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 compound.

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0030815 dated March 9, 2021, and all contents disclosed in the documents of that Korean patent application are incorporated herein by reference. 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 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 them.

[0003] An organic light-emitting device generally has a structure including a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode. The organic 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 the two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic 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 existing deposition processes have been developed to reduce process costs. In the early days, it was planned to develop organic light-emitting devices by coating all the layers of the organic light-emitting device using solution processes, but due to limitations in current technology, a hybrid process is being researched in which only HIL, HTL, and EML are processed using solution processes in a forward structure, and the subsequent processes utilize existing deposition processes.

[0006] Therefore, the present invention provides a novel material for organic light emitting devices that is 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 provides a novel compound and an organic light-emitting device containing the compound. [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, A1 is an aromatic ring having 6 to 60 carbon atoms; A2 is an aromatic ring having 6 to 60 carbon atoms or a heteroaromatic ring having 2 to 60 carbon atoms containing any one of N, O and S; A3 is an aromatic ring having 6 to 60 carbon atoms or a heteroaromatic ring having 2 to 60 carbon atoms containing any one of N, O and S; A4 is an aromatic ring having 6 to 60 carbon atoms; X is NR, where R is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; Y is B, n is an integer from 1 to 4.

[0011] The present invention also provides an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers contains 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, thereby realizing improved efficiency, low driving voltage, and / or improved life characteristics of the organic light-emitting device. [Brief description of the drawings]

[0013] [Figure 1] FIG. 1 is a diagram showing an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Diagram 2] FIG. 1 is a diagram showing 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 its understanding.

[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 is substituted or unsubstituted with a group in which two or more of the above-listed substituents are linked. 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 in which two phenyl groups are linked.

[0017] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it 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 a compound 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 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, but are not limited to these.

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

[0022] As used herein, 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 alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. 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 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, but are not limited thereto.

[0025] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include 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, but are not limited thereto.

[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 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 naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0027] In this specification, the fluorenyl group may be substituted, and two of the substituents may be bonded together 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 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 the number of carbon atoms is 2 to 60. Examples of heteroaryl include xanthene, thioxanthen, thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, acridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyrid ... Examples of such alkyl groups include, but are not limited to, dopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0029] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group. In this specification, the above-mentioned explanation regarding the heteroaryl is applicable to the heteroaryl in the heteroarylamine. In this specification, the above-mentioned explanation regarding the alkenyl group is applicable to the alkenyl group in the aralkenyl group. In this specification, the above-mentioned explanation regarding the aryl group is applicable to the arylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the heteroaryl is applicable to the heteroarylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the aryl group or the cycloalkyl group is applicable to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the above-mentioned explanation regarding the heteroaryl is applicable to the heterocycle, except that it is not a monovalent group but is formed by bonding two substituents.

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

[0031] Preferably, A1, A2, A3 and A4 are each independently a substituted or unsubstituted benzene ring.

[0032] Preferably, the formula 1 is represented by the following formula 1′: [ka] In the above Chemical Formula 1', n is an integer from 1 to 4; R1 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O and S, or a substituent represented by the following chemical formula 2; or two adjacent R1 are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, R2 is independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, a heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S, or a substituent represented by the following chemical formula 2; or two adjacent R2 are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms; R3 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S; or two adjacent R3 are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, or -O-(CH2) m -O-, where m is an integer from 1 to 4; R4 is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S, or a substituent represented by the following chemical formula 2, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; [ka] In the above Chemical Formula 2, L is a single bond or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; L1 and L2 each independently represent a single bond, a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S; n1 is an integer from 0 to 4, n2 is an integer from 0 to 4, n3 is 1 or 2.

[0033] Preferably, the formula 1' is represented by any one of the following formulas 1-1 to 1-6: [ka] In the above Chemical Formulas 1-1 to 1-6, R1 to R5, n1 and n2 are as defined above.

[0034] Preferably, n is 1, 2 or 3.

[0035] Preferably, n1 is 1, and R1 is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S, or a di(substituted or unsubstituted aryl having 6 to 10 carbon atoms)amino.

[0036] Preferably, n1 is 1 and R1 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

[0037] Preferably, n1 is 2, and R1's are bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms.

[0038] Preferably, n1 is 2 and R1 are linked together to form a substituent represented by any one of the following: [ka] .

[0039] Preferably, n2 is 1, and R2 is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S, or a di(substituted or unsubstituted aryl having 6 to 10 carbon atoms)amino.

[0040] Preferably, n2 is 1 and R2 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

[0041] Preferably, n2 is 2 and R2 are linked together to form a substituent represented by any one of the following: [ka] .

[0042] Preferably, n3 is 1 or 2, and each R3 is independently hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S, or a di(substituted or unsubstituted aryl having 6 to 10 carbon atoms)amino.

[0043] Preferably, n3 is 1 or 2, and each R3 is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

[0044] Preferably, n3 is 2, and R3 are bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, or -O-(CH2) m It forms --O--, where m is an integer of 1 to 3.

[0045] Preferably, n3 is 2 and R3 are linked together to form a substituent represented by any one of the following: [ka] .

[0046] Preferably, R4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituent group represented by the above chemical formula 2.

[0047] Preferably, R4 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, dimethylfluorenyl, diphenylfluorenyl, or any one selected from the group consisting of: [ka]

[0048] Preferably, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl having 6 to 10 carbon atoms.

[0049] Preferably, R5 is hydrogen, deuterium, or phenyl.

[0050] Representative examples of the compound represented by Formula 1 are as follows:

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] Meanwhile, the present invention provides a method for preparing the compound represented by Chemical Formula 1' as shown in the following Reaction Scheme 1, for example, and the compound represented by Chemical Formula 1 can be prepared by referring to this method. [ka]

[0067] In the above reaction scheme 1, the remaining definitions except for X are as defined above, and X is a halogen, preferably bromine or chlorine.

[0068] 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 changed according to those 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 further embodied in the preparation examples described below.

[0069] (Coating Composition) Meanwhile, the compound according to the present invention can 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. Therefore, the present invention provides a coating composition including the compound according to the present invention and a solvent.

[0070] The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, 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 Examples of solvents include polyhydric alcohols and derivatives thereof, such as glycol, 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 can be used alone or in combination of two or more. Preferably, toluene can be used as the solvent.

[0071] 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.

[0072] The viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. The concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.

[0073] The present invention also provides a method for forming an emitting layer using the above-mentioned coating composition, specifically, the method includes 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.

[0074] 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 blading, inkjet printing, screen printing, spraying, roll coating, and the like.

[0075] 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. The heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

[0076] (Organic light-emitting device) The present invention also provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. As an 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.

[0077] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or 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.

[0078] 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 is used as a dopant in the light-emitting layer.

[0079] 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. In addition, 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 one embodiment of the present invention is illustrated in FIG. 1 and FIG. 2.

[0080] 1 is a diagram showing 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. In this structure, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer.

[0081] 2 is a diagram showing 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 may be contained in the emitting layer.

[0082] 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 Chemical 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.

[0083] 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 an organic layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer may be formed thereon, and then a material to be used as the anode may be deposited thereon.

[0084] 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). However, the manufacturing method is not limited to this.

[0085] As an 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.

[0086] The positive electrode 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 positive electrode 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.

[0087] 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.

[0088] 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 from 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. 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, and polyaniline and polythiophene-based conductive compounds, but are not limited thereto.

[0089] The hole transport layer is a layer that receives holes from the hole injection layer and transports them 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 preferably a material with 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.

[0090] 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, 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, and the like.

[0091] 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 a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene, which have an arylamino group, 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.

[0092] 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 such an electron injection and transport material, a material that can easily receive electrons from the negative electrode and transfer them to the light-emitting layer and has high mobility with respect to electrons is preferable. Specific examples of the electron injection and transport material include, but are not limited to, 8-hydroxyquinoline Al complex; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; 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., can be used, but are not limited to these.

[0093] 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-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0094] The organic light emitting device according to the present invention can be a front-emitting, a back-emitting or a dual-emitting type, depending on the materials used.

[0095] Furthermore, the compound according to the present invention can be included in an organic solar cell or an organic transistor other than the organic light-emitting device.

[0096] Hereinafter, the compound represented by Formula 1 and the preparation of an organic light-emitting device including the same will be described in detail with reference to examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto. EXAMPLES

[0097] [Example] Example 1: Preparation of Compound 1 [ka]

[0098] Compound 1-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-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 for 4 hours. After the reaction, the reactants were cooled to room temperature and sufficiently diluted with CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 (73% yield).

[0099] Compound 1-d (1.0 eq.) and compound 1-e (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K2CO3 (aq.) (1.5 eq.) was added dropwise to the reaction mixture. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80°C and stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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-f (70% yield).

[0100] Compound 1-f (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-g (1.03 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 sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 (yield 83%).

[0101] Compound 1-h (1.05 eq.), NaOt-Bu (4.0 eq.), and compound 1-c (1.0 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, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 (yield 67%).

[0102] Compound 1-i (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 (70% yield). m / z[M+H] + 737.3

[0103] Example 2: Preparation of Compound 2 [ka]

[0104] Compound 2 was prepared in the same manner as in the preparation of Compound 1, except that Compound 2-a was used instead of Compound 1-g. m / z[M+H] + 757.6

[0105] Example 3: Preparation of Compound 3 [ka]

[0106] Compound 3 was prepared in the same manner as in the preparation of Compound 1, except that Compound 3-a was used instead of Compound 1-g. m / z[M+H] + 757.6

[0107] Example 4: Preparation of Compound 4 [ka]

[0108] Compound 4-a (1.0 eq.) and compound 4-b (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K2CO3 (aq.) (1.5 eq.) was added dropwise to the reaction mixture. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80°C and stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 4-c (yield 82%).

[0109] Next, compound 4 was prepared in the same manner as compound 1, except that compound 4-c was used instead of compound 1-g. m / z[M+H] + 797.4

[0110] Example 5: Preparation of Compound 5 [ka]

[0111] Compound 5 was prepared in the same manner as compound 4, except that compound 5-a was used instead of compound 4-a. m / z[M+H] + 797.4

[0112] Example 6: Preparation of Compound 6 [ka]

[0113] Compound 6 was prepared in the same manner as in the preparation of Compound 1, except that Compound 6-a was used instead of Compound 1-g. m / z[M+H] + 791.6

[0114] Example 7: Preparation of Compound 7 [ka]

[0115] Compound 7 was prepared in the same manner as in the preparation of Compound 1, except that Compound 7-a was used instead of Compound 1-g. m / z[M+H] + 749.5

[0116] Example 8: Preparation of Compound 8 [ka]

[0117] Compound 8 was prepared in the same manner as in the preparation of Compound 1, except that Compound 8-a was used instead of Compound 1-g. m / z[M+H] + 797.3

[0118] Example 9: Preparation of Compound 9 [ka]

[0119] Compound 9 was prepared in the same manner as in the preparation of Compound 1, except that Compound 9-a was used instead of Compound 1-g. m / z[M+H] + 731.4

[0120] Example 10: Preparation of Compound 10 [ka]

[0121] Compound 10-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-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 120°C and stirred for 3 hours. After the reaction, the reactants were cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 10-b (yield 63%).

[0122] Compound 10-c (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 10-d (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 sufficiently diluted with CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 10-e (yield 69%).

[0123] Compound 10-b (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 10-e (1.03 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 sufficiently diluted with CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 10-f (yield 79%).

[0124] Compound 10-f (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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 the mixture was 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 10 (yield 73%). m / z[M+H] + 661.5

[0125] Example 11: Preparation of Compound 11 [ka]

[0126] Compound 11 was prepared in the same manner as compound 10, except that compound 11-a was used instead of compound 10-c. m / z[M+H] + 647.4

[0127] Example 12: Preparation of Compound 12 [ka]

[0128] Compound 12 was prepared in the same manner as compound 10, except that compound 12-a was used instead of compound 10-c. m / z[M+H] + 675.3

[0129] Example 13: Preparation of Compound 13 [ka]

[0130] Compound 13 was prepared in the same manner as compound 10, except that compound 13-a was used instead of compound 10-c. m / z[M+H] + 661.5

[0131] Example 14: Preparation of Compound 14 [ka]

[0132] Compound 10-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 13-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 120°C and stirred for 2 hours. After the reaction, the reactants were cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 14-a (yield 72%).

[0133] Compound 14-b (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-g (1.03 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 sufficiently diluted with CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 14-c (yield 83%).

[0134] Compound 14-c (1.05 eq.), NaOt-Bu (4.0 eq.), and compound 14-a (1.0 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 sufficiently diluted with CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 14-d (yield 82%).

[0135] Compound 14-d (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 14 (76% yield). m / z[M+H] + 869.5

[0136] Example 15: Preparation of Compound 15 [ka]

[0137] Compound 15-a (1.0 eq.) and compound 4-b (2.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K2CO3 (aq.) (1.5 eq.) was added dropwise to the reaction mixture. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 15-b (yield 82%).

[0138] Next, compound 15 was prepared in the same manner as compound 14, except that compound 15-b was used instead of compound 14-b. m / z[M+H] + 837.5

[0139] Example 16: Preparation of Compound 16 [ka]

[0140] Compound 15-a (1.0 eq.) and compound 4-b (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K2CO3 (aq.) (1.5 eq.) was added dropwise to the reaction mixture. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80°C and stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 16-a (yield 64%).

[0141] Compound 16-a (1.0 eq.) and compound 16-b (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K2CO3 (aq.) (1.5 eq.) was added dropwise to the reaction mixture. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80°C and stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 16-c (yield 78%).

[0142] Next, compound 16 was prepared in the same manner as compound 14, except that compound 16-c was used instead of compound 14-b. m / z[M+H] + 913.5

[0143] Example 17: Preparation of Compound 17 [ka]

[0144] Compound 17 was prepared in the same manner as compound 14, except that compound 17-a was used instead of compound 14-c. m / z[M+H] + 769.5

[0145] Example 18: Preparation of Compound 18 [ka]

[0146] Compound 18 was prepared in the same manner as compound 14, except that compound 18-a was used instead of compound 14-c. m / z[M+H] + 685.4

[0147] Example 19: Preparation of Compound 19 [ka]

[0148] Compound 1-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-h (2.2 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 CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 19-a (yield 68%).

[0149] Compound 19-a (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 19 (73% yield). m / z[M+H] + 815.5

[0150] Example 20: Preparation of Compound 20 [ka]

[0151] Compound 20-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-h (2.2 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 CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 20-b (yield 62%).

[0152] Compound 20-b (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 20-c (1.03 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 sufficiently diluted with CHCl, and then washed with CHCl / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 20-d (yield 70%).

[0153] Compound 20-d (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 20 (76% yield). m / z[M+H] + 1190.30

[0154] Example 21: Preparation of Compound 21 [ka]

[0155] Compound 20-b (1.0 eq.) and compound 17-a (1.3 eq.) were placed in a round-bottom flask and dissolved in anhydrous dioxane (0.12 M). K2CO3 (aq.) (2.6 eq.) was added dropwise to the reaction mixture. Pd(t-Bu3P)2 (3 mol%) was added dropwise at a bath temperature of 120°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature and sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 21-a (yield 72%).

[0156] Compound 21-a (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 21 (yield 82%). m / z[M+H] + 1236.7

[0157] Comparative Example 1: Preparation of Comparative Compound F [ka]

[0158] Compound 1-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-b (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, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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-1 (yield 75%).

[0159] Compound F-1 (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 (yield 87%). m / z[M+H] + =659.6

[0160] Comparative Example 2: Preparation of Comparative Compound G [ka]

[0161] Compound G was prepared in the same manner as in Comparative Example 1, except that compound G-1 was used instead of compound 1-a. m / z[M+H] + =659.5

[0162] Comparative Example 3: Preparation of Comparative Compound H [ka]

[0163] Compound 1-c (1.0 eq.), NaOt-Bu (4.0 eq.), and compound H-1 (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 sufficiently diluted with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4, and the mixture was 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-2 (yield 79%).

[0164] Compound H-2 (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). 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, which was then washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4, and the mixture was 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 (yield 73%). m / z[M+H] + =725.5

[0165] Experimental Example 1 A glass substrate coated with a 500Å-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water with detergent dissolved in it. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned with a solvent of isopropyl and acetone, dried, and then the substrate was washed for 5 minutes and then transported to a glove box.

[0166] 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 20 wt / v% cyclohexanone 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 with Agilent 1200 series) was dissolved in 6 wt / v% toluene 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 compound 1 prepared above 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. After transferring to a vacuum deposition device, 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. On the electron injection and transport layer, LiF was sequentially deposited to a thickness of 10 Å and aluminum was deposited to a thickness of 1,000 Å to form a cathode.

[0167] [ka]

[0168] In the above process, the deposition rate of the organic material was maintained at 0.4-0.7 Å / sec, the deposition rate of LiF was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The degree of vacuum during deposition was 2×10 -7 ~5×10 -8 torr was maintained.

[0169] Experimental Examples 2-21

[0170] An organic light emitting device was manufactured in the same manner as in Example 1, except that a compound shown in Table 1 below was used instead of Compound 1 as a dopant in the light emitting layer.

[0171] Comparative Experimental Examples 1-3

[0172] An organic light emitting device was manufactured in the same manner as in Example 1, except that a compound shown in Table 1 below was used instead of Compound 1 as a dopant in the light emitting layer.

[0173] When a current was applied to the organic light emitting devices manufactured in the examples and comparative examples, 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. 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 initial brightness (500 nits) to decrease to 90%.

[0174] [Table 1]

[0175] As shown in Table 1 above, the organic light-emitting device containing 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]

[0176] 1 Board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Light-emitting layer 8 Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1': 【Chemistry 2】 In the above Chemical Formula 1', n is 1, 2 or 3; R １ are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O and S, or a substituent represented by the following chemical formula 2; or two adjacent R １ are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, R ２ are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O and S, or a substituent represented by the following chemical formula 2; or two adjacent R ２ are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms; 【Chemistry 10】 or 【Chemistry 11】 Forming R ３ are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S; or two adjacent R ３ are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, or —O—(CH ２ ) ｍ -O-, where m is an integer from 1 to 4; R ４ is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S, or a substituent represented by the following chemical formula 2, R ５ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; 【Chemistry 3】 In the above Chemical Formula 2, L is a single bond or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; L １ and L ２ each independently represents a single bond, a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms and containing at least one heteroatom selected from the group consisting of N, O, and S; Ar １ and Ar ２ each independently represents a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing at least one heteroatom selected from the group consisting of N, O, and S; n1 is an integer from 0 to 4, n2 is an integer from 0 to 4, n3 is 1 or 2.

2. The compound according to claim 1, wherein the formula 1' is represented by any one of the following formulas 1-1 to 1-6: 【Chemistry 4】 In the above Chemical Formulas 1-1 to 1-6, R １ ~R ５ , n1 and n2 are as defined in claim 1.

3. n1 is 1, R １ is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing at least one heteroatom selected from the group consisting of N, O, and S, or a di(substituted or unsubstituted aryl)amino having 6 to 10 carbon atoms.

4. n1 is 1, R １ The compound of claim 1, wherein is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

5. n1 is 2; R １ and are bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms.

6. n1 is 2; R １ The compound of claim 1, wherein: 【Chemistry 5】 。

7. n2 is 1, R ２ is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing at least one heteroatom selected from the group consisting of N, O, and S, or a di(substituted or unsubstituted aryl)amino having 6 to 10 carbon atoms.

8. n2 is 1, R ２ The compound of claim 1, wherein is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

9. n2 is 2, R ２ The compound of claim 1, wherein: 【Chemistry 6】 。

10. n3 is 1 or 2; R ３ are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 10 carbon atoms, a substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing at least one heteroatom selected from the group consisting of N, O, and S, or a di(substituted or unsubstituted aryl)amino having 6 to 10 carbon atoms.

11. n3 is 1 or 2; R ３ is each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

12. n3 is 2, R ３ are bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, or —O—(CH ２ ) ｍ The compound of claim 1 , which forms —O—, where m is an integer from 1 to 3.

13. n3 is 2, R ３ The compound of claim 1, wherein: 【Chemistry 7】 。

14. R ４ is a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a substituent represented by the chemical formula 2.

15. R ４ is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, dimethylfluorenyl, diphenylfluorenyl, or any one selected from the group consisting of: 【Chemistry 8】 。

16. R ５ The compound according to claim 1, wherein is hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl having 6 to 10 carbon atoms.

17. R ５ is hydrogen, deuterium, or phenyl.

18. The compound according to claim 1, wherein the compound represented by the formula 1' is any one selected from the group consisting of: 【Chemistry 9A】 【Chemistry 9B】 【Chemistry 9C】 【Chemistry 9D】 【Chemistry 9E】 【Chemistry 9F】 【Chemical 9G】 【Chemistry 9H】 【Chemistry 9I】 【Chemistry 9J】 【Chemistry 9K】 【Chemical 9L】 【Chemical 9M】 【Chemistry 9N】 [Chemical formula 9O] 。

19. An organic light-emitting device comprising a first electrode, a second electrode provided so as to face 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 according to any one of claims 1, 3, and 5 to 18.

20. The organic light-emitting device according to claim 19 , wherein the organic layer containing the compound is a light-emitting layer.

Images