WO2019177393A1

WO2019177393A1 - Compound and organic light emitting device comprising same

Info

Publication number: WO2019177393A1
Application number: PCT/KR2019/002950
Authority: WO
Inventors: 윤홍식; 홍완표; 김진주
Original assignee: 주식회사 엘지화학
Priority date: 2018-03-14
Filing date: 2019-03-14
Publication date: 2019-09-19
Also published as: CN111225895B; KR102230988B1; CN111225895A; KR20190108517A

Abstract

The present specification provides a compound of formula 1 and an organic light emitting device comprising same.

Description

Compound and organic light emitting device comprising same

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

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2018-0029680 filed with the Korea Intellectual Property Office on March 14, 2018, the entire contents of which are incorporated herein.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function as necessary. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of the material of the organic thin film is continuously required.

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

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

[Formula 1]

In Chemical Formula 1,

One of Ar1 and Ar2 is represented by the following formula (2),

The rest of Ar1 and Ar2 are substituted or unsubstituted aryl groups,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

[Formula 2]

In Formula 2, Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.

The compound according to the exemplary embodiment of the present application is used in an organic light emitting device to increase the brightness of the organic light emitting device, increase the lifespan, lower the driving voltage, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound Can be improved. Specifically, the compound according to the exemplary embodiment of the present invention has a structure having high electron acceptability because two substituents are bonded to one benzene ring of phenanthrene, and have excellent heat resistance, so that the appropriate deposition temperature may be I can keep it. In addition, since the compound according to the present invention has a high sublimation temperature and is capable of high purity by a sublimation purification method, contamination of the film forming apparatus or organic light emitting device for deposition during organic light emitting device manufacture is prevented.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.

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

[Description of the code]

1: substrate

2: anode

3: light emitting layer

4: cathode

5: hole injection layer

6: hole transport layer

7: electronic jersey

8: electron injection and transport layer

Hereinafter, this specification is demonstrated in detail.

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

Examples of substituents herein are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a 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 a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Alkyl groups; Cycloalkyl group; An alkoxy group; Silyl groups; Amine groups; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are linked" 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 linked.

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

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. 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 and the like It may be, but is not limited thereto.

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

In the present specification, the amine group is -NH ₂ ; Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of N-alkylheteroarylamine group, monoheteroarylamine group and diheteroarylamine group, carbon number 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, and 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenyl amine group and the like, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be naphthyl group, anthracene group, phenanthrene group, pyrenyl group, peryleneyl group, chrysene group, fluorene group, etc., but is not limited thereto.

In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, and the like. have. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60 or C2-C30. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophene group, dibenzothiophene group , Benzofuran group, dibenzofuran group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isoxoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxazine group, and condensation structures thereof, etc. There is, but is not limited to these.

In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, R1, R2, Ar1, Ar2, and Ar3 are the same as defined in Formula 1.

In an exemplary embodiment of the present specification, the remainder of the Ar1 and Ar2 other than the general formula (2) is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, the remainder of the Ar 1 and Ar 2 other than Chemical Formula 2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, the remainder of the formula (2) in the Ar1 and Ar2 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, the remainder other than Formula 2 of Ar1 and Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Or a naphthyl group.

In one embodiment of the present specification, the remainder other than Formula 2 of Ar1 and Ar2 is a phenyl group; Or a biphenyl group.

In one embodiment of the present specification, the remainder other than Formula 2 in Ar1 and Ar2 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, the remainder other than Formula 2 of Ar1 and Ar2 is a phenyl group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 36 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 36 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group including at least one of N, O, and S having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group containing at least one of O and S having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzonaphthofuran group; Or a substituted or unsubstituted benzonaphthothiophene group.

In one embodiment of the present specification, Ar3 is a deuterium or an aryl group unsubstituted or substituted with an aryl group; Or a heterocyclic group.

In one embodiment of the present specification, Ar3 is a deuterium or a phenyl group unsubstituted or substituted with an aryl group; Deuterium or a biphenyl group unsubstituted or substituted with an aryl group; Deuterium or a naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene groups unsubstituted or substituted with deuterium or an aryl group; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group.

In one embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; A biphenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; A naphthyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; Phenanthrene groups unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group.

In one embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with deuterium or a naphthyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present specification, R1 and R2 are hydrogen.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is selected from the following structural formulas.

In addition, the present specification provides an organic light emitting device including the compound described above.

In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

The organic material layer of the organic light emitting device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer has a thickness of 100 kPa to 500 kPa, preferably 200 kPa to 400 kPa.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a host.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer further includes a dopant material.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound and the dopant in a weight ratio of 1: 1 to 200: 1.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound and the dopant in a weight ratio of 20: 1 to 200: 1.

In an exemplary embodiment of the present application, the light emitting layer may include a pyrene-based compound, an anthracene-based compound, a boron-based compound, etc. as a dopant material, but is not limited thereto.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-1.

[Formula A-1]

In Chemical Formula A-1,

n is an integer of 1 or more,

Ar11 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

L11 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar12 and Ar13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,

When n is 2 or more, the structures in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-1 as a dopant of the light emitting layer.

According to an exemplary embodiment of the present application, the L11 is a direct bond.

According to an exemplary embodiment of the present application, n is 2.

In an exemplary embodiment of the present application, Ar11 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, or tert-butyl groups; Or a divalent chrysene group unsubstituted or substituted with deuterium, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

In one embodiment of the present application, Ar11 is a divalent pyrene group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present application, Ar12 and A1r3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present application, Ar12 and Ar13 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group; Or a heteroaryl group unsubstituted or substituted with an alkyl group.

In one embodiment of the present application, Ar12 and Ar13 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a methyl group, an ethyl group or an isopropyl group; Or a heteroaryl group.

According to an exemplary embodiment of the present application, Ar12 and Ar13 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group; Or a dibenzofuran group.

In one embodiment of the present application, Chemical Formula A-1 may be represented by the following structural formula.

In an exemplary embodiment of the present application, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, the hole injection layer, a hole transport layer, or a hole injection and transport layer comprises the compound.

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

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

In one embodiment of the present application, the organic light emitting device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers comprises the compound.

In one embodiment of the present application, the organic material layer further includes a hole injection layer.

In one embodiment of the present application, the organic material layer further comprises a hole transport layer.

In one embodiment of the present application, the organic material layer further includes an electron blocking layer.

In one embodiment of the present application, the organic material layer further includes an electron injection and transport layer.

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

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

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

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

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

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

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

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

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

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

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

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

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. 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), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. The hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material. The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and 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 light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is 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 with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.

The electron transporting layer is a layer for receiving electrons from the electron injection layer and transporting electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof 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 in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-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, 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-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer for blocking the arrival of the cathode of the hole, 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, and the like, 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 side emission type according to a material used.

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

<< 제조예Production Example >>

The compound represented by Chemical Formula 1 introduced bromo group through 9-chloroanthracene through bromination and introduced aryl or heteroaryl by Suzuki reaction. Thereafter, borates were introduced through a boration reaction, and finally, compounds of the embodiments were synthesized through the process of introducing phenanthrene groups.

제조예Production Example 1-1 1-1

Synthesis of Compound 1-A

50 g (235 mmol) of 9-chloroanthracene and 500 mL of chloroform were mixed and cooled to 0 ° C. Bromine 235 mL was slowly dropped at 0 ° C. and stirred at room temperature for 3 hours. After the reaction, the organic layer was extracted with an aqueous sodium thiosulfate solution, and then recrystallized twice with chloroform and hexane to obtain Compound 1-A (58.3 g) (yield 85%).

MS [M + H] ⁺ = 291

제조예Production Example 2-1 2-1

Synthesis of Compound 2-A

30 g (103 mmol) of 1-A, 103 mmol of [1,1'-biphenyl] -4-ylboronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice from chloroform and hexane to give 33.1 g of compound 2-A (yield 88%).

MS [M + H] ⁺ = 365

제조예Production Example 2-2 2-2

Synthesis of Compound 2-B

30 g (103 mmol) of 1-A, 103 mmol of [1,1'-biphenyl] -3-ylboronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 32.3 g of compound 2-B (yield 86%).

MS [M + H] ⁺ = 365

제조예Production Example 2-3 2-3

Synthesis of Compound 2-C

30 g (103 mmol) of 1-A, 103 mmol of naphthalen-1-ylboronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 28.3 g of compound 2-C (yield 81%).

MS [M + H] ⁺ = 339

제조예Production Example 2-4 2-4

Synthesis of Compound 2-D

30 g (103 mmol) of 1-A, 103 mmol of dibenzo [b, d] thiophen-4-ylboronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain 33.8 g of compound 2-D (yield 83%).

MS [M + H] ⁺ = 395

제조예Production Example 2-5 2-5

Synthesis of Compound 2-E

30 g (103 mmol) of 1-A, 103 mmol of (phenyl-d5) boronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 26.3 g of compound 2-E (yield 87%).

MS [M + H] ⁺ = 294

제조예Production Example 2-6 2-6

Synthesis of Compound 2-F

30 g (103 mmol) of 1-A, 103 mmol of dibenzo [b, d] furan-2-ylboronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 32.8 g of compound 2-F (yield 84%).

MS [M + H] ⁺ = 379

제조예Production Example 2-7 2-7

Synthesis of Compound 2-G

30 g (103 mmol) of 1-A, 103 mmol of naphtho [2,3-b] benzofuran-4-ylboronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (309 mmol) and tetrakistriphenylphosphinepalladium (2 mmol) were added and the mixture was stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice from chloroform and hexane to give 35.3 g of compound 2-G (yield 80%).

MS [M + H] ⁺ = 429

제조예Production Example 3-1 3-1

Synthesis of Compound 3-A

25.5 g (70 mmol) of 2-A, 70 mmol of bis (pinacolato) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The obtained solid was purified by column chromatography with chloroform / hexanes to give 27.8 g (yield 87%) of compound 3-A.

MS [M + H] < + > = 457

제조예Production Example 3-2 3-2

Synthesis of Compound 3-B

25.5 g (70 mmol) of 2-B, 70 mmol of bis (pinacolacto) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The obtained solid was purified by column chromatography with chloroform / hexanes to give 28.1 g (yield 88%) of compound 3-B.

MS [M + H] < + > = 457

제조예Production Example 3-3 3-3

Synthesis of Compound 3-C

23.7 g (70 mmol) of 2-C, 70 mmol of bis (pinacolato) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The obtained solid was purified by column chromatography with chloroform / hexanes to give 25.6 g (yield 85%) of compound 3-C.

MS [M + H] < + > = 431

제조예Production Example 3-4 3-4

Synthesis of Compound 3-D

27.6 g (70 mmol) of 2-D, 70 mmol of bis (pinacolacto) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexanes to give 27.9 g of compound 3-D (yield 82%).

MS [M + H] < + > = 487

제조예Production Example 3-5 3-5

Synthesis of Compound 3-E

20.6 g (70 mmol) of 2-E, 70 mmol of bis (pinacolacto) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexanes to give 23.2 g (yield 86%) of compound 3-E.

MS [M + H] < + > = 386

제조예Production Example 3-6 3-6

Synthesis of Compound 3-F

26.5 g (70 mmol) of 2-F, 70 mmol of bis (pinacolacto) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The resulting solid was purified by chloroform / hexane using column chromatography to give 27.6 g of compound 3-F (84% yield).

MS [M + H] < + > = 471

제조예Production Example 3-7 3-7

Synthesis of Compound 3-G

30 g (70 mmol) of 2-G, 70 mmol of bis (pinacolato) diboron, 140 mmol of potassium acetate and 250 mL of 1,4-dioxane were mixed and heated to 100 ° C. Palladium acetate 1mmol% was added thereto, and the mixture was stirred for 12 hours under reflux. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was distilled off to obtain a solid. The obtained solid was purified by column chromatography with chloroform / hexanes to give 24.6 g (yield 82%) of compound 3-G.

MS [M + H] < + > = 429

제조예Production Example 4-1 4-1

compound 1One Synthesis of

13.7 g (30 mmol) of compound 3-A, 30 mmol of 3-chloro-2-phenylphenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice from chloroform and hexane to obtain Compound 1 (11 g) (yield 63%).

MS [M + H] ⁺ = 583

제조예Production Example 4-2 4-2

compound

22 Synthesis of

13.7 g (30 mmol) of compound 3-B, 30 mmol of 3-chloro-2-phenylphenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain Compound 2 (11.4 g) (yield 65%).

MS [M + H] ⁺ = 583

제조예Production Example 4-3 4-3

compound

33 Synthesis of

12.9 g (30 mmol) of compound 3-C, 30 mmol of 3-chloro-2-phenylphenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give compound 3 (10.2 g) (yield 61%).

MS [M + H] ⁺ = 557

제조예Production Example 4-4 4-4

compound

44 Synthesis of

14.6 g (30 mmol) of compound 3-D, 30 mmol of 3-chloro-2-phenylphenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give compound 4 (11.6 g) (yield 63%).

MS [M + H] ⁺ = 613

제조예Production Example 4-5 4-5

compound

55 Synthesis of

11.6 g (30 mmol) of Compound 3-E, 30 mmol of 3-chloro-2-phenylphenanthene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice from chloroform and hexane to give compound 5 (9.8 g) (yield 64%).

MS [M + H] ⁺ = 512

제조예Production Example 4-6 4-6

compound

66 Synthesis of

14.1 g (30 mmol) of compound 3-F, 30 mmol of 2-chloro-3-phenylphenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give compound 6 (10.9 g) (yield 61%).

MS [M + H] ⁺ = 597

제조예Production Example 4-7 4-7

compound

77 Synthesis of

15.6 g (30 mmol) of compound 3-G, 30 mmol of 2-chloro-3-phenylphenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give compound 7 (12.6 g) (yield 65%).

MS [M + H] ⁺ = 647

제조예Production Example 4-8 4-8

Synthesis of Compound 8

13.7 g (30 mmol) of compound 3-A, 30 mmol of 3-chloro-2- (naphthalen-1-yl) phenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice from chloroform and hexane to give compound 8 (11.9 g) (yield 63%).

MS [M + H] ⁺ = 633

제조예Production Example 4-9 4-9

Synthesis of Compound 9

13.7 g (30 mmol) of compound 3-A, 30 mmol of 3-chloro-2- (naphthalen-2-yl) phenanthrene, 100 mL of 1,4-dioxane and 50 mL of water were mixed and heated to 60 ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain compound 9 (11.6 g) (yield 61%).

MS [M + H] ⁺ = 633

제조예Production Example 4-10 4-10

Synthesis of Compound 10

Mix compound 3-A 13.7 g (30 mmol), 2-([1,1'-biphenyl] -3-yl) -3-chlorophenanthrene 30 mmol, 100 mL of 1,4-dioxane and 50 mL water, and mix 60 Heated to ° C. Potassium phosphate (90 mmol) and tetrakistriphenylphosphinepalladium (0.4 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to obtain compound 10 (13 g) (yield 66%).

MS [M + H] ⁺ = 659

Using the same reaction as in the above scheme, various kinds of substituents may be introduced to synthesize a compound represented by Chemical Formula 1.

<< 실험예Experimental Example >>

Comparative Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. The hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.

Compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 Pa), which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. It was.

The compound N-([1,1'-bisphenyl] -4-yl) -N- (4- (11-([1,1'-biphenyl] -4-yl) having a film thickness of 100 kPa on the hole transport layer ) -11H-benzo [a] carbazole-5-yl) phenyl)-[1,1'-biphenyl] -4-amine (EB 1) (100 Pa) was vacuum deposited to form an electron blocking layer.

Subsequently, the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the electron blocking layer with a film thickness of 300 Pa.

The following compound ET1 and the following compound LiQ (Lithium Quinolate) were vacuum-deposited on the emission layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.

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 ^{- The} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁶ torr.

[HAT]

[NPB]

Experimental Example 1-1 to 1-10

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 1H was prepared in Preparation Examples 1-1 to 4-10, and the compound shown in Table 1 was used instead of Compound BH.

Comparative example 1-1 to 1-3

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound of the following BH1 to BH3 shown in Table 1 instead of the compound BH.

When the current is applied to the organic light emitting device manufactured by Comparative Example 1, Experimental Examples 1-1 to 1-10 and Comparative Examples 1-1 to 1-3, the results of measuring the voltage, efficiency, color coordinates are shown in Table 1 below. Shown in

구분division	화합물(발광층)Compound (light emitting layer)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	색좌표(x,y)Color coordinates (x, y)
비교예 1Comparative Example 1	BHBH	4.44.4	55	(0.16, 0.19)(0.16, 0.19)
실험예 1-1Experimental Example 1-1	화합물 1 Compound 1	4.14.1	1313	(0.15, 0.18)(0.15, 0.18)
실험예 1-2Experimental Example 1-2	화합물 2 Compound 2	4.04.0	1212	(0.16, 0.19)(0.16, 0.19)
실험예 1-3Experimental Example 1-3	화합물 3 Compound 3	4.04.0	1313	(0.16, 0.18)(0.16, 0.18)
실험예 1-4Experimental Example 1-4	화합물 4 Compound 4	4.14.1	1111	(0.15, 0.18)(0.15, 0.18)
실험예 1-5Experimental Example 1-5	화합물 5 Compound 5	3.93.9	1212	(0.16, 0.19)(0.16, 0.19)
실험예 1-6Experimental Example 1-6	화합물 6 Compound 6	4.04.0	1111	(0.15, 0.18)(0.15, 0.18)
실험예 1-7Experimental Example 1-7	화합물 7 Compound 7	3.93.9	1313	(0.15, 0.19)(0.15, 0.19)
실험예 1-8Experimental Example 1-8	화합물 8 Compound 8	4.04.0	1111	(0.16, 0.19)(0.16, 0.19)
실험예 1-9Experimental Example 1-9	화합물 9Compound 9	4.04.0	1111	(0.15, 0.19)(0.15, 0.19)
실험예 1-10Experimental Example 1-10	화합물10Compound 10	3.93.9	1313	(0.15, 0.18)(0.15, 0.18)
비교예 1-1Comparative Example 1-1	BH1BH1	4.24.2	77	(0.16, 0.20)(0.16, 0.20)
비교예 1-2Comparative Example 1-2	BH2BH2	4.34.3	66	(0.16, 0.21)(0.16, 0.21)
비교예 1-3Comparative Example 1-3	BH3BH3	4.24.2	77	(0.17, 0.20)(0.17, 0.20)

As shown in Table 1, the devices of Experimental Examples 1-1 to 1-10 using the compound having the structure of Formula 1 as the core, the voltage is lower than the device using the compound of Compound BH in Comparative Example 1, the efficiency is Ascending results were obtained.

In addition, when comparing with the devices of Comparative Examples 1-1 to 1-3 it can be seen that when the compound of the general formula (1) is applied to the device, the characteristics are improved both in terms of voltage and efficiency.

As shown in Table 1, the compound bonded to the substituents at

positions

2 and 3 of the phenanthrene according to the present invention was confirmed that it is possible to implement a low-voltage, high efficiency organic light emitting device having high conductivity of holes and electrons.

Claims

Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

One of Ar1 and Ar2 is represented by the following formula (2),

The rest of Ar1 and Ar2 are substituted or unsubstituted aryl groups,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

[Formula 2]

In Formula 2, Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
The compound of claim 1, wherein Formula 1 is represented by Formula 1-1 or 1-2:

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2, R1, R2, Ar1, Ar2, and Ar3 are the same as defined in claim 1.
The compound of claim 1, wherein the remainder other than Formula 2 in Ar1 and Ar2 is a substituted or unsubstituted phenyl group.
The method according to claim 1, wherein Ar3 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzonaphthofuran group; Or a substituted or unsubstituted benzonaphthothiophene group.
The method of claim 1, wherein Ar3 is deuterium, or an aryl group unsubstituted or substituted with an aryl group; Or a heterocyclic group.
The compound of claim 1, wherein R 1 and R 2 are hydrogen.
The compound of claim 1, wherein the compound represented by Chemical Formula 1 is selected from the following structural formulas:
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 7. device.
The organic light emitting diode of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
The organic light emitting device of claim 8, wherein the organic material layer comprises a hole blocking layer, and the hole blocking layer comprises the compound.
The organic light emitting device of claim 8, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
The organic light emitting device of claim 8, wherein 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, the hole transport layer, or the hole injection and transport layer includes the compound.