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 - 0030814, filed on Mar. 9, 2021, and all of the contents disclosed in the document of the Korean Patent Application are incorporated herein by reference in their entirety. The present invention relates to a novel compound and an organic light - emitting device including the same.

Background Art

[0002] Generally, the organic light - emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light - emitting devices that utilize the organic light - emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and many studies are being carried out due to their excellent luminance, driving voltage, and response speed characteristics.

[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 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 include a hole injection layer, a hole transport layer, a light - emitting layer, an electron transport layer, an electron injection layer, and the like. In such a structure of the 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.

[0004] There has been a continuous demand for the development of new materials for the organic substances used in such organic light - emitting devices.

[0005] On the other hand, recently, in order to reduce process costs, organic light-emitting devices using a solution process, particularly an inkjet process, instead of the existing vapor deposition process 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 a solution process. However, with current technology, there are limitations. Currently, only the HIL, HTL, and EML are formed using a solution process in a normal structure, and for subsequent processes, a hybrid process that utilizes the existing vapor deposition process is under research.

[0006] 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

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] The present invention provides a novel compound and an organic light-emitting device containing the same.

Means for Solving the Problems

[0009] The present invention provides a compound represented by the following Chemical Formula 1:

Chem.

[0010] The present invention also 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

[0011] 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 also be used in a solution process, and can achieve an improvement in efficiency, a low driving voltage, and / or an improvement in lifetime characteristics in the organic light-emitting device.

Brief Description of the Drawings

[0012]

Figure 1

Figure 2

Embodiments for Carrying Out the Invention

[0013] Hereinafter, a more detailed description will be given to assist in understanding the present invention.

[0014] (Definition of Terms) In this specification,

Chem.

Chem.

[0015] As used herein, the term "substituted or unsubstituted" means being substituted or unsubstituted 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 substituted or unsubstituted with a substituent 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.

[0016] In the present specification, the number of carbon atoms 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

[0017] In the present specification, the ester group may be substituted with an oxygen of the ester group by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, compounds having the following structural formulas may be used, but are not limited thereto.

Chemical formula

[0018] 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]

[0019] In this specification, examples of the silyl group specifically include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.

[0020] In this specification, examples of the boron group specifically include, but are not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.

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

[0022] 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 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 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.

[0023] 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 carbon number of the alkenyl group is 2 to 20. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number 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, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0024] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0025] 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 include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a fluorenyl group.

[0026] In this specification, the fluorenyl group may be substituted, or two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Chemical formula

[0027] 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 carbon atoms. 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, pyrimidyl group, triazinyl group, acridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinoprazinyl 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, etc., but is not limited thereto only.

[0028] In this specification, for the aryl groups in aralkyl groups, aralkenyl groups, alkylaryl groups, arylamine groups, and arylsilyl groups, the descriptions regarding the aryl groups mentioned above are applicable. In this specification, for the alkyl groups in aralkyl groups, alkylaryl groups, and alkylamine groups, the descriptions regarding the alkyl groups mentioned above are applicable. In this specification, for the heteroaryl in heteroarylamine, the descriptions regarding the heteroaryl mentioned above are applicable. In this specification, for the alkenyl groups in aralkenyl groups, the descriptions regarding the alkenyl groups mentioned above are applicable. In this specification, for arylene, except that it is a divalent group, the descriptions regarding the aryl groups mentioned above are applicable. In this specification, for heteroarylene, except that it is a divalent group, the descriptions regarding the heteroaryl mentioned above are applicable. In this specification, for hydrocarbon rings, except that they are not monovalent groups and are formed by bonding two substituents, the descriptions regarding the aryl groups or cycloalkyl groups mentioned above are applicable. In this specification, for heterocycles, except that they are not monovalent groups and are formed by bonding two substituents, the descriptions regarding the heteroaryl mentioned above are applicable.

[0029] (Compound) The present invention provides a compound represented by the above chemical formula 1.

[0030] Preferably, A1, A2, A3, and A4 are each independently a substituted or unsubstituted benzene ring.

[0031] Preferably, the above chemical formula 1 is represented by the following chemical formula 1': [Chemical formula]

[0032] In the above chemical formula 1', n1 and n2 are each independently 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, 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 R1s are bonded to each other to form substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aromatic ring having 6 to 60 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, substituted or unsubstituted aromatic ring having 6 to 60 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 3 to 6:

Chemical formula

Chemical formula

[0034] In the chemical formulas 3 to 6, n1, n2, R1, R2, R3, m1 and m2 are as defined above.

[0035] Preferably, n1 and n2 are each independently 1, 2 or 3.

[0036] Preferably, n3 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, 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.

[0037] Preferably, n3 is 1, and R1 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, or benzothiophenyl.

[0038] Preferably, n3 is 2, and R1 are bonded to each other to form a substituted or unsubstituted cycloalkyl having 5 to 6 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 10 carbon atoms, or -O-(CH2)m1 -O- is formed, where m1 is an integer from 1 to 3.

[0039] Preferably, n3 is 2, and R1 is combined with each other to form a substituent represented by any one of the following:

Chemical formula

[0040] Preferably, n4 is 1, and it is hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 10 carbon atoms, or 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.

[0041] Preferably, n4 is 2, and R2 is combined with each other to form a cycloalkyl having 5 to 6 carbon atoms which may be substituted or unsubstituted, an aromatic ring having 6 to 10 carbon atoms which may be substituted or unsubstituted, or -O-(CH2) m1 -O- is formed, where m2 is an integer from 1 to 3.

[0042] Preferably, n4 is 2, and R2 is combined with each other to form a substituent represented by any one of the following:

Chemical formula

[0043] Preferably, R3 is substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or the substituent represented by the chemical formula 2 above.

[0044] Preferably, L, L1, and L2 are each independently a single bond, phenylene, or naphthylene.

[0045] Preferably, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl.

[0046] Typical examples of the compound represented by Chemical Formula 1 are as follows:

Chem.

[0047]

Chem.

[0048]

Chem.

[0049]

Chem.

[0050]

Chem.

[0051]

Chem.

[0052]

Chem.

[0053]

Chem.

[0054]

Chem.

[0055]

Chem.

[0056]

Chem.

[0057]

Chem.

[0058] 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.

Chem.

[0059] In the above reaction formula 1, the definitions of the remaining parts except X are as defined above, and X is a halogen, preferably bromine or chlorine.

[0060] 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, which is preferably carried out in the presence of a base. The above production method will be further embodied in the production examples described below.

[0061] (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 can be 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 described above and a solvent.

[0062] 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.

[0063] 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.

[0064] In addition, 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%.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] (Organic light-emitting device) The present invention also provides an organic light-emitting device containing 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 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 the compound represented by Chemical Formula 1.

[0069] 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.

[0070] 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 is used as a dopant in the light-emitting layer.

[0071] In addition, the organic light-emitting device according to the present invention may be a normal-type organic light-emitting device having a structure 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 inverted-type organic light-emitting device having a structure 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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 the negative electrode can be deposited thereon for manufacturing.

[0076] 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.

[0077] 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.

[0078] 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, but are not limited thereto.

[0079] 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 it is not limited thereto.

[0080] 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, prevents the electrons of the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and 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 it is not limited thereto.

[0081] 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 it is not limited thereto.

[0082] The light-emitting layer can include 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.

[0083] 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 the substituents are substituted or unsubstituted with one or more 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.

[0084] The electron injection and transport layer is a layer that simultaneously functions as an electron transport layer and an electron injection layer, injecting electrons from the electrode and transporting 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 well receive electron injection from the negative electrode and transfer it to the 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, or nitrogen-containing 5-membered ring derivatives, etc. can also be used, but are not limited thereto.

[0085] 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.

[0086] The organic light-emitting device according to the present invention can be a front emission type, a back emission type, or a double-sided emission type depending on the materials used.

[0087] 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.

[0088] 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 by way of examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto.

Examples

[0089] [Examples] Example 1: Production of Compound 1

Chem.

[0090] 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 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-c (yield 89%).

[0091] Compound 1-d (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 1-c (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 100 °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-e (yield 79%).

[0092] Compound 1-e (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 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 82%).

[0093] 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 sat. 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 73%). m / z [M+H] + 663.5

[0094] Example 2: Preparation of Compound 2

Chemical formula

[0095] Compound 2-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 2-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 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 2-c (yield 81%).

[0096] Compound 2 was prepared in the same manner as the method for producing Compound 1 described above, except that Compound 2-c was used instead of Compound 1-f. m / z [M+H] + 771.3

[0097] Example 3: Preparation of Compound 3

Chemical formula

[0098] Compound 3 was prepared in the same manner as the method for producing Compound 2 described above, except that Compound 3-a was used instead of Compound 2-a and Compound 3-b was used instead of Compound 2-b. m / z [M+H] + 871.6

[0099] Example 4: Preparation of Compound 4

Chemical formula

[0100] Compound 4 was prepared in the same manner as the method for producing Compound 2 described above, except that Compound 4-a was used instead of Compound 2-a and Compound 4-b was used instead of Compound 2-b. m / z [M+H] + 687.2

[0101] Example 5: Preparation of Compound 5

Chem.

[0102] Compound 5 was prepared in the same manner as the preparation method of Compound 1, except that Compound 5-a was used instead of Compound 1-f. m / z [M+H] + 783.5

[0103] Example 6: Preparation of Compound 6

Chem.

[0104] Compound 6 was prepared in the same manner as the preparation method of Compound 1, except that Compound 6-a was used instead of Compound 1-f. m / z [M+H] + 739.5

[0105] Example 7: Preparation of Compound 7

Chem.

[0106] Compound 7-a (1.0 eq.) and Compound 7-b (2.1 eq.) were placed in a round-bottomed flask and dissolved in anhydrous THF (0.12 M). K2CO3(aq.) (3.0 eq.) was added dropwise to the reactants. Pd(PPh3)4 (3 mol%) was added dropwise at a bath temperature of 80 °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 give Compound 7-c (yield 87%).

[0107] Subsequent synthesis was carried out in the same manner as the method for producing Compound 1, except that Compound 7-c was used instead of Compound 1-f to produce Compound 7. m / z [M+H] + 783.4

[0108] Example 8: Production of Compound 8

Chemical formula

[0109] Compound 8 was produced in the same manner as the method for producing Compound 7, except that Compound 8-a was used instead of Compound 7-b. m / z [M+H] + 841.6

[0110] Example 9: Production of Compound 9

Chemical formula

[0111] 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] + 883.3

[0112] Example 10: Production of Compound 10

Chemical formula

[0113] Compound 10 was produced in the same manner as the method for producing Compound 7, except that Compound 10-a was used instead of Compound 7-b. m / z [M+H] + 915.3

[0114] Example 11: Production of Compound 11

Chemical formula

[0115] Compound 1-d (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 100 °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 11-a (yield 73%).

[0116] Compound 11-b (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 11-c (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and 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 11-d (yield 82%).

[0117] Compound 11-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 11-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 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 11-e (yield 72%).

[0118] Compound11-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 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 sat. Na2S2O3 (aq.) were sequentially added dropwise to the reaction mixture, 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 11 (yield 81%). m / z [M+H] + 663.4

[0119] Example 12: Preparation of Compound 12

Chemical formula

[0120] Compound 12 was prepared in the same manner as the method for preparing Compound 11, except that 12-a was used instead of Compound 11-b and Compound 12-b was used instead of Compound 11-c. m / z [M+H] + 635.4

[0121] Example 13: Preparation of Compound 13

Chemical formula

[0122] Compound 13 was prepared in the same manner as the method for preparing Compound 11, except that 13-a was used instead of Compound 11-b and Compound 13-b was used instead of Compound 11-c. m / z [M+H]+ 635.4

[0123] Example 14: Preparation of Compound 14

Chemical formula

[0124] Instead of compound 11-b 14-a and instead of compound 11-c, compound 14-b Compound 13 was prepared in the same manner as the method for preparing compound 11, except that the above compound was used. m / z [M+H] + 717.4

[0125] Example 15: Preparation of Compound 15 [Chemical formula]

[0126] Compound 15 was prepared in the same manner as the method for preparing compound 1, except that 15-a was used instead of compound 1-d. m / z [M+H] + 705.4

[0127] Example 16: Preparation of Compound 16 [Chemical formula]

[0128] Compound 16-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 1-c (1.05 eq.) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 100 °C, and the mixture was stirred for 2.5 hours. After the reaction, the reaction mixture was cooled to room temperature and diluted sufficiently with CH2Cl2, 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 65%).

[0129] Compound 16-b (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 100 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature and diluted thoroughly with CH2Cl2, 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-c (yield 88%).

[0130] Compound 16-c (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 16-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 the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature and diluted thoroughly with CH2Cl2, 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-e (yield 80%).

[0131] Compound 16-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 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 sat. Na2S2O3 (aq.) were sequentially added dropwise to the reaction mixture, 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 16 (yield 74%). m / z[M+H] + 1038.6

[0132] Example 17: Preparation of Compound 17

Chem.

[0133] Compound 17 was prepared in the same manner as the method for preparing Compound 16, except that 17-a was used instead of Compound 16-d. m / z [M+H] + 1098.6

[0134] Example 18: Preparation of Compound 18

Chem.

[0135] Compound 16-c (1.0 eq.) and Compound 18-a (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 stirred overnight. After the reaction, the reactants were cooled to room temperature, diluted sufficiently 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 18-b (yield 74%).

[0136] Compound 18-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 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 sat. 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 passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound 18 (yield 72%). m / z [M+H] + 1084.6

[0137] Example 19: Preparation of Compound 19 [Chemical formula]

[0138] Compound 19 was prepared in the same manner as the preparation method of Compound 18, except that 19-a was used instead of Compound 18-a. m / z [M+H] + 781.6

[0139] Example 20: Preparation of Compound 20 [Chemical formula]

[0140] Compound 20 was prepared in the same manner as the preparation method of Compound 18, except that 20-a was used instead of Compound 18-a. m / z [M+H] + 957.5

[0141] Example 21: Preparation of Compound 21 [Chemical formula]

[0142] Compound 21-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 1-c (2.1 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 21-b (yield 76%).

[0143] Compound 21-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 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 sat. Na2S2O3 (aq.) were sequentially added dropwise to the reaction mixture, and the organic layer was separated by washing with CH2Cl2 / H2O. The 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 21 (yield 75%). m / z [M+H] + 667.3

[0144] Example 22: Preparation of Compound 22

Chemical Structure

[0145] Compound 22 was prepared in the same manner as the method for preparing compound 21, except that 11-d was used instead of compound 1-c. m / z [M+H] + 667.3

[0146] Example 23: Preparation of Compound 23

Chemical Structure

[0147] Compound 23 was prepared in the same manner as the method for preparing compound 21, except that 13-c was used instead of compound 1-c. m / z [M+H] + 611.2

[0148] Example 24: Preparation of Compound 24

Chemical Structure

[0149] Compound 24 was produced in the same manner as the method for producing Compound 21, except that 12-c was used instead of Compound 1-c. m / z [M+H] + 611.2

[0150] Example 25: Production of Compound 25

Chemical formula

[0151] Compound 25 was produced in the same manner as the method for producing Compound 21, except that 14-c was used instead of Compound 1-c. m / z [M+H] + 723.4

[0152] Example 26: Production of Compound 26

Chemical formula

[0153] Compound 16-a (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound 1-c (2.1 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 26-a (yield 72%).

[0154] Compound 26-a (1.0 eq.), NaOt-Bu (4.0 eq.), and compound 16-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 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 26-b (yield 74%).

[0155] Compound 26-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 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 sat. 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 26 (yield 71%). m / z [M+H] + 1042.5

[0156] Example 27: Preparation of Compound 27

Chemical Structure

[0157] Compound 26-a (1.0 eq.) and compound 18-a (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 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 27-a (yield 82%).

[0158] Compound 27-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 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 sat. Na2S2O3(aq.) were added dropwise sequentially to the reactants, 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 27 (yield 75%). m / z[M+H] + 1088.5

[0159] Comparative Example 1: Preparation of Comparative Compound A

Chemical Structure

[0160] Compound 1-d (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 reaction mixture was cooled to room temperature and diluted thoroughly with CH2Cl2, 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 A-1 (yield 75%).

[0161] Compound A-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 sat. Na2S2O3(aq.) were sequentially added dropwise to the reaction mixture, 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 A (yield 87%). m / z [M+H] + = 659.6

[0162] Comparative Example 2: Preparation of Comparative Compound B

Chemical Structure

[0163] Compound B was prepared in the same manner as in the preparation method of Comparative Example 1, except that Compound B-1 was used instead of Compound 1-f. m / z [M+H] + = 659.5

[0164] Comparative Example 3: Preparation of Comparative Compound C

Chemical Structure

[0165] Compound 11-c (1.0 eq.), NaOt-Bu (4.0 eq.), and Compound C-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 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 passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound C-2 (yield 79%).

[0166] Compound C-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 well to room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 eq.) and sat. 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 passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to produce Compound C (yield 73%). m / z[M+H] + =725.5

[0167] [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 with 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. 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.

[0168] 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 a PC standard with an 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 evaporation apparatus, the following Compound S was vacuum-evaporated to a thickness of 350 Å on the light-emitting layer to form an electron injection and transport layer. On the electron injection and transport layer, LiF was evaporated to a thickness of 10 Å and aluminum was evaporated to a thickness of 1000 Å in sequence to form a cathode.

[0169]

Chemical formula

[0170] In the above process, the deposition rate of the organic substance was maintained at 0.4 to 0.7 Å / sec, the deposition rate of LiF was 0.3 Å / sec, and the deposition rate of aluminum was 2 Å / sec. The degree of vacuum during deposition was maintained at 2×10 -7 ~5×10 -8 torr.

[0171] Experimental Examples 2 to 27 An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds described in Table 1 below were used instead of Compound 1.

[0172] Comparative Experimental Examples 1 to 3 An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of Compound 1.

[0173] When a current was applied to the organic light-emitting devices manufactured in the above Experimental Examples and Comparative Experimental Examples, the driving voltage, external quantum efficiency (EQE), and lifetime were measured at a current density of 10 mA / cm 2 . The results are shown in Table 1 below. At this time, the external quantum efficiency (EQE) was obtained from "(number of photons emitted) / (number of charge carriers injected) × 100", and T90 means the time until the initial luminance (500 nit) decreased 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 showed excellent characteristics in terms of the efficiency, driving voltage, and lifetime of the organic light-emitting device.

Explanation of Reference Numerals

[0176] 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 2】 In the Chemical Formula 1', n1 and n2 are each independently an integer from 1 to 4, R １ is each 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 at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S; or two adjacent Rs １ are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, 【Chemical Formula 9】 or -O-(CH ２ ) ｍ１ -O- is formed, where m1 is an integer from 1 to 4, R ２ is each 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 at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O, and S; or two adjacent Rs ２ are bonded to each other to form a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, 【Chemical 10】 or -O-(CH ２ ) ｍ２ -O- is formed, where m2 is an integer from 1 to 4, R ３ 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 heteroaryl having 2 to 60 carbon atoms containing at least one heteroatom 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 3] In the 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 heteroarylene having 2 to 60 carbon atoms containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O, and S; Ar １ and Ar ２ each independently is a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a heteroaryl having 2 to 60 carbon atoms containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, n3 is an integer from 0 to 4, n4 are each independently an integer from 0 to 5.

2. The compound according to Claim 1, wherein the Chemical Formula 1' is represented by any one of the following Chemical Formulas 3 to 6: 【Chemical Formula 4】 【Chemical Formula 5】 In the Chemical Formulas 3 to 6, n1, n2, R １ , R ２ , R ３ , m1, and m2 are as defined in claim 1.

3. n3 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, or a heteroaryl having 8 to 12 carbon atoms containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, the compound according to claim 1.

4. n3 is 1, R １ is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, phenyl substituted with tert-butyl, benzofuranyl, dibenzofuranyl, or benzothiophenyl, the compound according to claim 1.

5. n3 is 2, R １ are joined to each other to form a substituted or unsubstituted C5-C6 cycloalkyl, 【Chemical 11】 、 or -O-(CH ２ ) ｍ１ -O- is formed, where m1 is an integer from 1 to 3, the compound according to claim 1.

6. n3 is 2, R １ which are joined to each other to form a substituent represented by any one of the following, the compound according to claim 1: ​ 。

7. n4 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, or a heteroaryl having 8 to 12 carbon atoms containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, the compound according to claim 1.

8. n4 is 2, R ２ are combined with each other to form a substituted or unsubstituted C5-C6 cycloalkyl, 【Chemical 12】 、 or -O-(CH ２ ) ｍ２ -O- is formed, where m2 is an integer from 1 to 3, the compound according to claim 1.

9. n4 is 2, R ２ which are combined with each other to form a substituent represented by any one of the following, the compound according to claim 1: 【Chemical Formula 7】 。

10. R ３ The compound according to claim 1, wherein R 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.

11. L, L １ and L ２ The compound according to claim 1, wherein each of L, L, and L is independently a single bond, phenylene, or naphthylene. It should be noted that there seems to be a repetition of "L" in the original text which might be a typo. The translated text has been adjusted according to the correct claim structure. If the actual claim has a different structure or more specific requirements, the translation may need to be further refined.

12. Ar １ and Ar ２ each independently is phenyl, biphenylyl, terphenylyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl, the compound according to claim 1.

13. 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 8A】 【Chemical 8B】 【Chemical Formula 8C】 【Chemical 8D】 【Chemical Formula 8E】 【Chemical Formula 8F】 【Chemical 8G】 [Chemical 8H] 【Chemical 8I】 [Chemical 8J] 【Chemical Formula 8K】 【Chemical Formula 8L】 。

14. 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 at least one of the organic layers contains the compound according to any one of Claims 1, 3, 5 to 13.

15. The organic light-emitting device according to Claim 14, wherein the organic layer containing the compound is a light-emitting layer.

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