KR102690833B1 - 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.

Description

Novel compound and organic light emitting device comprising the same}

The present invention relates to novel compounds and organic light-emitting devices containing them.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.

Organic light emitting devices generally have a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.

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

Meanwhile, recently, in order to reduce process costs, organic light-emitting devices have been developed using a solution process, especially an inkjet process, instead of the existing deposition process. In the early days, attempts were made to develop organic light emitting devices by coating all organic light emitting device layers using a solution process, but there are limitations to the current technology, so only HIL, HTL, and EML in the form of a fixed structure were performed using a solution process, and the subsequent processes were carried out using the existing deposition process. A hybrid process utilizing 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 at the same time can be used in a solution process.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to novel compounds and organic light-emitting devices containing them.

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

[Formula 1]

In 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 one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

However, cases where Ar ₂ is phenyl or anthracenyl are excluded.

In addition, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer includes the compound represented by Formula 1.

The compound represented by the above-mentioned formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can also be used in a solution process, and can improve efficiency, low driving voltage, and/or lifespan characteristics in organic light-emitting devices. there is.

Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Figure 2 shows 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 aid understanding.

(Definition of Terms)

In this specification, means a bond connected to another substituent.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; 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 of the above-exemplified substituents linked. . For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with 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-chain, or ring-chain 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 carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.

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

In this specification, the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be straight chain (linear) or branched (branched), and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups 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, etc., but is not limited to these.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, etc., but are not limited to these.

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 embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl 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, etc., but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, It can be etc. However, it is not limited to this.

In the present specification, heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as a heteroelement, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, etc., but is not limited to these.

In this specification, the aryl group among 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 this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding heteroaryl described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In this specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of heteroaryl described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above can be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of heteroaryl described above can be applied, except that the heterocycle is not monovalent and is formed by combining two substituents.

(compound)

Meanwhile, the present invention provides an anthracene derivative compound represented by Formula 1 above. At this time, in Formula 1, 'Excluding the case where Ar ₂ is phenyl or anthracenyl' means that Ar ₂ is not substituted or unsubstituted phenyl, and is not substituted or unsubstituted anthracenyl.

Previously, materials used in vacuum deposition processes had a problem in that they had very low solubility in solvents or had high solubility only in specific solvents, making them difficult to use in solution processes.

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

Therefore, the compound according to the present invention, which is represented by Formula 1 and excludes the compound in which Ar ₂ is phenyl or anthracenyl, has high solubility in organic solvents used in solution processes, such as toluene, and can be used as an organic light-emitting device. It can be used in the solution process during 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 can be prepared by the preparation method shown in Scheme 1 below, for example, when R ₁ to R ₁₆ are all hydrogen:

[Scheme 1]

In Scheme 1, the description of the substituent is as defined in Formula 1 above. Step 1-1 is a step of preparing intermediate compound I-1 through Suzuki coupling reaction between the starting material 2,2'-dibromo-1,1'-biphenyl and the compound A-1, Step 1-2 is a step of preparing the compound represented by Formula 1 through Suzuki coupling reaction between the intermediate compound I-1 and compound A-2. At this time, the Suzuki coupling reaction is preferably performed in the presence of a palladium catalyst and a base, and the production method can be more detailed in the production examples described later.

(Coating composition)

Meanwhile, the compound according to the present invention can form an organic layer, especially a light-emitting layer, of an organic light-emitting device through a solution process. Specifically, the compound can be used as a host material for the light-emitting layer. For this purpose, the present invention provides a coating composition comprising the compound and solvent according to the present invention described above.

The solvent is not particularly limited as long as it is capable of dissolving or dispersing the compound according to the present invention, and examples include 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 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-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyhydric acids 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, etc. alcohol and its derivatives; Alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate-based solvents such as butyl benzoate and methyl-2-methoxybenzoate; tetralin; Solvents such as 3-phenoxytoluene can be mentioned. In addition, the above-mentioned solvents may be used individually or two or more types of solvents may be mixed. Preferably, toluene can 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 as the dopant material will be provided later.

Additionally, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within this 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 accordingly, the coating composition containing the compound represented by Formula 1 is Suitable for use in solution processes.

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

The solution process uses the coating composition according to the present invention described above, and includes spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

(Organic light emitting device)

Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. In one example, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer includes the compound represented by Formula 1.

Additionally, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light emitting device according to the present invention may be an inverted type organic light emitting device 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.

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

Figure 2 shows 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 this 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 can be manufactured using materials and methods known in the art, except that the light emitting layer contains the compound according to the present invention and is manufactured according to the method described above.

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

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

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

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

The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode 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); Combinations of metals and oxides 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 are included, but are not limited to these.

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic 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 are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The hole injection layer is a layer that injects holes from an electrode. The hole injection material has the ability to transport holes, has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and has an excellent hole injection effect on the light-emitting layer or light-emitting material. A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. These include organic substances, anthraquinone, polyaniline, and polythiophene series conductive compounds, but are not limited to these.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and has high mobility for holes. The material is suitable. Specific examples include arylamine-based organic materials, conductive compounds, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

The light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with 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-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series compounds; Spiro compounds; Polyfluorene, rubrene, etc., 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 the above-mentioned formula (1). Alternatively, in addition to the compound represented by Formula 1, a condensed aromatic ring derivative or a heterocyclic ring-containing compound may be used as a host material. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

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 transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and is a material with high electron mobility. Suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. 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 with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. A compound that prevents movement 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. , preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

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

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

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

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

Manufacturing example 1: Preparation of Compound 1

Step 1-1: Intermediate Compound INT Manufacturing of -1

7.0 g (22.4 mmol, 1.0 eq) of 2,2'-dibromo-1,1'-biphenyl and 4.6 g (26.9 mmol, 1.2 eq) of 1-naphthalenyl boronic acid, 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 along with 150 ml toluene and 50 ml water. After the degassing process, the mixture was replaced with nitrogen, the temperature was raised to 100°C, and the mixture was stirred overnight. Afterwards, the product was cooled to room temperature and extracted with dichloromethane. Next, after removing moisture with magnesium sulfate, the mixture was adsorbed on dichloromethane and then subjected to column chromatography using hexane as a solvent to obtain 2.0 g (yield 25%) of the title compound.

Step 1-2: Preparation of Compound 1

2.0 g (5.6 mol, 1.0 eq) of the intermediate compound INT-1 prepared in step 1-1, 2.9 g (8.4 mmol, 1.5 eq) of 10-(naphthalen-1-yl)anthracene-9-ylboronic acid, and Pd ( 0.7 g (0.6 mmol, 0.1 eq) of PPh ₃ ) ₄ and 2.3 g (16.7 mmol, 3.0 eq) of potassium carbonate were added to 250 ml RBF along with 150 ml toluene and 50 ml water. After the degassing process, the mixture was replaced with nitrogen, the temperature was raised to 100°C, and the mixture was stirred overnight. Afterwards, the product was cooled to room temperature and extracted with dichloromethane. Next, after removing moisture with magnesium sulfate, adsorption into dichloromethane, column chromatography was performed using dichloromethane/hexane (1:10) as an eluent, and precipitation with dichloromethane/methanol gave 1.0 g of the title compound. . The LC-MS data of 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 using the same method as 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. The LC-MS data of prepared Compound 2 is as follows.

MS[M+H] ⁺ = 583.4

Manufacturing example 3: Preparation of Compound 3

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

MS[M+H] ⁺ = 583.4

Experiment example 1: Solubility experiment

Compounds 1 to 3 prepared in the above Preparation Example and the following compounds A to C were each dissolved in toluene to measure solubility, 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 more effective in toluene than not only compounds in which the substituent at position 10 of anthracene is substituted in the para position, but also compounds in which the Ar ₂ substituent is phenyl or anthracenyl. It can be seen that the solubility is significantly high.

Example 1: Manufacturing of organic light emitting device

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,500 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, the substrate was ultrasonic cleaned with a solvent of isopropyl alcohol and acetone, dried, and then washed for 5 minutes before transporting the substrate to a glove box.

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

On the hole transport layer, a composition prepared by dissolving Compound 1 prepared in Preparation Example 1 and the following dopant compound Dopant at a weight ratio of 90:10 and 1 wt% in toluene was spin-coated to a thickness of 40 nm, followed by a hot plate under N2 atmosphere. The coating composition was cured at 200°C for 30 minutes to form a light emitting layer.

Afterwards, it was transferred to a vacuum deposition machine and the compounds ETM1 (20 Å), LiF (12 Å), and Al (2000 Å) were sequentially deposited to produce a device with an electron transport layer, an electron injection layer, and a cathode. In the above process, the deposition rate of organic materials was maintained at 0.4 ~ 0.7 Å/sec, LiF on the cathode was maintained at 0.3 Å/sec, aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ 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 Example 1, except that the compounds listed in Table 2 below were used as the host of the light-emitting layer instead of Compound 1.

Experiment 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, the driving voltage, current efficiency, and lifespan (T50) were measured, and the results are shown in Table 2 below. T50 refers to the time it takes for luminance to decrease to 50% from the initial luminance.

compound
(luminous 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 has excellent characteristics in terms of current efficiency and lifespan compared to the organic light-emitting device using Comparative Example Compounds A to C as the host of the light-emitting layer. It can be seen that it represents

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: Electron injection layer

Claims (7)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
R ₁ to R ₁₆ are each independently hydrogen; or deuterium,
Ar ₁ is substituted or unsubstituted C _6-20 aryl,
Here, ‘substituted or unsubstituted’ means unsubstituted or substituted with deuterium,
Ar ₂ is any one selected from the group consisting of:

According to paragraph 1,
Ar ₁ is phenyl or naphthyl,
compound.
delete delete According to paragraph 1,
R ₁ to R ₁₆ are hydrogen,
compound.
According to paragraph 1,
The compound is any one selected from the group consisting of the following compounds:

.
first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer contains the compound according to any one of claims 1, 2, 5, and 6. Containing an organic light-emitting device.