Novel compound and organic light-emitting device using the same

Abstract

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

Description

[Technical field]

[0001] [Cross-reference to related applications] This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0185368 dated December 22, 2021, and all contents disclosed in the documents of that 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 technology]

[0003] In general, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, and are the subject of much research.

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

[0005] There is a continuing demand for the development of new organic materials for use in such organic light-emitting devices. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Means for solving the problem]

[0008] The present invention provides a compound represented by the following formula 1: [ka]

[0009] In the above Chemical Formula 1, n is an integer from 1 to 6; X is O or S; L 1 and L 2 each independently represents a single bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B, Ar 1 is cyano; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B, Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B.

[0010] The present invention also provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. Effect of the Invention

[0011] The compound represented by the above-mentioned Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can improve the efficiency, low driving voltage, and / or life characteristics of the organic light-emitting device. In particular, the compound represented by the above-mentioned Chemical Formula 1 can be used as a material for a hole injection layer, a hole transport layer, a hole injection layer and transport, an electron inhibiting layer, a light-emitting layer, an electron transport layer, or an electron injection layer. [Brief description of the drawings]

[0012] [Figure 1] The figure shows an example of an organic light-emitting device that is composed of a substrate 1, a positive electrode 2, an organic layer 3, and a negative electrode 4. [Diagram 2] 1 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 7, a light-emitting layer 8, a hole inhibiting layer 9, an electron transport layer 10, an electron injection layer 11, and a negative electrode 4. [Diagram 3] An example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 12, and a negative electrode 4 is shown. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The present invention will now be described in more detail for easier understanding.

[0014] The present invention provides a compound represented by Chemical Formula 1.

[0015] In this specification, [ka] and [ka] denotes a bond that is connected to another substituent.

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

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

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

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

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

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

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

[0023] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

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

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

[0026] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. 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 phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a fluorenyl group.

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

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

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

[0030] The compound represented by the formula 1 includes a dibenzofuran or dibenzothiophene containing one or more deuterium, an aryl- or heteroaryl-substituted triazine group bonded thereto, and an aryl or heteroaryl group, and does not include a nitrogen-containing heterocycle other than the triazine group. The compound satisfying the structure of the formula 1 exhibits low voltage and has excellent efficiency and life characteristics when applied to an organic light emitting device.

[0031] The formula 1 can be specifically represented by the following formula 1-1 or 1-2: [ka]

[0032] In the above Chemical Formulas 1-1 and 1-2, n, L 1 , L 2 , and Ar 1 ~Ar3 is as defined in Chemical Formula 1.

[0033] Preferably, n is an integer of 4-6.

[0034] In the above Chemical Formula 1, L 1 , L 2 , Ar 1 ~Ar 3 One or more hydrogen atoms may be replaced with deuterium.

[0035] Preferably, L 1 and L 2 are each independently a single bond; a substituted or unsubstituted arylene having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene having 2 to 20 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B. Preferably, the heteroatom of the heteroarylene may be O and / or S.

[0036] Preferably, L 1 and L 2 each independently represents a single bond; phenylene; or biphenylenesilyl; 1 and L 2 may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0037] Preferably, L 1 and L 2 are each independently a single bond; phenylene which is unsubstituted or substituted with one or more deuterium atoms; or biphenylylene which is unsubstituted or substituted with one or more deuterium atoms.

[0038] Preferably, L 1 and L 2 are each independently a single bond; phenylene; or biphenylylene.

[0039] Preferably, Ar 1is cyano; a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing one or more heteroatoms selected from the group consisting of O, S, Si, P and B. Preferably, the heteroatom of the heteroaryl may be O and / or S. 1 However, when it is aryl or heteroaryl, one or more hydrogens may be replaced by deuterium.

[0040] Preferably, Ar 1 is cyano; phenyl; biphenylyl; terphenylyl; triphenylenyl; benzofuranyl; benzothiophenyl; dibenzofuranyl; or dibenzothiophenyl, said substituents being optionally substituted with one or more deuterium atoms or optionally unsubstituted.

[0041] Preferably, Ar 1 is cyano; phenyl substituted or unsubstituted by one or more deuteriums; biphenylyl substituted or unsubstituted by one or more deuteriums; terphenylyl substituted or unsubstituted by one or more deuteriums; triphenylenyl substituted or unsubstituted by one or more deuteriums; benzofuranyl substituted or unsubstituted by one or more deuteriums; benzothiophenyl substituted or unsubstituted by one or more deuteriums; dibenzofuranyl substituted or unsubstituted by one or more deuteriums; or dibenzothiophenyl substituted or unsubstituted by one or more deuteriums.

[0042] Preferably, Ar 2 and Ar 3 is a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing one or more heteroatoms selected from the group consisting of O, S, Si, P and B. Preferably, the heteroatom of the heteroaryl may be O and / or S. 2 and Ar 3 may each be substituted with one or more deuterium atoms.

[0043] Preferably, Ar 2 and Ar3 are each independently phenyl; phenyl substituted with one or more substituents selected from the group consisting of halogen, cyano, trimethylsilyl, alkyl having 1 to 4 carbon atoms, and alkenyl having 1 to 4 carbon atoms; biphenylyl; terphenylyl; naphthyl; 9,9-dimethylfluorenyl; 9,9-diphenylfluorenyl; triphenylenyl; chrysenyl; dibenzofuranyl; phenyldibenzofuranyl; dibenzothiophenyl; or phenyldibenzothiophenyl, and the substituents may be substituted with one or more deuterium atoms or may be unsubstituted. On the other hand, the "phenyl substituted with one or more substituents selected from the group consisting of halogen, cyano, trimethylsilyl, alkyl having 1 to 4 carbon atoms, and alkenyl having 1 to 4 carbon atoms" may be, for example, fluorophenyl, cyanophenyl, trimethylsilylphenyl, dimethylphenyl, t-butylphenyl, or ethenylphenyl.

[0044] Preferably, Ar 2 and Ar 3each independently represents phenyl substituted or unsubstituted with one or more deuterium atoms; fluorophenyl substituted or unsubstituted with one or more deuterium atoms; cyanophenyl substituted or unsubstituted with one or more deuterium atoms; trimethylsilanophenyl substituted or unsubstituted with one or more deuterium atoms; dimethylphenyl substituted or unsubstituted with one or more deuterium atoms; t-butylphenyl substituted or unsubstituted with one or more deuterium atoms; ethenylphenyl substituted or unsubstituted with one or more deuterium atoms; biphenylyl substituted or unsubstituted with one or more deuterium atoms; terphenylyl substituted or unsubstituted with one or more deuterium atoms; substituted or unsubstituted naphthyl; 9,9-dimethylfluorenyl substituted or unsubstituted by one or more deuteriums; 9,9-diphenylfluorenyl substituted or unsubstituted by one or more deuteriums; triphenylenyl substituted or unsubstituted by one or more deuteriums; chrysenyl substituted or unsubstituted by one or more deuteriums; dibenzofuranyl substituted or unsubstituted by one or more deuteriums; phenyldibenzofuranyl substituted or unsubstituted by one or more deuteriums; dibenzothiophenyl substituted or unsubstituted by one or more deuteriums; or phenyldibenzothiophenyl substituted or unsubstituted by one or more deuteriums.

[0045] In the above Chemical Formula 1, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 20 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B; Ar 1 is cyano, a substituted or unsubstituted aryl having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing one or more heteroatoms selected from the group consisting of O, S, Si, P, and B; Ar 2 and Ar 3may be a substituted or unsubstituted aryl having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing one or more heteroatoms selected from the group consisting of O, S, Si, P, and B. In this case, preferably, the heteroatom of the heteroarylene or heteroaryl may be one or more selected from the group consisting of O and S.

[0046] In the above Chemical Formula 1, L 1 and L 2 are each independently a single bond, phenylene which is unsubstituted or substituted with one or more deuterium atoms, or biphenylylene which is unsubstituted or substituted with one or more deuterium atoms; Ar 1is cyano; phenyl substituted or unsubstituted by one or more deuteriums; biphenylyl substituted or unsubstituted by one or more deuteriums; terphenylyl substituted or unsubstituted by one or more deuteriums; triphenylenyl substituted or unsubstituted by one or more deuteriums; benzofuranyl substituted or unsubstituted by one or more deuteriums; benzothiophenyl substituted or unsubstituted by one or more deuteriums; dibenzofuranyl substituted or unsubstituted by one or more deuteriums; or dibenzothiophenyl substituted or unsubstituted by one or more deuteriums; phenyl substituted or unsubstituted by one or more deuteriums; fluorophenyl substituted or unsubstituted by one or more deuteriums; cyanophenyl substituted or unsubstituted by one or more deuteriums; trimethylsilanophenyl substituted or unsubstituted by one or more deuteriums; dimethylphenyl substituted or unsubstituted by one or more deuteriums; substituted or unsubstituted t-butylphenyl; ethenylphenyl substituted or unsubstituted by one or more deuteriums; biphenylyl substituted or unsubstituted by one or more deuteriums; terphenylyl substituted or unsubstituted by one or more deuteriums; naphthyl substituted or unsubstituted by one or more deuteriums; 9,9-dimethylfluorenyl substituted or unsubstituted by one or more deuteriums; 9,9-diphenylfluorenyl substituted or unsubstituted by one or more deuteriums; triphenylenyl substituted or unsubstituted by one or more deuteriums; chrysenyl substituted or unsubstituted by one or more deuteriums; dibenzofuranyl substituted or unsubstituted by one or more deuteriums; phenyldibenzofuranyl substituted or unsubstituted by one or more deuteriums; dibenzothiophenyl substituted or unsubstituted by one or more deuteriums; or phenyldibenzothiophenyl substituted or unsubstituted by one or more deuteriums.

[0047] Representative examples of the compound represented by Formula 1 are as follows:

[0048] [ka]

[0049] [ka]

[0050]

change

[0051]

change

[0052]

change

[0053]

change

[0054]

change

[0055]

change

[0056]

change

[0057]

change

[0058]

change

[0059]

change

[0060]

change

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] The present invention also provides a method for preparing the compound represented by Formula 1.

[0068] For example, the compound represented by Chemical Formula 1 can be prepared according to the following Reaction Scheme 1: [ka]

[0069] In the above reaction scheme 1, the remainder except for X' are the same as defined above, and X' is a halogen, more preferably bromo or chloro.

[0070] The above reaction scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction can be varied as known in the art.

[0071] The above-mentioned production method can be more specifically embodied in the production examples described below.

[0072] The present invention also provides an organic light-emitting device comprising the compound represented by Chemical Formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound represented by Chemical Formula 1.

[0073] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0074] The organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1. In particular, the compound according to the present invention may be used as a host in the light-emitting layer.

[0075] The organic layer may include a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the compound represented by Chemical Formula 1.

[0076] The organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate. The organic light emitting device according to the present invention may be an organic light emitting device having 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 an organic light emitting device according to an embodiment of the present invention is shown in Figures 1 to 3.

[0077] 1 shows an example of an organic light-emitting device including a substrate 1, a positive electrode 2, an organic layer 3, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be contained in the organic layer.

[0078] 2 shows an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 7, an emitting layer 8, a hole inhibiting layer 9, an electron transport layer 10, an electron injection layer 11, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the electron inhibiting layer, the emitting layer, the hole inhibiting layer, the electron transport layer, and the electron injection layer, and is, for example, included in the emitting layer.

[0079] 3 shows an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 7, an emitting layer 8, a hole inhibiting layer 9, an electron injection and transport layer 12, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the electron inhibiting layer, the emitting layer, the hole inhibiting layer, and the electron injection and transport layer, for example, in the emitting layer.

[0080] The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0081] For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a cathode, and an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and a material that can be used as an anode may be deposited thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an anode material, an organic layer, and an anode material on a substrate.

[0082] In addition, the compound represented by Formula 1 can be used to form an organic layer by a solution coating method as well as a vacuum deposition method during the preparation of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0083] 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 (WO2003 / 012890), but the manufacturing method is not limited to this.

[0084] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0085] The cathode material is preferably a material having a large work function so that holes can be easily injected into the organic layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2Examples of the conductive polymers include, but are not limited to: a combination of a metal such as Sb and an oxide; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0086] The negative electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2 / Al and other multi-layered materials, but are not limited to these.

[0087] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the positive electrode, has an excellent hole injection effect for the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

[0088] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer, and the hole transport material is a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer, and has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

[0089] The electron blocking layer prevents electrons injected from the anode from being transferred to the cathode without being recombined in the light emitting layer, thereby improving the efficiency of the organic light emitting device.

[0090] The light-emitting material is preferably a material that can emit light in the visible light range by receiving and combining holes and electrons transported from the hole transport layer and electron transport layer, respectively, and has good quantum efficiency for fluorescence or phosphorescence. 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0091] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocycle-containing compound. Specifically, the fused aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocycle-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc. In particular, in the present invention, the compound represented by Chemical Formula 1 may be used as a host material for the light-emitting layer, and in this case, low voltage, high efficiency, and / or long life characteristics of the organic light-emitting device may be obtained.

[0092] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and peripluranthene, which have arylamino groups, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the dopant materials include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0093] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the negative electrode and transfer them to the light emitting layer and has high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Alq 3These include, but are not limited to, complexes containing; organic radical compounds; hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to conventional techniques. In particular, examples of suitable cathode materials are conventional materials having low work functions, followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.

[0094] The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that has the ability to transport electrons, has an excellent electron injection effect from a negative electrode, an excellent electron injection effect for the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and has excellent thin-film forming ability.Specific examples of the compound include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0095] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0096] According to an embodiment of the present invention, the electron transport material and the electron injection material may be simultaneously deposited to form a single layer of electron injection and transport layers.

[0097] The organic light emitting device according to the present invention may be of a front emission type, a back emission type or a dual emission type depending on the materials used.

[0098] In addition, the compound represented by Chemical Formula 1 can be used in organic solar cells or organic transistors in addition to organic light emitting devices.

[0099] The compound represented by Formula 1 and the preparation of an organic light-emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0100] [Production Example] Production Example 1: Production of Compound 1 [ka]

[0101] (Production Example 1-1) Production of Intermediate 1-1 In a nitrogen atmosphere, 1-bromo-7-chlorodibenzo[b,d]furan-2,3,4,6,8,9-d6 (50g, 173.9mmol) and phenylboronic acid (21.2g, 173.9mmol) were added to 300ml of THF and stirred and refluxed. Then, potassium carbonate (72.1g, 521.6mmol) was dissolved in 100ml of water and added, and after stirring thoroughly, tetrakistriphenyl-phosphinopalladium (6g, 5.2mmol) was added. After reacting for 2 hours, it was cooled at room temperature, and the organic layer and aqueous layer were separated, and the organic layer was distilled. This was again added to 500mL of chloroform and dissolved, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce intermediate 1-1 (25.7 g, 52%, MS: [M+H]+=285.8).

[0102] (Production Example 1-2) Production of Intermediate 1-2 In a nitrogen atmosphere, intermediate 1-1 (50g, 175.6mmol) and bis(pinacolato)diboron (45g, 193.1mmol) were added to 350ml of dioxane and stirred and refluxed. Then, potassium acetate (50.6g, 526.7mmol) was added and thoroughly stirred, and then palladium dibenzylideneacetone palladium (3g, 5.3mmol) and tricyclohexylphosphine (3g, 10.5mmol) were added. After reacting for 7 hours, the organic layer was cooled to room temperature, filtered to remove salt, and the filtered organic layer was distilled. This was again added to 450mL of chloroform and dissolved, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce intermediate 1-2 (56.8 g, 86%, MS: [M+H]+=377.3).

[0103] (Production Example 1-3) Production of Compound 1 In a nitrogen atmosphere, intermediate 1-2 (30g, 79.7mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (27.4g, 79.7mmol) were added to 600ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (33.1g, 239.2mmol) was dissolved in 33ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (2.8g, 2.4mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1500mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce compound 1 (22.2 g, 50%, MS: [M+H]+=558.7).

[0104] Production Example 2: Production of Compound 2 [ka] Compound 1-2 (25.3 g, 57%, MS: [M+H]+=558.7) was prepared in the same manner as compound 1, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0105] Production Example 3: Production of Compound 3 [ka] Compound 3 (26.3 g, 52%, MS: [M+H]+=634.8) was prepared in the same manner as compound 1, except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0106] Production Example 4: Production of Compound 4 [ka] Compound 4 (28.1 g, 64%, MS: [M+H]+=674.9) was prepared in the same manner as compound 1, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0107] Production Example 5: Production of Compound 5 [ka] Compound 5 (32.1 g, 67%, MS: [M+H]+=572.7) was prepared in the same manner as compound 1, except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0108] Production Example 6: Production of Compound 6 [ka] Compound 6 (27.4 g, 62%, MS: [M+H]+=664.8) was prepared in the same manner as compound 1, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]thiophen-1-yl)-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0109] Preparation Example 7: Preparation of Compound 7 [ka]

[0110] (Production Example 7-1) Production of Intermediate 7-1 Intermediate 7-1 (45.2 g, 72%, MS: [M+H]+=361.9) was prepared in the same manner as in intermediate 1-1, except that [1,1'-biphenyl]-4-ylboronic acid was used instead of phenylboronic acid.

[0111] (Production Example 7-2) Production of Intermediate 7-2 Intermediate 7-2 (55 g, 88%, MS: [M+H]+=452.4) was prepared in the same manner as in the preparation of Intermediate 1-2.

[0112] (Production Example 7-3) Production of Compound 7 Compound 7 (21.8 g, 59%, MS: [M+H]+=558.7) was prepared in the same manner as compound 1, except that intermediate 7-2 was used instead of intermediate 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0113] Production Example 8: Production of Compound 8 [ka] Compound 8 (38.7 g, 70%, MS: [M+H]+=634.8) was prepared in the same manner as compound 7, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0114] Preparation Example 9: Preparation of Compound 9 [ka] Compound 9 (27.4 g, 54%, MS: [M+H]+=710.9) was prepared in the same manner as compound 7, except that 2-([1,1':3',1''-terphenyl]-4'-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0115] Preparation Example 10: Preparation of Compound 10 [ka]

[0116] (Production Example 10-1) Production of Intermediate 10-1 Intermediate 10-1 (45.2 g, 72%, MS: [M+H]+=361.9) was prepared in the same manner as in the preparation of intermediate 7-1, except that [1,1'-biphenyl]-3-ylboronic acid was used instead of [1,1'-biphenyl]-4-ylboronic acid.

[0117] (Production Example 10-2) Production of Intermediate 10-2 Intermediate 10-2 (45.7 g, 73%, MS: [M+H]+=452.4) was produced by carrying out the synthesis in a similar manner to the production method of intermediate 7-2.

[0118] (Production Example 10-3) Production of Compound 10 Compound 10 (21.4 g, 51%, MS: [M+H]+ = 634.8) was prepared in the same manner as compound 7, except that intermediate 10-2 was used instead of intermediate 7-2 and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0119] Preparation Example 11: Preparation of Compound 11 [ka] Compound 11 (33.5 g, 67%, MS: [M+H]+=724.9) was prepared in the same manner as compound 7, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0120] Preparation Example 12: Preparation of Compound 12 [ka] Compound 12 (31.1 g, 63%, MS: [M+H]+=740.9) was prepared in the same manner as compound 10, except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(dibenzo[b,d]thiophen-4-yl)-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0121] Preparation Example 13: Preparation of Compound 13 [ka]

[0122] (Production Example 13-1) Production of Intermediate 13-1 Intermediate 13-1 (34.7 g, 54%, MS: [M+H]+=370.9) was prepared in the same manner as in the preparation of intermediate 7-1, except that ([1,1'-biphenyl]-4-yl-d9)boronic acid was used instead of [1,1'-biphenyl]-4-ylboronic acid.

[0123] (Production Example 13-2) Production of Intermediate 13-2 Intermediate 13-2 (53 g, 85%, MS: [M+H]+=462.4) was prepared by carrying out the synthesis in a similar manner to the preparation of intermediate 7-2.

[0124] (Production Example 13-3) Production of Compound 13 Compound 13 (24.5 g, 67%, MS: [M+H]+=567.7) was prepared in the same manner as compound 7, except that intermediate 13-2 was used instead of intermediate 7-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0125] Preparation Example 14: Preparation of Compound 14 [ka]

[0126] (Production Example 14-1) Production of Intermediate 14-1 Intermediate 14-1 (37.9 g, 59%, MS: [M+H]+=370.9) was prepared in the same manner as in the preparation of intermediate 7-1, except that ([1,1'-biphenyl]-3-yl-d9)boronic acid was used instead of [1,1'-biphenyl]-4-ylboronic acid.

[0127] (Production Example 14-2) Production of Intermediate 14-2 Intermediate 14-2 (54.9 g, 88%, MS: [M+H]+=462.4) was prepared by carrying out the synthesis in a similar manner to the preparation of intermediate 7-2.

[0128] (Production Example 14-3) Production of Compound 14 Compound 14 (32.3 g, 68%, MS: [M+H]+=733.9) was prepared in the same manner as compound 7, except that intermediate 14-2 was used instead of intermediate 7-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0129] Preparation Example 15: Preparation of Compound 15 [ka]

[0130] (Production Example 15-1) Production of Intermediate 15-1 Intermediate 15-1 (52.4 g, 69%, MS: [M+H]+=438) was prepared in the same manner as in the preparation of intermediate 7-1, except that [1,1':3',1''-terphenyl]-5'-ylboronic acid was used instead of [1,1'-biphenyl]-4-ylboronic acid.

[0131] (Production Example 15-2) Production of Intermediate 15-2 Intermediate 15-2 (52 g, 86%, MS: [M+H]+=529.5) was prepared by carrying out the synthesis in a similar manner to the preparation of intermediate 7-2.

[0132] (Production Example 15-3) Production of Compound 15 Compound 15 (29.1 g, 62%, MS: [M+H]+ = 827) was prepared in the same manner as in the preparation of compound 7, except that intermediate 15-2 was used instead of intermediate 7-2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0133] Preparation Example 16: Preparation of Compound 16 [ka]

[0134] (Production Example 16-1) Production of Intermediate 16-1 Intermediate 16-1 (31.7 g, 64%, MS: [M + H] + = 301.8) was prepared in the same manner as intermediate 1-1, except that 1-bromo-7-chlorodibenzo [b, d] furan-2, 3, 4, 6, 8, 9-d6 and phenylboronic acid were used instead of 1-bromo-7-chlorodibenzo [b, d] furan-2, 3, 4, 6, 8, 9-d6 and [1, 1'-biphenyl] -4-ylboronic acid.

[0135] (Production Example 16-2) Production of Intermediate 16-2 Intermediate 16-2 (57.4 g, 88%, MS: [M+H]+=393.4) ​​was produced by carrying out the synthesis in a similar manner to the production method of intermediate 1-2.

[0136] (Production Example 16-3) Production of Compound 16 Compound 16 (24.1 g, 55%, MS: [M+H]+=574.8) was prepared in the same manner as in the preparation of compound 1, except that intermediate 16-2 was used instead of intermediate 1-2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0137] Preparation Example 17: Preparation of Compound 17 [ka] Compound 17 (34.8 g, 66%, MS: [M+H]+=690.9) was prepared in the same manner as compound 16, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0138] Preparation Example 18: Preparation of Compound 18 [ka]

[0139] (Production Example 18-1) Production of Intermediate 18-1 Intermediate 18-1 (44.1 g, 71%, MS: [M+H]+=377.9) was prepared in the same manner as in the preparation of intermediate 16-1, except that [1,1'-biphenyl]-4-ylboronic acid was used instead of phenylboronic acid.

[0140] (Production Example 18-2) Production of Intermediate 18-2 Intermediate 18-2 (43.5 g, 70%, MS: [M+H]+=469.2) was prepared by carrying out the synthesis in a similar manner to the preparation of intermediate 16-2.

[0141] (Production Example 18-3) Production of Compound 18 Compound 18 (19.5 g, 53%, MS: [M+H]+ = 574.8) was prepared in the same manner as compound 16, except that intermediate 18-2 was used instead of intermediate 16-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0142] Preparation Example 19: Preparation of Compound 19 [ka]

[0143] (Production Example 19-1) Production of Intermediate 19-1 Intermediate 19-1 (34.5 g, 53%, MS: [M + H] + = 375.9) was prepared in the same manner as in the preparation of intermediate 7-1, except that dibenzo [b, d] furan-1-ylboronic acid was used instead of [1, 1'-biphenyl] -4-ylboronic acid.

[0144] (Production Example 19-2) Production of Intermediate 19-2 The synthesis was carried out in a similar manner to the preparation of intermediate 7-2 to prepare intermediate 19-2 (46 g, 74%, MS: [M+H]+=467.4).

[0145] (Production Example 19-3) Production of Compound 19 Compound 19 (27.9 g, 67%, MS: [M+H]+ = 648.8) was prepared in the same manner as in the preparation of compound 7, except that intermediate 19-2 was used instead of intermediate 7-2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0146] Preparation Example 20: Preparation of Compound 20 [ka]

[0147] (Production Example 20-1) Production of Intermediate 20-1 Intermediate 20-1 (36.7 g, 54%, MS: [M + H] + = 391.9) was prepared in the same manner as in the preparation of intermediate 7-1, except that dibenzo [b, d] thiophen-2-ylboronic acid was used instead of [1, 1'-biphenyl] -4-ylboronic acid.

[0148] (Production Example 20-2) Production of Intermediate 20-2 Intermediate 20-2 (51.5 g, 80%, MS: [M+H]+=483.4) was prepared by carrying out the synthesis in a similar manner to the preparation of Intermediate 7-2.

[0149] (Production Example 20-3) Production of Compound 20 Compound 20 (32.8 g, 70%, MS: [M+H]+ = 754.9) was prepared in the same manner as in the preparation of compound 7, except that intermediate 20-2 was used instead of intermediate 7-2 and 2-chloro-4-phenyl-6-(1-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. EXAMPLES

[0150] Example 1 A glass substrate coated with a 100 nm-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned by placing it in distilled water with detergent dissolved in it. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was washed for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaning device. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition device.

[0151] On the thus prepared ITO transparent electrode, the following compound HI-A was thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer.

[0152] The following compound HAT was vacuum-deposited on the hole injection layer to form a first hole transport layer with a thickness of 5 nm, and the following compound HT-A was vacuum-deposited on the first hole transport layer to form a second hole transport layer with a thickness of 50 nm.

[0153] On the hole transport layer, the following compound HT-B was thermally vacuum deposited to a thickness of 45 nm to form an electron inhibiting layer.

[0154] On the electron inhibiting layer, the compound 1 prepared above and the following compound GD were vacuum-deposited in a weight ratio of 85:15 to a thickness of 40 nm to form a light-emitting layer.

[0155] On the light-emitting layer, the following compound ET-A was vacuum-deposited to a thickness of 5 nm to form a hole-blocking layer.

[0156] On the hole blocking layer, the following compound ET-B and the following compound LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injecting and transporting layer having a thickness of 35 nm.

[0157] Lithium fluoride (LiF) was deposited on the electron injecting and transporting layer to a thickness of 1 nm, and then aluminum was deposited to a thickness of 100 nm to form a negative electrode, thereby preparing an organic light emitting device.

[0158] During the above process, the deposition rate of the organic material was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The degree of vacuum during deposition was 1×10 -7 torr~5×10 -5 torr was maintained.

[0159] [ka]

[0160] Examples 2 to 25 and Comparative Examples 1 to 5 An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1.

[0161] For reference, in Examples 21 to 25 and Comparative Examples 4 to 5, the compounds shown in Table 1 below were used in a weight ratio of 1:1 instead of Compound 1-1 to manufacture organic light-emitting devices. For example, Example 21 is the same as Example 1 in which Compound 1 and Compound H-2 were used in a weight ratio of 1:1 instead of Compound 1-1. In Table 1 below, Compounds H-2, C1 to C3 are as follows, respectively.

[0162] [ka]

[0163] Experimental Example Each organic light-emitting device manufactured in the above examples and comparative examples was subjected to a current of 10 mA / cm 2 The voltage, efficiency, and luminescent color when a current was applied were measured, and the results are shown in Table 1. In addition, in order to confirm the life characteristics, a current of 20 mA / cm was applied to each of the organic light-emitting devices. 2When a current of 1000 nits was applied, the time it took for the luminance to decrease to 95% from the initial luminance (1600 nits) (T95, hr) was measured.

[0164] [Table 1]

[0165] In Table 1, Examples 1 to 20 and Comparative Examples 1 to 3 are examples of organic light-emitting devices using a single host in the light-emitting layer, and Examples 21 to 25 and Comparative Examples 4 and 5 are examples of devices using two types of hosts in the light-emitting layer.

[0166] Referring to Table 1, it can be seen that the organic light emitting device according to the embodiment using the compound of Chemical Formula 1 of the present invention has higher efficiency, lower driving voltage, and especially improved life characteristics, compared to the organic light emitting device according to the comparative example, not only when one type of host is used in the light emitting layer, but also when two types of hosts are used.

[0167] From the above results, it can be seen that when the compound of Formula 1 is used as a host for an organic light emitting device, the device exhibits low voltage, high efficiency, and long life characteristics. [Explanation of symbols]

[0168] 1 Board 2 Positive electrode 3 Organic layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7 Electron suppression layer 8. Light-emitting layer 9 Hole Blocking Layer 10 Electron transport layer 11 Electron injection layer 12 Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, n is an integer from 4 to 6, X is O or S; L １ and L ２ each independently represents a single bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B, Ar １ is cyano; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B, Ar ２ and Ar ３ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of O, S, Si, P, and B.

2. L １ and L ２ is each independently a single bond; phenylene which is unsubstituted or substituted with one or more deuterium atoms; or biphenylylene which is unsubstituted or substituted with one or more deuterium atoms.

3. Ar １ is cyano; phenyl; biphenylyl; terphenylyl; triphenylenyl; benzofuranyl; benzothiophenyl; dibenzofuranyl; or dibenzothiophenyl, The Ar １ The compound of claim 1 , wherein is unsubstituted or substituted with one or more deuterium atoms.

4. Ar ２ and Ar ３ are each independently phenyl; phenyl substituted with one or more substituents selected from the group consisting of halogen, cyano, trimethylsilyl, alkyl having 1 to 4 carbon atoms, and alkenyl having 1 to 4 carbon atoms; biphenylyl; terphenylyl; naphthyl; 9,9-dimethylfluorenyl; 9,9-diphenylfluorenyl; triphenylenyl; chrysenyl; dibenzofuranyl; phenyldibenzofuranyl; dibenzothiophenyl; or phenyldibenzothiophenyl; Ar ２ and Ar ３ is independently substituted or unsubstituted with one or more deuterium atoms.

5. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 。

6. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6 , wherein the organic layer containing the compound is a light-emitting layer.

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