WO2020130528A1 - Compound and organic light emitting diode comprising same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting diode comprising same.

Description

Compound and organic light emitting device comprising same

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0164384, filed with the Korean Patent Office on December 18, 2018, the entire contents of which are incorporated herein.

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, 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. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for such organic light-emitting devices continues to be required.

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

The present invention provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl A group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

Any one of R ₁ to R ₈ is combined with L ₃ ,

L ₁ and L ₂ are the same as or different from each other, and each independently, a substituted or unsubstituted arylene group,

L ₃ is a direct bond,

Ar ₁ and Ar ₂ 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,

m and n are the same as or different from each other, and each independently, an integer from 0 to 2,

When m is 2, L ₁ is the same as or different from each other,

When n is 2, L ₂ is the same as or different from each other.

In addition, the present invention is a first electrode; A second electrode provided opposite to the first electrode; And it provides an organic light emitting device comprising one or more layers of an organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound.

The compound according to an 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 this, it is possible to improve efficiency, improve a low driving voltage, and/or life characteristics in the organic light emitting device.

1 shows an organic light emitting diode according to an exemplary embodiment of the present specification.

2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.

[Description of codes]

1: Substrate

2: first electrode

3: organic layer

4: Second electrode

5: hole injection layer

6: hole transport layer

7: Electronic suppression layer

8: emitting layer

9: Hole bottom layer

10: electron injection and transport layer

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

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

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

The term "substitution" 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 to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to deuterium; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with 1 or 2 or more substituents selected from the group consisting of substituted or unsubstituted substituents, or having no substituents. For example, the "substituent in which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specific examples include methyl groups; Ethyl group; Propyl group; n-propyl group; Isopropyl group; Butyl group; n-butyl group; Isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethyl butyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; Heptyl group; n-heptyl group; 1-methylhexyl group; Cyclopentyl methyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; Isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; Cyclobutyl group; Cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; Cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl group; Cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specifically, a methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; p-methylbenzyloxy group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluorenylamine group and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 20 carbon atoms, and more preferably 6 to 20 carbon atoms. 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 is preferably 6 to 20 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms. Specifically, as the monocyclic aryl group, a phenyl group; Biphenyl group; It may be a terphenyl group, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 30 carbon atoms, and more preferably 10 to 20 carbon atoms. Specifically, a polycyclic aryl group is a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group and the like, but is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

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

In the present specification, the heteroaryl group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms 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, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline group (phenanthroline); Isooxazolyl group; Thiadiazolyl group; Phenothiazinyl group and dibenzofuranyl group, and the like, but is not limited thereto.

In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-1 to 1-4, L ₁ , L ₂ , R ₁ to R _8, Ar ₁ , Ar ₂ , m, and n are as defined in Chemical Formula 1.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from each other, and each independently an substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from each other, and each independently an arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from each other, and each independently an unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent Terphenyl group, substituted or unsubstituted naphthalene group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent triphenylene group, or substituted or unsubstituted 2 It is a pseudo fluorene group.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted divalent ratio. It is a phenyl group.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from each other, and each independently a phenylene group, a naphthalene group, or a divalent biphenyl group.

In one embodiment of the present specification, L ₁ and L ₂ are phenylene groups.

In one embodiment of the present specification, L ₁ and L ₂ are naphthalene groups.

In one embodiment of the present specification, L ₁ and L ₂ are divalent biphenyl groups.

In one embodiment of the present specification, L ₁ and L ₂ are each independently a phenylene group, a naphthalene group, or a divalent biphenyl group.

In one embodiment of the present specification, L ₃ is a direct bond.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero atom having 3 to 30 carbon atoms. It is an aryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as each other, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as each other, and are substituted aryl groups having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as each other, and are unsubstituted aryl groups having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as each other and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same and substituted heteroaryl groups having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same and unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as each other, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are different from each other.

In one embodiment of the present specification, Ar ₁ is a substituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₁ is an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ is a substituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ is an unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₂ is an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar ₂ is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₂ is a substituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₂ is an unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently is one of the following substituents.

The dotted line is a site binding to L1 and L2, and Rx is an alkyl group or an aryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrene group, a triphenylene group, a fluorene group, and dibenzo A furan group or a dibenzothiophene group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, triphenylene group, fluorene group, dibenzofuran group, or dibenzothiophene group is deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, It is substituted or unsubstituted with any one or more substituents selected from the group consisting of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrene group, a triphenylene group, a fluorene group, and dibenzo A furan group or a dibenzothiophene group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrene group, triphenylene group, fluorene group, dibenzofuran group, or dibenzothiophene group is deuterium, nitrile group, halogen group, substituted or unsubstituted carbon number 1 It is substituted or unsubstituted with any one or more substituents selected from the group consisting of an alkyl group of 10 to 10, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, a substituent that does not bind to L ₃ in R ₁ to R ₈ is hydrogen, deuterium, a nitrile group, a halogen group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, silyl group substituted with alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In one embodiment of the present specification, a substituent that does not bind to L ₃ in R ₁ to R ₈ is hydrogen; heavy hydrogen; Nitrile group; F; Br; Cl; I; Nitro group; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Terbutyl group; Methoxy group; Ethoxy group; Butoxy group; Terbutoxy group; A silyl group substituted with a methyl group, an ethyl group, or a terbutyl group; Phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Phenanthrene group; Anthracene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Or a triazine group.

In one embodiment of the present specification, a substituent that does not bind to L ₃ in R ₁ to R ₈ is hydrogen.

In one embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

In this specification, when it is said that a part "includes" a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise specified.

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

The organic light emitting device of the present invention comprises 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 layer of the organic material layer may include the aforementioned compound.

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

In FIG. 1, a structure of an organic light emitting device in which the first electrode 2, the organic material layer 3, and the second electrode 4 are sequentially stacked on the substrate 1 is illustrated.

1 illustrates an organic light emitting device and is not limited thereto.

In FIG. 2, the first electrode 2 on the substrate 1, the hole injection layer 5, the hole transport layer 6, the electron suppressing layer 7, the light emitting layer 8, the hole blocking layer 9, the electron injection and The structure of the organic light emitting device in which the transport layer 10 and the second electrode 4 are sequentially stacked is illustrated. The compound of the present invention can be used for the hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole blocking layer electron injection and transport layer, but is preferably used for the electron suppression layer.

2 illustrates an organic light emitting device and is not limited thereto.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula 1 above.

In an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer includes the compound of Formula 1 You can.

In one embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or the electron injection and transport layer includes the compound of Formula 1 You can.

In an exemplary embodiment of the present invention, the organic material layer includes an electron suppression layer, and the electron suppression layer may include the compound of Formula 1.

In an exemplary embodiment of the present invention, the organic material layer includes a hole blocking layer, and the hole blocking layer may include a compound represented by Chemical Formula 1.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof To form an anode, and then form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer containing the compound of Formula 1, and deposit a material that can be used as a cathode thereon. It can be prepared by. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, but are not limited thereto.

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

As the hole injection material, a hole injection material can be well injected from the anode at a low voltage, and it is preferable that a high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the cathode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic compounds, anthraquinones, and polyaniline-based conductive polymers, and the like, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable as a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

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

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

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using the compound.

The present specification also provides a method of manufacturing an organic light emitting device formed using the compound.

Examples of dopant materials include aromatic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound A compound in which at least one arylvinyl group is substituted with an arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including 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 or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, and 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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that prevents the cathode 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 complex, and the like, but are not limited thereto.

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

The organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except for forming one or more organic material layers using the above-described compounds.

The method for manufacturing the compound of Formula 1 and the production of the organic light emitting device using the same are described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

In the following reaction scheme, various kinds of intermediates can be synthesized according to the type and number of substituents by appropriately selecting a known starting material by those skilled in the art. Reaction types and reaction conditions may be those known in the art.

[Correction by Rule 91 28.01.2020]

[Correction by Rule 91 28.01.2020]

[Correction by Rule 91 28.01.2020]

When the preparation formulas described in the examples of the present specification and the intermediates are appropriately combined on the basis of common technical knowledge, all the compounds of Formula 1 described herein can be prepared.

Preparation Example 1

Compound A-1 (7.78 g, 15.44 mmol), and compound a1 (4.50 g, 14.71 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (2.83 g, 29.41 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.15 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 310 mL of ethyl acetate to prepare compound 1 (7.12 g, yield: 66%).

MS[M+H] ⁺ = 730

Preparation Example 2

Compound B-1 (7.72 g, 15.34 mmol), and compound a2 (4.50 g, 14.61 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then NaOtBu (2.81 g, 29.22 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.07 g, 0.15 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare compound 2 (6.58 g, yield: 62%).

MS[M+H] ⁺ = 732

Preparation Example 3

Compound C-1 (8.43 g, 16.76 mmol), and compound a3 (4.50 g, 15.96 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.07 g, 31.91 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.16 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 180 mL to prepare compound 3 (5.37 g, yield: 48%).

MS[M+H] ⁺ = 716

Preparation Example 4

Compound D-1 (7.38 g, 14.67 mmol), and compound a4 (4.50 g, 13.98 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (2.69 g, 27.95 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.07 g, 0.14 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 250 mL to prepare compound 4 (7.12 g, yield: 68%).

MS[M+H] ⁺ = 746

Preparation Example 5

Compound A-2 (7.73 g, 13.98 mmol), and compound a5 (4.50 g, 13.31 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then NaOtBu (2.56 g, 26.63 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.07 g, 0.13 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare compound 5 (6.34 g, yield: 59%).

MS[M+H] ⁺ = 812

Preparation Example 6

Compound B-2 (7.72 g, 15.34 mmol), and compound a6 (4.50 g, 14.61 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then NaOtBu (2.81 g, 29.22 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.07 g, 0.15 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 230 mL to prepare compound 6 (7.54 g, yield: 66%).

MS[M+H] ⁺ = 782

Preparation Example 7

Compound C-2 (9.27 g, 16.76 mmol), and compound a7 (4.50 g, 15.96 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.07 g, 31.91 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.16 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 180 mL to prepare compound 7 (6.68 g, yield: 55%).

MS[M+H] ⁺ = 756

Preparation Example 8

Compound D-2 (10.62 g, 19.21 mmol), and compound a8 (4.50 g, 18.29 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.52 g, 36.59 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 210 mL to prepare compound 8 (5.96 g, yield: 45%).

MS[M+H] ⁺ = 720

Preparation Example 9

Compound A-3 (10.87 g, 18.03 mmol), and compound a9 (4.50 g, 17.18 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.30 g, 34.35 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.09 g, 0.17 mmol) was added, followed by heating and stirring for 6 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with tetrahydrofuran 240 mL to prepare compound 9 (8.06 g, yield: 54%).

MS[M+H] ⁺ = 812

Preparation Example 10

Compound B-3 (12.28 g, 20.37 mmol), and compound a10 (4.50 g, 19.40 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then NaOtBu (3.73 g, 38.79 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.10 g, 0.19 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure, and recrystallized with 210 mL of ethyl acetate to prepare compound 10 (9.11 g, yield: 62%).

MS[M+H] ⁺ = 756

Preparation Example 11

Compound C-3 (10.47 g, 17.37 mmol), and compound a11 (4.50 g, 16.54 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then NaOtBu (3.18 g, 33.09 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.17 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 210 mL to prepare compound 11 (6.68 g, yield: 55%).

MS[M+H] ⁺ = 796

Preparation Example 12

Compound D-3 (10.47 g, 19.21 mmol), and compound a12 (4.50 g, 16.54 mmol) were dissolved in 230 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.18 g, 33.09 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.17 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 250 mL to prepare compound 12 (8.76 g, yield: 76%).

MS[M+H] ⁺ = 856

Preparation Example 13

Compound A-4 (16.75 g, 30.29 mmol), and compound a13 (4.50 g, 28.85 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (5.54 g, 57.69 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.15 g, 0.29 mmol) was added, followed by heating and stirring for 2 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare compound 13 (12.06 g, yield: 66%).

MS[M+H] ⁺ = 630

Preparation 14

Compound B-4 (10.24 g, 20.37 mmol), and compound a14 (4.50 g, 19.40 mmol) were completely dissolved in 210 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.73 g, 8.79 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.10 g, 0.19 mmol) was added thereto, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 220 mL to prepare compound 14 (5.83 g, yield: 46%).

MS[M+H] ⁺ = 706

Preparation 15

Compound C-4 (11.54 g, 22.94 mmol), and compound a15 (4.50 g, 21.84 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then NaOtBu (4.20 g, 43.69 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.11 g, 0.22 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 210 mL of ethyl acetate to prepare compound 15 (7.77 g, yield: 52%).

MS[M+H] ⁺ = 680

Preparation Example 16

Compound D-4 (12.68 g, 22.94 mmol), and compound a16 (4.50 g, 21.84 mmol) were dissolved in 230 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (4.20 g, 43.69 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.11 g, 0.22 mmol) was added, followed by heating and stirring for 2 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 210 mL of ethyl acetate to prepare compound 16 (6.38 g, yield: 43%).

MS[M+H] ⁺ = 680

Preparation Example 17

Compound A-5 (11.75 g, 20.37 mmol), and compound a17 (4.50 g, 19.40 mmol) were dissolved in 230 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.73 g, 38.79 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.10 g, 0.19 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 220 mL of ethyl acetate to prepare compound 17 (9.32 g, yield: 66%).

MS[M+H] ⁺ = 730

Preparation Example 18

Compound B-5 (12.08 g, 21.53 mmol), and compound a18 (6.50 g, 21.10 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.04 g, 31.66 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.11 g, 0.21 mmol) was added, followed by heating and stirring for 2 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 230 mL to prepare compound 18 (8.37 g, yield: 55%).

MS[M+H] ⁺ = 716

Preparation Example 19

Compound C-5 (8.61 g, 15.34 mmol), and compound a19 (4.50 g, 14.61 mmol) were completely dissolved in 210 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (2.81 g, 29.22 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.07 g, 0.15 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized with 210 mL of acetone to prepare compound 19 (6.95 g, yield: 59%).

MS[M+H] ⁺ = 806

Preparation Example 20

Compound D-5 (11.75 g, 20.37 mmol), and compound a20 (4.50 g, 19.40 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.73 g, 38.79 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.10 g, 0.19 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 210 mL of acetone to prepare compound 20 (9.35 g, yield: 66%).

MS[M+H] ⁺ = 730

Preparation Example 21

Compound A-6 (7.78 g, 15.44 mmol), and compound a21 (4.50 g, 14.71 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (2.83 g, 29.41 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.15 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 310 mL of ethyl acetate to prepare compound 21 (7.12 g, yield: 66%).

MS[M+H] ⁺ = 730

Preparation Example 22

Compound B-6 (10.43 g, 19.21 mmol), and compound a22 (4.50 g, 18.29 mmol) were completely dissolved in 290 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.52 g, 36.59 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 290 mL of ethyl acetate to prepare compound 22 (8.46 g, yield: 65%).

MS[M+H] ⁺ = 730

Preparation Example 23

Compound C-6 (9.79 g, 18.03 mmol), and compound a23 (4.50 g, 17.18 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.30 g, 34.35 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.09 g, 0.17 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare compound 23 (7.49 g, yield: 60%).

MS[M+H] ⁺ = 730

Preparation Example 24

Compound D-6 (9.43 g, 17.37 mmol), and compound a24 (4.50 g, 16.54 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (3.18 g, 33.09 mmol) was added. Then, bis(tri-tert-butylphosphine) palladium (0) (0.08 g, 0.17 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, the xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare compound 24 (5.33 g, yield: 44%).

MS[M+H] ⁺ = 736

Example 1-1

A glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,000 에 was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as the detergent, and distilled water filtered secondarily by a filter (filtration) of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

A compound of the following compound HI1 and the following compound HI2 was thermally vacuum-deposited to a thickness of 100 Pa to a ratio of 98:2 (molar ratio) on the prepared ITO transparent electrode, thus forming a hole injection layer. A compound (1150 진공) represented by the following Chemical Formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, an electron suppressing layer was formed by vacuum-depositing Compound 1 on the hole transport layer with a thickness of 50 mm 2. Subsequently, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD as a film thickness of 200 mm 2 on the electron suppressing layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing a compound represented by the following Chemical Formula HB1 with a thickness of 50 mm 2 on the light emitting layer. Subsequently, on the hole blocking layer, a compound represented by the following Chemical Formula ET1 and a compound represented by the following Chemical Formula LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 MPa. On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 순차적 were sequentially deposited to form a negative electrode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- An} organic light emitting device was manufactured by maintaining ⁷ to 5×10 ^-6 torr.

Examples 1-2 to Examples 1-24

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound shown in Table 1 instead of Compound 1.

Comparative Examples 1-1 to 1-7

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound shown in Table 1 instead of Compound 1. The compounds of EB2, EB3, EB4, EB5, EB6, EB7, and EB8 used in Table 1 below are as follows.

Experimental Example 1

When current was applied to the organic light-emitting device manufactured in the above Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

	Compound (electron suppression layer)	Voltage (V@10mA/cm 2 )	Efficiency (cd/A@10mA/cm 2 )	Color coordinate (x,y)	T95(hr)
Example 1-1	Compound 1	4.43	6.47	(0.145, 0.046)	235
Example 1-2	Compound 2	4.62	6.56	(0.147, 0.044)	245
Example 1-3	Compound 3	4.66	6.51	(0.144, 0.043)	245
Example 1-4	Compound 4	4.74	6.35	(0.147, 0.044)	220
Example 1-5	Compound 5	4.79	6.35	(0.144, 0.044)	225
Example 1-6	Compound 6	4.58	6.54	(0.144, 0.043)	245
Example 1-7	Compound 7	4.57	6.56	(0.144, 0.046)	235
Example 1-8	Compound 8	4.75	6.35	(0.146, 0.046)	255
Example 1-9	Compound 9	4.71	6.33	(0.147, 0.044)	255
Example 1-10	Compound 10	4.52	6.51	(0.144, 0.043)	255
Example 1-11	Compound 11	4.60	6.52	(0.144, 0.043)	250
Example 1-12	Compound 12	4.63	6.50	(0.144, 0.044)	250
Example 1-13	Compound 13	4.49	6.69	(0.144, 0.044)	235
Example 1-14	Compound 14	4.48	6.68	(0.144, 0.043)	255
Example 1-15	Compound 15	4.57	6.54	(0.144, 0.043)	245
Example 1-16	Compound 16	4.55	6.56	(0.146, 0.045)	255
Examples 1-17	Compound 17	4.44	6.65	(0.147, 0.044)	250
Example 1-18	Compound 18	4.54	6.54	(0.144, 0.043)	245
Examples 1-19	Compound 19	4.52	6.52	(0.146, 0.045)	250
Example 1-20	Compound 20	4.41	6.65	(0.147, 0.044)	255
Example 1-21	Compound 21	4.43	6.67	(0.147, 0.044)	250
Example 1-22	Compound 22	4.71	6.46	(0.146, 0.045)	225
Example 1-23	Compound 23	4.72	6.44	(0.147, 0.044)	220
Example 1-24	Compound 24	4.45	6.69	(0.147, 0.044)	250
Comparative Example 1-1	EB2	4.96	5.68	(0.141, 0.045)	120
Comparative Example 1-2	EB3	5.23	5.46	(0.143, 0.046)	75
Comparative Example 1-3	EB4	5.45	5.73	(0.143, 0.044)	90
Comparative Example 1-4	EB5	6.02	4.32	(0.144, 0.045)	45
Comparative Example 1-5	EB6	6.62	4.18	(0.143, 0.046)	50
Comparative Example 1-6	EB7	6.75	4.09	(0.143, 0.044)	65
Comparative Example 1-7	EB8	6.82	4.01	(0.144, 0.045)	55

As shown in Table 1, the organic light emitting device using the compound of the present invention as an electron suppressing layer exhibited excellent properties in terms of efficiency, driving voltage and stability of the organic light emitting device. In Examples 1-1 to 1-24, when an amine group-branched chain biphenyl group (phenylene group substituted with a phenyl group)-polycyclic heteroaryl group is sequentially used as an electron suppressing layer, a branched chain biphenyl group is an amine It shows that it has a low voltage and high efficiency by acting to push electrons a little more, and dibenzofuran has high stability to electrons, and thus has a long life. Comparative Example 1-1 does not have a branched chain biphenyl group, so it can transfer electrons to amine groups. There is no boosting role, and Comparative Examples 1-2 and 1-3 are aryl amines with branched biphenyl groups connected to the dibenzofuran 3 position, and exhibited poor properties in terms of efficiency, driving voltage, and stability. Comparative Example 1-4 is an aryl amine to which 9H-pyrido[3,4-b]indole is linked, and the balance of the device is completely collapsed.

Comparative Examples 1-5 to 1-7 use a compound in which the linking group connecting L3 and an amine group in Formula 1 of the present specification is an unsubstituted phenyl group or a phenyl group substituted with a methyl group, and does not play a role of boosting electrons to the amine group. Because of this, the organic light emitting device exhibited poor properties in terms of efficiency, driving voltage, and stability.

Although the preferred embodiment (electron suppression layer) of the present invention has been described through the above, the present invention is not limited thereto, and can be implemented by various modifications within the scope of the claims and detailed description of the invention. It belongs to the scope of the invention.

Claims (10)

1. Compound represented by the formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl A group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

   Any one of R ₁ to R ₈ is combined with L ₃ ,

   L ₁ and L ₂ are the same as or different from each other, and each independently, a substituted or unsubstituted arylene group,

   L ₃ is a direct bond,

   Ar ₁ and Ar ₂ 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,

   m and n are the same as or different from each other, and each independently, an integer from 0 to 2,

   When m is 2, L ₁ is the same as or different from each other,

   When n is 2, L ₂ is the same as or different from each other.
2. The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-4:

   [Formula 1-1]

   

   [Formula 1-2]

   

   [Formula 1-3]

   

   [Formula 1-4]

   

   In Chemical Formulas 1-1 to 1-4, L ₁ , L ₂ , R ₁ to R _8, Ar ₁ , Ar ₂ , m, and n are as defined in Chemical Formula 1.
3. The method according to claim 1, wherein L ₁ And L ₂ Is The same as or different from each other, each independently A compound having a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
4. The method according to claim 1, wherein Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. compound.
5. The method according to claim 1, wherein Formula 1 is any one selected from the following compounds:

   

   

   

   

   

   

   

   

   

   

   
6. A first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound of claim 1. Light emitting element.
7. The method according to claim 6, The organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, the hole injection layer, hole transport layer, or the hole injection and transport layer comprises the compound.
8. The method according to claim 6, The organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.
9. The method according to claim 6, The organic layer comprises an electron suppression layer, the electron suppression layer is an organic light emitting device comprising the compound.
10. The method according to claim 6, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound.

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