WO2018225940A1 - Novel heterocyclic compound and organic light-emitting element using same - Google Patents

Abstract

The present invention relates to a novel heterocyclic compound and a light-emitting element comprising the same.

Description

 [Name of invention]

 Novel heterocyclic compound and organic light emitting device using the same

Technical Field

 Cross Citation with Related Applications

 This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0070988 dated June 7, 2017 and Korean Patent Application No. 10-2017-0160633 dated November 28, 2017. All content disclosed in the literature is included as part of this specification. The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same.

[Technology behind the invention]

 In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic electroluminescent device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted. The organic EL device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to increase the efficiency and stability of the organic EL device, the organic layer is often formed of a multilayer structure composed of different materials. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. .

 When the voltage is applied between the two electrodes in the structure of the organic EL 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 electrons meet each other. When this axtone falls back to the ground, it glows.

For the organic material used in the organic electroluminescent device as described above, the development of new materials is continuously required. Prior Art Documents

 [Patent literature]

 (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 (2000.08.16)

[Content of invention]

 Problem to be solved

 The present invention is to provide a novel heterocyclic compound as an organic electroluminescent compound.

 The present invention also provides an organic electroluminescent device comprising the heterocyclic compound.

[Measures of problem]

 According to the present invention there is provided a compound represented by the following formula (1):

 [Formula 1]

 In Chemical Formula 1,

 Each X is independently N or CR0, at least two of X are N,

R ⁰ is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group C _1-30 alkyl group, C ₂ ᅳ ₃₀ alkenyl group, C ₂ ᅳ ₃₀ alkynyl group, d ᅳ ₃₀ alkoxy group, C ₀ aryloxy group, or C _A C ₆ ᅳ ₅₀ aryl group unsubstituted or substituted with a _6-30 aryl group; Or deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C _1-30 , an alkenyl group of C _2-30 , C ₂ , including any one or more heteroatoms selected from the group consisting of N, O, and S Or a C _2-50 heteroaryl group which is unsubstituted or substituted with an alkynyl group of _-30 , an alkoxy group of C _1-30, an aryloxy group of C _{6 30} , or an aryl group of C _M0 , and Y is O or S,

U and L ² are each independently a direct bond; Or unsubstituted or deuterium, halogen, amino, nitrile, nitro, C _1-30 alkyl, C _2-30 alkenyl, C _2-30 alkynyl, C _1-30 alkoxy, € _6-30 aryloxy group, or C _6-20 arylene group substituted with a C _6-30 aryl group,

 m and n are each independently an integer of 0 to 2,

Ar ⁱ and Ar ² are each independently hydrogen; Distillate; Deuterium, halogen, amino group, nitrile group, nitro group, C _1-30 alkyl group, C _2-30 alkenyl group, C _2-30 alkynyl group, C _1-30 alkoxy group, C _6-30 aryl jade group, or an aryl group substituted with a C _6-30 aryl or unsubstituted C ₆ -50; Or N, O, and includes any one or more heteroatoms selected from the group consisting of S and C heteroaryl group substituted with an aryl group or a non-substituted C _{2- 50 6-30,} and

Ar ³ is a C6_6o aryl group. In addition, according to the present invention,

 An organic electroluminescent device comprising 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;

 At least one layer of the organic material layer is provided with an organic electroluminescent device comprising a compound represented by the formula (1).

【Effects of the Invention】

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

[Brief Description of Drawings]

 FIG. 1 shows an example of an organic electroluminescent 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 electroluminescent device composed 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 shown. ^"

[Specific contents to carry out invention]

 Hereinafter, the compound and the organic electroluminescent device including the same according to the embodiments of the present invention will be described in detail to help the benefit of the present invention. Unless expressly stated herein, the terminology is merely for reference to particular embodiments and is not intended to limit the invention. As used herein, the singular forms “a”, “an” and “the” include plural forms as well, unless the phrases clearly indicate the opposite.

 As used herein, the meaning of "includes" specifies a particular characteristic, region, integer, step, operation, element and / or component, and other specific characteristics, region, integer, step, operation, element, component and / or component. Except for the presence or addition of armies, it is not.

In the present specification, the mark of the formula indicates a part in which the group is connected to another group. 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; What is thioxy 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 one of the N, ᄋ, and S atoms It means substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including the above, or substituted or unsubstituted with two or more substituents in the above-described substituents. For example, the substituent "to which the ^π 2 or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group and may be interpreted as a substituent to which two phenyl groups are linked. In the present specification, the alkyl group may be straight or branched chain. The carbon number is not particularly limited but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20. 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, and specific examples of the alkyl group include methyl, ethyl, propyl, η-propyl, isopropyl, butyl, η-butyl, isobutyl, tert-butyl, sec -Butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4-methyl -2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnuclear, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2-propylpentyl, n-nonyl, 2,2- Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isonuclear, 2-methylpentyl, 4-methylnuclear, 5-methylnuclear, and the like, but are not limited to these. The group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20. According to another embodiment, the alke The carbon number of the alkyl group is 2 to 10. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples of the alkenyl group 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- Mono, 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, an alkynyl group is a monovalent group in a form in which one hydrogen atom is removed from an alkyne having 2 to 30 carbon atoms or a derivative thereof. 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. In the present specification, a fluorenyl group may be substituted, and two substituents may form a binder spiro structure with each other. 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 ring group including one or more of O, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic group are thiophene group, a furan group, a group of blood, imidazole group, thiazole group, oxazole group, oxadiazole group, a triazole group, a pyridyl group, a non-pyridyl group, a pyrimidinyl group, _a, triazole oscillator, triazole Drowsiness, acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolin group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, iso Quinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thia Zolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, ^{Phenothiazinyl} groups, dibenzofuranyl groups, and the like, but are not limited thereto. In the present specification, the description of the aryl group described above may be applied except that arylene is a divalent group. Except that the heteroarylene is a divalent group, the description of the heterocyclic group described above may be applied. On the other hand, according to one embodiment of the invention, a compound represented by the following formula (1) is provided.

 [Formula 1]

As a result of continuous studies by the present inventors, the compound represented by Chemical Formula 1 has two substituent groups introduced into one of the two benzene rings constituting the dibenzofuran or dibenzothiophene group, and the structural formula With the features, it is possible to improve the efficiency and lifespan characteristics of the organic EL device. In Formula 1, X is each independently N or CR ⁰ , and at least two of X is N. Wherein R ⁰ is hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C _1-30 alkyl group, C _2-30 alkenyl group, C _2-30 alkynyl group, C _1-30 alkoxy group, C6-30 aryloxy group Or a C _6-50 aryl group unsubstituted or substituted with a C _6-30 aryl group; Or N, O, and which contains one or more heteroatoms selected from the group consisting of S and deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkenyl group of C _1-30 alkyl group, C ₂ of _30, C _{2 30} the alkynyl group, may be an a C _1-30 alkoxy group, C ₆ ^ aryloxy, substituted or unsubstituted, a C _6-30 aryl or C _2-50 heteroaryl.

Preferably, X is N or CH, respectively, and at least two of X may be N. In Formula 1, Υ is O or S. In Formula 1, L ⁱ and L ² are each independently a direct bond; Or unsubstituted or heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C _1-30, C ₂ - ₃₀ alkenyl, C _2. C _6-20 arylene group substituted with ₃₀ alkynyl group, C alkoxy group, ^ aryloxy group, or C _6-30 aryl group. In Formula 1, m and n are each independently an integer of 0 to 2. Specifically, m and n may be each independently 0 or 1. In Formula 1, Ar ¹ and Ar ² are each independently hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C _1-30 alkyl group, C _2-30 alkenyl group, C _2-30 alkynyl group, C _1-30 alkoxy group, C _6-30 aryl jade C _6-50 aryl group which is unsubstituted or substituted with an aryl group of C _6-30 ; Or a C _2-50 heteroaryl group which contains one or more heteroatoms selected from the group consisting of N, O and S and which is optionally substituted with an aryl group of C _6-30 .

Preferably, Ar ⁱ and Ar ² are each independently hydrogen or an aryl group of C _6-50 . In Formula 1, Ar ³ is an aryl group of C _{6 0} .

Specifically, Ar ³ may be a phenyl group, biphenyl group, terphenyl group, natyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, or substituted or unsubstituted fluorenyl group. . Specifically, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6:

 [Formula 1-1]

[Formula 1-3]

[Formula 1-4]

[Formula 1-6]

In Chemical Formulas 1-1 to 1-6,

X, Y, U, L ² , m, Ar, Ar ² , and Ar ³ are each as defined in Chemical Formula 1. Representative examples of the compound represented by Formula 1 are as follows:

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

-2-13 1-2-14 1-2-15 1-2-16

-2-21 1-2-22 1-2-23 1-2-24

-2-41 1-2-42 1-2-43 1-2-44

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

-6-13 1-6-14 1-6-15 1-6-16

The compound represented by Chemical Chemistry 1 may be prepared by the same method as in Scheme 1 below. The manufacturing method may be more specific in the production examples to be described later.

In the reaction form 1,

X ¹ to X ³ are each independently -CI, -Br, -I, -OTf, -ONf,-are the same groups as i, and χι and X ² are different groups;

X, VII, ΙΛ L ² , m, Ar ⁱ , Ar ² , and Ar ³ are the same as defined in Chemical Formula 1. On the other hand, according to another embodiment of the invention, there is provided an organic electroluminescent device comprising a compound represented by the formula (1).

 For example, according to the present invention, there is provided an organic electroluminescent device comprising 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. ; At least one layer of the organic material layer is provided with an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1.

The organic material layer of the organic electroluminescent device of the present invention may have a single layer structure, or may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic EL 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 electroluminescent element is not limited to this and is less It may comprise a number of organic layers.

 In addition, the organic layer may include a hole injection layer / a hole transport layer, or a layer for simultaneously injecting and transporting a hole, the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole is represented by the formula (1) 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 material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.

 In addition, the electron transport layer, the electron injection layer, or the layer for simultaneously transporting electrons and electron injection comprises a compound represented by the formula (1).

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

 In addition, the organic electroluminescent device according to the present invention may be an organic electroluminescent 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 electroluminescent device according to the present invention may be an organic electroluminescent 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 EL device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

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

2 shows an example of an organic electroluminescent device composed 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 shown. In the structure as shown in FIG. 2, the compound represented by Chemical Formula 1 may include at least one of the hole injection layer, the hole transport layer, and the electron transport layer; Preferably it may be included in the hole transport layer. On the other hand, the organic electroluminescent device according to the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer comprises a compound represented by the formula (1).

 In addition, when the organic EL 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 EL 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 EL 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 EL device. Here, solution coating means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, coating, and the like, but is not limited thereto.

 In addition to the method described above, an organic EL device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (WO 2003/012890). 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 vanadium, chromium, copper, zinc / gold, and the like. Metals or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); 조합 a combination of a metal and an oxide, such as ^η Ο: Α1 or SN02: 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 negative electrode 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 Li0 ₂ / Al, and the like, but are not limited thereto.

 The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer. To the electron injection layer or electron injection material of the excited excitons. The compound which prevents 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 matter, nucleonitrile-nucleated azatriphenylene-based organic material, quinacridone-based organic material, and perylene Organic, 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 capable of transporting holes from the anode or the hole injection layer and transferring the holes to the light emitting layer. This is suitable.

Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a nonconjugated portion together. 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 of the light emitting material include 8-hydroxyquinoline aluminum complex (Alq 3); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (P-phenylenevinylene) (PPV) family; 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, srylyl 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, and a styrylamine compound may be substituted or unsubstituted. 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 transporting material is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transporting material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. This is suitable. Specific examples of the electron transporting material include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; 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 the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the 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.

 Specific examples of the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyranone dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, and Tron and the like, derivatives thereof, metal complex compounds and 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 and bis (8-hydroxyquinolinato) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h ] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium, etc. There is, but is not limited to this.

 The organic electroluminescent 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 is in addition to the organic electroluminescent device It can be applied to organic solar cells or organic transistors. Hereinafter, preferred embodiments will be presented to aid in understanding the invention. However, the following examples are only to illustrate the invention, not limited to the invention only.

1-1-1A under 1-1-1 B nitrogen stream, the compound 1-1-1A (20 Ό g, 60.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine ( 16.3 g, 60.9 mmol) and potassium carbonate (19.6 g, 141.1 mmol) were added to THF (250 mL) and stirred with heat. tetrakis (triphenylphosphine) palladium (0) (2.11 g, 1.83 mmol) was added thereto, followed by heating and stirring for 4 hours. After cooling to room temperature, ethanol slurry was purified to prepare the compound ll-lB (25 g, yield 94.7%) (MS: [M + H] ⁺ = 434).

Under nitrogen stream, the compound ll-lB (25 g, 5 g 6 mmol), [1,1'-biphenyl] -4-yl boronic acid (11.4 g, 57.6 mmol) and potassium carbonate (15.9 g, 115.2 mmol) Was added to THF (300 mL) and stirred with heat. Potassium acetate (0.39 g, 1.73 mmol) and s-phos (1.41 g, 3.46 mmol) ligands were added and stirred under heating for 2 hours. After cooling to room temperature, the ethanol slurry was purified to prepare compound 1-1-1 (29 g, yield 91.3%) (MS: [M + H] ⁺ = 5 ⁵ 2).

 1-1 -2A -1-2B 1 -1-2 under nitrogen stream, compound 1-1-2A (20.0 g, 58.0 mmol), 2-chloro-4,6-diphenyl-1,3,5- Triazine (15.5 g, 58.0 mmol) and potassium carbonate (16.0 g, 116.1 mmol) were added to THF (250 mL) and stirred with heat.

Tetrakis (triphenylphosphine) palladium (0) (2.01 g, 1.74 mmol) was added thereto, followed by heating and stirring for 4 hours. After cooling to room temperature, ethane was slurry purified to prepare Compound 1-1-2B (24.0 g, yield 92.0%) (MS: [M + H] ⁺ = 450).

Under nitrogen stream, the compound ll-2B (24 g, 53.3 mmol), biphenyl] -4-yl boronic acid (10.6 g, 53.3 mmol) and potassium carbonate (14.7 g, 106.6 mmol) were added to THF (300 mL). It stirred by heating. Potassium acetate (0.36 g, 1.60 mmol) and s-phos (1.31 g, 3.20 mmol) ligands were added and stirred under heating for 2 hours. Purified with silver and then purified by ethanol slurry to prepare compound 1-1-2 (28 g, yield 92.6%) (MS: [M + H] ⁺ = 568).

1-1 -3 A -1-3B 1-1-3 Under nitrogen stream, compound 1-1-3 A (20.0 g, 60.9 mmol), 2-chloro-4,6-diphenyl-1,3, 5-triazine (16.3 g, 60.9 mmol) and potassium carbonate (16.8 g, 121.8 mmol) was added to THF (250 mL) and stirred with heating.

Tetrakis (triphenylphosphine) palladium (0) (2.11 g, 1.83 mmol) was added thereto, followed by heating and stirring for 4 hours. After cooling to room temperature, the ethanol slurry was purified to prepare compound 1-1-3B ( ²⁴ .5 g, yield 9Z8%) (MS: [M + H] ⁺ = ⁴ 3 ⁴ )

Under a stream of nitrogen, the compound ll-3B (24.5 g, 56.5 mmol), triphenylene-1-yl boronic acid (15.4 g, 56.5 mmol) and potassium carbonate (15.6 g, 112.9 mmol) were added to THF (300 mL). The mixture was heated and stirred. Potassium acetate (0.38 g, 1.69 mmol) and s-phos (0.69 g, 3.39 mmol) ligands were added and stirred under heat for 2.5 hours. After cooling to room temperature, the ethanol slurry was purified to prepare compound 1-1-3 (33 g, yield 93.5%) (MS: [M + H] ⁺ = 626).

 Compound 1-1-14A (20.0 g, 58.0 mmol), 4-chloro-2,6-diphenylpyrimidine (15.5 g, 58.0 mmol) and potassium carbonate under 1-1-14A-14B-14 nitrogen stream (16.0 g, 116.1 mmol) was added to THF (250 mL) and stirred with heat.

Tetrakis (triphenylphosphine) palladium (0) (2.01 g, 1.74 mmol) was added thereto, followed by heating and stirring for 5 hours. After stirring at room temperature, ethanol slurry was purified to prepare the compound lll ⁴ B ( ²⁴ g, yield 9 1%) (MS: [Μ + Η] ⁺ = 4 ⁴⁹ ).

Under a stream of nitrogen, the compound ll-14B (27 g, 53.5 mmol), (4-naphthalen-1-yl) phenyl) boronic acid (13.3 g, 53.5 mmol) and potassium carbonate (14.8 g, 106.9 mmol) were added to THF (300). mL) and heated and stirred. Potassium acetate (0.36 g, 1.60 mmol) and s-phos (1.31 g, 3.20 mmol) ligands were added and stirred under heating for 3 hours. After cooling to room temperature, the ethanol slurry was purified and the compound 1-1-14 (30 g, Yield 91.2%) was prepared (MS: [M + H] ⁺

-1-23A 1-1-23B 1-1-23 Under nitrogen stream, compound 1-1-23A (20.0 g, 60.9 mmol), 2-chloro-4,6-diphenylpyrimidine (16.2 g, 60.9 mmol) and potassium carbonate (16.8 g, 121.8 mmol) were added to THF (250 mL) and stirred with heating. tetr akis (tripheny lphosphine) palladium (O) (2.11 g, 1.83 mmol) was added thereto, followed by heating and stirring for 5 hours. Purified with silver and then purified by ethanol slurry to give the compound 1-1-23B (23.5 g, yield 89.2%) (MS: [M + H] ⁺ = 449).

Under a stream of nitrogen, the compound ll-23B (23.5 g, 54.3 mmol), (4-naphthalen-1-yl) phenyl) boronic acid (16.2 g, 54.3 mmol) and potassium carbonate (15.0, 108.6 mmol) were added to THF (300). mL) and heated and stirred. Potassium acetate (0.37 g, 1.63 mmol) and s-phos (1.33 g, 3.26 mmol) ligands were added and stirred under heating for 3 hours. After cooling to room temperature, ethanol slurry was purified to prepare compound 1-1-23 (34 g, yield 96.3%) (MS: [M + H] ⁺ = 651).

1-1-25A 1-1-25B 1-1-25 Under nitrogen stream, the compound 1-1-25A (20.0 g, 58.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (15.5 g, 58.0 mmol) and potassium carbonate (16.0 g, 116.1 mmol) was added to THF (250 mL) and stirred with heating.

Tetrakis (triphenylphosphine) palladium (0) (2.01 g, 1.74 mmol) was added thereto, followed by heating and stirring for 5 hours. After cooling to room temperature, ethanol slurry was purified to prepare the compound ll-25B (23 g, yield 91.4%) (MS: [M + H] ⁺ = 434).

Under nitrogen stream, the compound ll-25B (23 g, 53.0 mmol), 2- (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3, 2-dioxabororene (17.0 g, 53.0 mmol) and potassium carbonate (14.6 g, 106.0 mmol) were added to THF (300 mL) and stirred with heat. Potassium acetate (0.36 g, 1.59 mmol) and s-phos (1.30 g, 3.18 mmol) ligands were added and stirred under heating for 3 hours. Purified with silver and then purified by ethanol slurry to prepare the compound 1-1-25 (29 g, yield 92.2%) ol (MS: [M + H] ⁺ = 592).

 1-1-30A 1-1-30B 1-1-30 Under nitrogen stream, compound 1-1-30A (20.0 g, 58.0 mmol), 2-chloro-4,6-diphenyl-1,3,5 Triazine (15.5 g, 58.0 mmol) and potassium carbonate (16.0 g, 116.1 mmol) were added to THF (250 mL) and stirred with heat.

Tetrakis (triphenylphosphine) palladium (0) (2.01 g, 1.74 mmol) was added thereto, followed by heating and stirring for 5 hours. After cooling to room temperature, ethanol slurry was purified to prepare the compound ll-30B (24 g, yield 92.3%) (MS: [M + H] ⁺ = 450).

Under nitrogen stream, compound ll-30B (24 g, 53.3 mmol), (9,9-diphenyl-9H- Fluoren-2-yl) boronic acid (19.3 g, 53.3 mmol) and potassium carbonate (14.7 g, 106.6 mmol) were added to THF (300 mL) and stirred with heat. Potassium acetate (0.36 g, 1.60 mmol) and s-phos (1.31 g, 3.20 mmol) ligands were added and stirred under heating for 3 hours. After cooling to room temperature, the ethanol slurry was purified to prepare compound 1-1-30 (36 g, yield 92.3%) (MS: [M + H] ⁺ = 732).

 -1A 1-1-1B 1-1-31 [1,1 '-biphenyl] -4-yl boronic acid instead of 4,4,5,5-tetramethyl-2- (4- (pyrene-1- 1) phenyl)-

Compound 1-1-31 was prepared by the same method as the preparation of Compound 1-1-1 according to Synthesis Example 1, except that 1,3,2-dioxabororene was used (MS: [M + H] ⁺ = 676).

 1-1 -14 A 1-1-14B 1-1-52

Of compound 1-1-14 according to Synthesis Example 4, except that 9,9'-spirobi [fluorene] -2-yl boronic acid is substituted for (4-naphthalen-1-yl) phenyl) boronic acid Manufacturing and In the same manner, compound 1-1-52 was prepared (MS: [M + H] ⁺ = 729).

1-2-5

1 -2-5A 1-2-5B under a stream of nitrogen, the above compound 1-2-5 A (20.0 g, 60.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine ( 16.3 g, 60.9 mmol) and potassium carbonate (16.8 g, 121.8 mmol) were added to THF (250 mL) and stirred with heat.

Tetrakis (triphenylphosphine) palladium (0) (2.11 g, 1.83 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. A nyaenggak to room temperature, and then was purified to prepare a slurry of ethanol proceeds mall-2-5B compound l (g 24, yield 9% ^{4 7.)} (MS: [M + H] ⁺ 3 = ^{4 4).}

Under nitrogen stream, the compound l-2-5B (24 g, 55.3 mmol), 4,4,5,5-tetramethyl- ^2- ( ^4- (naphthalene- ² -yl) phenyl) -I, ³ , ^2- Dioxabororene (18.3 g, 55.3 mmol) and potassium carbonate (15.3 g, 110.6 mmol) were added to THF (300 mL) and stirred with heat. Potassium acetate (0.37 g, 1.66 mmol) and s-phos (1.36 g, 3.32 mmol) ligands were added and stirred under heating for 3 hours. After cooling to room temperature, ethanol slurry was purified to prepare the compound 1-2-5 (30 g, 90.4% of water) (MS: [M + H] ⁺ = 602).

1-2-5A 1-2-5B 1-2-27 ^4,4, 5,5-Tetramethyl-2- ^(4- (naphthalen-2-yl) phenyl) - 1,3,2-dioxa-beam Lauren instead of ^(4- (9,9-dimethyl -9H- fluorene Compound 1-2-27 was prepared by the same method as the preparation of Compound 1-2-5 according to Synthesis Example 10, except that orene-2-yl) phenyl) boronic acid was used (MS: [M + H] ⁺ = 668).

 1-2-55A 1-2-55B

 1-2-55 2-Chloro-4,6-diphenyl 2- (4-bromophenyl) -4,6-diphenyl- instead of 4,3,5-triazine

Compound 1-2-55B was prepared by the same method as the preparation of Compound 1-2-5B according to Synthesis Example 10, except that 1,3,5-triazine was used (MS: [M + H ] ⁺ = 34).

Use 1-2-55B instead of 1-2-5B and use 4,4,5,5-tetramethyl-2- (4- (naphthalen-2-yl) phenyl) -1,3,2-dioxaborolene Compound 1- according to Synthesis Example 10, except that 4,4,5,5-tetramethyl-2- (triphenylene-1-yl) -1,3,2-dioxabororene was used instead. Compound 1-2-55 was prepared by the same method as the preparation of 2-5 (MS: [M + H] ⁺ = 702).

 1-2-63A 1-2-63B 1-2-63

Except that the additive compound 1-2-63 The compound A instead 1-2-5A, and the compound 1- ² _ ⁶³ B in the same way as the production of the compounds according to the 1-2-5B Synthesis Example 10 Prepared (MS: [M + H] < + > = ⁴⁵ 0).

Use compound 1-2-63B instead of compound 1-2-5B and use 4,4,5,5-tetramethyl-2- (4- (naphthalen-2-yl) phenyl) -1,3,2- According to Synthesis Example 10, except that 4,4,5,5-tetramethyl-2- (phenanthrene-3-yl) -1,3,2-dioxabororene was used instead of dioxabororene. compound was prepared as the compound 1-2-63 1-2-5 theta Joe ^"as the method of (MS: [M + H] + = 591).

 1-3-1 A 1-3-1 B 1-3- 'Under nitrogen stream, compound 1-3-1 A (20.0 g, 53.6 mmol), 2-chloro-4,6-diphenyl-1, 3,5-triazine (14.4 g, 53.6 mmol) and potassium carbonate (14.8 g, 107.2 mmol) were added to THF (250 mL) and stirred with heat.

Tetrakis (triphenylphosphine) palladium (0) (1.85 g, 1.61 mmol) was added and 5 hours Stirring while heating. Purified with silver and then purified by ethanol slurry to prepare the compound 1-3-1β (24.5 g, yield 92.6%) (MS: [M + H] ⁺ = 478).

Under a stream of nitrogen, the compound l-3-lB (24.5 g, 51.2 mmol), 4,4,5,5-tetramethyl-2- (4- (naphthaljan-2-yl) phenyl) -1,3, 2-dioxa.borolene (10.1 g, 51.2 mmol) and potassium carbonate (14.2 g, 102.4 mmol) were added to THF (300 mL) and stirred with heat. Potassium acetate (0.35 g, 1.54 mmol) and s-phos (1.26 g, 3.07 mmol) ligands were added and stirred under heating for 3 hours. After cooling to room temperature, ethanol slurry was purified to prepare the compound 1-3-1 (28 g, yield 92.2%) (MS: [M + H] ⁺ = 552).

1-3-6A 1-3-6B 1-3-6 Compound 1-3-1B according to Synthesis Example 14, except that Compound 1-3-6A was used instead of Compound 1-3-1 A Compounds 1-3-6B were prepared by the same method as the preparation of (MS: [M + H] ⁺ = 494).

Synthesis except that compound 1-3-6B was used instead of compound 1-3-1B and (4- (naphthalen-2-yl) phenyl) boronic acid was used instead of biphenyl] -4-yl boronic acid Compound 1-3-6 was prepared by the same method as the preparation of the compound 1-3-1 according to Example 14 (MS: [M + H] ⁺ = 618).

Same as the preparation of Compound 1-3-1 according to Synthesis Example 14, except that (9,9-dimethyl-9Η-fluoren-2-yl) boronic acid was used instead of biphenyl] -4-ylboronic acid Compound 1-3-25 was prepared by the method (MS: [Μ + Η] ⁺ = 592).

1-3-52Α 1-3-52Β 1-3-52 The compound 1-3-52A was used instead of the compound 1-3-1A and 2-chloro-4,6-diphenyl-1,3,5 Compound 1- in the same manner as in the preparation of Compound 1-3-1B according to Synthesis Example 14, except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine was used instead of triazine. 3-52B was prepared (MS: [M + H] ⁺ = ⁴ 93).

Using compound 1-3-52B instead of compound 1-3-1B and using (9,9-diphenyl-9H-fluoren-4-yl) boronic acid instead of biphenyl]-4-yl boronic acid Except, Compound 1-3-52 was prepared by the same method as the preparation of Compound 1-3-1 according to Synthesis Example 14 (MS: [M + H] ⁺ = 807).

 1 -4-8A 1-4-8

^, The compound with the compound 1-3-1 1-4-8B A instead of methods, such as the production of the compound 1-3-1B according to Synthesis Example 14, except for using the compound 1-4-8A (MS: [M + H] ⁺ = 494).

Compound 1-4-8B was used instead of compound 1-3-1B and 4,4,5,5-tetramethyl-2- (4- (phenanthrene-9-) was used instead of biphenyl] -4-yl boronic acid. The compound 1-4-8 was prepared by the same method as the preparation of the compound 1-3-1 according to Synthesis Example 14, except that one) phenyl) -1,3,2-dioxabororene was used. (MS: [M + H] ⁺ = 668).

1-4-56A 1 -4-56B 1 -4-56 The compound 1-4-56A was used instead of the compound 1-4-8A and 2-chloro-4,6-diphenyl-1,3,5- Preparation of the compound 1-4-8B according to Synthesis Example 18, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of triazine In the same manner, 1-4-56B was prepared (MS: [M + H] ⁺ = 542). Compound 1-4-56B was used instead of compound 1-4-8B and 4,4,5,5-tetramethyl-2- (4- (phenanthrene-9-yl) phenyl) -1,3,2 Synthesis Example 18, except that 4,4,5,5-tetramethyl-2- (triphenylene-1-yl) -1,3,2-dioxabororene was used instead of dioxabororene. Compound 1-4-56 was prepared by the same method as the preparation of Compound 1-4-8 (MS: [M + H] ⁺ = 718).

1-4-59A 1-4-59B 1-4-59 The compound 1-4-59 A is used instead of the compound 1-4-8A and 2-chloro-4,6-diphenyl-1,3,5 Compound 1-4- according to Synthesis Example 18, except that 2- (4-chloronaphthalen-1-yl) -4,6-diphenyl-1,3,5-triazine was used instead of -triazine Compound 1-4-59B was prepared in the same manner as in the preparation of 8B (MS: [M + H] ⁺ = 542).

Compound 1-4-59B was used instead of compound 1-4-8B and 4,4,5,5-tetramethyl-2- (4- (phenanthrene-9-yl) phenyl) -1,3,2 Except for using 2- (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabororene instead of dioxabororene And, Compound ^1-4 _ ⁵ 9 was prepared by the same method as the preparation of Compound 1-4-8 according to Synthesis Example 18 (MS: [Μ + Η] ⁺ = ⁷ 1 ⁸ ).

An additive compound 1-5-29B was prepared by the same method as the preparation of compound 1-4-8B according to Synthesis Example 18, except that Compound 1-5-29 A was used instead of Compound 1-4-8A. (MS: [Μ + Η] ⁺ = 526)

Compound 1-5-29B was used instead of compound 1-4-8B and 4,4,5,5-tetramethyl-2- (4- (phenanthrene-9-yl) phenyl) -1,3,2 Using 2- (9,9-diphenyl-9Η-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolene instead of dioxabororene except for the compound I- ⁵ in the same manner as in Preparation of the compound 1-4-8 according to the Preparation example 18, it was prepared the ^{29 (MS: [Μ + Η} ] + = 7 1 6).

Compound 1-5-32B was prepared by the same method as the preparation of Compound 1-5-29B according to Synthesis Example 21, except that Compound 1-5-32A was used instead of Compound 1-5-29A. (MS: [M + H] ⁺ = ⁵⁴ 2).

Use of compound 1-5-32B instead of compound 1-5-29B and 2- (9,9-diphenyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1 4,4,5,5-tetramethyl-2- (4- (pyren-1-yl) phenyl) -1,3,2-dioxabororene instead of, 3,2-dioxabororene Except, Compound 1-5-32 was prepared by the same method as the preparation of Compound 1-5-29 according to Synthesis Example 21 (MS: [M + H] ⁺ = 692).

 1 -5-51 A 1 -5-51 B The compound 1-5-51 A is used instead of the compound 1-5-29A and 2-chloro-4,6-diphenyl-1,3,5-triazine Compound 1-5-51B was prepared by the same method as the preparation of Compound 1-5-29B according to Synthesis Example 21, except that 4-chloro-2,6-diphenylpyrimidine was used instead (MS [M + H] < + > = 525).

Use of compound 1-5-51B instead of compound 1-5-29B and 2- (9,9-diphenyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1 Same as the preparation of Compound 1-5-29 according to Synthesis Example 21, except that 9,9'-spirobibi [fluorene] -2-yl boronic acid was used instead of, 3,2-dioxaborolene. Compound 1-5-51 was prepared by the method (MS: [M + H] ⁺ = 713).

1-5-58 A 1-5-58B 1-5-58 The compound 1-5-58A is used instead of the compound 1-5-29A and 2-chloro-4,6-diphenyl-1,3,5 Compound 1- in the same manner as in the preparation of Compound 1-5-29B according to Synthesis Example 21, except that 4- (2-chlorophenyl) -2,6-diphenylpyrimidine was used instead of triazine. 5-58B was prepared (MS: [Μ + Η] ⁺ = 617).

 Use of compound 1-5-58B instead of compound 1-5-29B and 2- (9,9-diphenyl-9Η-fluoren-2-yl) -4,4,5,5-tetramethyl-1 Instead of, 3,2-dioxaborolene

Biphenyl] _ ₄ _ doing the compound 1-5-58 In the same way, and the preparation of the compound 1-5-29 of the above Synthesis Example 21 except that the acid was prepared (MS: [M + H] ⁺ = 643).

Compound 1-6-5B was prepared by the same method as the preparation of Compound 1-5-29B, according to Synthesis Example 21, except that Compound 1-6-5A was used instead of Compound 1-5-29A. (MS: [M + H] ⁺ = 43 ⁴ ).

Use of compound 1-6-5B instead of compound 1-5-29B and 2- (9,9-diphenyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1 Addition of the above compound in the same manner as in the preparation of Compound 1-5-29 according to Synthesis Example 21, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of 3,2-dioxabororene Compound 1-6-5 was prepared (MS: [M + H] ⁺ = 602).

1-6-24A 1-6-24B 1-6-24 The compound 1-6-24A is used instead of the compound 1-6-5A and 2-chloro-4,6-diphenyl-1,3,5- Compound 1-6-24B was prepared by the same method as the preparation of Compound 1-6-5B according to Synthesis Example 25, except that 2-chloro-4,6-diphenylpyrimidine was used instead of triazine. (MS: [M + H] ⁺ = 433).

Compound 1-6-24B is used instead of Compound 1-6-5B and 4,4,5,5-tetramethyl-2- (4- (instead of (4- (naphthalen-1-yl) phenyl) boronic acid) Compound 1-6 in the same manner as in the preparation of Compound 1-6-5 according to Synthesis Example 25, except that phenanthrene-9-yl) phenyl) -1,3,2-dioxabororene was used. -24 was prepared (MS: [M + H] ⁺ = 667).

 1-6-49A 1-6-49B 1-6-49

The compound producing the compound 1-6- ⁴ 9Β in the same way as the production of the compound 1-6-5B, according to the above Synthesis Example 25 except that instead of using the compound 1-6-49A 1-6-5A (MS: [M + H] ⁺ = 4 ⁷ 8).

Compound 1-6-49B was used instead of Compound 1-6-5B and 9,9'-spirobi [fluorene] -2-ylboronic acid was substituted for (4- (naphthalen-1-yl) phenyl) boronic acid. Except for the use, the compound 1-6-49 was prepared by the same method as the preparation of the compound 1-6-5 according to Synthesis Example 25 (MS: [M + H] ⁺ = 714).

1-6-64A 1-6-64B 1-6-64 Compound 1-6-64A was used instead of Compound 1-6-5A and 4-chloro-2,6-diphenylpyrimidine was substituted for 2-chloro-4,6-diphenyl-1,3,5-triazine. Compound 1-6-64B was prepared by the same method as the preparation of Compound 1-6-5B according to Synthesis Example 25, except that (MS: [Μ + Η] ⁺ = 493).

 Instead of compound 1-6-5B, use compound 1-6-64B (4- (naphthalene-

Compound 1-6-64 was prepared by the same method as the preparation of Compound 1-6-5 according to Synthesis Example 25, except that phenanthrene-3-yl boronic acid was used instead of 1-yl) phenyl) boronic acid. Prepared (MS: [M + H] ⁺ = 591). Example 1

 A glass substrate coated with a thickness of 1,000 A of ITO (indium tin oxide) 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 following compound [HI-A] was vacuum-deposited to a thickness of 600 A on the prepared πΌ transparent electrode to form a hole injection layer. 50 A and the following compound [HT-A] (600 A) were sequentially vacuum-deposited on the hole injection layer to form nucleitrile hexasatriphenylene (HAT) of the following formula to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to form a light emitting layer at a thickness of 200 A. Compound 1-1-1 and [LiQ] (Lithiumquinolate) were vacuum-deposited on the emission layer in a 1: 1 weight ratio The electron week and the transport layer were formed to a thickness of 350A. Lithium fluoride (LiF) and aluminum at 1,000 A thickness were sequentially deposited on the electron injection and transport layer to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 A / sec, the lithium fluoride of the cathode was maintained at 0.3 A / sec, and the aluminum was maintained at the deposition rate of 2 A / sec. An organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁸ torr.

Examples 2 to 28

To the embodiment in place of the compound 1-1-1 of the electron transporting layer in Example 1, except that the compounds described in Table 1 and the ^'was prepared in the organic light emitting device in the same manner as in Example 1.

Comparative Example 1

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

Comparative Example 2

 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following compound ET2 instead of the compound 1-1-1 of the electron transport layer in Example 1. [ET2]

Comparative Example 3

The following compound ET3 instead of compound 1-1-1 of the electron transport layer in Example 1 An organic light-emitting device was manufactured in the same manner as in Example 1, except that it was used.

[ET3]

Comparative Example 4

 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following compound ET4 instead of the compound 1-1-1 of the electron transport layer in Example 1.

 [ET4]

Comparative Example 5

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following compound ET5 instead of the compound 1-1-1 of the electron transport layer in Example 1. [ET5]

Comparative Example 6

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET6 was used instead of Compound 1-1-1 of the electron transport layer in Example 1.

Test Example

The driving voltage and the luminous efficiency of the organic light emitting diodes of Examples 1 to 28 and Comparative Examples 1 to 6 were measured at a current density of 10 mA / cm ² , and 90% of the initial luminance was measured at a current density of 20 mA / cm ² . The time to become (LT90) was measured. The results are shown in Table 1 below. _// u O-ss _oS SSM _ld AV

Referring to Table 1, the organic light emitting device manufactured by applying the compound of Synthesis Example to the electron transport layer showed excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device. In particular, the organic light emitting diodes manufactured by applying the compounds of the synthesis examples to the electron transport layer exhibited lower voltage and higher efficiency than the organic light emitting diodes of the comparative examples.

[Explanation of code]

 Board

 Light emitting layer

 cathode

 Hole injection layer

 Hole transport layer

 Light emitting layer

 Electron transport layer

Claims

Claims [Claim 1] A compound represented by the following formula (1):

 [Formula 1]

In Chemical Formula 1,

Each X is independently N or CR ⁰ , at least two of X are N,

R ⁰ is hydrogen; heavy hydrogen; Deuterium, halogen, amino, nitrile, nitro,

The alkyl group, C2-30 alkenyl group of C _1-30, C _2-30 alkynyl group, an alkoxy group, an aryloxy group of C _6-30, or c aryl group optionally substituted in the _{6 and 30} of the C _{1-30 Unsubstituted} aryl group of c _6-50 ; Or deuterium, halogen, amino group, nitrile group, nitro group, C _1-30 alkyl group, c ₂ ^ alkenyl group, c _2- containing at least one hetero atom selected from the group consisting of N, O and S; A heteroaryl group of C _{2 50} which is unsubstituted or substituted with an alkynyl group of ₃₀ , an alkoxy group of c _1-30, an aryloxy group of c _6-30 , or an C _6-30 aryl group, and Y is O or S ego,

L ⁱ and L ² are each independently a direct bond; Or unsubstituted or deuterium, halogen, amino, nitrile, nitro, C _1-30 alkyl, C _2-30 alkenyl, C _2-30 alkynyl, C _1-30 alkoxy, C an aryl group of C _6-20 aryl substituted with a group of _30, - _6-30 aryloxy, or C ₆ m and n are each independently an integer of 0 to 2,

Ar ⁱ and Ar ² are each independently hydrogen; heavy hydrogen; Deuterium, halogen, amino group, nitrile group, nitro group, C _1-30 alkyl group, C ₂ ᅳ ₃₀ alkenyl group, C _2-30 alkynyl group, C _1-30 alkoxy group, C _M0 aryloxy group, or an aryl group that is not substituted with a C _6-30 aryl or substituted C _6- 50; Or a C ₂ ᅳ 5 ₀ heteroaryl group which includes one or more heteroatoms selected from the group consisting of N, O and S and is optionally substituted with an aryl group of C _6-30 ,

Ar ³ is a C ₆ _ 6o aryl group.

[Claim 2]

 The method of claim 1,

 Formula 1 is represented by any one of the following Formula 1-1 to 1-6, Compound:

 [Formula 1-1]

[Formula 1-2]

[Formula 1-5]

 In Chemical Formulas l-l to 1-6,

X, Y,,, m, n, Ar, Ar ² , and Ar ³ are each as defined in Chemical Formula 1.

[Claim 3]

 Article ： according to claim I,

Each X is independently N or CH, and at least two of X are N.

[Claim 4]

 The method of claim 1,

 M and n are each independently 0 or 1;

[Claim 5]

 The method of claim 1,

Ar ⁱ and Ar ² are each independently hydrogen or a C ₆ ᅳ ₅₀ aryl group.

[Claim 6]

 The method of claim 1 wherein.

Ar ³ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, a phenanthryl group, a pyrenyl group, a perrylenyl group, chrysenyl group, or a substituted or unsubstituted fluorenyl group.

[Claim port Ί \

 The method of claim 1,

Compound represented by Formula 1 is any one selected from the group consisting of a compound of the formula:

-2-21 1-2-22 1-2-23 1-2-24

-2-41 1-2-42 1-2-43 1-2-44

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

_{//: /} O _Z6 S ₀₈ S2XI2 ₀₆ ss ₈ sAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

Z.Z6C00 / 8T0ZaM / X3d 0176SZZ / 810Z OAV

87 [Claim 8]

 An organic electroluminescent device comprising 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;

 At least one of the organic material layer is an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1.