KR20200020459A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound represented by chemical formula 1, and to an organic light emitting device using the same. The compound improves the efficiency, low driving voltage and/or service life properties in the organic light emitting device.

Description

Novel compound and organic light emitting device comprising the same

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

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

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

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

Recently, organic light emitting devices using a solution process, in particular, an inkjet process, have been developed in order to reduce process costs. In the early days, organic light emitting devices were developed by coating all organic light emitting device layers by solution process, but there are limitations in current technology, so only HIL, HTL, and EML are used as solution process in regular structure, and further processes are conventional deposition processes. A hybrid process that utilizes is under study.

Accordingly, the present invention provides a novel organic light emitting device that can be used in an organic light emitting device and can be used in a solution process at the same time.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by Chemical Formula 1.

The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting device, and may also be used in a solution process, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting device. have.

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 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.
3 shows GC-MS data of Compound 1 prepared in Preparation Example 1. FIG.

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

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

Means a bond connected to another substituent.

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

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

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

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

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

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

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

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

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

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

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

In the present specification, the heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl Groups, phenothiazinyl groups, dibenzofuranyl groups and the like, but are not limited thereto.

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

On the other hand, the present invention provides an anthracene derivative compound represented by the formula (1).

The conventional materials used in the vacuum deposition process have a problem that the solubility in the solvent is very low, or the solubility in only a specific solvent is high and thus difficult to be used in the solution process.

However, the compound according to the present invention has a structure represented by Chemical Formula 1 as described in detail below, and has high solubility in a solvent, and thus may be used in a solution process in manufacturing an organic light emitting device.

(compound)

The compound of the present invention is represented by the formula (1).

In Formula 1, Ar ₁ and Ar ₂ may each independently be C _6-20 aryl unsubstituted or substituted with C _1-10 alkyl.

Specifically, Ar ₁ and Ar ₂ may each independently be phenyl, phenyl substituted with C _1-4 alkyl, naphthyl, or naphthyl substituted with C _1-4 alkyl.

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

.

.

For example, the compound is any one selected from the group consisting of the following compounds:

On the other hand, the compound represented by the formula (1) can be prepared by the same production method as in Scheme 1 below.

Scheme 1

In Reaction Scheme 1, Ar ₁ and Ar ₂ are the same as defined in Formula 1. Specifically, the steps 1-1, 1-3, and 1-5 are a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and a reactor for the Suzuki coupling reaction is changed as known in the art. This is possible. In addition, steps 1-2 and 1-4 are reactions in which a bromo group is introduced into an intermediate compound, which is preferably performed using a bromosuccinimide reagent. The manufacturing method may be more specific in the production examples to be described later.

(Coating Composition)

On the other hand, the compound according to the invention can form an organic layer, in particular a light emitting layer of the organic light emitting device by a solution process. Specifically, the compound may be used as a host material of the light emitting layer. To this end, the present invention provides a coating composition comprising a compound and a solvent according to the present invention described above.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention. For example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o Chlorine solvents such as dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Polyhydric compounds such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol Alcohols and derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; Sulfoxide solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; Benzoate solvents such as butyl benzoate and methyl-2-methoxybenzoate; Tetralin; And solvents such as 3-phenoxytoluene. In addition, the solvent mentioned above may be used individually by 1 type, or 2 or more types of solvent may be mixed and used for it.

In addition, the coating composition may further include a compound used as a dopant material, the description of the compound used in the dopant material will be described later.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, the coating is easy in the above range. In addition, the concentration of the compound according to the invention in the coating composition is preferably from 0.1 wt / v% to 20 wt / v%.

The solubility (wt%) of the coating composition in the solvent may be 2 or more and less than 10, preferably 3 or more and less than 10, more preferably 5 or more and less than 10, based on the solvent toluene. Coating compositions comprising the compound of interest are suitable for use in solution processes.

The present invention also provides a method of forming a light emitting layer using the coating composition described above. Specifically, coating the light emitting layer according to the present invention on the anode, or on the hole transport layer formed on the anode in a solution process; And heat treating the coated coating composition.

The solution process is to use the coating composition according to the present invention described above, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited to these.

In the heat treatment step, the heat treatment temperature is preferably 150 to 230 ℃. The heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably carried out in an inert gas atmosphere such as argon, nitrogen.

(Organic Light Emitting Element)

In another aspect, the present invention provides an organic light emitting device comprising a compound represented by the formula (1). In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by Chemical Formula 1.

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

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

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 the light emitting layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that the light emitting layer includes the compound according to the present invention and is manufactured as described above.

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

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

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

As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SNO ₂ : Sb; Conductive compounds such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic compounds, anthraquinone, and polyaniline and polythiophene-based conductive compounds, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

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

The light emitting layer may include a host material and a dopant material as described above. As the host material, a compound represented by Chemical Formula 1 may be used. Alternatively, a condensed aromatic ring derivative or a hetero ring-containing compound may be further used as a host material in addition to the compound represented by Formula 1 above. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group. At least one arylvinyl group is substituted with the above-described arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting 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 Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer for injecting electrons from an electrode, has 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, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. It is not limited to this.

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

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

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 only for illustrating the present invention, and the scope of the present invention is not limited thereto.

Production Example  1: Preparation of Compound 1

Step 1-1: Preparation of Intermediate Compound A1

2-bromoanthracene (5 g, 19.45 mmol), naphthalen-1-ylboronic acid (4 g, 23.3 mmol), potassium carbonate (8.1 g, 58 mmol) was added 65 ml of toluene, 20 ml of ethanol, 20 ml of water The temperature was raised to 90 ° C. and dissolved. Pd (PPh ₃ ) ₄ (1.1 g, 0.97 mmol) was added thereto and reacted at 90 ° C. for about 24 hours. The temperature was lowered, the organic layer was extracted with ethyl acetate [EA], water was removed with magnesium sulfate [MgSO ₄ ], and the residual catalyst was adsorbed with charcoal, and then filtered through celite and silica. The filtrate was concentrated, slightly dissolved in methylene chloride and precipitated in ethanol to obtain 8.4 g of a white solid intermediate compound A1.

Step 1-2: Preparation of Intermediate Compound A2

The intermediate compound A1 (8.8 g, 28.91 mmol) and N-bromosuccinimide (5.4 g, 30.4 mmol) obtained in step 1-1 were added to 200 ml of DMF to dissolve the reaction, and the reaction was performed at room temperature for about 3 hours. I was. The reaction was quenched with water and filtered using water and methanol to give a brown solid. The solid was dissolved using excess THF and EA, and brine was added to extract the organic layer. Water was removed with magnesium sulfate [MgSO ₄ ], concentrated and precipitated in ethanol to give 4.1 g of a yellow solid intermediate compound A2.

Step 1-3: Preparation of Intermediate Compound A3

The intermediate compound A2 (4.1 g, 10.69 mmol), phenylboronic acid (1.95 g, 16.04 mmol) obtained in the above step 1-2, and potassium carbonate (4.4 g, 32.07 mmol) were added to 100 ml of toluene, 30 ml of ethanol, and water. After putting into 30 ml, the temperature was dissolved by heating to 100 ° C. Pd (PPh ₃ ) ₄ (0.61 g, 0.53 mmol) was added thereto and reacted at 100 ° C. for about 3 hours. The temperature was lowered, the organic layer was extracted with ethyl acetate [EA], water was removed with magnesium sulfate [MgSO ₄ ], and the residual catalyst was adsorbed with charcoal, and then filtered through celite and silica. The filtrate was adsorbed onto silica and subjected to column chromatography to obtain about 1.4 g of intermediate compound A3.

Step 1-4: Preparation of Intermediate Compound A4

Intermediate compound A3 (1.4 g, 3.68 mmol) and N-bromosuccinimide (0.67 g, 3.79 mmol) obtained in Step 1-3 were added to 20 ml of DMF to dissolve the reaction and reacted at room temperature for about 3 hours. I was. The reaction was quenched with water and filtered using water and methanol to give a brown solid. The solid was dissolved using excess THF and EA, and brine was added to extract the organic layer. Water was removed with magnesium sulfate [MgSO ₄ ], concentrated and precipitated in ethanol to obtain 1.4g of a yellow solid intermediate compound A4.

Step 1-5: Preparation of Compound 1

4,4,5,5-tetramethyl-2- (3- (10- (naphthalen-1-yl) anthracene-9-yl) phenyl) -1,3,2-dioxaborolane (2.3 g, 4.6 mmol), the intermediate compound A4 (1.4 g, 3.05 mmol) obtained in the above steps 1-4, potassium carbonate (1.3 g, 9.15 mmol) was added to 30 ml of toluene, 5 ml of ethanol, and 5 ml of water, and then the temperature was 90 ° C. Warmed up and melted. Pd (PPh ₃ ) ₄ (1.06 g, 9.15 mmol) was added thereto and reacted at 90 ° C. for about 3 hours. The temperature was lowered, the organic layer was extracted with ethyl acetate [EA], water was removed with magnesium sulfate [MgSO ₄ ], and the residual catalyst was adsorbed with charcoal, and then filtered through celite and silica. The filtrate was adsorbed on silica and subjected to column chromatography to obtain 1.8 g of compound 1. GC-MS data of the prepared compound 1 is shown in FIG. 3.

Production Example  2: Preparation of Compound 2

The title compound was prepared in the same manner as in Preparation Example 1, except that (4- (tert-butyl) phenyl) boronic acid was used instead of phenylboronic acid in steps 1-3 of Preparation Example 1.

MS [M + H] ⁺ = 816.37

Production Example  3: Preparation of Compound 4

The title compound was prepared in the same manner as in Preparation Example 1, except that (4- (tert-butyl) phenyl) boronic acid was used instead of naphthalen-1-ylboronic acid in Step 1-1 of Preparation Example 1.

MS [M + H] ⁺ = 766.35

Production Example  4: Preparation of Compound 5

Preparation of the title compound was carried out in the same manner as in Preparation Example 1, except that naphthalene-1ylboronic acid boronic acid was used instead of phenylboronic acid in steps 1-3 of Preparation Example 1.

MS [M + H] ⁺ = 810.32

Experimental Example  1: Solubility Experiment

Example  1-1 to 1-4

The solubility was measured by dissolving the compounds prepared in Preparation Examples 1 to 4 in toluene, respectively, and the results are shown in Table 1 below.

Comparative example  1-1

Compound A was dissolved in toluene to measure solubility, and the results are shown in Table 1 below.

[Compound A]

compound Solubility (wt%) Example 1-1 Compound 1 5 Example 1-2 Compound 2 > 10 Example 1-3 Compound 4 > 10 Example 1-4 Compound 5 5 Comparative Example 1-1 Compound A One

As shown in Table 1, the compound represented by the formula (1) of the present invention, it can be seen that the solubility in toluene is significantly higher than that of Comparative Example Compound A without the Ar ₁ substituent.

Example  2-1: Fabrication of Organic Light-Emitting Element

A glass substrate coated with a thin film of ITO at 500 kPa was placed in distilled water in which detergent was dissolved, and ultrasonically washed. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. 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.

On the thus prepared ITO transparent electrode, a composition in which the ratio of VNPB and p-dopant were mixed at a weight ratio of 0.8: 0.2 was spin-coated, and cured at a temperature of 220 ° C. for 30 minutes in a hot plate under a nitrogen atmosphere to form a hole injection layer having a thickness of 400 μm. .

On the hole injection layer thus formed, spin-coated a solution of N, N, N ', N'-tetra (4-biphenyl) diaminobiphenylene (hereinafter abbreviated as TBDB) in toluene and spin coated on a hot plate. Heat treatment was performed at 30 ° C. for 30 minutes to form a hole transport layer having a thickness of 200 μs. Compound 1 prepared in Preparation Example 1 was spin-coated by dissolving the compound 1 prepared in Preparation Example 1 on the formed hole transport layer and heat-treated at 180 ° C. for 30 minutes to form a light emitting layer having a thickness of 350 Pa. This was introduced into a vacuum vapor deposition apparatus, and when the base pressure was 2x10-5 Pa or less, LiF (200 Pa) and Al (1,000 Pa) were deposited in order to manufacture an organic light emitting device. In the above process, the deposition rate of LiF was maintained at 0.01 to 0.05 nm / s, and the deposition rate of materials other than LiF was maintained at 0.1 to 0.5 nm / s.

Example  2-2 to Example  2-4 and Comparative example  2-1

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compound shown in Table 2 was used instead of the compound 1 of Preparation Example 1.

Experimental Example  2: Evaluation of organic light emitting device characteristics

When a current is applied to the organic light emitting diodes manufactured in Examples 2-1 to 2-4 and Comparative Example 2-1, the driving voltage, current efficiency, quantum efficiency (QE), brightness, and lifetime (T90) are measured. The results are shown in Table 2 below. T90 means the time taken for the luminance to decrease to 90% from the initial luminance.

compound
(Light emitting layer
Host) Driving voltage
(V
@ 10mA / cm ² ) Current efficiency
(cd / A
@ 10mA / cm ² ) QE
(%) Luminance
(cd / m ² ) T90
(hr
@ 10mA / cm ² ) Example 2-1 Compound 1 4.41 8.25 8.01 825.33 41 Example 2-2 Compound 2 4.62 7.54 7.50 754.65 35 Example 2-3 Compound 4 4.64 7.51 5.09 751.75 31 Example 2-4 Compound 5 4.43 8.16 7.97 816.48 38 Comparative Example 2-1 Compound A 7.90 2.75 2.30 275.16 10

As shown in Table 2, the organic light emitting device using the compound of the present invention as a host of the light emitting layer, compared to the organic light emitting device using the Comparative Example Compound A without the Ar ₁ substituent as the host of the light emitting layer, the driving voltage, current efficiency and All showed excellent properties in terms of stability.

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 (6)

A compound represented by formula (1):
[Formula 1]

In Chemical Formula 1,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently C _6-20 aryl unsubstituted or substituted with C _1-10 alkyl,
compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently unsubstituted phenyl, phenyl substituted with C _1-4 alkyl, unsubstituted naphthyl, or naphthyl substituted with C _1-4 alkyl,
compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of
compound:

.
The method of claim 1,
The compound is any one selected from the group consisting of the following compounds:

A first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer comprises a compound according to any one of claims 1 to 5. .

Images