3, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group.

According to an exemplary embodiment of the present specification, in Formula 3, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.

According to an exemplary embodiment of the present specification, in Formula 3, Ar7 to Ar10 are the same as or different from each other, and each independently an alkyl group or an aryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 3, Ar7 to Ar10 are the same as or different from each other, and each independently an alkyl group or a phenyl group unsubstituted or substituted with an aryl group; Or a biphenyl group.

According to an exemplary embodiment of the present specification, in Formula 3, Ar7 to Ar10 are the same as or different from each other, and each independently a methyl group or a phenyl group unsubstituted or substituted with a phenyl group; Or a biphenyl group.

According to an exemplary embodiment of the present specification, Formula 3 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the emission layer includes a compound represented by Formula 4 below.

[Formula 4]

In Formula 4,

Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, in Formula 4, Ar11 and Ar12 are the same as or different from each other, and each independently an alkyl group or an aryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Chemical Formula 4, Ar11 and Ar12 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 an aryl group; Terphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Anthracenyl group substituted with an aryl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Triphenylenyl group; Or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, in Formula 4, Ar11 and Ar12 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, or a phenyl group unsubstituted or substituted with a naphthyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; An anthracenyl group substituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a phenanthrenyl group, or a triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Triphenylenyl group; Or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, Formula 4 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the emission layer includes a compound represented by Formula 5 below.

[Formula 5]

In Formula 5,

X; is O or S,

Ar13 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, in Chemical Formula 5, X'is O.

According to an exemplary embodiment of the present specification, in Chemical Formula 5, X'is S.

According to an exemplary embodiment of the present specification, in Formula 5, Ar13 is an aryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 5, Ar13 is a phenyl group unsubstituted or substituted with an aryl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, in Formula 5, Ar13 is a phenyl group, or a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 5 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the emission layer includes the compounds represented by Chemical Formulas 4 and 5.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Formula 4 or 5.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Chemical Formula 4.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Chemical Formula 5.

According to an exemplary embodiment of the present specification, the emission layer includes compounds represented by Chemical Formulas 4 and 5 as a host of the emission layer. Specifically, the host is a blue host.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Chemical Formula 4 or 5 as a host of the emission layer.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Formula 4 as a host of the emission layer.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Chemical Formula 5 as a host of the emission layer.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Chemical Formula 4 as a blue host of the emission layer.

According to an exemplary embodiment of the present specification, the emission layer includes the compound represented by Chemical Formula 5 as a blue host of the emission layer.

The organic material layer of the organic light emitting device of the present specification 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.

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 diode 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 according to an exemplary embodiment of the present specification, and may further include another organic material layer.

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

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.

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.

In the organic light emitting device of the present specification, except that the first organic material layer includes at least one of the compounds represented by Formula 1 and Formula 2, and the second organic material layer includes the compound represented by Formula 3 It can be made with materials and methods known in the art.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic material layer, and a cathode 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 prepared by forming an anode, 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 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 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.

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 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, and thus 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, and when the organic light emitting device of the present specification includes an additional hole transport layer in addition to the hole transport layer including the compound represented by Formula 1 , As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes 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 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 2 above. In the case of including an additional electron blocking layer in addition to the electron 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.

As the light-emitting material of the light-emitting layer, a material capable of emitting light in the visible region by transporting and combining 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, 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. Host materials include condensed aromatic ring derivatives or hetero ring-containing compounds. 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, styrylamine 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 A compound in which at least one arylvinyl group is substituted on the arylamine, and 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, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, one or more selected from the following compounds may be used as the topant material, but is not limited thereto.

According to an exemplary embodiment of the present specification, the light emitting layer includes the dopant, 0.1% to 10% by weight of the dopant, and preferably 0.5% to 4% by weight.

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 light emitting layer. In addition to the electron transport layer including the compound represented by Chemical Formula 3, the organic light emitting device of the present specification In the case of including a transport layer, the electron transport material is a material capable of transferring electrons from the cathode to the light emitting layer, and a material having high mobility for electrons 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, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring 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 specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light-emitting device in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors.

The fabrication of the organic light emitting device will be described in detail in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

< Comparative example 1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made 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.

A hole injection layer was formed by thermally vacuum evaporating a compound of the following compound [HI-1] and the following compound [HI-2] to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared ITO transparent electrode, which is an anode.

[HI-1] [ HI-2]

The following compound [HT-1] (1150Å), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.

[HT-1]

Subsequently, the following compound [EB-1] (100Å) with a film thickness of 50Å was vacuum deposited on the hole transport layer to form an electron blocking layer.

[ EB -One]

Subsequently, a light emitting layer was formed by vacuum depositing the following compound [BH] and compound [BD] in a weight ratio of 25:1 with a film thickness of 200 Å on the electron blocking layer.

[BH] [BD ]

[HB-1] [ ET-1]

[ LiQ ]

The compound [HB-1] was vacuum-deposited on the light-emitting layer with a film thickness of 50 Å on the hole transport layer to form a hole blocking layer.

Subsequently, on the hole blocking layer, compound [ET-1] and compound [LiQ] (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 to form a layer for simultaneously injecting and transporting electrons at a thickness of 310 Å.

Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 2,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

Was the deposition rate of the organic material in the above process, maintaining the range of 0.4 to 0.7Å / sec, the lithium fluoride of the cathode was 0.3Å / sec, aluminum was deposited at a rate of 2Å / sec, the degree of vacuum during the deposition to 2Х10 ^-7 By maintaining 5Х10 ^-6 torr, an organic light emitting device was manufactured.

< Comparative example 1-2>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-1 was used instead of Compound [HT-1] in Comparative Example 1-1.

< Comparative example 1-3>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-2 was used instead of Compound [HT-1] in Comparative Example 1-1.

< Comparative example 1-4>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-3 was used instead of Compound [HT-1] in Comparative Example 1-1.

< Comparative example 1-5>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-4 was used instead of Compound [HT-1] in Comparative Example 1-1.

< Comparative example 1-6>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 1-5 was used instead of Compound [HT-1] in Comparative Example 1-1.

< Comparative example 1-7>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-1 was used instead of Compound [EB-1] in Comparative Example 1-1.

< Comparative example 1-8>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-2 was used instead of Compound [EB-1] in Comparative Example 1-1.

< Comparative example 1-9>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-3 was used instead of Compound [EB-1] in Comparative Example 1-1.

< Comparative example 1-10>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 2-4 was used instead of Compound [EB-1] in Comparative Example 1-1.

< Comparative example 1-11>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-1 was used instead of Compound [ET-1] in Comparative Example 1-1.

< Comparative example 1-12>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-2 was used instead of Compound [ET-1] in Comparative Example 1-1.

< Comparative example 1-13>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-3 was used instead of Compound [ET-1] in Comparative Example 1-1.

< Comparative example 1-14>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that Compound 3-4 was used instead of Compound [ET-1] in Comparative Example 1-1.

< Example 1-1>

The same as in Comparative Example 1-1, except that the compound 1-1 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-2>

The same as in Comparative Example 1-1, except that the compound 1-1 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-3>

The same as in Comparative Example 1-1, except that the compound 1-1 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-4>

The same as in Comparative Example 1-1 except that the compound 1-1 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-5>

The same as in Comparative Example 1-1, except that the compound 1-2 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-6>

The same as in Comparative Example 1-1, except that the compound 1-2 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-7>

The same as in Comparative Example 1-1, except that the compound 1-2 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-8>

The same as in Comparative Example 1-1, except that the compound 1-2 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-9>

The same as in Comparative Example 1-1, except that the compound 1-3 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-10>

The same as in Comparative Example 1-1, except that the compound 1-3 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-11>

The same as in Comparative Example 1-1, except that the compound 1-3 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-12>

The same as in Comparative Example 1-1, except that the compound 1-3 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-13>

The same as in Comparative Example 1-1, except that the compound 1-4 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-14>

The same as in Comparative Example 1-1, except that the compound 1-4 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-15>

The same as in Comparative Example 1-1, except that the compound 1-4 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-16>

The same as in Comparative Example 1-1, except that the compound 1-4 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-17>

The same as in Comparative Example 1-1, except that the compound 1-5 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-18>

The same as in Comparative Example 1-1, except that the compound 1-5 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-19>

The same as in Comparative Example 1-1, except that the compound 1-5 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-20>

The same as in Comparative Example 1-1, except that the compound 1-5 was used instead of the compound [HT-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-21>

The same as in Comparative Example 1-1, except that the compound 2-1 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-22>

The same as in Comparative Example 1-1, except that the compound 2-1 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-23>

The same as in Comparative Example 1-1, except that the compound 2-1 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-24>

The same as in Comparative Example 1-1, except that the compound 2-1 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-25>

The same as in Comparative Example 1-1, except that the compound 2-2 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-26>

The same as in Comparative Example 1-1, except that the compound 2-2 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-27>

The same as in Comparative Example 1-1, except that the compound 2-2 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-28>

The same as in Comparative Example 1-1, except that the compound 2-2 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-29>

The same as in Comparative Example 1-1 except that the compound 2-3 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-30>

The same as in Comparative Example 1-1, except that the compound 2-3 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-31>

The same as in Comparative Example 1-1, except that the compound 2-3 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-32>

The same as in Comparative Example 1-1, except that the compound 2-3 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-33>

The same as in Comparative Example 1-1, except that the compound 2-4 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-1 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-34>

The same as in Comparative Example 1-1, except that the compound 2-4 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-2 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-35>

The same as in Comparative Example 1-1, except that the compound 2-4 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-3 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-36>

The same as in Comparative Example 1-1, except that the compound 2-4 was used instead of the compound [EB-1] in Comparative Example 1-1, and the compound of the following 3-4 was used instead of the compound [ET-1]. The organic light emitting device was manufactured by the method.

< Example 1-37>

In Comparative Example 1-1, compound 1-1 was used instead of compound [HT-1], compound 2-2 was used instead of compound [EB-1], and the following 3-1 was used instead of compound [ET-1] An organic light emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the compound of was used.

< Comparative example 1-15>

In Comparative Example 1-1, except that the compound [HT-2] was used instead of the compound [HT-1], and the compound 3-1 was used instead of the compound [ET-1], An organic light emitting device was manufactured in the same manner.

< Comparative example 1-16>

In Comparative Example 1-1, except that the compound [EB-2] was used instead of the compound [EB-1], and the compound 3-2 was used instead of the compound [ET-1], An organic light emitting device was manufactured in the same manner.

< Comparative example 1-17>

In Comparative Example 1-1, compound 1-1 was used instead of compound [HT-1], compound 2-2 was used instead of compound [EB-1], and compound [ET-] was used instead of compound [ET-1] 2], an organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1.

Hole transport layer Electron blocking layer Electron transport layer Voltage
(V) Luminance (CD/A) T95
(hr) Comparative Example 1-1 [HT-1] [EB-1] [ET-1] 4.46 5.86 230 Comparative Example 1-2 1-1 [EB-1] [ET-1] 4.19 6.02 260 Comparative Example 1-3 1-2 [EB-1] [ET-1] 4.18 6.03 255 Comparative Example 1-4 1-3 [EB-1] [ET-1] 4.11 6.08 265 Comparative Example 1-5 1-4 [EB-1] [ET-1] 4.21 6.15 235 Comparative Example 1-6 1-5 [EB-1] [ET-1] 4.12 6.06 285 Comparative Example 1-7 [HT-1] 2-1 [ET-1] 4.06 6.28 270 Comparative Example 1-8 [HT-1] 2-2 [ET-1] 4.03 6.22 285 Comparative Example 1-8 [HT-1] 2-3 [ET-1] 4.02 6.29 275 Comparative Example 1-10 [HT-1] 2-4 [ET-1] 4.05 6.27 270 Comparative Example 1-11 [HT-1] [EB-1] 3-1 3.94 6.17 325 Comparative Example 1-12 [HT-1] [EB-1] 3-2 3.96 6.13 320 Comparative Example 1-13 [HT-1] [EB-1] 3-3 3.97 6.14 305 Comparative Example 1-14 [HT-1] [EB-1] 3-4 3.94 6.12 310 Example 1-1 1-1 [EB-1] 3-1 3.49 6.43 330 Example 1-2 1-1 [EB-1] 3-2 3.48 6.46 365 Example 1-3 1-1 [EB-1] 3-3 3.47 6.48 350 Example 1-4 1-1 [EB-1] 3-4 3.48 6.48 345 Example 1-5 1-2 [EB-1] 3-1 3.56 6.40 325 Example 1-6 1-2 [EB-1] 3-2 3.57 6.48 360 Example 1-7 1-2 [EB-1] 3-3 3.58 6.47 345 Example 1-8 1-2 [EB-1] 3-4 3.59 6.49 345 Example 1-9 1-3 [EB-1] 3-1 3.54 6.48 335 Example 1-10 1-3 [EB-1] 3-2 3.55 6.47 365 Example 1-11 1-3 [EB-1] 3-3 3.56 6.46 350 Example 1-12 1-3 [EB-1] 3-4 3.51 6.45 345 Example 1-13 1-4 [EB-1] 3-1 3.52 6.49 345 Example 1-14 1-4 [EB-1] 3-2 3.53 6.48 375 Example 1-15 1-4 [EB-1] 3-3 3.54 6.47 360 Example 1-16 1-4 [EB-1] 3-4 3.49 6.46 355 Example 1-17 1-5 [EB-1] 3-1 3.54 6.41 335 Example 1-18 1-5 [EB-1] 3-2 3.55 6.49 370 Example 1-19 1-5 [EB-1] 3-3 3.56 6.48 355 Example 1-20 1-5 [EB-1] 3-4 3.57 6.48 355 Example 1-21 [HT-1] 2-1 3-1 3.71 6.60 335 Example 1-22 [HT-1] 2-1 3-2 3.72 6.62 360 Example 1-23 [HT-1] 2-1 3-3 3.73 6.64 350 Example 1-24 [HT-1] 2-1 3-4 3.77 6.66 345 Example 1-25 [HT-1] 2-2 3-1 3.75 6.52 325 Example 1-26 [HT-1] 2-2 3-2 3.74 6.57 370 Example 1-27 [HT-1] 2-2 3-3 3.76 6.51 350 Example 1-28 [HT-1] 2-2 3-4 3.78 6.53 345 Example 1-29 [HT-1] 2-3 3-1 3.79 6.56 330 Example 1-30 [HT-1] 2-3 3-2 3.71 6.57 375 Example 1-31 [HT-1] 2-3 3-3 3.75 6.55 345 Example 1-32 [HT-1] 2-3 3-4 3.73 6.54 340 Example 1-33 [HT-1] 2-4 3-1 3.74 6.53 335 Example 1-34 [HT-1] 2-4 3-2 3.71 6.51 365 Example 1-35 [HT-1] 2-4 3-3 3.70 6.50 355 Example 1-36 [HT-1] 2-4 3-4 3.73 6.54 355 Example 1-37 1-1 2-2 3-1 3.42 6.74 380 Comparative Example 1-15 [HT-2] [EB-1] 3-1 4.34 6.13 280 Comparative Example 1-16 [HT-1] [EB-2] 3-2 4.05 5.93 290 Comparative Example 1-17 1-1 2-2 [ET-2] 3.92 6.09 250

When an electric current was applied to the organic light-emitting devices fabricated in Examples 1-1 to 1-37 and Comparative Examples 1-1 to 1-17, the results of Table 1 were obtained. The blue organic light-emitting device of Comparative Example 1-1 used a material that has been widely used in the past. Compound [HT-1] as a hole transport layer, compound [EB-1] as an electron blocking layer, and compound [ET-1] as an electron transport layer It is a structure that uses ].

According to Table 1, Comparative Examples 1-2 to 1-6 used the compound of Formula 1 according to an exemplary embodiment of the present specification instead of the compound [HT-1] used as a conventional hole transport layer, and Comparative Example 1- 7 to 1-10 used the compound of Formula 2 according to an exemplary embodiment of the present specification instead of the compound [EB-1] used as the conventional electron blocking layer, and Comparative Examples 1-11 to 1-14 were Instead of the compound [ET-1] used as the transport layer, an organic light-emitting device including the compounds of Formula 1, Formula 2, and Formula 3 was manufactured by using the compound of Formula 3 according to an exemplary embodiment of the present specification.

Examples 1-1 to 1-20 are organic light emitting devices using Chemical Formula 1 of the present specification as a hole transport layer and Chemical Formula 3 of the present specification as an electron transport layer, and the organic light emitting device of Examples 1-1 to 1-20 In the light emitting device, the overall driving voltage is 10 to 12% lower and the lifespan is 30% longer than the organic light emitting device of Comparative Examples 1-2 to 1-14 each including Formula 1, Formula 2 and Formula 3 of the present specification. Showed the result.

In particular, the driving voltage of the organic light emitting device of Examples 1-1 to 1-4 using Compound 1-1 as the hole transport layer and Compounds 3-1 to 3-4, which are compounds of Formula 3 of the present specification, as the electron transport layer Was the lowest, and Examples 1-2, 1-6, 1-10, in which compounds 1-1 to 1-5, which are compounds of Formula 1 in the present specification, were used as the hole transport layer, and compound 3-2 was used as the electron transport layer. The lifetimes of organic light-emitting devices 1-14 and 1-18 were measured for the longest.

Examples 1-21 to 1-36 are organic light emitting devices using Chemical Formula 2 of the present specification as an electric barrier layer and Chemical Formula 3 of the present specification as an electron transport layer. The organic light-emitting device showed a result that overall luminous efficiency was increased by 5 to 8% or more, and the lifespan was measured to be 30% or more longer than that of the organic light-emitting device including Chemical Formulas 1, 2, and 3 of the present specification.

Example 1-37 showed the best properties as an organic light-emitting device including the compound of Chemical Formula 1 of the present specification as a hole transport layer, Chemical Formula 2 of the present specification as an electron blocking layer, and Chemical Formula 3 of the present specification as an electron transport layer.

In Comparative Example 1-15, the compound [HT-2] in which two polycyclic aryl groups are bonded to the core structure of the present formula 1, which is widely used in the prior art, is used as a hole transport layer, and compound 3-1 of the present specification is used as the compound When used instead of [ET-1], the voltage increased significantly by more than 10%. In particular, in the case of the compound [HT-2], since the glass transition temperature (Tg) is less than 100°C, thermal stability is poor, so that the lifespan of the organic light emitting device is greatly reduced, and efficiency is decreased.

Comparative Example 1-16 is an organic light-emitting device using a compound [EB-2] in which a tricyclic heterocyclic group, which is a substituent of Formula 2 in the present specification, is connected in a para direction instead of a meta direction as an electron blocking layer, and the device efficiency is 10% or more The result was greatly reduced.

Comparative Example 1-17 is an organic light-emitting device using a compound [ET-2] having terphenyl as a core instead of naphthalene, which is the core of Chemical Formula 3 of the present specification, as an electron transport layer, and the lifespan of the device was significantly reduced.

Through this, the organic light emitting device including at least one first organic material layer including at least one of Chemical Formulas 1 and 2 and the second organic material layer including Chemical Formula 3 has improved driving voltage and luminous efficiency, especially lifespan characteristics. I could confirm.

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: electron blocking layer
90: electron transport layer
100: electron injection layer

Claims (15)

anode;
A negative electrode provided to face the positive electrode;
A light emitting layer provided between the anode and the cathode;
At least one first organic material layer provided between the anode and the emission layer; And
An organic light-emitting device comprising a second organic material layer provided between the cathode and the emission layer,
The first organic material layer includes at least one of compounds represented by the following Chemical Formulas 1 and 2,
The second organic material layer is an organic light emitting device including a compound represented by the following formula (3):
[Formula 1]

In Formula 1,
Any one of Ar1 to Ar4 is a polycyclic aryl group, the rest are the same as or different from each other, and each independently a monocyclic aryl group,
[Formula 2]

In Formula 2,
Ar5 and Ar6 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,
Y1 is a group represented by any one of the following structures,

,

In the above structure,
X is O or S,
R1 to R8 are hydrogen, or adjacent groups are bonded to each other to form an aromatic ring,
[Formula 3]

In Chemical Formula 3,
At least one of X1 to X3 is N, the rest are CH,
At least one of X4 to X6 is N, the rest are CH,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar7 to Ar10 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group. The organic light-emitting device of claim 1, wherein the first organic material layer includes a hole transport layer and an electron blocking layer, and the hole transport layer includes a compound represented by Formula 1. The organic light-emitting device of claim 1, wherein the first organic material layer includes a hole transport layer and an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 2. The method of claim 1, wherein the first organic material layer includes a hole transport layer and an electron blocking layer, the hole transport layer includes a compound represented by Formula 1, and the electron blocking layer includes a compound represented by Formula 2 Organic light emitting device. The method according to claim 1, wherein the second organic material layer is 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 represented by Formula 3 An organic light-emitting device comprising the compound to be displayed. The organic light-emitting device of claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
The definition of Ar1 to Ar4 is the same as defined in Chemical Formula 1. The organic light-emitting device of claim 1, wherein the formula 2 is represented by the following formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,
The definitions of R1 to R8, X, Ar5, and Ar6 are the same as those defined in Chemical Formula 2. The organic light-emitting device of claim 1, wherein Formula 3 is represented by any one of the following Formulas 3-1 to 3-8:
[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

In Formulas 3-1 to 3-8,
The definitions of X1 to X6, L1, L2, and Ar7 to Ar10 are as defined in Chemical Formula 3. The organic light-emitting device of claim 1, wherein Formula 1 is selected from the following compounds:

The organic light-emitting device of claim 1, wherein Formula 2 is selected from the following compounds:

The organic light-emitting device of claim 1, wherein Formula 3 is selected from the following compounds:

The organic light-emitting device of claim 1, wherein the emission layer comprises a compound represented by the following Formula 4:
[Formula 4]

In Formula 4,
Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group. The organic light-emitting device of claim 12, wherein Formula 4 is selected from the following compounds:

The organic light-emitting device of claim 1, wherein the emission layer comprises a compound represented by the following formula (5):
[Formula 5]

In Formula 5,
X'is O or S,
Ar13 is a substituted or unsubstituted aryl group. The organic light-emitting device of claim 14, wherein Formula 5 is selected from the following compounds:

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