WO2018110887A1 - Heterocyclic compound, and organic light-emitting element comprising same - Google Patents

Abstract

The present invention provides a heterocyclic compound having a novel structure, and an organic light-emitting element comprising the heterocyclic compound.

Description

 [Name of invention]

 Heterocyclic compound and organic light emitting device comprising the same

 Technical Field

 Cross Citation with Related Application (s)

 This application is filed with Korean Patent Application No. 10-2016-

Claiming the benefit of priority based on 0170676, all the contents disclosed in the literature of the relevant Korean patent application are incorporated as part of this specification. The present invention relates to a heterocyclic compound having a novel structure and an organic light emitting device including the same.

 Background Art

 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, brightness, driving voltage and Many studies have been conducted because of excellent response speed characteristics. 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material charge is often composed of a multilayer structure composed of different materials, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport insect. It may be made of an electron injection insect. 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, electrons are injected into the organic layer, and excitons are formed when the injected holes and the electrons meet each other. The axtone glows when it falls back to the ground. There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices.

 Prior Art Documents

[Patent literature] (Patent Document 0001) Korean Patent Publication No. 2000-0051826

 [Content of invention]

 [Problem to solve]

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

 [Solution of problem]

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

 In Chemical Formula 1,

 X is 0 or S,

Ri to ¾ are each independently hydrogen or deuterium, at least one of ¾ to is deuterium, and any one of to R ₄ is the following Chemical Formula 2,

!八^ is substituted or unsubstituted C ₁₀ - ₂₀ is aryl. In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Chemical Formula 1. to provide.

 【Effects of the Invention】

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

 [Brief Description of Drawings]

 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.

 2 shows a substrate 1, an anode 2, a hole injection layer 5, and a hole transport layer 6. The example of the organic light emitting element which consists of the light emitting layer 7, the electron carrying layer 8, and the cathode 4 is shown.

 [Specific contents to carry out invention]

 Hereinafter, in order to help the understanding of the present invention will be described in more detail.

In the present specification, means a bond connected to another compound. As used herein, the term "substituted or unsubstituted" may mean substituted or unsubstituted by R ^a , ^ is deuterium, halogen, cyano group, nitro group, amino group, alkyl group having 1 to 40 carbon atoms, carbon number At least one of 1 to 40 haloalkyl group, substituted or unsubstituted 0, N, Si and S containing at least one heteroalkyl group having 1 to 40 carbon atoms, substituted or unsubstituted 0, N, Si and S It may include a heterohaloalkyl group having 1 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms In the present specification, the halogen may be fluorine, chlorine, bromine or iodine. In particular, an alkyl group having 1 to 40 carbon atoms may be a straight chain alkyl group having 1 to 40 carbon atoms; a straight chain alkyl group having 1 to 20 carbon atoms; Linear alkyl groups of 1 to 10; Branched or cyclic alkyl groups having 3 to 40 carbon atoms; Branched or cyclic alkyl groups having 3 to 20 carbon atoms; Or a branched or cyclic alkyl group having 3 to 10 carbon atoms. More specifically, the alkyl group having 1 to 40 carbon atoms is methyl group, ethyl group, n—propyl group, i so-propyl group, n-butyl group, i so-butyl group, t-butyl group, n-pentyl group, i so- Pentyl group, neo-pentyl group or cyclonuclear group. However, the present invention is not limited thereto. In the present specification, the heteroalkyl group having 1 to 40 carbon atoms is each independently one or more carbon atoms of 0, N. It may be substituted with Si or S. For example, as an example of a linear alkyl group, a heteroalkyl group in which carbon number 1 of the n-butyl group is substituted with 0 is an n-propoxy group, a heteroalkyl group substituted with N is an n ᅳ propylamino group, and a heteroalkyl group substituted with Si is n Is a propylsilyl group, and the heteroalkyl group substituted with S is an n-propylthio group. For example, as the branched alkyl group, the heteroalkyl group in which the carbon number 1 of the neo-pentyl group is substituted with 0 is a t-butoxy group, the heteroalkyl group substituted with N is a _t -butylamino group, and the heteroalkyl group substituted with Si is t A -butylsilyl group, and the heteroalkyl group substituted with S is a t-butylthio group. In addition, as an example of a cyclic alkyl group, the heteroalkyl group in which the carbon number 2 of the cyclonuclear group is substituted with 0 is 2-tetrahydropyranyl group, and the heteroalkyl group substituted with N is 2-piperidinyl group. , a heterocyclic group substituted by Si 1-sila-and haeksil (1-si la- cyc lohexyl) based upon a ^{^} cycles, the heteroaryl group is substituted by S 2-thio-tetrahydro pyranyl (2-tetrahydrothiopyranyl) group is . Specifically, the heteroalkyl group having 1 to 40 carbon atoms has a straight, branched or cyclic hydroxyalkyl group having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxy groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxyalkyl groups having 2 to 40 carbon atoms; Linear, branched or cyclic aminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylamino groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylaminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic silylalkyl (oxy) groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silyl groups having 1 to 40 carbon atoms; Straight chain, branched chain of 1 to 40 carbon atoms, or Cyclic alkyl (oxy) silylalkyl (oxy) groups; Linear, branched or cyclic mercatoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylthio groups having 1 to 40 carbon atoms; Or a straight, branched or cyclic alkylthioalkyl group having 2 to 40 carbon atoms. More specifically, the heteroalkyl group having 1 to 40 carbon atoms has a hydroxymethyl group, a methoxy group, an ethoxy group, η-propoxy group, i so-propoxy group, t-subspecial group, cyclonuclear special group, mesospecial methyl group, i so -Propoxymethyl group, cyclonucleooxymethyl group, 2-tetrahydropyranyl (l-tetr ahydr opyr any l) 7 l, aminomethyl group, methylamino group, _η -propylamino group, t-butylamino group ᅳ methylaminopropyl group, 2- Piperidinyl group, n-propylsilyl group. Trimethylsilyl group dimethylmethoxysilyl group, ^' t-butylsilyl group, 1-sila-cyclonuclear chamber (1-si ^' la-cyc lohexyl) group, n_propylthio group, t-butylthio group or 2-Dtra Hydrotepyyranyl (2-tetrahydrothiopyranyl) groups, and the like. However, the present invention is not limited thereto. In the present specification, an alkenyl group having 2 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkenyl group. Specifically, the alkenyl group having 2 to 40 carbon atoms has a straight chain alkenyl group having 2 to 40 carbon atoms; Linear alkenyl groups having 2 to 20 carbon atoms; Linear alkenyl groups having 2 to 10 carbon atoms; Branched alkenyl groups having 3 to 40 carbon atoms; Branched alkenyl groups having 3 to 20 carbon atoms; Branched alkenyl groups having 3 to 10 carbon atoms; Cyclic alkenyl groups having 5 to 40 carbon atoms; Cyclic alkenyl groups having 5 to 20 carbon atoms; Or a cyclic alkenyl group having 5 to 10 carbon atoms. More specifically, the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, propenyl group, butenyl group, pentenyl group, or cyclonucleenyl group. However, the present invention is not limited thereto. In the present specification, the aryl group having 6 to 20 carbon atoms may be a monocyclic aryl group or a polycyclic aryl group. Specifically, the aryl group having 6 to 20 carbon atoms may be a phenyl group, a biphenyl group or a terphenyl group as a monocyclic aryl group, and a naphthyl group, anthracenyl group, phenanthryl group, triphenylenyl group, pyrenyl group as a polycyclic aryl group. It may be a perrylenyl group, chrysenyl group or fluorenyl group. In addition, the aryl group having 6 to 20 carbon atoms may have a structure in which two or more selected from the group consisting of a monocyclic aryl group and a polycyclic aryl group are connected to each other. Specifically, the aryl group having 6 to 20 carbon atoms may have a structure in which a polycyclic aryl group and / or a monocyclic aryl group are linked to the polycyclic aryl group. More specifically, the aryl group having 6 to 20 carbon atoms may be a naphthylphenyl group, anthracenylphenyl group phenanthrylphenyl group, fluorenylphenyl group, phenylnaphthyl group or phenylanthracenyl group. However, the present invention is not limited thereto. In the present specification, the fluorenyl group may be substituted, two substituents are bonded to each other

Occation,

Could be such. However, the present invention is not limited thereto. The present invention provides a compound represented by Formula 1 in the present invention. If hayeoteul used as a light emitting layer host material of dibenzofuran or dibenzothiophene when directly bonded to anthracene increases the HOMO Highest Occupi ed Mo l ecu l ar Orbi tal) energy rebael of molecular organic light-emitting device is represented by Formula 1, ^"hole In addition, it is possible to reduce the driving voltage by smoothly injecting In addition, in the case of Ar1 CUHM aryl group, the thermal stability is increased, so that the molecular weight is suitable for thermal vacuum deposition, and stability in the manufacturing process of the organic light emitting device can be ensured. Has a higher atomic weight than hydrogen, resulting in a less vibrational mode, which increases the non-radioactive decay time and especially the stability of triplet excitons in an excited state. Generated by singlet excitons Amplification of the phenomenon (Tr iplet-Tr iplet Fusion; TTF) can contribute to the efficiency and lifetime of blue fluorescence. In Chemical Formula 1, ¾ to ¾ are each independently hydrogen or deuterium, at least one of R ₈ is deuterium, and any one of R ₄ is Formula 2 below. According to the bonding position of Formula 2, Formula 1 is represented by the following Formula 1-1, 1-2, 1-3. Or 1-4:

[Formula 1 一 3]

 In Chemical Formula 1—1 to 1-4,

 X and Ar ^ l definition is the same as in claim 1,

In Chemical Formula 1-1. R and R ₃ to ¾ are each independently hydrogen or deuterium. And at least one of R ₈ is deuterium,

In Formula 1-2, R ₂ to ¾ are each independently hydrogen or deuterium, at least one of ¾ to ¾ is deuterium,

In Formula 1-3,, and ¾ to ¾ are each independently hydrogen or deuterium, at least one of ¾, R ₂ and R ₄ to ¾ is deuterium,

In Formula 1-4, to R ₃ and R ₈ are each independently hydrogen or deuterium, at least one of ^ to ¾ and to ¾ is deuterium. Preferably, in Formula 1-1 and above, ¾; R ₄ ; R ₅ ; ; R ₇ ; R ₈ ; i and; Re and; Ri, ₃ and; ₅ to; Or Ri and R ₃ to R ₈ are deuterium, with the remainder being hydrogen. More preferably, the In Formula 1-1 and R ₃ to R ₈ , Rs and R ₄ ; R ₅ to; Or ¾ and R ₃ to R ₈ are deuterium and the remainder is hydrogen. Also, preferably, in Formulas 1-2 to R ₈ , R ₂ ; R ₃ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₂ and ¾; R ₆ and R ₈ ; R ₂ to; To; Or ¾ to ¾ is deuterium and the remainder is hydrogen. More preferably, in Formula 1-2, R ₂ to ¾; R ₅ to R ₈ ; Or R ₂ to R ₈ are deuterium, and the remainder are hydrogen. Also preferably, in Formulas 1-3 of R ₁ R ₂ and R ₄ ,

Ri; ; ; ; R ₆ ; R ₇ ; ; ₂ and ₄ ; R ₆ and ¾; Ri, R ₂ and R ₄ ; R ₅ to or, and to ¾ are deuterium and the remainder is hydrogen. More preferably, in Formulas 1-3, R ₂ and R ₄ to, Ri, R ₂ and; R ₅ to R ₈ ; Or, R ₂ and R 4 to ¾ are deuterium and the remainder is hydrogen. Also preferably, among Formulas 1-4 and R ₅ to R ₈ , R, ..; R ₂ ; ¾; R ₅ ; R ₆ ; ₇ ; ; Ri and ¾: _' ¾ and R ₈ ; Ri to R ₃ ; R ₅ to ^' .

; Or R! To R ₃ and R ₅ to R ₈ deuterium, with the remainder being hydrogen. More preferably. In Formulas 1-4 to and R ₅ to, Ri to R ₃ ; R ₅ to; Or R _L to and R ₅ to ¾ deuterium, with the remainder being hydrogen. Preferably, A is naphthyl, phenylnaphthyl, phenanthrenyl, or triphenylenyl. The compound represented by Formula 1 may be selected from the group consisting of the following compounds:

10

11





한편， 상기 화학식 1-1로 표시되는 화합물은 하기 반응식 1과 같은 법으로 제조할 수 있으며 , 화학식 1, 1-2, 1-3, 및 1-4에도 적용할 수 있다.

Meanwhile, the compound represented by Chemical Formula 1-1 may be prepared by the same method as in Scheme 1 below, and may be applied to Chemical Formulas 1, 1-2, 1-3, and 1-4. Can be.

In Reaction Scheme 1, the remaining definitions except for X 'are as defined above, and X' is halogen, more preferably brolo or chloro. The reaction 1 is preferably performed in the presence of a paralysis catalyst and a base as a Suzuki coupling reaction, and a reactor for the Suzuki coupling reaction can be changed as known in the art. The production method may be more specified in the production examples to be described later. In addition, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one example. The present invention comprises 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 multi-layer structure in which two or more layers of organic material packs 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 the organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller 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 holes, the hole injection layer, holes The transport layer, or the layer for simultaneously injecting and transporting a hole may include the compound represented by Chemical Formula 1. In addition, the organic layer may include a light emitting insect, and the light emitting layer may include a compound represented by Chemical Formula 1. The organic layer may include an electron transport layer, an electron injection layer, or a layer for simultaneously transporting and injecting electrons, and the electron transport layer, an electron injection layer, or a layer for simultaneously transporting and injecting electrons may be represented by Formula 1 above. It may include a compound represented. 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 insect 3, and a cathode 4. 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 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, except that at least one layer of the organic material layer comprises a compound represented by the formula (1) It may be made of materials and methods known in the art. 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, a metal oxide or a metal oxide having a conductivity or a metal on a substrate by using a physical vapor deposition deposition (PVD) method such as sputtering or e-beam evaporat ion An alloy is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport insect may be formed thereon, and then, a material usable 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. Also. The compound represented by Chemical Formula 1 may be formed into an organic material charge by a solution coating method as well as a vacuum deposition method in manufacturing an organic light emitting device. Here, the solution coating method is spin coating, dip coating, doctor blading. Inkjet printing, screen printing, spraying, roll coating and the like, but is not limited to these. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material charge and an anode material from a cathode material on a substrate 0V0 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 Metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ^{Η η} 0: A1 or SN0 ₂ : a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene KPED0T), polypyri 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 magnesium, calcium, sodium, potassium, titanium, indium, and yttrium. Metals such as lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or U¾ / A1, and the like, but are not limited thereto. The hole injection layer is a layer for injecting holes from the electrode. The hole injection material has a capability of transporting holes, and has excellent hole injection effects at the anode, and excellent holes for light emitting or light emitting materials. The compound which has an injection effect, prevents the movement of the excitons which generate | occur | produced in the luminescent charge to an electron injection layer or a battery-injection material, and is excellent in thin film formation ability is preferable. It is preferred that the highest occupied molecul ar orbital (H0M0) of the hole injection material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material is a metal porphyrin (porphyr in), oligothiophene, arylamine series of organic matter, hex nitrile hex-aza triphenylene ^■ organic substance in the series, quinacridone (qu inacr i done) organic substance in the series, Fe Perylene organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The hole transport layer is a material 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 as a hole transport material. Materials with high mobility for holes are suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, 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 include 8—hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimer i zed styryl compounds; BAlq; 10-hydroxybenzoquinoline—metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (P-phenylenevinylene) (PPV) family; Spi ro 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. Condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, and phenanthrene compounds. And pulluloranthene compounds. Heterocyclic containing compounds include, but are not limited to carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, and the like. Specifically, the light emitting layer may include a compound represented by Formula 1 as the host material. In particular, it is possible to provide an organic light emitting device having excellent efficiency by using the compound represented by Formula 1 as a host material of the blue light emitting layer. The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complex 1, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamino group. The styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and an aryl group and a silyl group. Alkyl group. One or two or more substituents selected from the group consisting of a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styryl amine, styryl diamine styryl triamine, styryl tetraamine and the like, but is not limited thereto. In addition, the metal complex includes a lychee complex, a back complex, and the like, but is not limited thereto. The electron transport layer is a layer that receives electrons from the electron injection charge and transports the electrons to the light emitting charge, and the electron transport material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. Suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes including Al q 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 layer or silver worm. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum worm or silver layer. The electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting 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. Specifically, fluorenone, anthraquinodimethane, diphenoquinone. Thiopyran dioxide, oxazole, oxadiazole. Triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone and the like, derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto. As said metal complex compound, 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] quinolina Earth, zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0-crezolato) gallium, bis (2-methyl-8-quinolinato) ) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like. 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. Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Production example]

In a two-necked flask, dibenzo [b, d] furan- (18 (50.0 g, 283.7 麵 ol) was dissolved in acetic acid (500 ml) by heating under argon atmosphere. Bromine (17 ml, 340.4 隱 ol) After slowly adding dropwise, the mixture was stirred for 20 hours while cooling to room temperature. Washed with water and recrystallized with methanol to obtain intermediate A (30.3 g. Yield 42%. MS: [M + H] + = 254).

 B

Dibenzo [b, d] furan-d8 (50.0 g, 283.7 隱₀ 1) was dissolved in THF (500 ml) under a nitrogen atmosphere in a dried three-necked flask and 1.6M n-butyl with stirring at -78 ^° C. Lithium (186 ml, 297.9 mniol) was slowly added dropwise. When the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining at -78 ^° C. Thereafter, trimethyl borate (38.3 g, 368.8 Pa ol) was slowly added dropwise, and then raised to room temperature and stirred for 1 hour. After the reaction was completed, 2N HC1 aqueous solution (200 ml) was added dropwise at room temperature, followed by stirring for 30 minutes. Transfer the reaction mixture to a separatory funnel and then the organic layer was extracted using water and ethyl acetate, and concentrated under reduced pressure, CH ₂ C1 was recrystallized in _two nucleic acid intermediates B * obtained (29.8 g, yield 48%, _MS:.. [ M + H] ⁺ = 219). Preparation Example 3 Preparation of Intermediate C

 C-1

1,3-dimethoxybenzene—2, 4, 5,6 ᅳ (14 (50.0 g, 351.6 麵 ol)) was dissolved in THF (500 ml) under a nitrogen atmosphere in a dried three-neck flask at -10 ^° C. 1.6 M n-butyllithium (231 ml, 369.2 画 ol) was slowly added dropwise with stirring, after which the addition was completed, the mixture was stirred for 4 more hours at the same degree, and then cooled to -78 ^° C and trimethyl borate (47.5 g, 457.1 mniol) was slowly added dropwise, followed by stirring overnight at room temperature. After reaction was completed, 2N HC1 aqueous solution was added dropwise. After acidification it was stirred for 30 minutes. The reaction solution was transferred to a separatory funnel, the organic layer was extracted with water and ethyl acetate, concentrated under reduced pressure, and recrystallized with nucleic acid to obtain Intermediate C-1 (45.5 g, yield 70%, MS: [M + H] ⁺ = 185).

Intermediate 01 (45.0 g, 243.2 mmol), 1-bromo-2-fluorobenzene (46.8 g. 267.6 μl ol) were dissolved in THF (675 ml) in a three neck flask and K ₂ CO ₃ (134.5 g, 973.0 mmol) ) Was dissolved in water (338 ml). Pd (PPh ₃ ) ₄ (H.2 g, 9.7 mmol) was added thereto, and the mixture was stirred for 8 hours under reflux conditions under argon. After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel, extracted with water and ethyl acetate. The extract was dried over MgS0 ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography. Intermediate 0 2-1- was obtained (44.6 g, yield 78%. MS: [M + H] ⁺ -235).

Intermediate 02 (40.0 g, 276.3 μl) and acetic acid (240 ml) HBr (160 ml) were added to a three neck flask and stirred overnight under reflux conditions. When the reaction was finished, the solution was cooled to room temperature and water (500 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give Intermediate C-3 (32.4 g, yield 92%, MS: [M + H] ⁺ = 207).

Intermediate 03 (30.0 g, 144.8 mmol), ₂ CO ₃ (40.0 g, 289.5 mmol) and NMP (400 nil) were added to a three neck flask and stirred at 120 ^° C overnight. After the reaction was completed, the reaction solution was stirred with silver, and water (500 ml) was added dropwise to the reaction solution. After that, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give intermediate C-4 (23.0 g, yield 85%, MS: [M + H] ⁺ = 187). .

Intermediate C-4 (20 g, 106.8 mmol) was dissolved in acetonitrile (560 ml) in a three-necked flask, and then triethylamine (24 ml, 170.9 隱 ol), perfluoro-1-butane Sulfonyl fluoride (29 ml, 160.2 mmol) was added and stirred at room temperature overnight. When the reaction was completed, the mixture was diluted with ethyl acetate, transferred to a separatory funnel, washed with an aqueous 0.5 M sodium bisulfate solution, and the organic layer was extracted. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give Intermediate C (36.1 g, yield 72%, MS: [M + H] ⁺ = 469). Preparation Example 4 Preparation of Intermediate D

 Step 1) Preparation of Intermediate D-1

 D-1

Put a 30 wt% aqueous solution of hydrogen peroxide (60 ml, 529.6 mmol) in a two-necked flask and add pen-d5-ol (50.0 g, 504.3 μl) and iodine (64.8 g, 252.2 mmol) to distilled water (500 ml). After melting. Stir at 50 ^° C for 24 h. After the reaction was completed, an aqueous solution of sodium thiosulfate was added thereto, followed by stirring. The reaction solution was transferred to a separating funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give intermediate D-1 (54.2 g, yield 48%, MS: [M + H] ⁺ = 224). .

 D-1 D-2

Intermediate D-1 (50.0 g, 223.2 mmol), NBS (41.7 g, 234.3 mmol) and DMF (1000 mL) were added to a two-necked flask and stirred for 8 hours at room temperature under argon atmosphere. After completion of reaction, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give intermediate D-2 (57.3 g, yield 85%, MS: [M ^′ + H] ⁺ = 302 ). Step 3) Preparation of Intermediate D— 3

3 ball. Dissolve intermediate D-2 (55.0 g, 182.2 瞧 ol), (2-fluorophenyl) boronic acid (28.0 g, 200.4 隱 ol) in THF (825 ml) in a flask and add 2C0 ₃ (100.7 g, 728.7 画 ol) Was dissolved in water (413 ml). Pd (PPh ₃ ) ₄ (8.4 g, 7.3 Pa) was added thereto, and the mixture was stirred for 8 hours under reflux conditions under argon. When the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give Intermediate D-3 (36.9 g, yield 75%. MS: [M + H] ⁺ = 270).

 D-3 D

In a three-necked flask intermediate I ⁾ -3 (36.0 g, 133.3 μl), K ₂ CO ₃ (36.8 g, 266.5 mmol). NMP (470 ml) was added and stirred at 120 ^° C overnight. After the reaction was completed, the reaction solution was cooled to silver and water (500 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give Intermediate D (21.0 g, yield 63%, MS: [M + H] ⁺ = 250). Preparation Example 5 Preparation of Intermediate E

Step 1) Preparation of Intermediate E-1

 E-1

In a three-necked flask, intermediate D-K50.0 g, 223.2 μl ol) and (5-bromo-2-fluorophenyl) boronic acid (53.7 g, 245.5 μl) were dissolved in THF (750 ml) and K ₂ C0 ₃ (123.4 g, 892.7 μl) was dissolved in water (375 ml). Pcl (PPh ₃ ) ₄ (10.3 g, 8.9 麵 ol) was added thereto, followed by stirring for 8 hours under argon atmosphere reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give intermediate E—Γ (45.4 g, yield 75V MS: [M + H] ⁺ = 271).

In a three-necked flask, intermediate E-K45.0 g, 166.0 μl ol), ₂ CO ₃ (45.9 g ′ 332.0 μl ol), NMP (585 ml) were added and stirred at 120 ° C. overnight. When the reaction was finished, the solution was decanted and added dropwise with water (60Q ml) little by little. The reaction solution was then transferred to a separatory funnel, and the organic insects were extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give Intermediate E (25.4 g, 61% water, MS: [M + H] ⁺ = 251). Preparation Example 6 Preparation of Intermediate F

Dibenzo [b, d] thiophene-d8 (30.0 g, 156.0 μl ol) was dissolved in acetic acid (300 ml) in a two-necked flask by heating under argon atmosphere. Bromine (10 ml, 187.2 mmol) was slowly added dropwise thereto, followed by stirring for 20 hours while cooling to room temperature. After the reaction was completed, the resulting solid was filtered, washed with acetic acid and water and recrystallized with methanol to obtain intermediate F (16.0 g, yield 38%, MS: [M + H] ⁺ = 270).

EXAMPLE

 Example 1 Preparation of Compound 1

9 microbromoanthracene (15.0 g, 58.3 mmol) in a three neck flask. Bis (pinacolato) diboron (1g 8 g, 70.0 mmol), Pd (dba) ₂ (0.7 g, 1.2 mmol), tricyclonucleosilphosphine (0.7 g, 2.3 mmol), K0Ac (11.5 g, 116.7 mmol), 1,4-dioxane (225 ml) was added, and the mixture was stirred for 12 hours under argon atmosphere reflux conditions. After the reaction was completed, the reaction solution was cooled to silver, and the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 1-a (14.7 g, yield 83%, MS: [M + H] ⁺ = 304). . Step 2) Preparation of Compound 1-b

In a three-necked flask, compound la (14.0 g, 46.0 μl ol), intermediate A (12.9 g, 50.6 μl ol) were dissolved in THF (210 ml) and ₂ CO ₃ (25.4 g, 184.1 mmol) was added to water (105 ml). Melted in. Pcl (PPh ₃ ) ₄ (2.1 g, 1.8 Pa) was added thereto, and the mixture was stirred for 8 hours under reflux conditions under argon. When the reaction is finished, after cooling to room temperature. The reaction solution was transferred to a separatory funnel and extracted with water and ethyl acetate. The extract was dried over MgS0 ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give compound 1-b (12.6 g, yield 78%, MS: [M + H] ⁺ = 351).

To a two-necked flask, add compound lb (12.0 g, 34.1 隱 ol), NBS (6.4 g, 35.9 mmol), and DMF (240 mL). It was stirred for 8 hours at room temperature under argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgS0 ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give compound 1-c (12.9 g, yield 88%, MS: [M + H] ⁺ = 403). Step 4) Preparation of Compound 1

In a three-necked flask, compound lc (12.5 g, 29.0 μl ol), naphthalene-2-ylboronic acid (5.5 g, 32.0 mmol) was dissolved in THF (190 ml), and K ₂ CO ₃ (16.1 g, 116.2 μl) was dissolved in water. Dissolved in (94 nil). Pd (PPh ₃ ) ₄ (1.3 g, 1.2 隱 ol) was added thereto, and the mixture was stirred for 8 hours under reflux condition under argon atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature and the reaction solution was transferred to a separatory funnel. . Extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, the sample was purified by silica gel column chromatography, and then sublimed to obtain Compound 1 (4..9 g, yield 35%, MS: [M]. + H] ⁺ = 478).

실시예 1의 단계 4에서， 나프탈렌 -2-일보론산 대신 나프탈렌ᅳ 1- 일보론산을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 2를 제조하였다 (4.7 g, 수율 34%, MS: [M+H]⁺= 478). 실시예 3: 화합물 3의 제조

실시예 1의 단계 4에서， 나프탈렌— 2-일보론산 대신 페난쓰렌 -9- 일보론산을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로_.화합물 3을 제조하였다 (5.7 g, 수율 37%, MS: [M+H]⁺= 528).

In Step 4 of Example 1, except that naphthalene-2-ylboronic acid was used instead of naphthalene-2-ylboronic acid, Compound 2 was prepared by the same method as the preparation of Compound 1 (4.7 g, Yield 34%, MS: [M + H] ⁺ = 478). Example 3: Preparation of Compound 3

In the same manner as in the preparation of Compound 1, in Step 4 of Example 1, except that phenanthrene-9-ylboronic acid was used instead of naphthalene—2-ylboronic acid _. Compound 3 was prepared (5.7 g, yield 37%, MS: [M + H] ⁺ = 528).

실시예 1의 단계 4에서， 나프탈렌 -2-일보론산 대신 (4-페닐나프탈렌— 1-일)보론산을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 4를 제조하였다 (5.1 g, 수율 32%ᅳ MS: [M+H]⁺= 554). 실시예 5: 화합물 5의 제조

In Step 4 of Example 1, Compound 4 was prepared by the same method as the preparation of Compound 1, except that (4-phenylnaphthalene-1-yl) boronic acid was used instead of naphthalene-2-ylboronic acid (5.1 g, yield 32% ms MS: [M + H] ⁺ = 554). Example 5: Preparation of Compound 5

Step 1) Preparation of Compound 5—a

In a three-necked flask, 9-bromoanthracene (14.0 g, 54.4 μl ol) and intermediate B (13.1 g, 59.9 μl ol) were dissolved in THF (210 ml) and K ₂ CO ₃ (30.1 g, 217.8 μl ol) was watered. (105 ml) was dissolved. Pd (PPh ₃ ) ₄ (2.5 g, 2.2 瞧₀ 1) was added thereto, and the mixture was stirred for 8 hours under reflux condition of argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgS0 ₄ , filtered and concentrated, and then sampled. Purification by silica gel column chromatography gave compound 5-a (14.4 g. Yield 75%, MS: [M + H] ⁺ = 351).

Compound 5—a (14.0 g, 39.8 μl ol), NBS (7.4 g, 41.8 μl ol) and DMF (280 ml) were added to a two neck flask and stirred for 8 hours at room temperature under an argon atmosphere. After the reaction was completed, the reaction solution was transferred to a separatory funnel. The organic insects were extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and filtered. After concentration, the sample was purified by silica gel column chromatography to give compound 5-b (13.2 g, yield 77%, MS: [M + H] ⁺ = 403). Step 3) Preparation of Compound 5

실시예 1의 단계 4에서, 화합물 1— c 대신 화합물 5-b를 사용한 것을 제외하고는， 화합물 1의 제조 방법과 동일한 방법으로 화합물 5를 제조하였다 (4.3 g, 수율 31%, MS: [M+H]⁺= 478).

In Step 4 of Example 1, Compound 5 was prepared by the same method as the preparation of Compound 1, except that Compound 5-b was used instead of Compound 1-c (4.3 g, yield 31%, MS: [M]. + H] ⁺ = 478).

In Step 4 of Example 1, the same method as for preparing Compound 1, except that Compound 5-b was used instead of Compound 1-c and naphthalene- 1- _ylboronic acid was used instead of naphthalene-2- _ylboronic acid Compound 6 was prepared by the method (4.4 g, yield 32%, MS: [M + H] ⁺ = 478). Example 7: Preparation of Compound 7

 7

In Step 4 of Example 1, except that Compound 5-b was used instead of Compound 1-c and (6-phenylnaphthalen-2-yl) boronic acid was used instead of naphthalen-2-ylboronic acid, Compound 7 was prepared by the same method as the preparation method (5.0 g, yield 31%, MS: M + H] ⁺ -554).

In step 4 of Example 1, the same method as for preparing compound 1, except that compound 5-b was used instead of compound 1-c and triphenylene- 2-ylboronic acid was used instead of naphthalene-2-ylboronic acid Compound 8 was prepared ^' by the method (6.2 g, yield 37%, MS: [M + H] ⁺ = 578). Example 9: Preparation of Compound 9

Step 1) Preparation of Compound 9—a

In a three-necked flask, dissolve Compound 1—a (15.0 g, 49.3 mmol), Intermediate C (25.5 g. 54.2 μl) in THFC225 ml, and ₂ CO ₃ (27.3 g, 197.2 mmol) in water (113 ml). Melted. Pd (PPh ₃ ) ₄ (2.3 g, 2.0 Pa ol) was added thereto and stirred for 8 hours under argon atmosphere reflux conditions. When the reaction is over, after cooling to room temperature. The reaction solution was transferred to a separatory funnel and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to give compound 9-a (11 ᅳ 6 g, yield 68%, MS: [M + H] ⁺ = 347).

In Step 3 of Example 1, except that Compound 9-a was used instead of Compound 1-b, Compound 9-b was prepared by the same method as the method for preparing Compound 1-c (11.9 g, yield 88%, MS: [M + H] ⁺ = 426). Step 3) Preparation of Compound '9

 9

In Step 4 of Example 1, except that Compound 9-b was used instead of Compound 1-c, Compound 9 was prepared by the same method as the preparation of Compound 1 (4.3 g, Yield 34%, MS: [M + H] ⁺ = 474). Example 10 Preparation of Compound 10

In Example 1 step 4, the compound 1-c instead of using the compound 9-b, and _{naphthalene-2} and _ the same procedures as in the process for producing the compound 1, but instead of daily acid was used to form the 9-phenanthryl sseuren eu Daily acid Compound 10 was prepared (4.4 g. Yield 31%, MS: [M + H] ⁺ = 524). Example 11: Preparation of Compound 11

실시예 1의 단계 2에서， 중간체 A 대신 중간체 D를 사용한 것을 제외하고는, 화합물 1-b의 제조 방법과 동일한 방법으로 화합물 11— a를 제조하였다 (11.4 g, 수율 71%, MS: [M+H]⁺= 347).

In Step 2 of Example 1, except that Intermediate D was used instead of Intermediate A, Compound 11-a was prepared by the same method as the preparation of Compound 1-b (11.4 g, Yield 71%, MS: [M + H] ⁺ = 347).

In Step 3 of Example 1, except that Compound 11-a was used instead of Compound 1-b, Compound 11-b was prepared by the same method as the method for preparing Compound 1-c (11.5 g, 85% yield, MS: [M + H] ⁺ = 426).

In Step 4 of Example 1, except that Compound 11-b was used instead of Compound 1-c, Compound 11 was prepared by the same method as the preparation of Compound 1 (4.5 g, 35% yield, MS: [M]. + H] ⁺ = 474). Example 12: Preparation of Compound 12

실시예 1의 단계 4에서， 화합물 1-c 대신 화합물 11— b를 사용하고， 나프탈렌 _₂ᅳ일보론산 대신 나프탈렌 -1-일보론산을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 12를 제조하였다 (4.1 g, 수율 32%， MS: [M+H]⁺= 474).

In the same manner as in the preparation of Compound 1, in Step 4 of Example 1, except that Compound 11-b was used instead of Compound 1-c and naphthalene-1-ylboronic acid was used instead of naphthalene _ ₂ xylboronic acid Compound 12 was prepared (4.1 g, yield 32%, MS: [M + H] ⁺ = 474).

^

 13

In Example 11, Compound 13 was prepared by the same method as the method for preparing Compound 11, except that Intermediate E was used instead of Intermediate D, and phenanthren-9-ylboronic acid was used instead of naphthalene-2-ylboronic acid. 4.3 g, MS: [M + H] = 525).

Compound 14 was prepared in the same manner as in the preparation of Compound 11, except that Intermediate E & was used instead of Intermediate D in Example 11, and naphthalene- 1-ylboronic acid was used instead of naphthalene—2—ilboronic acid (4.5 g, MS: [M + H] ⁺ = 475). Example 15: Preparation of Compound 15

 15

In Example 11, except that Intermediate F was used instead of Intermediate D. Compound 15 was prepared by the same method as the compound 11 preparation (5.3 g. MS: [M + H] ⁺ = 494),

Experimental Example

 Experimental Example 1

IT0 (Indium Tin Oxide) was a thin film coated glass substrate with a thickness of 1,400A was put in distilled water dissolved in detergent and washed with ultrasonic waves. Fischer Co.'s Decon ™ C0N705 product was used as a detergent, and distilled water was filtered secondly with a 0.22 sterilizing filter of Millerpore Co.'s product. After washing IT0 for 30 minutes, the ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried and then 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 HI—Α compound and the following HAT ′ CN compound were thermally vacuum deposited to a thickness of 650 A and a thickness of 50 A, respectively, on the πΌ transparent electrode thus prepared to form a hole injection layer. The following HT-A compound was vacuum deposited to a thickness of 600 A on the hole injection layer to form a hole transport layer. The following HT—B compound was thermally vacuum deposited to a thickness of 50 A on the hole transport layer to form an electron blocking layer. The light emitting layer was formed by vacuum depositing Compound 1 and the following BD compound on the electronic blocking layer at a thickness of 200 A at a weight ratio of 96: 4. The following ET-A compound was vacuum-deposited to a thickness of 50 A on the luminescent charge to form a hole blocking layer. The following ET-B compound and the following Liq compound were thermally vacuum-deposited to a thickness of 310 A on a weight ratio of 1: 1 to form an electron transport layer on the hole blocking layer. The following _{L iq} compound was vacuum deposited to a thickness of 5 A on the electron transport layer to form an electron injection layer. Magnesium and silver were sequentially deposited on the electron injection layer at a weight ratio of 10: 1 to 120A, and aluminum was deposited to 1000A to form a cathode, thereby manufacturing an organic light emitting device.

Experimental Examples 2 to 15

 An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of the compound 1 in Experimental Example 1. Comparative Experiments 1 to 8

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1. In Table 1 below, the compounds of BH-A, BH-B, BH-C, BH-D, BH-E, BH-F, BH-G and BH-H are as follows.

BH-E BH-F BH-G BH-H Applying a current to the organic light emitting device manufactured in the above Experimental Example and Comparative Experimental Example to measure the voltage, efficiency, lifetime (T95) and the results are shown in Table 1 below. In this case, the voltage and efficiency were measured by applying a current density of 10 mA / cm ² , and T95 means the time until the initial luminance decreased to 95% at a current density of 20 mA / cm ² .

 [Table 1]

Hose Voltage (V) Efficiency (cd / A) Life (T95, hr) _. Substance (@ 10 mA / cm ² ) (@ 10 mA / cm ² ) (@ 20 mA / cni ² ) Experimental Example 1 Compound 1 3.32 6.07 65 Experimental Example 2 Compound 2 3.31 6.03 60 Experimental Example 3 Compound 3 3.33 6.08 66 Experimental Example 4 Compound 4 3.34 6. 11 68 Experiment 5 Compound 5 3.44 6.07 67 Experiment 6 Compound 6 3.45 6.09 65 Experiment 7 Compound 7 3.48 6. 10 63 Experiment 8 Compound 8 3.44 6.06 61 Experiment 9 Compound 9 3.35 5.71 55 Experiment 10 Compound 10 3.34 5.66 53 Experiment 11 Compound 11 3.30 5.88 59 Experiment 12 Compound 12 3.39 5.80 58 Experimental Example 13 Compound 13 3.38 5.55 51 Experimental Example 14 Compound 14 3.36 5.56 50 Experimental Example 15 Compound 15 3.33 6.02 60 Comparative Experiment 1 BH-A 4.25 5. 13 40 Comparative Experiment 2 BH-B 3.81 5. 10 20 Comparative Experiment Example 3 BH-C 3.71 5.21 20 Comparative Experiment 4 BH-D 4.81 3. 12 10 Comparative Experiment 5 BH-E 4.80 3.51 13 Comparative Experiment 6 BH-F 5.28 2. 12 5 Comparative Experiment 7 BH-G 3.31 5. 10 40 Comparative Example 8 BH-H 3.35 5.06 41 Compared with the BH-A structure of Comparative Example 1, the HOMO energy level was higher than when the dibenzofuran or dibenzothiophene was directly bonded to the anthracene. Higher and easier injection of holes, the driving voltage was lowered. As seen in Comparative Experiment 2 and Comparative Example 3, even if dibenzofuran or dibenzothiophene is directly bonded to anthracene, such as BH-B or BH-C, when there is only a phenyl group on the opposite side, the molecular weight is Too small to reduce thermal stability, which resulted in reduced efficiency and lifetime. BH-D increased molecular weight by introducing substituent ¾ to dibenzofuran to ensure thermal stability. Comparative Experimental Example with BH-E and BH-F applied 4. Comparative Experimental Example 5 and Comparative Experimental Example 6 are ^. Rather, it resulted in higher voltage, lower efficiency, and lower lifetime. As a result of the above results, it is confirmed that a dibenzofuran or a dibenzothiophene is directly bonded to anthracene, and an aryl group having 10 to 20 carbon atoms is opposite to the blue light emitting layer host. have. In addition, deuterium has a higher atomic weight than hydrogen and thus has a small oscillation mode, which increases the non-radioactive decay time in the excited state, and in particular, increases the stability of the triplet excitons. The increased stability of triplet excitons can eventually amplify the TTF phenomenon and contribute to the efficiency and lifetime improvement of blue fluorescence. The results of Experimental Examples 1 to 15 described in Table 1 show such effects well when compared with Comparative Experimental Example 7 and Comparative Experimental Example 8 in which deuterium is not substituted. From the results of the experimental examples, the more deuterium is contained in dibenzofuran or dibenzothiophene, the more the deuterium is located in the anthracene where the triplet excitons are mainly located. The closer it is, the greater the effect. As a result, when the material having the structure of Formula 1 is used as the blue light emitting layer host of the organic electroluminescent device, a low voltage, high efficiency, long life device can be obtained.

 [Explanation of code]

 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

[Patent Claims]  [Claim 1]  Compound represented by the following formula (1):  [

 In Chemical Formula 1,  X is 0 or S, Ri to ¾ are each independently hydrogen or deuterium, at least one of ¾ to R ₈ is deuterium, any one of R ₃ to R ₄ is the following Formula 2,

₂₀ is an aryl - Arr ^ substituted or unsubstituted C _10. [Claim 2]  The method of claim 1,  Formula 1 is represented by the following Formula 1-1, 1-2, 1-3, or 1-4. compound:

[Formula 1-2]

 In Chemical Formula 1—1 to 1-4,  X and Ar are as defined in claim 1, In Formula 1-1, ¾ and R ₃ to ¾ are each independently hydrogen or deuterium, at least one of ¾ and ¾ to R ₈ is deuterium, In Chemical Formula 1-2, R ₂ to ¾ each independently represent hydrogen and hydrogen, at least one of R ₂ to R ₈ is deuterium, In Formula 1-3, ¾ and to ¾ are each independently hydrogen or deuterium, at least one of R ₂ and R ₄ to is deuterium, In Formula 1-4, R ₃ and R ₅ to ¾ are each independently hydrogen or deuterium, and at least one of ¾ to ¾ and R ₅ to ¾ is deuterium. [Claim 3]  The method of claim 2, In Ri and R ₃ to R ₈ of the formula 1-1, R ₃ R ₈ ; Ri and R ₃ ; R ₆ and R ₈ ; R _1; R ₃ and R ₄ ; R ₅ to; Or ¾ Deuterium, the rest being hydrogen.  compound. [Billing Hing-4]  The method of claim 2, wherein. In R ₂ to ¾ of Formula 1-2, ¾; R ₃ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; ; ¾ and R ₄ ; R ₆ and R ₈ ; ᅵ to R ₄ ; R ₅ to ¾; Or R ₂ to ¾ are deuterium, the remainder is hydrogen,  compound. [Claim 5]  The method of claim 2, In Formula 1-3, and R ₄ to ¾; R ₂ ; ₄ ; ; ; R ₇ ; R ₈ ; R ₂ and R4; And; Ri, R ₂ and R4; R ₅ to I; Or Ri, ₂ and ¾ to ¾ are deuterium, the remainder being hydrogen,  compound. [Claim 6]  The method of claim 2, Among ¾ to ¾ and R ₅ to R ₈ of Formula 1-4, R ₂ ; R ₃ ; R ₅ ; ¾; R ₇ ; ; i and; R ₆ and R8; i to I¾; R ₅ to R8; Or Ri to I and R ₅ to deuterium, the remainder being hydrogen,  compound. [Claim 7]  In that U term,  八！ ^ is naphthyl, phenylnaphthyl, phenanthrenyl, or triphenylenyl. [Claim 8]  The method of claim 1, Wherein said compound is selected from the group consisting of: OS

ΪΪ.880ΪΪ / 8Ϊ0Ζ OAV

_/// O ₁₆ ss _Z J02Ml _> d-880Π8 _Ϊ 0ΖA ₇

[Claim 9] A first electrode; A second electrode provided to face the first electrode; And said At least one organic light emitting device provided between an electrode and the second electrode, wherein at least one of the organic material layer comprises the compound of claim 1, Organic light emitting device.