KR102006433B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light emitting device using the same.

Description

Novel hetero-cyclic compound and organic light emitting device comprising the same

The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. The organic layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2013-073537

The present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1).

In Chemical Formula 1,

R ₁ and R ₂ are each independently substituted or unsubstituted C _1-60 alkyl or substituted or unsubstituted C _6-60 aryl,

L ₁ , L ₂ and L ₃ are each independently a direct bond, or a substituted or unsubstituted C _6-60 arylene,

X ₁ , X ₂ and X ₃ are each independently N or CR ′, provided that at least one of them is N,

R 'is hydrogen or substituted or unsubstituted C _1-60 alkyl,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted C _5-60 heteroaryl, pyridinyl, pyrimidinyl, tria, including one or more of O and S; Genyl, carbazolyl, isoquinolinyl or quinazolinyl, provided that at least one of Ar ₁ and Ar ₂ is substituted or unsubstituted C _5-60 heteroaryl, pyri containing at least one of O and S Dinil, pyrimidinyl, triazinyl, carbazolyl, isoquinolinyl or quinazolinyl.

In addition, the present invention 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 provides an organic light emitting device including the compound of the present invention.

The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.

Hereinafter, the present invention will be described in more detail to aid in understanding the present invention.

The present invention provides a compound represented by the following formula (1).

In Chemical Formula 1,

R ₁ and R ₂ are each independently substituted or unsubstituted C _1-60 alkyl or substituted or unsubstituted C _6-60 aryl,

L ₁ , L ₂ and L ₃ are each independently a direct bond, or a substituted or unsubstituted C _6-60 arylene,

X ₁ , X ₂ and X ₃ are each independently N or CR ′, provided that at least one of them is N,

R 'is hydrogen or substituted or unsubstituted C _1-60 alkyl,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted C _5-60 heteroaryl, pyridinyl, pyrimidinyl, tria, including one or more of O and S; Genyl, carbazolyl, isoquinolinyl or quinazolinyl, provided that at least one of Ar ₁ and Ar ₂ is substituted or unsubstituted C _5-60 heteroaryl, pyri containing at least one of O and S Dinil, pyrimidinyl, triazinyl, carbazolyl, isoquinolinyl or quinazolinyl.

및

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

And

Means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O and S atoms, or two or more substituents of the above-described substituents connected or substituted. . 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 and can be interpreted as a substituent to which two phenyl groups are linked.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, 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 However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.

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 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 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.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

And so on. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxdiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group and the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.

Preferably, the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 1-1 to 1-5.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Chemical Formulas 1-1 to 1-5,

R _1- , R ₂ , L ₁ , L ₂ , L ₃ , Ar ₁ and Ar ₂ are as defined above.

Preferably, L ₁ , L ₂ and L ₃ may each independently be any one selected from the group consisting of:

일 수 있다.Further, preferably, L ₁ , L ₂ and L ₃ are each independently a direct bond or

Can be.

Preferably, R ₁ and R ₂ may each independently be methyl or benzyl.

Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of:

.

.

However, in this case, at least one of these is selected from the following compounds.

.

.

Preferably, the compound represented by Formula 1 may be any one selected from the group consisting of:

.

.

Of the compounds represented by Chemical Formula 1, when L is not a single bond, it may be prepared by a preparation method such as the following Schemes 1 to 3. In the case where L is a single bond, it may be prepared by the same method as in Scheme 4 below.

First, according to Schemes 1-1 to 1-3, first intermediates 1, 2, 3 can be prepared.

Scheme 1-1

Scheme 1-2

Scheme 1-3

Next, according to Scheme 2, the first intermediate 1, 2, 3 as a reactant, the second intermediate 4, 5, 6 can be prepared.

Scheme 2

Finally, according to Scheme 3 with the second intermediate 4, 5, 6 as a reactant, the compound of formula 1 of the present invention can be prepared.

Scheme 3

When passing through the second intermediate, a compound in which L ₁ is a direct bond can be prepared.

According to another embodiment of the present invention, the compound of formula 1 of the present invention may be prepared according to Scheme 4 by using the first intermediate 1, 2, 3 as a reactant.

Scheme 4

In Schemes 1-1 to 1-3, Schemes 2, 3, and 4, R ₁ , R _2, L ₁ , L _2, L _3, Ar ₁ , and Ar ₁ are as defined above. The type of reactor and catalyst used in the above reaction scheme can be appropriately changed. The manufacturing method may be more specific in the production examples to be described later.

The production of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

The present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1. In one embodiment, the present invention 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 comprises a compound represented by Chemical Formula 1. do.

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

The organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole may be represented by Formula 1 above. It includes a compound represented.

In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

In addition, the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).

In addition, the electron transport layer, the electron injection layer, or a layer for simultaneously injecting and transporting electrons includes a compound represented by the formula (1). In particular, the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability. In addition, when the compound represented by Chemical Formula 1 is used in an organic material layer capable of simultaneously injecting and transporting electrons, an n-type dopant used in the art may be mixed and used.

In addition, the organic material layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.

In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of 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 an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

The organic light emitting device according to the present invention 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 represented by Chemical Formula 1. In addition, 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited 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 represented by Formula 1 may be formed as an organic 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 the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, the second electrode is an anode.

As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material 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); Combinations of oxides with metals such as ZnO: Al or SNO ₂ : 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 the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer 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 anode material and the HOMO of the surrounding organic 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. The hole transport layer is a material that can transport holes from an anode or a hole injection layer to a light emitting layer. This 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 carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group. At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, 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 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 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 for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, and the 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 organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The production of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

<Preparation Example 1> Preparation of Compound 1

[Compound 1]

Compound A (8.46g, 21.58mmol), (4- (4,6-di (pyridin-2-yl) -1,3,5-triazin-2-yl) phenyl) boronic in 500ml round bottom flask under nitrogen atmosphere acid (10.34g, 29.14mmol) is completely dissolved in 280ml of tetrahydrofuran, 2M potassium carbonate solution (140ml) is added, and tetrakis- (triphenylphosphine) palladium (0.76g, 0.66mmol) is added for 3 hours. Stirring while heating. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of tetrahydrofuran to prepare compound 1 (8.12 g, 56%).

MS [M + H] ⁺ = 668

<Preparation Example 2> Preparation of Compound 2

[Compound 2]

Compound A (7.15g, 18.24mmol), (3- (4,6-di (pyridin-2-yl) -1,3,5-triazin-2-yl) phenyl) boronic in 500ml round bottom flask under nitrogen atmosphere acid (8.74g, 24.62mmol) is completely dissolved in 260ml of tetrahydrofuran, 2M potassium carbonate solution (130ml) is added, and tetrakis- (triphenylphosphine) palladium (0.63g, 0.55mmol) is added for 4 hours. Stirring while heating. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of tetrahydrofuran to prepare Compound 2 (7.25 g, 60%).

MS [M + H] ⁺ = 668

<Preparation Example 3> Preparation of Compound 3

[Compound 3]

Compound A (6.27g, 15.99mmol), (4- (4-phenyl-6- (4- (pyridin-2-yl) phenyl) -1,3,5-triazin-2 in 500ml round bottom flask under nitrogen atmosphere -yl) phenyl) boronic acid (9.29g, 21.59mmol) was dissolved completely in 240ml of tetrahydrofuran, then 2M potassium carbonate solution (120ml) was added, and tetrakis- (triphenylphosphine) palladium (0.55g, 0.48mmol) ) Was added and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of tetrahydrofuran to prepare compound 3 (6.08 g, 51%).

MS [M + H] ⁺ = 743

<Preparation Example 4> Preparation of Compound 4

[Compound 4]

Compound A (5.96g, 15.20mmol), (4- (4,6-di (pyridin-4-yl) -1,3,5-triazin-2-yl) phenyl) boronic in 500ml round bottom flask under nitrogen atmosphere acid (7.29g, 20.53mmol) is completely dissolved in 240ml of tetrahydrofuran, 2M potassium carbonate solution (120ml) is added, and tetrakis- (triphenylphosphine) palladium (0.53g, 0.46mmol) is added for 4 hours. Stirring while heating. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of tetrahydrofuran to prepare compound 4 (7.76 g, 76%).

MS [M + H] ⁺ = 668

<Preparation Example 5> Preparation of Compound 5

[Compound 5]

Compound A (6.74g, 17.19mmol), (3- (4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazin- 2-yl) phenyl) boronic acid (8.00g, 18.05mmol) was dissolved completely in 220ml of tetrahydrofuran, then 2M aqueous potassium carbonate solution (110ml) was added, and tetrakis- (triphenylphosphine) palladium (0.60g, 0.52 mmol), and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 18 ml of tetrahydrofuran to prepare compound 5 (6.35 g, 49%).

MS [M + H] ⁺ = 756

<Production Example 6> Preparation of Compound 6

[Compound 6]

Compound A (5.96g, 15.20mmol), (3- (4-phenyl-6- (3- (pyridin-2-yl) phenyl) -1,3,5-triazin-2 in 500ml round bottom flask under nitrogen atmosphere -yl) phenyl) boronic acid (8.83g, 20.53mmol) was completely dissolved in 180ml of tetrahydrofuran, then 2M potassium carbonate solution (90ml) was added, and tetrakis- (triphenylphosphine) palladium (0.53g, 0.46mmol) ) Was added and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 190 ml of tetrahydrofuran to prepare compound 6 (4.78 g, 42%).

MS [M + H] ⁺ = 743

<Production Example 7> Preparation of Compound 7

[Compound 7]

Compound D (10.10g, 20.86mmol), 2-chloro-4,6-di (pyridin-2-yl) -1,3,5-triazine (4.88g, 18.14mmol) in 500ml round bottom flask in nitrogen atmosphere After completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (0.63g, 0.54mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of acetonitrile to prepare compound 7 (6.16 g, 57%).

MS [M + H] ⁺ = 592

<Preparation Example 8> Preparation of Compound 8

[Compound 8]

Tetra compound D (9.59g, 19.81mmol), 4-chloro-2-phenyl-6- (4- (pyridin-2-yl) phenyl) pyrimidine (6.47g, 18.86mmol) in 500ml round bottom flask in nitrogen atmosphere After completely dissolved in 200 ml of hydrofuran, 2 M aqueous potassium carbonate solution (100 ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (0.65 g, 0.57 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of acetonitrile to prepare compound 8 (8.43 g, 67%).

MS [M + H] ⁺ = 666

<Preparation Example 9> Preparation of Compound 9

[Compound 9]

Tetra compound D (9.59g, 19.81mmol), 4-chloro-2-phenyl-6- (3- (pyridin-2-yl) phenyl) pyrimidine (6.47g, 18.86mmol) in a 500ml round bottom flask in a nitrogen atmosphere After completely dissolved in 200ml of hydrofuran 2M. Aqueous potassium carbonate solution (100 ml) was added, tetrakis- (triphenylphosphine) palladium (0.65 g, 0.57 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of acetonitrile to prepare compound 9 (8.43 g, 67%).

MS [M + H] ⁺ = 666

<Preparation Example 10> Preparation of Compound 10

[Compound 10]

In a 500 ml round-bottom flask in a nitrogen atmosphere, compound D (7.71g, 15.93mmol), 2-chloro-6-phenyl-4- (4- (pyridin-2-yl) phenyl) pyridine (5.19g, 15.18mmol) After completely dissolved in 210 ml of hydrofuran, 2M aqueous potassium carbonate solution (100 ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (0.53 g, 0.46 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 190 ml of acetonitrile to prepare compound 10 (6.95 g, 69%).

MS [M + H] ⁺ = 665

<Preparation Example 11> Preparation of Compound 11

[Compound 11]

Compound D (9.35g, 19.32mmol), 8- (4- (4-chloro-6-phenyl-1,3,5-triazin-2-yl) phenyl) quinoline (7.25g) in 500ml round bottom flask in nitrogen atmosphere , 18.40 mmol) was completely dissolved in 200 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (100 ml) was added thereto, followed by addition of tetrakis- (triphenylphosphine) palladium (0.63 g, 0.54 mmol), followed by heating and stirring for 4 hours. . The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 200 ml of acetonitrile to prepare compound 11 (7.22 g, 55%).

MS [M + H] ⁺ = 717

<Preparation Example 12> Preparation of Compound 12

[Compound 12]

Compound A (5.29 g, 13.49 mmol), (3- (4-phenyl-6- (4- (pyridin-3-yl) phenyl) -1,3,5-triazin-2 in a 500 ml round bottom flask under nitrogen atmosphere -yl) phenyl) boronic acid (6.09 g, 14.17 mmol) was completely dissolved in 160 ml of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (80 ml), and tetrakis- (triphenylphosphine) palladium (0.47 g, 0.40 mmol). ) Was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 150 ml of tetrahydrofuran to prepare compound 12 (6.27 g, 63%).

MS [M + H] ⁺ = 743

<Preparation Example 13> Preparation of Compound 13

[Compound 13]

Compound E (9.53g, 19.69mmol), 2-chloro-4-phenyl-6- (4- (pyridin-2-yl) phenyl) -1,3,5-triazine (5.89) in 500ml round bottom flask in nitrogen atmosphere g, 17.12 mmol) was completely dissolved in 220 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (110 ml) was added, followed by addition of tetrakis- (triphenylphosphine) palladium (0.59 g, 0.51 mmol), followed by heating and stirring for 4 hours. It was. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 ml of acetonitrile to prepare compound 13 (10.07 g, 69%).

MS [M + H] ⁺ = 590

<Preparation Example 14> Preparation of Compound 14

[Compound 14]

Compound E (8.53g, 17.63mmol), 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (dibenzo [b, d] thiophen-2 in 500ml round bottom flask under nitrogen atmosphere -yl) -1,3,5-triazine (8.53 g, 78.63 mmol) was completely dissolved in 210 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (105 ml), and tetrakis- (triphenylphosphine) palladium (0.64 g, 0.56 mmol), and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270ml of acetonitrile to prepare Compound 14 (10.25g, 70%).

MS [M + H] ⁺ = 786

<Preparation Example 15> Preparation of Compound 15

[Compound 15]

Compound B (5.38 g, 13.72 mmol), (3- (4-phenyl-6- (3- (pyridin-2-yl) phenyl) -1,3,5-triazin-2 in a 500 ml round bottom flask under nitrogen atmosphere -yl) phenyl) boronic acid (6.79g, 15.78mmol) was completely dissolved in 180ml of tetrahydrofuran, then 2M potassium carbonate solution (90ml) was added, and tetrakis- (triphenylphosphine) palladium (0.48g, 0.41mmol) ) Was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of ethyl acetate to obtain Compound 15 (8.13 g, 80%).

MS [M + H] ⁺ = 743

<Preparation Example 16> Preparation of Compound 16

[Compound 16]

Compound F (11.91g, 24.62mmol), 2-chloro-4,6-di (pyridin-4-yl) -1,3,5-triazine (6.97g, 25.91mmol) in 500ml round bottom flasks under nitrogen atmosphere After completely dissolved in 220 ml of tetrahydrofuran, an aqueous 2M potassium carbonate solution (110 ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (0.70 g, 0.61 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 ml of ethyl acetate to obtain compound 16 (11.33 g, 74%).

MS [M + H] ⁺ = 592

<Preparation Example 17> Preparation of Compound 17

[Compound 17]

Compound F (9.69g, 20.02mmol), 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (in a 500ml round bottom flask in nitrogen atmosphere) 7.52g, 21.06mmol) was completely dissolved in 200ml of tetrahydrofuran, 2M potassium carbonate solution (100ml) was added, tetrakis- (triphenylphosphine) palladium (0.73g, 0.63mmol) was added and heated for 5 hours. Stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 200 ml of tetrahydrofuran to prepare compound 17 (12.23 g, 74%).

MS [M + H] ⁺ = 680

<Example 18> Preparation of compound 18

[Compound 18]

Compound F (10.20g, 21.07mmol), 2-chloro-4-phenyl-6- (3- (pyridin-2-yl) phenyl) -1,3,5-triazine (7.63) in 500ml round bottom flask in nitrogen atmosphere g, 22.18 mmol) was completely dissolved in 200 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (100 ml) was added, followed by addition of tetrakis- (triphenylphosphine) palladium (0.77 g, 0.67 mmol), followed by heating and stirring for 6 hours. It was. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of tetrahydrofuran to prepare compound 18 (9.79 g, 66%).

MS [M + H] ⁺ = 667

<Preparation Example 19> Preparation of Compound 19

[Compound 19]

Compound C (6.86g, 17.50mmol), (3- (4-phenyl-6- (4- (pyridin-2-yl) phenyl) -1,3,5-triazin-2 in 500ml round bottom flask under nitrogen atmosphere -yl) phenyl) boronic acid (7.15g, 16.63mmol) was dissolved completely in 210ml of tetrahydrofuran, then 2M potassium carbonate solution (105ml) was added, and tetrakis- (triphenylphosphine) palladium (0.61g, 0.53mmol) ) Was added and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to prepare compound 19 (10.07 g, 77%).

MS [M + H] ⁺ = 743

<Preparation Example 20> Preparation of compound 20

 [Compound 20]

Compound C (8.03g, 20.48mmol), (4- (4-phenyl-6- (4- (quinolin-8-yl) phenyl) -1,3,5-triazin-2 in 500ml round bottom flask under nitrogen atmosphere -yl) phenyl) boronic acid (10.32g, 21.51mmol) was dissolved completely in 200ml of tetrahydrofuran, then 2M potassium carbonate solution (100ml) was added, and tetrakis- (triphenylphosphine) palladium (0.71g, 0.61mmol) ) Was added and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to prepare compound 20 (10.19 g, 63%).

MS [M + H] ⁺ = 793

<Preparation Example 21> Preparation of compound 21

[Compound 21]

Compound D (5.93g, 12.25mmol), 3- (4-chloro-6-phenyl-1,3,5-triazin-2-yl) -9-phenyl-9H-carbazole (in a 500ml round bottom flask in a nitrogen atmosphere 5.29g, 12.25mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M potassium carbonate solution (120ml) was added, and tetrakis- (triphenylphosphine) palladium (0.42g, 0.37mmol) was added and heated for 3 hours. Stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of acetonitrile to prepare Compound 21 (6.39 g, 69%).

MS [M + H] ⁺ = 755

<Preparation Example 22> Preparation of Compound 22

[Compound 22]

Compound A (6.17g, 15.74mmol), (3- (4- (4- (9H-carbazol-9-yl) phenyl) -6-phenyl-1,3,5-triazin in 500ml round bottom flask under nitrogen atmosphere -2-yl) phenyl) boronic acid (8.15g, 15.74mmol) was completely dissolved in 200ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (100ml) was added, followed by tetrakis- (triphenylphosphine) palladium (0.47g, 0.40 mmol) was added thereto, followed by stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 170 ml of tetrahydrofuran to prepare Compound 22 (10.09 g, 77%).

MS [M + H] ⁺ = 831

Preparation of <Production Example 23> Compound 23

[Compound 23]

Compound E (8.69g, 17.96mmol), 2- (4-chloro-6-phenyl-1,3,5-triazin-2-yl) -9-phenyl-9H-carbazole (in a 500ml round bottom flask in a nitrogen atmosphere 7.76g, 17.96mmol) was completely dissolved in 230ml of tetrahydrofuran, 2M potassium carbonate solution (115ml) was added, tetrakis- (triphenylphosphine) palladium (0.62g, 0.54mmol) was added and heated for 3 hours. Stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 ml of acetonitrile to prepare Compound 23 (9.76 g, 72%).

MS [M + H] ⁺ = 755

< Experimental 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 100 kPa on the prepared ITO transparent electrode to form a hole injection layer.

[HAT]

The following compound 4,4 '-(9-phenyl-9H-carbazole-3,6-diyl) bis (N, N-diphenylaniline) [HT 1] (1150 kV), which is a material for transporting holes on the hole injection layer, was vacuumed. It was deposited to form a hole transport layer.

[HT 1]

Subsequently, the following compound [EB 1] was vacuum deposited to a film thickness of 100 kPa on the hole transport layer to form an electron blocking layer.

[EB 1]

Subsequently, BH and BD as described below were vacuum-deposited at a weight ratio of 25: 1 on the electron blocking layer to form a light emitting layer.

[BH] [BD]

[HB 1] [ET 1]

[LiQ]

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

Subsequently, Compound ET 1 and Compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 310 Å. Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 Å 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, the degree of vacuum upon deposition ⅹ10 2 ^-7 The organic light emitting device was manufactured by maintaining ˜5 × 10 ⁻⁶ torr.

< Example  1-1 to 1-16

The organic light emitting device was manufactured by the same method as Experimental Example 1, but using the compound shown in Table 1 below instead of Compound HB 1 used in Experimental Example 1.

< Comparative example  1>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the following compound of HB 2 was used instead of compound EB 1 in Example 1-1.

[HB 2]

< Comparative example  2>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the compound of EB 3 below instead of compound EB 1 in Example 1-1.

[EB 3]

When the current was applied to the organic light emitting devices manufactured by Experimental Example 1, Examples 1-1 to 1-16, Comparative Example 1 and Comparative Example 2, the voltage, efficiency, color coordinates and lifespan were measured and the results are as follows. Table 1]. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1300 nits).

division compound
(Hole blocking layer) Voltage
(V @ 10mA
/ cm ² ) efficiency
(cd / A @ 10mA
/ cm ² ) Color coordinates
(x, y) T95
(hr) Experimental Example 1 HB 1 5.15 47.51 (0.141, 0.045) 225 Example 1-1 Compound 3 4.73 46.83 (0.142, 0.044) 260 Example 1-2 Compound 5 4.52 48.02 (0.140, 0.044) 260 Example 1-3 Compound 6 4.81 47.74 (0.139, 0.047) 270 Example 1-4 Compound 8 4.65 47.95 (0.141, 0.047) 280 Example 1-5 Compound 9 4.77 47.85 (0.142, 0.044) 280 Example 1-6 Compound 10 4.86 47.76 (0.140, 0.044) 290 Example 1-7 Compound 12 4.75 47.84 (0.139, 0.047) 275 Example 1-8 Compound 13 4.84 47.77 (0.141, 0.047) 270 Example 1-9 Compound 14 4.69 47.98 (0.138, 0.046) 275 Example 1-10 Compound 15 4.68 47.93 (0.139, 0.047) 275 Example 1-11 Compound 17 4.67 47.95 (0.141, 0.047) 270 Example 1-12 Compound 18 4.68 47.93 (0.139, 0.047) 275 Example 1-13 Compound 19 4.67 47.95 (0.141, 0.047) 270 Example 1-14 Compound 21 4.63 47.87 (0.141, 0.045) 280 Example 1-15 Compound 22 4.55 48.16 (0.142, 0.046) 265 Example 1-16 Compound 23 4.87 47.78 (0.141, 0.045) 260 Comparative Example 1 HB 2 5.05 45.55 (0.141, 0.045) 225 Comparative Example 2 HB 3 5.90 45.11 (0.143, 0.048) 235

As shown in Table 1, the organic light emitting device manufactured by using the compound of the present invention as a hole blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Comparative Examples 1 of Spirobifluorene Core and Comparative Example 2 of 9,10-dimetylfluorene Core The organic light emitting device manufactured by using the compound as a hole blocking layer exhibits the characteristics of low voltage, high efficiency and long life.

The core of the present invention has a relatively higher content of electrons than Spirobifluorene and 9,10-dimetylfluorene cores, and when used as a hole blocking layer has a strength in the voltage and efficiency without reducing the life.

As shown in Table 1, the other compounds of the present invention was confirmed that the hole blocking ability is excellent can be applied to the organic light emitting device.

< Example  2-1 to 2-22>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compounds 1 to 23 instead of ET 1 as the electron transport layer in Experimental Example 1.

< Comparative example  3>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound of ET 2 instead of using ET 1 as the electron transport layer in Experimental Example 1.

[ET 2]

< Comparative example  4>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound of ET 3 instead of using ET 1 as the electron transport layer in Experimental Example 1.

 [ET 3]

< Comparative example  5>

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of ET 4 instead of using ET 1 as the electron transport layer in Example 1.

[ET 4]

When the current was applied to the organic light emitting diodes manufactured according to Examples 2-1 to 2-22 and Comparative Examples 3 to 5, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in the following [Table 2]. Indicated. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1300 nits).

division compound
(Electronic transport layer) Voltage
(V @ 10mA
/ cm ² ) efficiency
(cd / A @ 10mA
/ cm ² ) Color coordinates
(x, y)
T95 (hr) Example 2-1 Compound 1 4.50 46.51 (0.140, 0.045) 285 Example 2-2 Compound 2 4.63 46.33 (0.141, 0.046) 275 Example 2-3 Compound 3 4.61 46.52 (0.142, 0.047) 300 Example 2-4 Compound 4 4.51 46.61 (0.142, 0.045) 305 Example 2-5 Compound 5 4.62 46.76 (0.138, 0.046) 285 Example 2-6 Compound 6 4.53 46.55 (0.142, 0.047) 295 Example 2-6 Compound 7 4.64 46.68 (0.141, 0.045) 280 Example 2-7 Compound 8 4.65 46.77 (0.142, 0.044) 290 Example 2-8 Compound 9 4.56 46.89 (0.141, 0.046) 310 Example 2-9 Compound 10 4.67 46.63 (0.143, 0.045) 295 Example 2-10 Compound 11 4.68 46.47 (0.138, 0.044) 285 Example 2-11 Compound 12 4.69 45.75 (0.142, 0.045) 275 Example 2-12 Compound 13 4.58 46.84 (0.142, 0.044) 290 Example 2-13 Compound 14 4.69 45.63 (0.141, 0.046) 280 Example 2-14 Compound 15 4.55 46.75 (0.143, 0.045) 295 Example 2-15 Compound 16 4.63 45.61 (0.138, 0.044) 295 Example 2-16 Compound 17 4.55 46.41 (0.142, 0.045) 300 Example 2-17 Compound 18 4.46 47.11 (0.141, 0.046) 280 Example 2-18 Compound 19 4.58 46.82 (0.141, 0.045) 295 Example 2-19 Compound 20 4.67 46.36 (0.138, 0.045) 295 Example 2-20 Compound 21 4.63 45.59 (0.142, 0.044) 300 Example 2-21 Compound 22 4.54 46.72 (0.142, 0.045) 280 Example 2-22 Compound 23 4.65 45.72 (0.141, 0.046) 295 Comparative Example 3 ET 2 4.85 44.91 (0.143, 0.047) 235 Comparative Example 4 ET 3 4.92 45.13 (0.143, 0.045) 205 Comparative Example 5 ET 4 4.87 44.84 (0.143, 0.045) 185

As shown in Table 2, in the case of the organic light emitting device manufactured using the compound of the present invention as an electron transport layer, it shows excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

The compound of Comparative Example 1 of Spirobifluorene core and Comparative Example 2 of 9,10-dimetylfluorene core shows lower voltage, higher efficiency and longer life than organic light emitting device manufactured using electron transport layer.

The core of the present invention has a relatively higher content of electrons than Spirobifluorene and 9,10-dimetylfluorene cores, and when used as an electron transport layer, the lifespan is increased by 15% to 30%, showing strength in voltage and efficiency.

In Comparative Examples 4 and 5 in which benzoimidazole is substituted with a triazine substituted, it can be seen that the lifespan is greatly decreased.

Although the preferred embodiments (hole blocking layer, electron transport layer) of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. This also belongs to the scope of the invention.

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

Claims (9)

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

In Chemical Formula 1,
R ₁ and R ₂ are each independently substituted or unsubstituted C _1-60 alkyl or substituted or unsubstituted C _6-60 aryl,
L ₁ , L ₂ and L ₃ are each independently a direct bond, or a substituted or unsubstituted C _6-60 arylene,
X ₁ , X ₂ and X ₃ are each independently N or CR ′, provided that at least one of them is N,
R 'is hydrogen or substituted or unsubstituted C _1-60 alkyl,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted C _5-60 heteroaryl, pyridinyl, pyrimidinyl, tria, including one or more of O and S; Genyl, carbazolyl, isoquinolinyl or quinazolinyl, provided that at least one of Ar ₁ and Ar ₂ is substituted or unsubstituted C _5-60 heteroaryl, pyri containing at least one of O and S Diyl, pyrimidinyl, triazinyl, carbazolyl, isoquinolinyl or quinazolinyl.
The method of claim 1,
The compound represented by Formula 1 is any one selected from compounds represented by Formulas 1-1 to 1-5, wherein:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Chemical Formulas 1-1 to 1-5,
R ₁ , R ₂ , L ₁ , L ₂ , L ₃ , Ar ₁ and Ar ₂ are as defined in claim 1.
The method of claim 1,
R ₁ and R ₂ are each independently methyl or benzyl.
The method of claim 1,
L ₁ , L ₂ and L ₃ are each independently a direct bond or any one selected from the group consisting of:

.
The method of claim 1,
L ₁ , L ₂ and L ₃ are each independently a direct bond or

Phosphorus, compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

.
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 comprises a compound according to any one of claims 1 to 7. That is, an organic light emitting device.
The method of claim 8,
The organic material layer containing the compound is an electron injection layer; Electron transport layer; Or a layer that simultaneously performs electron injection and electron transport.

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