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 - 0030816, filed on March 9, 2021, and all the contents disclosed in the document of the Korean patent application are incorporated herein by reference.

[0002] The present invention relates to a novel compound and an organic light - emitting device containing the same.

Background Art

[0003] Generally, the organic light - emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light - emitting devices using the organic light - emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and many studies have been carried out due to their excellent luminance, driving voltage, and response speed characteristics.

[0004] 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 often has a multilayer structure composed of different substances in order to improve the efficiency and safety of the organic light - emitting device. For example, it may consist of a hole injection layer, a hole transport layer, a light - emitting layer, an electron transport layer, an electron injection layer, etc. In such a structure of an organic light - emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode and electrons are injected from the negative electrode. When the injected holes and electrons come into contact, an exciton is formed, and when this exciton falls back to the ground state again, light is emitted.

[0005] There has been a continuous demand for the development of new materials for the organic substances used in such organic light - emitting devices.

[0006] On the one hand, recently, in order to reduce process costs, organic light-emitting devices that use solution processes, particularly inkjet processes, instead of existing vapor deposition processes have been developed. In the early days, attempts were made to develop organic light-emitting devices by coating all organic light-emitting device layers using solution processes. However, current technology has limitations. Currently, only HIL, HTL, and EML are formed using solution processes in a normal structure, and subsequent processes involve research on hybrid processes that utilize existing vapor deposition processes.

[0007] Therefore, the present invention provides a novel material for an organic light-emitting device that is used in an organic light-emitting device and can be used in a solution process.

Prior Art Documents

Patent Documents

[0008]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0009] The present invention provides a novel compound and an organic light-emitting device containing the same.

Means for Solving the Problems

[0010] The present invention provides a compound represented by the following Chemical Formula 1:

Chemical Formula

[0011] Further, the present invention provides an organic light-emitting device including 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 one or more of the organic layers contain a compound represented by Chemical Formula 1.

Advantages of the Invention

[0012] The compound represented by Chemical Formula 1 described above can be used as a material for the organic layer of an organic light-emitting device, can be used in a solution process, and can improve the efficiency, lower the driving voltage, and / or improve the lifetime characteristics in an organic light-emitting device.

Brief Description of the Drawings

[0013]

Figure 1

Figure 2

Embodiments for Carrying Out the Invention

[0014] Hereinafter, a more detailed description will be given to assist in understanding the present invention.

[0015] (Definition of Terms) In this specification,

Chem.

[0016] As used herein, the term "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfinyl group; an arylsulfinyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or a heteroaryl containing one or more of N, O, and S atoms, or being unsubstituted, or being substituted with or unsubstituted with a group in which two or more of the exemplified substituents are linked. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may also be interpreted as a substituent in which two phenyl groups are linked.

[0017] In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, compounds having the following structures may be used, but are not limited thereto.

Chemical formula

[0018] In the present specification, 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 at the oxygen of the ester group. Specifically, compounds having the following structural formulas may be used, but are not limited thereto.

Chemical formula

[0019] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, compounds having the following structures may be used, but are not limited thereto. [Chemical formula]

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

[0021] In this specification, examples of the boron group specifically include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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

[0023] In this specification, the alkyl group may be linear or branched, and its carbon number 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 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 the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0024] In this specification, the alkenyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to still another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to still another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0025] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to still another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to still another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0026] In this 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. Examples of the monocyclic aryl group may include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. Examples of the polycyclic aryl group may include, but are 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 substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Chemical formula

[0028] As used herein, heteroaryl is heteroaryl containing one or more of O, N, Si, and S as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl include xanthene, thioxanthene, thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidinyl group, triazinyl group, acridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolyl group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but is not limited thereto.

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

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

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

[0032] Preferably, the above Chemical Formula 1 is represented by the following Chemical Formula 1': [Chemical Formula] In the above Chemical Formula 1', Ar is a benzene ring condensed with two adjacent rings, n is an integer from 1 to 4, Each 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, heteroaryl having 2 to 60 carbon atoms containing any 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 R1s are bonded to each other to form substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, or -O-(CH2) m1 -O- is formed, where m1 is an integer from 1 to 4, Each R2 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 heteroaryl having 2 to 60 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S; or two adjacent R2s are bonded to each other to form substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, or -O-(CH2) m2 -O- is formed, where m2 is an integer from 1 to 4, R3 is hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, heteroaryl having 2 to 60 carbon atoms containing any 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,

Chemical formula

[0033] Preferably, the chemical formula 1’ is represented by any one of the following chemical formulas 1-1 to 1-9 according to the condensation position of Ar:

Chemical formula

[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 heteroaryl having 8 to 12 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S, or 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 is bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, or -O-(CH2) m1 -O- is formed, where m is an integer from 1 to 3.

[0038] Preferably, n1 is 2, and R1 are bonded to each other to form a substituent represented by any one of the following:

Chemical formula

[0039] Preferably, each n2 is independently 1 or 2, and each R2 is independently hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a heteroaryl having 8 to 12 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S; or two adjacent R2 are bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, or -O-(CH2) m2 -O- is formed, where m2 is an integer from 1 to 3.

[0040] Preferably, each n2 is independently 1 or 2, and each R2 is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, dimethylfluorenyl, diphenylfluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl; or two adjacent R2 are bonded to each other to form a substituent represented by any one of the following:

Chemical formula

[0041] Preferably, R3 is substituted or unsubstituted alkyl having 1 to 10 carbon atoms.

[0042] Preferably, R3 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, dimethylfluorenyl, or diphenylfluorenyl.

[0043] Preferably, R3 is a substituent represented by the chemical formula 2. In the chemical formula 2, L is a single bond or phenylene, L1 and L2 are each independently a single bond, phenylene, naphthylene, or dimethylfluorenediyl, Ar1 is phenyl, naphthyl, dimethylfluorenyl, or benzofuranyl, Ar2 is dimethylfluorenyl or dimethylbenzofuranyl, and the Ar1 and Ar2 are each independently unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

[0044] Preferably, in the chemical formula 2, L1 and L2 are each independently a single bond, phenylene, or naphthylene. Preferably, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl. More preferably, the chemical formula 2 is diphenylamino.

[0045] Typical examples of the compound represented by the chemical formula 1 are as follows:

[0046]

Chem.

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Chem.

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Chem.

[0050]

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[0051]

Chem.

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Chem.

[0053]

Chem.

[0054]

Chem.

[0055]

Chem.

[0056]

Chem.

[0057]

Chem.

[0058]

Chem.

[0059]

Chem.

[0060]

Chem.

[0061] [Chemical]

[0062] [Chemical]

[0063] [Chemical]

[0064] [Chemical]

[0065] [Chemical]

[0066] [Chemical]

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[0069] [Chemical]

[0070] [Chemical]

[0071] [Chemical]

[0072]

Chem.

[0073]

Chem.

[0074] On the one hand, as an example, the present invention provides a method for producing a compound represented by the above chemical formula 1’ as shown in the following reaction formula 1, and the compound represented by the chemical formula 1 can also be produced with reference to this.

[0075]

Chem.

[0076] In the above reaction formula 1, the definitions of the remaining parts except X are as defined above, X is a halogen, more preferably chlorine or bromine.

[0077] The above step 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed by those known in the art. The above step 2 is to react with BI3, and it is preferably carried out in the presence of a base. The above production method will be further embodied in the production examples described below.

[0078] (Coating composition) On the other hand, the compound according to the present invention can form an organic layer of an organic light-emitting device, particularly a light-emitting layer, in a solution process. Specifically, the compound is used as a dopant material for the light-emitting layer. Therefore, the present invention provides a coating composition containing the compound according to the present invention and a solvent as described above.

[0079] The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention. As an example, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate; polyhydric alcohols and their derivatives such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol; alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide; benzoate solvents such as butyl benzoate, methyl-2-methoxybenzoate; tetralin; solvents such as 3-phenoxytoluene. Further, the above-mentioned solvents can be used alone or in combination of two or more solvents. Preferably, toluene can be used as the solvent.

[0080] In addition, the coating composition can further contain a compound used as a host material, and the description of the compound used as the host material will be described later. Further, the coating composition can contain a compound used as a dopant material, and the description of the compound used as the dopant material will be described later.

[0081] Further, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. Further, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.

[0082] The present invention also provides a method for forming a light-emitting layer using the above-described coating composition. Specifically, it includes a step of coating the above-described light-emitting layer according to the present invention on a positive electrode or on a hole transport layer formed on the positive electrode by a solution process, and a step of heat-treating the coated coating composition.

[0083] The solution process uses the above-described coating composition according to the present invention, and means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

[0084] In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. Further, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. Further, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

[0085] (Organic light-emitting device) The present invention also provides an organic light-emitting device including the compound represented by Chemical Formula 1. As an example, the present invention is an organic light-emitting device including a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound represented by Chemical Formula 1.

[0086] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. 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 it may include a smaller number of organic layers.

[0087] Further, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1. In particular, the compound according to the present invention can be used as a dopant in the light-emitting layer.

[0088] 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. Further, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverted 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 the organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

[0089] FIG. 1 is a diagram showing 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 the chemical formula 1 may be included in the light-emitting layer.

[0090] FIG. 2 is a diagram showing 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 injection and transport layer 8, and a negative electrode 4. In this structure, the compound represented by the chemical formula 1 may be included in the light-emitting layer.

[0091] The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers contain the compound represented by the chemical formula 1. Further, when the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0092] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially laminating a positive electrode, an organic layer, and a negative electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal, a metal oxide having conductivity, or an alloy thereof is deposited on the substrate to form a positive electrode, and then a hole injection layer, a hole transport layer, a light-emitting layer, and an organic layer including an electron transport layer are formed thereon. After that, a substance used as a negative electrode can be deposited thereon for manufacturing.

[0093] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a negative electrode material, an organic layer, and a positive electrode material on a substrate (International Publication No. 2003 / 012890). However, the manufacturing method is not limited thereto.

[0094] 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.

[0095] As the positive electrode material, a material having a large work function is preferably used so that hole injection into the organic layer becomes smooth. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline. However, it is not limited only to these.

[0096] As the negative electrode material, it is preferably a material with a small work function so that electron injection into the organic layer is facilitated. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0097] The hole injection layer is a layer that injects holes from the electrode. As the hole injection material, it has the ability to transport holes, has an excellent hole injection effect from the positive electrode, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material, and prevents the electrons of the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material. Also, a compound with excellent thin film forming ability is preferred. 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. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive compounds such as polyaniline and polythiophene, but are not limited thereto.

[0098] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the hole transport material, it is a material that can receive hole transport from the positive electrode or the hole injection layer and transfer it to the light-emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic substances, conductive compounds, and block copolymers in which both a conjugated part and a non-conjugated part are present, but are not limited thereto.

[0099] The light-emitting layer can contain a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0100] Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, examples of the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periflanthene having an arylamino group, etc. Examples of the styrylamine compounds are compounds in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 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. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. Also, examples of the metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0101] The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting the received electrons to a 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 well receive electron injection from a negative electrode and transfer it to a light-emitting layer, and has a high mobility with respect to electrons is suitable. Specific examples of the electron injection and transport material include an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex; a triazine derivative, etc., but are not limited thereto. Alternatively, LiF, NaF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc. can also be used, but are not limited thereto.

[0102] Examples of the metal complex compound include lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolate), aluminum bis(2-methyl-8-quinolinato)(1-naphtholate), gallium bis(2-methyl-8-quinolinato)(2-naphtholate), etc., but are not limited thereto.

[0103] The organic light-emitting device according to the present invention can be a front emission type, a rear emission type, or a double-sided emission type depending on the materials used.

[0104] In addition to organic light-emitting devices, the compounds according to the present invention can also be included in organic solar cells or organic transistors.

[0105] Hereinafter, the production of the compound represented by the chemical formula 1 and the organic light-emitting device containing the same will be specifically described 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

[0106] Example 1: Production of Compound 1

Chemical formula

[0107] Compound 1-d (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 1-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 the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 1-f (yield 89%).

[0108] Compound 1-f (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 the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted well with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4, and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 1-g (yield 69%).

[0109] Compound 1-g (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 the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was cooled well to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and saturated Na2S2O3 (aq.) were sequentially added dropwise to the reaction mixture, washed with CH2Cl2 / H2O, and the organic layer was separated. Water was removed with MgSO4, and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 1 (yield 70%). m / z [M+H] + 689.6

[0110] Example 2: Preparation of Compound 2

Chemical formula

[0111] Compound 2 was prepared in the same manner as the method for preparing compound 1, except that compound 2-a was used instead of compound 1-e. m / z [M+H] + 737.3

[0112] Example 3: Preparation of Compound 3

Chemical formula

[0113] Compound 3 was prepared in the same manner as the method for preparing Compound 1, except that Compound 3-a was used instead of Compound 1-e. m / z [M+H] + 661.5

[0114] Example 4: Preparation of Compound 4

Chem.

[0115] Compound 4 was prepared in the same manner as the method for preparing Compound 1, except that Compound 4-a was used instead of Compound 1-d. m / z [M+H] + 689.6

[0116] Example 5: Preparation of Compound 5

Chem.

[0117] Compound 5 was prepared in the same manner as the method for preparing Compound 1, except that Compound 5-a was used instead of Compound 1-d. m / z [M+H] + 675.4

[0118] Example 6: Preparation of Compound 6

Chem.

[0119] Compound 6 was prepared in the same manner as the method for preparing Compound 1, except that Compound 6-a was used instead of Compound 1-d. m / z [M+H] + 703.4

[0120] Example 7: Preparation of Compound 7

Chem.

[0121] Compound 1-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 1-f (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 7-a (yield 80%).

[0122] Compound 7-b (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 7-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 reaction mixture was cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 7-d (yield 83%).

[0123] Compound 7-d (1.05 eq.), NaOt-Bu (4.0 eq.), and Compound 7-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 reaction mixture was cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 7-e (yield 72%).

[0124] Compound 7-e (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 reactants, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reactants were cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and saturated Na2S2O3 (aq.) were sequentially added dropwise to the reactants, and the organic layer was separated by washing with CH2Cl2 / H2O. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 7 (yield 72%). m / z [M+H] + 897.6

[0125] Example 8: Preparation of Compound 8

Chemical Structure

[0126] Compound 8-a (1.0 eq.) and Compound 8-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 reactants. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred for 4 hours. After the reaction, the reactants were cooled to room temperature, diluted sufficiently with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 8-c (yield 64%).

[0127] Compound 8-c (1.0 eq.) and compound 8-d (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 reactants. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred for 4 hours. After the reaction, the reactants were cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 8-e (yield 78%).

[0128] Next, compound 8 was produced in the same manner as the method for producing compound 7, except that compound 8-e was used instead of compound 7-b. m / z [M+H] + 941.4

[0129] Example 9: Production of compound 9

Chemical formula

[0130] Compound 8-a (1.0 eq.) and compound 8-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 reactants. Pd(PPh3)4 (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred overnight. After the reaction, the reactants were cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 9-a (yield 82%).

[0131] Next, compound 9 was produced in the same manner as the method for producing compound 7, except that compound 9-a was used instead of compound 7-b. m / z [M+H] + 865.4

[0132] Example 10: Preparation of Compound 10

Chem.

[0133] Compound 10 was prepared in the same manner as the preparation method of Compound 7, except that Compound 10-a was used instead of Compound 7-d. m / z [M+H] + 797.6

[0134] Example 11: Preparation of Compound 11

Chem.

[0135] Compound 11 was prepared in the same manner as the preparation method of Compound 7, except that Compound 11-a was used instead of Compound 7-d. m / z [M+H] + 713.5

[0136] Example 12: Preparation of Compound 12

Chem.

[0137] Compound 12 was prepared in the same manner as the preparation method of Compound 7, except that Compound 1-f was used instead of Compound 7-d. m / z [M+H] + 719.4

[0138] Example 13: Preparation of Compound 13

Chem.

[0139] Compound 13 was prepared in the same manner as the preparation method of Compound 7, except that Compound 5-b was used instead of Compound 7-d. m / z [M+H]+ 719.4

[0140] Example 14: Preparation of Compound 14

Chemical Structure

[0141] Compound 4-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 2-a (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, diluted well with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 14-a (yield 69%).

[0142] Compound 14-a (2.05 eq.), NaOt-Bu (4.0 eq.), and Compound 1-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 the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted well with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 14-b (yield 79%).

[0143] Compound 14-b (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 reactants, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reactants were cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and saturated Na2S2O3 (aq.) were sequentially added dropwise to the reactants, and the mixture was washed with CH2Cl2 / H2O to separate the organic layer. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 14 (yield 72%). m / z [M+H] + 815.4

[0144] Example 15: Preparation of Compound 15

Chemical Structure

[0145] Compound 15 was prepared in the same manner as the method for preparing Compound 14, except that Compound 5-b was used instead of Compound 14-a. m / z [M+H] + 691.4

[0146] Example 16: Preparation of Compound 16

Chemical Structure

[0147] Compound 16-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 1-f (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 the mixture was stirred overnight. After the reaction, the reactants were cooled to room temperature, diluted sufficiently with CH2Cl2, and then washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 16-b (yield 63%).

[0148] Compound 16-b (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 16-c (1.2 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 the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature and diluted well with CH2Cl2, then washed with CH2Cl2 / brine and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 16-d (yield 71%).

[0149] Compound 16-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 the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was cooled well to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and saturated Na2S2O3(aq.) were sequentially added dropwise to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 16 (yield 69%). m / z [M+H] + 1094.6

[0150] Example 17: Preparation of Compound 17

Chemical Structure

[0151] Compound 16-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 reactants. Pd(t-Bu3P)2 (3 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reactants were cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 17-b (yield 79%).

[0152] Compound 17-b (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 reactants, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reactants were cooled sufficiently to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and saturated Na2S2O3(aq.) were added dropwise to the reactants in sequence, washed with CH2Cl2 / H2O, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce compound 17 (yield 70%). m / z[M+H] + 1140.6

[0153] [Comparative Example] Comparative Example 1: Preparation of Comparative Compound F [Chemical formula]

[0154] 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 the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4, and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound F-1 (yield 75%).

[0155] 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 the mixture was 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 saturated Na2S2O3 (aq.) were sequentially added dropwise to the reaction mixture, washed with CH2Cl2 / H2O, and the organic layer was separated. Water was removed with MgSO4, and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound F (yield 87%). m / z [M+H] + =659.6

[0156] Comparative Example 2: Preparation of Comparative Compound G

Chemical Structure

[0157] Compound G was prepared in the same manner as in Comparative Example 1, except that Compound G-1 was used instead of Compound 1-b. m / z [M+H] + =659.5

[0158] Comparative Example 3: Preparation of Comparative Compound H

Chemical Structure

[0159] 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 the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, diluted thoroughly with CH2Cl2, washed with CH2Cl2 / brine, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound H-2 (yield 79%).

[0160] 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 the mixture was 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 saturated Na2S2O3 (aq.) were sequentially added dropwise to the reaction mixture, washed with CH2Cl2 / H2O, and the organic layer was separated. Water was removed with MgSO4 and the solution was passed through a Celite-Florisil-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound H (yield 73%). m / z [M+H] + = 725.5

[0161] [Experimental Example] Experimental Example 1 A glass substrate with a thin film coating of ITO (indium tin oxide) with a thickness of 500 Å was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, a product of Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered through a filter of a product of Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents of isopropyl and acetone, dried, and then the substrate was cleaned for 5 minutes, and then the substrate was transported to a glove box.

[0162] 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 in which the Compound 1 manufactured above and the following Compound R (weight ratio of 2:98) were dissolved in 2 wt / v% cyclohexanone 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 apparatus, the following Compound S was vacuum-deposited on the light-emitting layer to form an electron injection and transport layer with a thickness of 350 Å. On the electron injection and transport layer, LiF was deposited to a thickness of 10 Å and aluminum was deposited to a thickness of 1000 Å in sequence to form a cathode.

[0163]

Chemical formula

[0164] 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 0.3 Å / sec, the deposition rate of aluminum was 2 Å / sec, and the degree of vacuum during deposition was maintained at 2×10 -7 ~5×10 -8 torr.

[0165] Experimental Examples 2 - 17 An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 as the dopant in the light-emitting layer.

[0166] Comparative Experimental Examples 1 - 3 An organic light-emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound described in Table 1 below was used instead of Compound 1 as the dopant in the light-emitting layer.

[0167] When a current was applied to the organic light-emitting devices fabricated in the experimental examples and comparative experimental examples, the driving voltage, external quantum efficiency (EQE), and lifetime at a current density of 10 mA / cm 2 are shown in Table 1 below. At this time, the external quantum efficiency (EQE) was determined from "(number of photons emitted) / (number of charge carriers injected) × 100", and T90 means the time until the initial luminance (500 nit) decreases to 90%.

[0168]

Table 1

[0169] As shown in Table 1 above, the organic light-emitting device containing the compound of the present invention in the light-emitting layer showed excellent characteristics in terms of the efficiency, driving voltage, and lifetime of the organic light-emitting device.

Explanation of Reference Numerals

[0170] 1 Substrate 2 Anode 3 Light-emitting layer 4 Cathode 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': 【Chemical 1】 In the Chemical Formula 1', Ar is a benzene ring condensed with two adjacent rings, n is an integer from 1 to 4, n1 is 1 or 2, When n1 is 1, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 10 carbon atoms, substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing any one or more heteroatoms selected from the group consisting of N, O and S, or di(substituted or unsubstituted aryl having 6 to 10 carbon atoms)amino, When n1 is 2, R1 is bonded to each other to form substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, or -O-(CH2)m1-O-, where m1 is an integer from 1 to 3, n2 is each independently an integer from 1 to 3, R2 is each independently hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 8 to 12 carbon atoms containing any one or more heteroatoms selected from the group consisting of N, O and S; or two adjacent R2 are bonded to each other to form substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, or -O-(CH2)m2-O-, where m2 is an integer from 1 to 3, R3 is substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or a substituent represented by the following Chemical Formula 2, 【Chemical 2】 In the Chemical Formula 2, L is a single bond, or 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 heteroarylene having 2 to 60 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S; Ar １ and Ar ２ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a heteroaryl having 2 to 60 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

2. The compound according to Claim 1, wherein the Chemical Formula 1' is represented by any one of the following Chemical Formulas 1-1 to 1-9: 【Chemical 3】 In the Chemical Formulas 1-1 to 1-9, R １ , R ２ , R ３ , n1 and n2 are as defined in claim 1.

3. The compound according to Claim 1, wherein n is 1, 2 or 3.

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

5. n1 is 2, R １ are joined to each other to form a substituent represented by any one of the following: The compound according to claim 1 【Chemical Formula 4】

6. n2 is each independently 1 or 2, R ２ is each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, dimethylfluorenyl, diphenylfluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl; or two adjacent Rs ２ are bonded to each other to form a substituent represented by any one of the following: The compound according to claim 1. 【Chemical Formula 5】

7. R ３ is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, dimethylfluorenyl, or diphenylfluorenyl, the compound according to claim 1.

8. R ３ is a substituent represented by the above chemical formula 2, In the Chemical Formula 2, L is a single bond, or phenylene, L １ and L ２ are each independently a single bond, phenylene, naphthylene, or dimethylfluorenediyl, Ar １ is phenyl, naphthyl, dimethylfluorenyl, or benzofuranyl, Ar ２ is dimethylfluorenyl or dimethylbenzofluorenyl, and Said Ar １ and Ar ２ are each independently unsubstituted or substituted with an alkyl having 1 to 10 carbon atoms, the compound according to claim 1.

9. The compound according to Claim 1, wherein the compound represented by the Chemical Formula 1' is any one selected from the group consisting of the following: [Chemical Formula 6] 【Chemical Formula 7】 【Chemical Formula 8】 【Chemical Formula 9】 【Chemical 10】 【Chemical 11】 【Chemical 12】 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical Formula 18】 【Chemical Formula 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemical Formula 24】 【Chemical 25】 【Chemical 26】 【Chemical 27】 【Chemical 28】 【Chemical 29】 【Chemical Formula 30】 【Chemical 31】 【Chemical 32】 【Chemical 33】 。

10. An organic light-emitting device including a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 9.

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

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