KR102601117B1 - 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 is 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,

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

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 Formula 1 described above can be used as a material for the organic layer of an organic light-emitting device, can also be used in a solution process, and can improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device. 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 an example of an organic light emitting device 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 was done.
Figure 3 shows GC-MS data of Compound 1 prepared in Preparation Example 1.

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

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 the present 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 or 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 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, isoxazolyl group, thiadiazolyl group group, phenothiazinyl group, and dibenzofuranyl group, but are 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 the present 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.

Meanwhile, the present invention provides an anthracene derivative compound represented by Formula 1 above.

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 a structure represented by Chemical Formula 1 and has high solubility in solvents, so it can be used in a solution process when manufacturing an organic light-emitting device.

(compound)

The compound of the present invention is represented by Formula 1 above.

In Formula 1, Ar ₁ and Ar ₂ may each independently be unsubstituted or C _6-20 aryl 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:

Meanwhile, the compound represented by Chemical Formula 1 can be prepared, for example, by a production method as shown in Scheme 1 below.

[Scheme 1]

In Scheme 1, the descriptions of Ar ₁ and Ar ₂ are as defined in Formula 1 above. Specifically, steps 1-1, 1-3 and 1-5 are Suzuki coupling reactions, which are preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction is changed according to what is known in the art. This is possible. Additionally, steps 1-2 and 1-4 are reactions for introducing a bromo group into the intermediate compound, and are preferably performed using a bromosuccinimide reagent. The manufacturing method may be further detailed in the manufacturing 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.

Additionally, 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%.

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, and thus expressed in Formula 1 A coating composition containing the compound is suitable for use in a solution process.

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 an example of an organic light emitting device 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 was done. 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 PVD (physical vapor deposition) 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 polymer; 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 heterocycle-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, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.

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 represented by Formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.

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: Preparation of intermediate compound A1

2-Bromoanthracene (5 g, 19.45 mmol), naphthalen-1-ylboronic acid (4 g, 23.3 mmol), and potassium carbonate (8.1 g, 58 mmol) were added to 65 ml of toluene, 20 ml of ethanol, and 20 ml of water. The temperature was raised to 90°C and melted. Pd(PPh ₃ ) ₄ (1.1 g, 0.97 mmol) was added and reacted at 90°C for about 24 hours. The temperature was lowered, the organic layer was extracted with ethyl acetate [EA], moisture was removed with magnesium sulfate [MgSO ₄ ], the remaining 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 white solid intermediate Compound A1.

Step 1-2: Preparation of intermediate compound A2

Intermediate compound A1 (8.8 g, 28.91 mmol) and N-bromosuccinimide (5.4 g, 30.4 mmol) obtained in step 1-1 were dissolved in 200 ml of DMF and then reacted at room temperature for about 3 hours. I ordered it. After quenching the reaction with water, the reaction was filtered using water and methanol to obtain a brown solid. This solid was dissolved using an excessive amount of THF and EA, and then brine was added to extract the organic layer. After removing moisture with magnesium sulfate [MgSO ₄ ], it was concentrated and precipitated in ethanol to obtain 4.1 g of yellow solid intermediate Compound A2.

Step 1-3: Preparation of intermediate compound A3

Intermediate compound A2 (4.1 g, 10.69 mmol), phenylboronic acid (1.95 g, 16.04 mmol), and potassium carbonate (4.4 g, 32.07 mmol) obtained in step 1-2 were mixed with 100 ml of toluene, 30 ml of ethanol, and water. After adding it to 30 ml, the temperature was raised to 100°C to dissolve it. Pd(PPh ₃ ) ₄ (0.61 g, 0.53 mmol) was added and reacted at 100°C for about 3 hours. The temperature was lowered, the organic layer was extracted with ethyl acetate [EA], moisture was removed with magnesium sulfate [MgSO ₄ ], the remaining 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 steps 1-3 were dissolved in 20 ml of DMF and then reacted at room temperature for about 3 hours. I ordered it. After quenching the reaction with water, the reaction was filtered using water and methanol to obtain a brown solid. This solid was dissolved using an excessive amount of THF and EA, and then brine was added to extract the organic layer. After removing moisture with magnesium sulfate [MgSO ₄ ], it was concentrated and precipitated in ethanol to obtain 1.4 g of yellow solid intermediate Compound A4.

Steps 1-5: Preparation of Compound 1

4,4,5,5-Tetramethyl-2-(3-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)-1,3,2-dioxaborane (2.3g, 4.6 mmol), intermediate compound A4 (1.4 g, 3.05 mmol) obtained in steps 1-4, and potassium carbonate (1.3 g, 9.15 mmol) were added to 30 ml of toluene, 5 ml of ethanol, and 5 ml of water, and the temperature was adjusted to 90°C. It was melted by raising the temperature to . Pd(PPh ₃ ) ₄ (1.06 g, 9.15 mmol) was added and reacted at 90°C for about 3 hours. The temperature was lowered, the organic layer was extracted with ethyl acetate [EA], moisture was removed with magnesium sulfate [MgSO ₄ ], the remaining 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 1.8 g of Compound 1. GC-MS data of prepared Compound 1 is shown in Figure 3.

Manufacturing example 2: Preparation of Compound 2

The title compound was prepared using the same method as 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

Manufacturing example 3: Preparation of Compound 4

The title compound was prepared using the same method as 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

Manufacturing example 4: Preparation of Compound 5

The title compound was prepared using the same method as Preparation Example 1, except that naphthalene-1ylboronic acid was used instead of phenylboronic acid in steps 1-3 of Preparation Example 1.

MS[M+H] ⁺ = 810.32

Experiment example 1: Solubility experiment

Example 1-1 to 1-4

The compounds prepared in Preparation Examples 1 to 4 were each dissolved in toluene to measure solubility, and the results are shown in Table 1 below.

Comparative example 1-1

Compound A below 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, it can be seen that the compound represented by Formula 1 of the present invention has a significantly higher solubility in toluene than Comparative Example Compound A without an Ar ₁ substituent.

Example 2-1: Manufacturing of organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 500 Å was placed in distilled water with dissolved detergent and washed with ultrasonic waves. At this time, a detergent from Fisher Co. was used, and distilled water filtered twice through 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, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

A composition of VNPB and p-dopant mixed at a weight ratio of 0.8:0.2 was spin-coated on the prepared ITO transparent electrode and cured at 220°C for 30 minutes on a hot plate under a nitrogen atmosphere to form a hole injection layer with a thickness of 400Å. .

On the hole injection layer formed in this way, a solution of N,N,N',N'-tetra(4-biphenyl)diaminobiphenylene (hereinafter abbreviated as TBDB) dissolved in toluene was spin-coated and heated at 200°C on a hot plate. Heat treatment was performed at ℃ for 30 minutes to form a hole transport layer with a thickness of 200 Å. Compound 1 prepared in Preparation Example 1 was dissolved in toluene and spin-coated on the formed hole transport layer, followed by heat treatment at 180°C for 30 minutes to form a 350Å-thick light-emitting layer. This was introduced into a vacuum deposition device, and when the base pressure became 2x10-5 Pa or less, LiF (200Å) and Al (1,000Å) were sequentially deposited 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 Example 2-1, except that the compounds listed in Table 2 below were used instead of Compound 1 of Preparation Example 1.

Experiment example 2: Evaluation of organic light emitting device characteristics

When current was applied to the organic light emitting device manufactured in Examples 2-1 to 2-4 and Comparative Example 2-1, the driving voltage, current efficiency, quantum efficiency (QE), luminance, and lifespan (T90) were measured, The results are shown in Table 2 below. T90 refers to the time it takes for luminance to decrease to 90% from the initial luminance.

compound
(luminous layer
host) driving voltage
(V
@10mA/cm ² ) Current efficiency
(cd/A
@10mA/cm ² ) QE
(%) Luminance
(cd/ ^m2 ) 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 the host of the light _- emitting layer has higher driving voltage, current efficiency, and All showed excellent characteristics 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)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
Ar ₁ and Ar ₂ are each independently C _6-60 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, and alkyl.
According to paragraph 1,
Ar ₁ and Ar ₂ are each independently C _6-20 aryl unsubstituted or substituted with C _1-10 alkyl,
compound.
According to paragraph 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.
According to paragraph 1,
Ar ₁ and Ar ₂ are each independently selected from the group consisting of:
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 includes the compound according to any one of claims 1 to 5. .