Novel compound and organic light-emitting device using the same

Abstract

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

Description

[Technical field]

[0001] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Background technology]

[0002] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. Organic light emitting devices using organic light emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and are the subject of much research.

[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 the conventional deposition process have been developed to reduce process costs. In the early days, attempts were made to develop organic light-emitting devices by coating all the 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 HIL, HTL, and 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 simultaneously 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] In the above Chemical Formula 1, X is O or S; R1's are each independently an alkyl group having 1 to 60 carbon atoms, an alkyl group having 1 to 60 carbon atoms substituted with cyano, a halogen atom, a nitro group, or a cyano group, or two adjacent R1's are bonded to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms; n1 is 1 or 2, R2 is hydrogen or deuterium; R3 is hydrogen, deuterium, or halogen.

[0010] The present invention also 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

[0011] 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, thereby improving the efficiency, lowering the driving voltage, and / or improving the life characteristics of the organic light-emitting device. [Brief description of the drawings]

[0012] [Figure 1] An example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4 is shown. [Diagram 2] 1 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 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 negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The present invention will now be described in more detail to aid in understanding the invention.

[0014] (Definition of terms) In this specification, [ka] denotes a bond that is connected to another substituent.

[0015] 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, and 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, and may be interpreted as a substituent with two phenyl groups linked together.

[0016] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a base of the following structure, but is not limited thereto. [ka]

[0017] 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 a group represented by the following structural formula, but is not limited thereto. [ka]

[0018] In this specification, the number of carbon atoms of the imido group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the imido group may be a base having the following structure, but is not limited thereto. [ka]

[0019] 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.

[0020] 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.

[0021] In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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 monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a nabutyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0026] 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 this.

[0027] In this specification, heteroaryl refers to 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.

[0028] 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, except that it is a divalent group. In this specification, the heteroaryl group described above can be applied to the heteroarylene, except that it is a divalent group. In this specification, the aryl group or cycloalkyl group described above can be applied to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the heterocyclic ring can be applied to the heteroaryl, except that it is not a monovalent group but is formed by bonding two substituents.

[0029] (compound) The present invention provides a compound represented by Chemical Formula 1.

[0030] Preferably, the formula 1 is represented by any one of the following formulas 1-1 to 1-4: [ka] [ka] In the above Chemical Formulas 1-1 to 1-4, R1 is independently an alkyl group having 1 to 60 carbon atoms, an alkyl group having 1 to 60 carbon atoms substituted with cyano, a halogen atom, a nitro group, or a cyano group; R2 is hydrogen or deuterium; R3 is hydrogen, deuterium, or halogen; R4 is hydrogen, deuterium, or -CO- (alkyl having 1 to 60 carbon atoms).

[0031] Preferably, each R1 is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanoisopropyl, cyanobutyl, cyanoisobutyl, cyanotert-butyl, fluoro, chloro, nitro, or cyano.

[0032] Preferably, R3 is hydrogen or deuterium.

[0033] Preferably, R4 is hydrogen, deuterium, or methylcarbonyl.

[0034] Representative examples of the compound represented by Formula 1 are as follows: [ka]

[0035] [ka]

[0036] Meanwhile, the present invention provides a method for preparing the compound represented by the above-mentioned Formula 1, as shown in the following Reaction Scheme 1: [ka]

[0037] The step 1 is a Grignard reaction using Mg (magnesium), and the production method is more specifically embodied in the production examples described below.

[0038] Step 2 is a reaction of the product of step 1 with an organolithium compound. The organolithium compound that can be used in the reaction can be appropriately selected depending on the compound to be produced, and for example, lithium hydride can be used. The production method will be more specifically described in the production examples described below.

[0039] 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.

[0040] (Coating composition) Meanwhile, the compound according to the present invention can form an organic layer, particularly an electron transport layer or an electron injection layer, of an organic light emitting device by a solution process, and to this end, the present invention provides a coating composition comprising the compound according to the present invention and a solvent.

[0041] 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; and ethylene glycol. Examples of the solvents 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 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; and 3-phenoxytoluene. The above-mentioned solvents may be used alone or in combination of two or more. Toluene may preferably be used as the solvent.

[0042] 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.

[0043] Furthermore, the present invention provides a method for forming an emitting layer using the above-mentioned coating composition, specifically comprising the steps of coating the above-mentioned emitting layer according to 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.

[0044] The solution process uses the coating composition according to the present invention as described above, and includes, but is not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spraying, roll coating, and the like.

[0045] 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 performed in an atmosphere of an inert gas such as argon or nitrogen.

[0046] (Organic light-emitting device) The present invention also provides an organic light-emitting device comprising a 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 a compound represented by Chemical Formula 1.

[0047] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, but may have 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 thereto, and may include a smaller number of organic layers.

[0048] In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Chemical Formula 1.

[0049] 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. 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.

[0050] 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.

[0051] 2 shows an example of an organic light-emitting device including a substrate 1, a positive electrode 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 negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in the electron transport layer or the electron injection layer.

[0052] 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.

[0053] 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, a light emitting layer, and an electron transport layer may be formed thereon, and a material usable as an anode may be deposited thereon.

[0054] In addition to this 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 (WO 2003 / 012890), but the manufacturing method is not limited thereto.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] The organic light emitting device according to the present invention may include a hole transport layer between the electron inhibiting layer and the anode.

[0059] The hole transport layer receives holes from the hole injection layer and transports them to the light emitting layer. A material that can receive holes from the anode or the hole injection layer and move them to the light emitting layer and has high mobility for holes is suitable as the hole transport material.

[0060] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0061] The organic light emitting device according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary.

[0062] 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 on 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. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.

[0063] Specific examples of hole injection materials include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0064] The organic light emitting device according to the present invention may include an electron transport layer between the light emitting layer and the negative electrode.

[0065] The electron transport layer receives electrons from the negative electrode or the electron injection layer formed on the negative electrode, transports the electrons to the light-emitting layer, and suppresses the transport of holes in the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the negative electrode and transfer them to the light-emitting layer and has high mobility for electrons is suitable.

[0066] Specific examples of the electron transport material include, but are not limited to, Al complex of 8-hydroxyquinoline; complex containing Alq3; organic radical compound; hydroxyflavone-metal complex. The electron transport layer can be used with any desired cathode material as used by the prior art. In particular, examples of suitable cathode materials are conventional materials with low work function, followed by an aluminum or silver layer. In particular, cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum or silver layer.

[0067] The organic light emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the negative electrode, if necessary.

[0068] The electron injection layer is a layer that injects electrons from an electrode, and it is preferable to use a compound that has the ability to transport electrons, has an effect of injecting electrons from a negative electrode, has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin-film forming ability.

[0069] Specific examples of materials that can be used in the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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

[0076] [Example] Example 1: Preparation of Compound 1 (Step 1) [ka]

[0077] Magnesium (1,241 mg, 51.0520 mmol) and anhydrous tetrahydrofuran (25 mL) were added to the flask and stirred at room temperature. 1-Bromo-4-fluoro-2-methoxybenzene (7 g, 34.1430 mmol, 4.38 mL) was added to the flask, followed by a small amount of iodine. The flask was heated to 80°C and stirred for 1 hour. The flask was cooled to room temperature again, and diphenylphosphinyl chloride (7.964 g, 32.5172 mmol, 6.42 mL) dissolved in anhydrous tetrahydrofuran (25 mL) was slowly added. The mixture was stirred at room temperature for 15 hours. The mixture was heated and refluxed for 3 hours. The flask was cooled again to room temperature, and methanol (20 mL) was added to terminate the reaction. The solvent was removed using an evaporator, and the solid was removed by filtration using an excess amount of chloroform to obtain a lower layer of chloroform solution. The solvent was removed using an evaporator and the solution was dried to obtain (4-fluoro-2-methoxyphenyl)diphenylphosphine oxide (7.8 g).

[0078] (Step 2) [ka]

[0079] (4-Fluoro-2-methoxyphenyl)diphenylphosphine oxide (7.8 g, 25.2984 mmol) prepared in step 1 and dichloromethane (20 mL) were added to the flask and stirred at -5 ° C for 30 minutes. Tribromoborane (6.972 g, 27.8282 mmol, 2.68 mL) was slowly added to the flask while keeping the flask at -5 ° C, and the mixture was stirred for 15 hours while warming to room temperature. The reaction was terminated using methanol (15 mL), and the reaction solution was neutralized using a saturated aqueous solution of sodium bicarbonate. The reaction solution was extracted using chloroform. The solvent of the extracted organic layer was removed, and the minimum amount of chloroform was used to precipitate with hexane to obtain (4-fluoro-2-hydroxyphenyl)diphenylphosphine oxide (5.5 g).

[0080] (Step 3) [ka]

[0081] The (4-fluoro-2-hydroxyphenyl)diphenylphosphine oxide (5.5 g, 17.6124 mmol) produced in step 2 above and anhydrous acetonitrile (103 mL) were added to the flask and stirred for 5 minutes. Lithium hydride (140 mg, 17.6124 mmol) was added to the flask and stirred for 24 hours. After the reaction was completed, the reaction solution was filtered using acetonitrile to obtain a solid. The obtained solid was sublimated to obtain compound 1 (3 g). m / z:312.07

[0082] Example 2: Preparation of Compound 2 (Step 1) [ka]

[0083] Magnesium (1.266g, 52.0574mmol) and anhydrous tetrahydrofuran (25mL) were added to the flask and stirred at room temperature. 1-Bromo-2-methoxy-4-methylbenzene (7g, 34.8155mmol, 5.03mL) was added to the flask, followed by a small amount of iodine. The flask was heated to 80°C and stirred for 1 hour. The flask was cooled to room temperature again, and diphenylphosphinyl chloride (7.846g, 33.1576mmol, 6.33mL) was dissolved in anhydrous tetrahydrofuran (25mL) and slowly added. Stirred at room temperature for 15 hours. Heated and refluxed for 3 hours. The flask was cooled again to room temperature, and methanol (20mL) was added to terminate the reaction. The solvent was removed using an evaporator, and the solid was removed by filtration using an excess amount of chloroform to obtain a lower layer of chloroform solution. The solvent was removed using an evaporator and the solution was dried to obtain (2-methoxy-4-methylphenyl)diphenylphosphine oxide (10.6 g).

[0084] (Step 2) [ka]

[0085] (2-Methoxy-4-methylphenyl)diphenylphosphine oxide (10.6 g, 32.8845 mmol) and dichloromethane (25 mL) prepared in the previous step 1 were added to a flask and stirred at -5°C for 30 minutes. Tribromoborane (9.062 g, 36.1730 mmol, 3.49 mL) was slowly added to the flask while keeping the flask at -5°C, and the mixture was stirred for 15 hours while warming to room temperature. The reaction was terminated using methanol (15 mL), and the reaction solution was neutralized using a saturated aqueous solution of sodium bicarbonate. The reaction solution was extracted using chloroform. The solvent of the extracted organic layer was removed, and the mixture was precipitated with hexane using a minimum amount of chloroform to obtain (2-hydroxy-4-methylphenyl)diphenylphosphine oxide (6.5 g).

[0086] (Step 3) [ka]

[0087] The (2-hydroxy-4-methylphenyl)diphenylphosphine oxide (6.5 g, 21.0820 mmol) prepared in step 2 and anhydrous acetonitrile (125 mL) were added to the flask and stirred for 5 minutes. Lithium hydride (168 mg, 21.0820 mmol) was added to the flask and stirred for 24 hours. After the reaction was completed, the reaction solution was filtered using acetonitrile to obtain a solid. The obtained solid was sublimated to obtain compound 2 (4.3 g). m / z:308.10

[0088] Example 3: Preparation of Compound 3 (Step 1) [ka]

[0089] Magnesium (1.266g, 52.0574mmol) and anhydrous tetrahydrofuran (25mL) were added to the flask and stirred at room temperature. (2-bromo-5-methylphenyl)(methyl)sulfane (7g, 32.2402mmol) was added to the flask, followed by a small amount of iodine. The flask was heated to 80°C and stirred for 1 hour. The flask was cooled to room temperature again, and diphenylphosphinyl chloride (7.629g, 32.2402mmol, 6.15mL) dissolved in anhydrous tetrahydrofuran (25mL) was slowly added. Stirred at room temperature for 15 hours. Heated and refluxed for 3 hours. The flask was cooled again to room temperature, and methanol (20mL) was added to terminate the reaction. The solvent was removed using an evaporator, and the residue was filtered using an excess amount of chloroform to remove the solids. A lower layer of a chloroform solution was obtained, and the solvent was removed using an evaporator. The solution was dried to obtain (4-methyl-2-(methylthio)phenyl)diphenylphosphine oxide (10.9 g).

[0090] (Step 2) [ka]

[0091] (4-Methyl-2-(methylthio)phenyl)diphenylphosphine oxide (10.9 g, 32.2104 mmol) prepared in the previous step 1 and dichloromethane (25 mL) were added to the flask and stirred at -5°C for 30 minutes. Tribromoborane (8.876 g, 35.4314 mmol, 3.41 mL) was slowly added to the flask while keeping the flask at -5°C, and the mixture was stirred for 15 hours while warming to room temperature. The reaction was terminated using methanol (15 mL), and the reaction solution was neutralized using a saturated aqueous solution of sodium bicarbonate. The reaction solution was extracted using chloroform. The solvent of the extracted organic layer was removed, and the mixture was precipitated with hexane using a minimum amount of chloroform to obtain (2-mercapto-4-methylphenyl)diphenylphosphine oxide (6.1 g).

[0092] (Step 3) [ka]

[0093] The (2-mercapto-4-methylphenyl)diphenylphosphine oxide (6.1 g, 18.8051 mmol) prepared in the previous step 2 and anhydrous acetonitrile (110 mL) were added to the flask and stirred for 5 minutes. Lithium hydride (150 mg, 18.8051 mmol) was added to the flask and stirred for 24 hours. After the reaction was completed, the reaction solution was filtered using acetonitrile to obtain a solid. The obtained solid was sublimated to obtain compound 3 (3.8 g). m / z:324.07

[0094] Example 4: Preparation of Compound 4 (Step 1) [ka]

[0095] Magnesium (1.091 g, 44.8571 mmol) and anhydrous tetrahydrofuran (25 mL) were added to the flask and stirred at room temperature. 1-Bromo-4-(tert-butyl)-2-methoxybenzene (7.294 g, 30.00 mmol) was added to the flask, followed by a small amount of iodine. The flask was heated to 80°C and stirred for 1 hour. The flask was cooled to room temperature again, and diphenylphosphinyl chloride (6.761 g, 28.5714 mmol, 5.45 mL) dissolved in anhydrous tetrahydrofuran (25 mL) was slowly added. Stirred at room temperature for 15 hours. Heated and refluxed for 3 hours. The flask was cooled again to room temperature, and methanol (20 mL) was added to terminate the reaction. The solvent was removed using an evaporator, and the mixture was filtered using an excess amount of chloroform to remove the solids. The lower layer of the chloroform solution was obtained, and the solvent was removed using an evaporator and dried to obtain (4-(tert-butyl)-2-methoxyphenyl)diphenylphosphine oxide (10.4 g).

[0096] (Step 2) [ka]

[0097] (4-(tert-butyl)-2-methoxyphenyl)diphenylphosphine oxide (10.4 g, 28.5385 mmol) prepared in the previous step 1 and dichloromethane (25 mL) were added to a flask and stirred at -5°C for 30 minutes. Tribromoborane (7.864 g, 31.3923 mmol, 3.02 mL) was slowly added to the flask while keeping the flask at -5°C, and the mixture was stirred for 15 hours while warming to room temperature. The reaction was terminated using methanol (15 mL), and the reaction solution was neutralized using a saturated aqueous solution of sodium bicarbonate. The reaction solution was extracted using chloroform. The solvent of the extracted organic layer was removed, and the mixture was precipitated with hexane using a minimum amount of chloroform to obtain (4-(tert-butyl)-2-hydroxyphenyl)diphenylphosphine oxide (8.4 g).

[0098] (Step 3) [ka]

[0099] The (4-(tert-butyl)-2-hydroxyphenyl)diphenylphosphine oxide (8.4 g, 23.9726 mmol) produced in the previous step 2 and anhydrous acetonitrile (100 mL) were added to the flask and stirred for 5 minutes. Lithium hydride (191 mg, 23.9726 mmol) was added to the flask and stirred for 24 hours. After the reaction was completed, the reaction solution was filtered using acetonitrile to obtain a solid. The obtained solid was sublimated to obtain compound 4 (5.5 g). m / z:356.15

[0100] Example 5: Preparation of Compound 5 (Step 1) [ka]

[0101] Magnesium (1.272 g, 52.3333 mmol) and anhydrous tetrahydrofuran (25 mL) were added to the flask and stirred at room temperature. (2-Bromo-5-(tert-butyl)phenyl)(methyl)sulfane (9.072 g, 35 mmol) was added to the flask, followed by a small amount of iodine. The flask was heated to 80°C and stirred for 1 hour. The flask was cooled to room temperature again, and diphenylphosphinyl chloride (8.788 g, 33.3333 mmol, 7.09 mL) dissolved in anhydrous tetrahydrofuran (25 mL) was slowly added. Stirred at room temperature for 15 hours. Heated and refluxed for 3 hours. The flask was cooled again to room temperature, and methanol (20 mL) was added to terminate the reaction. The solvent was blown off using an evaporator, filtered using an excess amount of chloroform, and the solid was removed to obtain a lower layer of chloroform solution. The solvent was removed using an evaporator and the solution was dried to obtain (4-(tert-butyl)-2-(methylthio)phenyl)diphenylphosphine oxide (12.7 g).

[0102] (Step 2) [ka]

[0103] (4-(tert-butyl)-2-(methylthio)phenyl)diphenylphosphine oxide (12.7 g, 33.3780 mmol) prepared in the previous step 1 and dichloromethane (25 mL) were added to a flask and stirred at -5 ° C for 30 minutes. Tribromoborane (9.198 g, 36.7158 mmol, 3.54 mL) was slowly added to the flask while keeping the flask at -5 ° C, and the mixture was stirred for 15 hours while warming to room temperature. The reaction was terminated using methanol (15 mL), and the reaction solution was neutralized using a saturated aqueous solution of sodium bicarbonate. The reaction solution was extracted using chloroform. The solvent of the extracted organic layer was removed, and the mixture was precipitated with hexane using a minimum amount of chloroform to obtain (4-(tert-butyl)-2-mercaptophenyl)diphenylphosphine oxide (9.6 g).

[0104] (Step 3) [ka]

[0105] The (4-(tert-butyl)-2-mercaptophenyl)diphenylphosphine oxide (9.6 g, 26.1965 mmol) produced in the previous step 2 and anhydrous acetonitrile (100 mL) were added to the flask and stirred for 5 minutes. Lithium hydride (208 mg, 26.1965 mmol) was added to the flask and stirred for 24 hours. After the reaction was completed, the reaction solution was filtered using acetonitrile to obtain a solid. The obtained solid was sublimated to obtain compound 5 (6.2 g). m / z:372.13

[0106] [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 ultrasonically cleaned twice with distilled water 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.

[0107] On the ITO transparent electrode, a coating composition in which the following compound p-dopant and the following compound HIL (weight ratio of 2:8) were dissolved in cyclohexanone at 5 wt% was spin-coated (2500 rpm) and heat-treated (cured) at 230°C for 30 minutes to form a hole injection layer having a thickness of 1000 Å. On the hole injection layer, a coating composition in which the following polymer HTL (Mn: 27,900; Mw: 35,600; measured by GPC using PC Standard using Agilent 1200 series) was dissolved in toluene at 2 wt% was spin-coated (2500 rpm) and heat-treated at 230°C for 20 minutes to form a hole transport layer having a thickness of 1000 Å. On the hole transport layer, a coating composition in which the following compound A and the following compound Dopant (weight ratio of 98:2) were dissolved in cyclohexanone at 2 wt % was spin-coated (2000 rpm) and heat-treated at 145° C. for 15 minutes to form a 400 Å-thick light-emitting layer.

[0108] On the light-emitting layer, a coating composition prepared by dissolving 2 wt% of the following compound ETL and the compound prepared in Example 1 (weight ratio of 3:7) in ethylene glycol and 1-propanol (volume ratio of 8:2) was spin-coated (2000 rpm) and heat-treated at 145° C. for 10 minutes to form an electron injection and transport layer with a thickness of 300 Å. Aluminum was deposited on the electron injection and transport layer with a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0109] [ka]

[0110] During the above process, the deposition rate of aluminum was kept at 2 Å / sec, and the vacuum during deposition was kept at 2×10 -7 ~5×10 -8 torr was maintained.

[0111] Experimental Examples 2 to 5 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1.

[0112] Comparative Experimental Examples 1-3 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that Compound C1 (LiQ; 8-quinolinolato lithium), Compound C2, and Compound C3 were used instead of Compound 1.

[0113] [ka]

[0114] 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, current efficiency and lifetime at a current density of 1000 nits are shown in Table 1. Here, lifetime (T90) refers to the time it takes for the luminance to decrease to 90% from the initial luminance (500 nits).

[0115] [Table 1]

[0116] As shown in Table 1, when the compound according to the present invention is used, the driving voltage is lower, the current efficiency is higher, and the life span is improved compared to the case where the comparative compound including commonly used LiQ is used. [Explanation of symbols]

[0117] 1. Substrate 2...Positive electrode 3. Emitting layer 4...Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Emitting layer 8...Electron transport layer 9...Electron injection layer

Claims

1. A compound 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, X is O or S; R 1 is independently an alkyl group having 1 to 60 carbon atoms, an alkyl group having 1 to 60 carbon atoms substituted with cyano, a halogen atom, a nitro group, or a cyano group; R 2 is hydrogen or deuterium; R 3 is hydrogen, deuterium, or halogen; R 4 is —CO— (alkyl having 1 to 60 carbon atoms).

2. R １ is each independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanoisopropyl, cyanobutyl, cyanoisobutyl, cyanotert-butyl, fluoro, chloro, nitro, or cyano.

3. R ３ The compound of claim 1 , wherein is hydrogen or deuterium.

4. The compound represented by any one of the chemical formulas 1-1 to 1-4 is any one selected from the group consisting of the following compounds according to claim 1: 【Chemistry 4】 【Chemistry 5】 。

5. 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 4.

6. The organic light-emitting device according to claim 5 , wherein the organic layer containing the compound is an electron transport layer or an electron injection layer.

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