KR20200072645A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same, wherein the compound is represented by chemical formula 1.

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, the organic light emitting phenomenon refers to a phenomenon that converts 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, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

Meanwhile, an organic light emitting device using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process to reduce process cost. In the early days, all organic light-emitting device layers were coated with a solution process to develop an organic light-emitting device, but there are limitations in current technology, so only HIL, HTL, and EML are used as a solution process in the form of a regular structure, and the subsequent process is an existing deposition process. A hybrid process that utilizes is being studied.

Accordingly, the present invention provides a novel organic light emitting device material 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,

R ₁ to R ₁₆ are each independently hydrogen; heavy hydrogen; Or substituted or unsubstituted C _1-60 alkyl,

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

However, the case where Ar ₂ is phenyl or anthracenyl is excluded.

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 a compound represented by Chemical Formula 1, and provides an organic emission element.

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

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), an electron injection layer (9) and a cathode (4) An example of an organic light emitting device is shown.

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

(Definition of Terms)

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

Means a linkage to another substituent.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" 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 connected.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

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 (linear) or branched (branched), and the number of carbon atoms 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 are 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 a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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, styrenyl 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 an exemplary 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 is not limited thereto.

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

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

It can be back. However, it is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as heterogeneous elements, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene group, furan group, pyrrol 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, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino group Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), an isooxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, an arylamine group, and an arylsilyl group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group. In the present specification, the heteroarylamine of the heteroaryl may be applied to the description of the heteroaryl described above. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heteroaryl described above 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 aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this 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.

(compound)

Meanwhile, the present invention provides an anthracene derivative compound represented by Chemical Formula 1. At this time, in Formula 1, the meaning of'except when Ar ₂ is phenyl or anthracenyl' means that Ar ₂ is not a substituted or unsubstituted phenyl, and is not a substituted or unsubstituted anthracenyl.

Materials previously used in the vacuum deposition process, there is a problem that the solubility in a solvent is very low, or it is difficult to be used in a solution process because the solubility is high only in a specific solvent.

However, the compound according to the present invention has an aryl or heteroaryl substituent at positions 9 and 10 of anthracene, as described in detail below, and a 2,2'-biphenyldiyl linker with a substituent at position 10 It has a connected structure. When the anthracene and the substituent are connected through the 2,2'-biphenyldiyl linker, the steric hindrance effect is large compared to the case where the substituent at the 10th position of the conventional anthracene is substituted with a para or meta position. The intermolecular packing is not easy, solubility in an organic solvent may be increased.

Therefore, the compound according to the present invention in which Ar ₂ is phenyl or anthracenyl, as represented by Chemical Formula 1, is excluded, and the organic light-emitting device has high solubility in an organic solvent used in a solution process, for example, a solvent such as toluene. It can be used for solution processing in manufacturing.

Preferably, Ar ₁ is phenyl or naphthyl. For example, Ar ₁ is phenyl, 1-naphthyl, or 2-naphthyl.

Preferably, Ar ₂ is any one selected from the group consisting of:

In the above,

X ₁ is O, S, NZ ₃ , or CZ ₄ Z ₅ ,

X ₂ is O, or S,

Z ₁ to Z ₅ are each independently C _1-10 alkyl, or C _6-20 aryl.

More preferably, Z ₁ , Z ₂ , Z ₃ and Z ₄ are methyl, and Z ₃ is phenyl.

Most preferably, Ar ₂ is any one selected from the group consisting of:

Preferably, R ₁ to R ₁₆ are all hydrogen.

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

On the other hand, the compound represented by Formula 1, for example, when R ₁ to R ₁₆ are all hydrogen, can be prepared by the same production method as in Scheme 1 below:

[Scheme 1]

In Reaction Scheme 1, description of the substituent is as defined in Chemical Formula 1. The step 1-1 is a step of preparing the intermediate compound I-1 through a Suzuki coupling reaction of the starting material 2,2'-dibromo-1,1'-biphenyl with the compound A-1, wherein Step 1-2 is a step of preparing a compound represented by Chemical Formula 1 through a Suzuki coupling reaction between the intermediate compound I-1 and Compound A-2. At this time, the Suzuki coupling reaction is preferably a method performed in the presence of a palladium catalyst and a base, and the production method may be more specific in the preparation examples described below.

(Coating composition)

On the other hand, the compound according to the present invention can form an organic material layer, particularly a light emitting layer, of an organic light emitting device by a solution process. Specifically, the compound may be used as a host material for 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-based solvents such as dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon-based 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; Polyvalent values of 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, etc. Alcohols and derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; Sulfoxide-based 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 above-described solvent may be used alone or in combination of two or more solvents. Preferably, toluene may be used as the solvent.

In addition, the coating composition may further include a compound used as a dopant material, and a 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, and the coating is easy in the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.

Preferably, the solubility (wt%) of the coating composition in the solvent is 1.0 to 10.0, more preferably 2.5 to 10.0 based on the solvent toluene, and thus the coating composition comprising the compound represented by Chemical Formula 1 is It is suitable for use in solution processing.

In addition, the present invention provides a method of forming a light emitting layer using the above-described coating composition. Specifically, the step of coating the light emitting layer according to the present invention described above on the positive electrode or the hole transport layer formed on the positive electrode in a solution process; And heat-treating the coated coating composition.

The solution process refers to the use of the coating composition according to the present invention described above, which means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

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

(Organic light emitting element)

In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one example, 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 a compound represented by Chemical Formula 1, and provides an organic emission element.

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

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

2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), an electron injection layer (9) and a cathode (4) An example of an organic light emitting device is shown. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

The organic light-emitting device according to the present invention can be made of materials and methods known in the art, except that the light-emitting layer contains the compound according to the present invention and is prepared as described above.

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

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

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (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, and the second electrode is an anode.

The positive electrode material is usually a material having a large work function 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), and indium zinc oxide (IZO); Metal and oxide combinations 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, but are not limited thereto.

The cathode material is preferably 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; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferred that the high 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 layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic compounds, anthraquinones, polyaniline and polythiophene-based conductive compounds, and the like, 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 the hole transport material, the hole is transported from the anode or the hole injection layer to the hole and is transported to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive compounds, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based compounds; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

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

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons Suitable. Specific examples include the Al complex 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 those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, LiF, NaF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid , Preoleenylidene methane, anthrone and the like, and derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, 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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

Manufacturing example 1: Preparation of compound 1

Step 1-1: Intermediate compound INT -1 Preparation

2,2'-dibromo-1,1'-biphenyl 7.0 g (22.4 mmol, 1.0 eq) and 1-naphthalenyl boronic acid 4.6 g (26.9 mmol, 1.2 eq), Pd (PPh ₃ ) ₄ 2.6 g (2.2 mmol, 0.1 eq), and 9.3 g (67.3 mmol, 3.0 eq) of potassium carbonate were added to 250 ml RBF with 150 ml toluene and 50 ml water. After the degassing process, nitrogen was replaced and then the temperature was raised to 100°C and stirred overnight. Thereafter, the product was cooled to room temperature, and then extracted with dichloromethane. Next, after moisture removal with magnesium sulfate, 2.0 g (25% yield) of the title compound was obtained by adsorption to dichloromethane and column chromatography using hexane as a solvent.

Step 1-2: Preparation of compound 1

Intermediate compound INT-1 prepared in step 1-1 2.0 g (5.6 mol, 1.0 eq) and 10-(naphthalen-1-yl) anthracene-9-ylboronic acid 2.9 g (8.4 mmol, 1.5 eq), Pd ( PPh ₃ ) ₄ 0.7 g (0.6 mmol, 0.1 eq), and potassium carbonate 2.3 g (16.7 mmol, 3.0 eq) were added to 250 ml RBF with 150 ml toluene and 50 ml water. After the degassing process, nitrogen was replaced and then the temperature was raised to 100°C and stirred overnight. Thereafter, the product was cooled to room temperature, and then extracted with dichloromethane. Next, after removing moisture with magnesium sulfate, after adsorbing on dichloromethane, column chromatography was performed using dichloromethane/hexane (1:10) as an eluent, and precipitated with dichloromethane/methanol to obtain 1.0 g of the title compound. . LC-MS data of the prepared compound 1 is as follows.

MS[M+H] ⁺ =583.4

Manufacturing example 2: Preparation of compound 2

1.5 g of the title compound was obtained in the same manner as in Preparation Example 1, except that 2-naphthalenyl boronic acid was used instead of 1-naphthalenyl boronic acid in Step 1-1 of Preparation Example 1. LC-MS data of the prepared compound 2 is as follows.

MS[M+H] ⁺ =583.4

Manufacturing example 3: Preparation of compound 3

Preparation Example 2, except that 10-(naphthalen-2-yl)anthracene-9-ylboronic acid was used instead of 10-(naphthalen-1-yl)anthracene-9-ylboronic acid in Step 1-2 of Preparation Example 2 Using the same method as 2, 2.6 g of the title compound was obtained. LC-MS data of the prepared compound 3 is as follows.

MS[M+H] ⁺ =583.4

Experimental Example 1: Solubility experiment

The solubility was measured by dissolving Compounds 1 to 3 and Compounds A to C prepared in Preparation Example in toluene, respectively, and the results are shown in Table 1.

[Compound A] [Compound B] [Compound C]

compound Solubility (wt%) Compound 1 3.5 Compound 2 3.0 Compound 3 3.5 Compound A 0.6 Compound B 2.0 Compound C 1.2

As shown in Table 1, the compound represented by Formula 1 of the present invention is toluene compared to the compound in which the substituent at position 10 of anthracene is substituted to the para position, as well as the compound in which the Ar ₂ substituent is phenyl or anthracenyl. It can be seen that the solubility to is remarkably high.

Example 1: Preparation of organic light emitting device

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,500 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone, followed by drying, and then the substrate was washed for 5 minutes and then transferred to a glove box.

The PEDOT:PSS was spin-coated on the prepared ITO transparent electrode to coat the coating composition having a thickness of 30 nm, and then cured the coating composition on a hot plate under an N ₂ atmosphere at 220° C. for 30 minutes to form a hole injection layer. . After spin coating the composition in which the following compound HTM1 is dissolved in organic solvent toluene at 1 wt% on the hole injection layer to a thickness of 40 nm, and curing the coating composition on a hot plate under an N2 atmosphere at 200° C. for 30 minutes, the hole transport layer Formed.

On the hole transport layer, the composition 1 prepared in Preparation Example 1 and the following dopant compound Dopant in a weight ratio of 90:10, spin-coated a composition dissolved in 1 wt% in toluene to a thickness of 40 nm, and then hot plated in an N2 atmosphere. At 200°C, the coating composition was cured under the conditions of 30 minutes to form a light emitting layer.

Subsequently, a compound having an electron transport layer, an electron injection layer, and a cathode was fabricated by sequentially depositing compounds ETM1 (20 Å), LiF (12 Å), and Al (2000 Å) by transferring to a vacuum evaporator. In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the LiF of the cathode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2x10 ^-7 to 5x10. ^-8 torr was maintained.

The materials used in the above examples are as follows.

Example 2, Example 3 and Comparative example 1 to 3

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

Experimental Example 2: Evaluation of organic light emitting device characteristics

When current was applied to the organic light emitting devices manufactured in Examples 1 to 3 and Comparative Examples 1 to 3, driving voltage, current efficiency, and lifetime (T50) were measured and the results are shown in Table 2 below. T50 means the time required for the luminance to decrease from the initial luminance to 50%.

compound
(Light emitting layer
Host) Driving voltage
(V
@20mA/cm ² ) Current efficiency
(cd/A
@20mA/cm ² ) T50
(hr
@20mA/cm ² ) Example 1 Compound 1 4.73 4.90 46 Example 2 Compound 2 4.47 4.63 52 Example 3 Compound 3 4.56 4.72 65 Comparative Example 1 Compound A 4.91 4.55 30 Comparative Example 2 Compound B 4.62 4.43 39 Comparative Example 3 Compound C 4.75 4.40 41

As shown in Table 2, the organic light-emitting device using the compound of the present invention as the host of the light-emitting layer, compared to the organic light-emitting device using Comparative Examples Compounds A to C as the host of the light-emitting layer, has excellent properties in terms of current efficiency and life. Can be seen.

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
9: Electronic injection layer

Claims (7)

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

In Chemical Formula 1,
R ₁ to R ₁₆ are each independently hydrogen; heavy hydrogen; Or substituted or unsubstituted C _1-60 alkyl,
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
However, the case where Ar ₂ is phenyl or anthracenyl is excluded.
According to claim 1,
Ar ₁ is phenyl or naphthyl,
compound.
According to claim 1,
Ar ₂ is any one selected from the group consisting of,
compound:

In the above,
X ₁ is O, S, NZ ₃ , or CZ ₄ Z ₅ ,
X ₂ is O, or S,
Z ₁ to Z ₅ are each independently C _1-10 alkyl, or C _6-20 aryl.
According to claim 3,
Z ₁ , Z ₂ , Z ₃ and Z ₄ are methyl,
Z ₃ is phenyl,
compound.
According to claim 1,
R ₁ to R ₁₆ are hydrogen,
compound.
According to 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 6. .

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