Novel compound and organic light-emitting device using the same

Abstract

The present invention provides a novel compound and an organic light-emitting device including the same. JPEG2024521759000144.jpg42170

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0071681 filed on June 2, 2021, and all contents disclosed in the documents of the Korean patent application are incorporated by reference as part of this specification. The present invention relates to a novel compound and an organic light-emitting device including the same. [Background technology]

[0002] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, and therefore many researches are being conducted on these devices.

[0003] An organic light emitting device generally has a structure including a positive electrode, a negative electrode, and an organic material layer between the positive electrode and the negative electrode. The organic material layer is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic material layer. When the injected holes and electrons come into contact with each other, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0004] There is a continuing demand for the development of new organic materials for use in such organic light emitting devices.

[0005] Meanwhile, in recent years, organic light-emitting devices that use solution processes, especially inkjet processes, instead of conventional deposition processes have been developed to reduce process costs. Initially, attempts were made to develop organic light-emitting devices by coating all layers of the organic light-emitting device using solution processes, but current technology has limitations, so research is being conducted on a hybrid process in which only the hole injection layer (HIL), hole transport layer (HTL), and emission layer (EML) are processed using solution processes in a fixed structure, and subsequent processes utilize conventional deposition processes.

[0006] Therefore, the present invention provides a novel organic light emitting device material that can be used in organic light emitting devices and is also solution processable. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0008] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Means for solving the problem]

[0009] The present invention provides a compound represented by the following formula 1: [ka]

[0010] In the above Chemical Formula 1, Ar1 is a furan or thiophene fused to two adjacent rings; Ar2 is benzene, benzofuran, or benzothiophene fused to an adjacent ring; Each R1 is independently hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or two adjacent R1 are bonded to each other to form -O-(CH2) m -O-, where m is an integer from 1 to 4; R2 is hydrogen, deuterium, or a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; R3 is hydrogen, deuterium, or a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; However, in the formula 1, adjacent two R1 are bonded to each other to form -O-(CH2) m Contains one or more -O-.

[0011] The present invention further provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. Effect of the Invention

[0012] The compound represented by the above-mentioned Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can be used in solution process, and can bring about improved efficiency, low driving voltage, and / or improved lifetime characteristics in the organic light-emitting device. [Brief description of the drawings]

[0013] [Figure 1] The figure illustrates an example of an organic light-emitting device that is composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Diagram 2] 1 illustrates an example of an organic light-emitting device consisting of a substrate 1 , a positive electrode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 7 , an electron injection and transport layer 8 , and a negative electrode 4 . DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The present invention will now be described in more detail to aid in understanding the invention.

[0015] (Definition of terms) In this specification, [ka] or [ka] denotes a bond that is connected to another substituent.

[0016] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, or heteroaryl containing one or more of N, O, and S atoms, or that two or more of the above-listed substituents are linked to each other to be substituted or unsubstituted. For example, the "substituent with two or more substituents linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent with two phenyl groups linked together.

[0017] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but the carbon number is preferably 1 to 40. Specifically, the carbonyl group may have a structure as shown below, but is not limited thereto. [ka]

[0018] In this specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be an ester group having the following structural formula, but is not limited thereto. [ka]

[0019] In this specification, the number of carbon atoms of the imido group is not particularly limited, but is preferably 1 to 25. Specifically, the imido group may have a structure as shown below, but is not limited thereto. [ka]

[0020] In this specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0021] In this specification, specific examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0022] In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0023] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include, but are not limited to, 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.

[0024] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include, but are not limited to, 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, a stilbenyl group, and a styrenyl group.

[0025] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and in one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0026] 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, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, or a fluorenyl group, but is not limited thereto.

[0027] In the present specification, the fluorenyl group may be substituted, and two of the substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to these.

[0028] In this specification, heteroaryl is heteroaryl containing one or more of O, N, Si and S as a hetero element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of heteroaryl include, but are not limited to, xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

[0029] In this specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group can be applied to the aryl group described above. In this specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamine group can be applied to the alkyl group described above. In this specification, the heteroaryl in the heteroarylamine can be applied to the heteroaryl group described above. In this specification, the alkenyl group in the aralkenyl group can be applied to the alkenyl group described above. In this specification, the aryl group described above can be applied to the arylene group, except that it is a divalent group. In this specification, the heteroaryl group described above can be applied to the heteroarylene group, except that it is a divalent group. In this specification, the aryl group or cycloalkyl group described above can be applied to the hydrocarbon condensed ring, except that it is not a monovalent group but a group formed by bonding two substituents. In this specification, the above description of heteroaryl is applicable to a fused hetero ring, except that the fused hetero ring is not a monovalent group but is a group formed by bonding two substituents.

[0030] (compound) The present invention provides a compound represented by Chemical Formula 1.

[0031] Preferably, the above-mentioned Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-4 depending on the fused ring position of Ar1: [ka] [ka]

[0032] In the above Chemical Formulas 1-1 to 1-4, Ar2 and R1 to R3 are defined as above.

[0033] Preferably, the above-mentioned Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-5 to 1-9 depending on the fused ring position of Ar2:

[0034] [ka] [ka] [ka]

[0035] In the above chemical formulas 1-5 to 1-9, Ar1 and R1 to R3 are defined as above. Preferably, each R1 is independently hydrogen, deuterium, alkyl having 1 to 10 carbon atoms, or aryl having 6 to 20 carbon atoms, or two adjacent R1 are bonded to each other to form [ka] or [ka] Form.

[0036] Preferably, each R1 is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, or phenyl, or two adjacent R1 are bonded to each other to form [ka] ,or [ka] Form.

[0037] Preferably, R2 is hydrogen, deuterium, or alkyl having 1 to 10 carbon atoms.

[0038] Preferably, R2 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl.

[0039] Preferably, R3 is hydrogen, deuterium, or alkyl having 1 to 10 carbon atoms.

[0040] Preferably, R3 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl.

[0041] Representative examples of the compound represented by Formula 1 are as follows:

[0042] [ka]

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[0092] Meanwhile, the present invention provides a method for preparing the compound represented by Formula 1, as shown in the following Reaction Scheme 1: [ka]

[0093] In the above reaction scheme 1, the definitions except for Y are the same as those described above, and Y is a halogen, preferably bromo or chloro.

[0094] The step 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction can be varied as known in the art. The step 2 is a reaction with BI3, which is preferably carried out in the presence of a base. The preparation method is more specifically described in the preparation examples described below.

[0095] Meanwhile, the organic layer containing the compound according to the present invention can be formed by utilizing various methods such as vacuum deposition and solution processing, and the solution processing will be described in detail below.

[0096] (Coating Composition) Meanwhile, the compound according to the present invention can be used to form an organic layer, particularly an emission layer, of an organic light-emitting device by solution processing. Specifically, the compound can be used as a dopant material for the emission layer. To this end, the present invention provides a coating composition comprising the compound according to the present invention and a solvent.

[0097] The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and examples thereof include chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-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-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; ethylene glycol, ethyl glycerol ... Examples of the solvent include polyhydric alcohols and derivatives thereof, such as ethanol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexaneol; 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; and 3-phenoxytoluene. The above-mentioned solvents may be used alone or in combination of two or more. Toluene may be used as the solvent.

[0098] The coating composition may further include a compound used as a host material, which will be described later. The coating composition may further include a compound used as a dopant material, which will be described later.

[0099] The viscosity of the coating composition is preferably 1 cP or more. Furthermore, in consideration of the ease of coating of the coating composition, the viscosity of the coating composition is preferably 10 cP or less. Furthermore, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% or more. Furthermore, in order to allow the coating composition to be optimally coated, the concentration of the compound according to the present invention in the coating composition is preferably 20 wt / v% or less.

[0100] Furthermore, the present invention provides a method for forming a light-emitting layer using the above-mentioned coating composition, which comprises the steps of coating the above-mentioned light-emitting layer of the present invention on a positive electrode or on a hole transport layer formed on a positive electrode by a solution process; and heat-treating the coated coating composition.

[0101] The solution process is a process using the coating composition according to the present invention, and refers to processes such as spin coating, dip coating, doctor blade, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0102] The heat treatment temperature in the heat treatment step is preferably 150 to 230° C. The heat treatment time is preferably 1 minute to 3 hours, more preferably 10 minutes to 1 hour. Furthermore, the heat treatment is preferably carried out in an atmosphere of an inert gas such as argon or nitrogen.

[0103] (Organic light-emitting device) The present invention also provides an organic light-emitting device comprising the compound represented by Chemical Formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound represented by Chemical Formula 1.

[0104] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure or a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited to these, and may include a smaller number of organic layers.

[0105] Furthermore, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1. In particular, the compound according to the present invention may be used as a dopant for the light-emitting layer.

[0106] In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate. Furthermore, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (inverted type) in which a negative electrode, one or more organic layers, and a positive electrode 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 shown in Figures 1 and 2.

[0107] 1 shows an example of an organic light emitting device including a substrate 1, a positive electrode 2, a light emitting layer 3, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

[0108] 2 shows an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an emitting layer 7, an electron injection and transport layer 8, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 can be contained in the emitting layer.

[0109] The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0110] For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic layer, and an anode on a substrate. In this case, a metal, a conductive metal oxide, or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and organic layers including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer may be formed thereon, and a material that can be used as an anode may be deposited thereon.

[0111] In addition to the above method, an organic light emitting device can be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (WO2003 / 012890). However, the manufacturing method is not limited to these.

[0112] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0113] The cathode material is preferably a material having a large work function so that holes can be easily injected into the organic layer.Specific examples of the cathode material include, but are not limited to, 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 SnO2:Sb; and conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0114] The negative electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0115] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the positive electrode, has an excellent hole injection effect for the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably 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 materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone-based organic materials, and polyaniline-based and polythiophene-based conductive compounds, but are not limited thereto.

[0116] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer, and is suitable for use as a hole transport material that has high mobility for holes.Specific examples include, but are not limited to, arylamine-based organic compounds, conductive compounds, and block copolymers having both conjugated and non-conjugated portions.

[0117] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the fused aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocyclic ring-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc.

[0118] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periflanthene, which have arylamino groups, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the dopant materials include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0119] The electron injection and transport layer is a layer that simultaneously functions as an electron transport layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the electron adjustment layer. As the electron injection and transport material, a material that can easily receive electrons injected from the negative electrode and transfer them to the light-emitting layer and has high mobility for electrons is suitable. Specific examples of the electron injection and transport material include, but are not limited to, 8-hydroxyquinoline Al complex; complex containing Alq3; organic radical compound; hydroxyflavone-metal complex; triazine derivatives, etc. Alternatively, LiF, NaF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives, etc. may be used, but are not limited to these.

[0120] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0121] In addition to the above-mentioned materials, the light-emitting layer, hole-injection layer, hole-transport layer, electron-transport layer, and electron-injection layer may further include inorganic compounds such as quantum dots or polymer compounds.

[0122] The quantum dots may be, for example, colloidal quantum dots, alloy quantum dots, core-shell quantum dots, or core quantum dots. Quantum dots containing elements belonging to groups 2 and 16, 13 and 15, 13 and 17, 11 and 17, or 14 and 15, such as cadmium (Cd), selenium (Se), zinc (Zn), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead (Pb), gallium (Ga), and arsenic (As), are used.

[0123] The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a dual emission device, and may be a bottom emission device which requires relatively high luminous efficiency.

[0124] Furthermore, the compound according to the present invention can be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

[0125] The compound represented by Formula 1 and the preparation of an organic light-emitting device including the same will be described in detail in the following examples. However, the examples are for illustrating the present invention, and the scope of the present invention is not limited thereto. EXAMPLES

[0126] [Example] Example 1: Preparation of Compound 1 [ka]

[0127] Compound 1-a (1.0 eq.), NaOt-Bu (4 eq.), and compound 1-b (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). At a bath temperature of 100°C, Pd(t-Bu3P)2 (5 mol%) was added dropwise and stirred for 2 hours. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 1-c (76% yield).

[0128] Compound 1-d (1.0 eq.), NaOt-Bu (4 eq.), and compound 1-c (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120°C and stirred for 4 hours. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 1-e (81% yield).

[0129] Compound 1-f (1.0 eq.), NaOt-Bu (4 eq.), and compound 1-g (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 100°C and stirred for 2 hours. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 1-h (82% yield).

[0130] Compound 1-h (1.0 eq.), NaOt-Bu (4 eq.), and compound 1-e (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120°C and stirred overnight. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 1-i (73% yield).

[0131] Compound 1-i (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03M). BI3 (2.0 eq.) was slowly added dropwise to the reaction mixture and stirred overnight at a bath temperature of 80°C. After the reaction, the reaction mixture was cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and sat.Na2S2O3 (aq.) were added dropwise to the reaction mixture in order, and the organic layer was separated by washing with CH2Cl2 / H2O. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 1 (78% yield). m / z[M+H] + 805.6

[0132] Example 2: Preparation of Compound 2 [ka] Compound 2 was prepared in the same manner as Compound 1, except that Compound 2-a was used instead of Compound 1-f. m / z[M+H] + 757.5

[0133] Example 3: Preparation of Compound 3 [ka] Compound 3 was prepared in the same manner as Compound 1, except that Compound 3-a was used instead of Compound 1-g. m / z[M+H] + 731.4

[0134] Example 4: Preparation of Compound 4 [ka] Compound 4 was prepared in the same manner as Compound 1, except that Compound 4-a was used instead of Compound 1-a. m / z[M+H] + 821.3

[0135] Example 5: Preparation of Compound 5 [ka] Compound 5 was prepared in the same manner as Compound 4, except that Compound 2-c was used instead of Compound 1-h. m / z[M+H] + 773.5

[0136] Example 6: Preparation of Compound 6 [ka] Compound 6 was prepared in the same manner as Compound 4, except that Compound 3-b was used instead of Compound 1-h. m / z[M+H] + 747.4

[0137] Example 7: Preparation of Compound 7 [ka] Compound 7 was prepared in the same manner as Compound 1, except that Compound 7-a was used instead of Compound 1-a. m / z[M+H] + 805.6

[0138] Example 8: Preparation of Compound 8 [ka] Compound 8 was prepared in the same manner as Compound 1, except that Compound 8-a was used instead of Compound 1-a. m / z[M+H] + 821.7

[0139] Example 9: Preparation of Compound 9 [ka]

[0140] Compound 2-a (1.0 eq.), NaOt-Bu (4 eq.), and compound 9-a (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 100°C and stirred for 2 hours. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 9-b (87% yield).

[0141] Compound 9-c (1.0 eq.), NaOt-Bu (4 eq.), and compound 9-b (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 100°C and stirred overnight. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 9-d (73% yield).

[0142] Compound 9-d (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03M). BI3 (2.0 eq.) was slowly added dropwise to the reaction mixture and stirred overnight at a bath temperature of 80°C. After the reaction, the reaction mixture was cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and sat.Na2S2O3 (aq.) were added dropwise to the reaction mixture in sequence, and the organic layer was separated by washing with CH2Cl2 / H2O. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound 9 (76% yield). m / z[M+H] + 799.5

[0143] Example 10: Preparation of Compound 10 [ka] Compound 10 was prepared in the same manner as Compound 9, except that Compound 10-a was used instead of Compound 9-a. m / z[M+H] + 831.5

[0144] Example 11: Preparation of Compound 11 [ka] Compound 11 was prepared in the same manner as Compound 1, except that Compound 11-a was used instead of Compound 1-f. m / z[M+H] + 791.5

[0145] Example 12: Preparation of Compound 12 [ka] Compound 12 was prepared in the same manner as Compound 1, except that Compound 12-a was used instead of Compound 1-f. m / z[M+H] + 819.6

[0146] Example 13: Preparation of Compound 13 [ka] Compound 13 was prepared in the same manner as Compound 9, except that Compound 13-a was used instead of Compound 9-c. m / z[M+H] + 841.5

[0147] [Comparative Example] Comparative Example 1: Preparation of Comparative Compound F [ka]

[0148] Compound 1-d (1.0 eq.), NaOt-Bu (4.0 eq.), and compound Fa (2.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120°C and stirred overnight. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound Fb (75% yield).

[0149] Compound Fb (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03M). BI3 (2.0 eq.) was slowly added dropwise to the reaction mixture and stirred overnight at a bath temperature of 80°C. After the reaction, the reaction mixture was cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and sat.Na2S2O3 (aq.) were added dropwise to the reaction mixture in order, and the organic layer was separated by washing with CH2Cl2 / H2O. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound F (87% yield). m / z[M+H] + =659.6

[0150] Comparative Example 2: Preparation of Comparative Compound G [ka] Compound G was prepared in the same manner as in Comparative Example 1, except that compound Ga was used instead of compound Fa. m / z[M+H] + =659.5

[0151] Comparative Example 3: Preparation of Comparative Compound H [ka]

[0152] Compound Ha (1.0 eq.), NaOt-Bu (4.0 eq.), and compound Hb (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120°C and stirred overnight. After the reaction, the reactants were cooled to room temperature and thoroughly diluted with CH2Cl2, then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound Hc (79% yield).

[0153] Compound Hc (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03M). BI3 (2.0 eq.) was slowly added dropwise to the reaction mixture and stirred overnight at a bath temperature of 80°C. After the reaction, the reaction mixture was cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and sat.Na2S2O3 (aq.) were added dropwise to the reaction mixture in order, and the organic layer was separated by washing with CH2Cl2 / H2O. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The solution that passed through was concentrated under reduced pressure and purified by column chromatography to produce compound H (73% yield). m / z[M+H] + =725.5

[0154] [Experimental Example] Experimental Example 1 A glass substrate coated with a 500Å-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent dissolved therein and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was washed for 30 minutes, then repeatedly washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning was complete, the substrate was ultrasonically cleaned with a solvent of isopropyl and acetone, dried, and then washed for 5 minutes before being transported to a glove box.

[0155] On the ITO transparent electrode, a coating composition in which the following compound O and compound P (weight ratio of 2:8) were dissolved in cyclohexanone at 20 wt / v% was spin-coated (4000 rpm) and heat-treated (cured) at 200°C for 30 minutes to form a hole injection layer with a thickness of 400 Å. On the hole injection layer, a coating composition in which the following compound Q (Mn: 27,900; Mw: 35,600; measured by GPC using PC Standard using Agilent 1200 series) was dissolved in toluene at 6 wt / v% was spin-coated (4000 rpm) and heat-treated at 200°C for 30 minutes to form a hole transport layer with a thickness of 200 Å. On the hole transport layer, a coating composition prepared by dissolving the previously prepared compound 1 and the following compound R (weight ratio of 2:98) in cyclohexanone at 2 wt / v% was spin-coated (4000 rpm) and heat-treated at 180° C. for 30 minutes to form a light-emitting layer with a thickness of 400 Å.

[0156] After transferring to a vacuum deposition machine, the following compound S was vacuum deposited on the light-emitting layer to a thickness of 350 Å to form an electron injection and transport layer. LiF was sequentially deposited on the electron injection and transport layer to a thickness of 10 Å and aluminum was deposited to a thickness of 1000 Å to form a cathode. [ka]

[0157] In the above process, the deposition rate of the organic material was maintained at 0.4~0.7Å / sec, LiF at 0.3Å / sec, and aluminum at 2Å / sec. The vacuum during deposition was 2*10 -7 ~5×10 -8 torr was maintained.

[0158] Experimental Examples 2-12 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that a compound shown in Table 1 below was used instead of Compound 1 as a dopant in the emission layer.

[0159] Comparative Experimental Examples 1-3 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that a compound shown in Table 1 below was used instead of Compound 1 as a dopant in the emission layer.

[0160] When a current was applied to the organic light emitting devices manufactured in the above experimental example and comparative experimental example, the current was 10 mA / cm 2 The results of measuring the driving voltage, external quantum efficiency (EQE) and lifetime at a current density of 1000 nits are shown in Table 1. Here, the external quantum efficiency (EQE) is calculated by (number of emitted photons) / (number of injected charge carriers) x 100, and T90 is the time it takes for the brightness to decrease to 90% from the initial brightness (500 nits).

[0161] [Table 1]

[0162] As shown in Table 1, the organic light emitting device including the compound of the present invention in the light emitting layer exhibited excellent properties in terms of efficiency, driving voltage and life span of the organic light emitting device. [Explanation of symbols]

[0163] 1. Substrate 2...Positive electrode 3. Emitting layer 4...Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Emitting layer 8. Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, Ar １ is a furan or thiophene fused to two adjacent rings, Ar ２ is a benzene, benzofuran, or benzothiophene fused to an adjacent ring, R １ are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or two adjacent R １ are bonded to each other to form -O-(CH ２ ) ｍ -O-, where m is an integer from 1 to 4; R ２ is hydrogen, deuterium, or a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; R ３ is hydrogen, deuterium, or a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; However, in the formula 1, two adjacent R １ are bonded together to form -O-(CH ２ ) ｍ Contains one or more -O-.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: 【Chemistry 2】 【Chemistry 3】 In the above Chemical Formulas 1-1 to 1-4, Ar ２ and R １ ~R ３ is as defined in claim 1.

3. R １ are each independently hydrogen, deuterium, alkyl having 1 to 10 carbon atoms, or aryl having 6 to 20 carbon atoms, or two adjacent R １ are combined with each other, 【Chemistry 4】 or 【Chemistry 5】 The compound of claim 1 , which forms:

4. R １ are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, or phenyl, or two adjacent R １ are combined with each other, 【Chemistry 6】 or 【Chemistry 7】 The compound of claim 1 , which forms:

5. R ２ is hydrogen, deuterium, or alkyl having 1 to 10 carbon atoms.

6. R ２ is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl.

7. R ３ is hydrogen, deuterium, or alkyl having 1 to 10 carbon atoms.

8. R ３ is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl.

9. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of: 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemistry 56】 【Chemistry 57】 。

10. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound according to any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10 , wherein the organic layer containing the compound is a light-emitting layer.

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