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. 10-2021-0023634 filed on February 22, 2021 and Korean Patent Application No. 10-2022-0022275 filed on February 21, 2022, and all contents disclosed in the documents of said Korean patent applications 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] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, and therefore many researches are being conducted on these devices.

[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. In such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons come into contact with each other, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[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 provides a novel compound and an organic light-emitting device including the compound. [Means for solving the problem]

[0008] The present invention provides a compound represented by the following formula 1: [Chemical formula 1] [ka] In the above Chemical Formula 1, L is a single bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms and containing one or more heteroatoms selected from N, O, and S; L1 and L2 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Ar1 and Ar2 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 one or more heteroatoms selected from N, O, and S; L' is a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Q is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; R is deuterium; or phenyl substituted with deuterium; n is an integer from 1 to 8.

[0009] The present invention also provides an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers contains a compound represented by Chemical Formula 1. Effect of the Invention

[0010] 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, lower the driving voltage, and / or improve the life characteristics of the organic light emitting device. [Brief description of the drawings]

[0011] [Figure 1] FIG. 1 is a diagram showing an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Diagram 2] 1 is a diagram showing an example of an organic light-emitting element 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 3, an electron transport layer 8, an electron injection layer 9 and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will now be described in more detail to aid in understanding the invention.

[0013] (Definition of terms) In this specification, [ka] and [ka] denotes a bond that is connected to another substituent.

[0014] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, or heteroaryl containing one or more of N, O, and S atoms, or that the group is substituted or unsubstituted with two or more of the above-listed substituents. For example, the "substituent with two or more substituents connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent with two phenyl groups connected. As one example, the term "substituted or unsubstituted" may be interpreted as meaning "unsubstituted or substituted with one or more, for example, 1 to 5, substituents selected from the group consisting of deuterium, halogen, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms." Furthermore, in this specification, the term "substituted with one or more substituents" may be interpreted as meaning, for example, "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents."

[0015] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferably 1 to 40. Specifically, the carbonyl group may have a structure as shown below, but is not limited thereto. [ka]

[0016] In this specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto. [ka]

[0017] 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 substituent having the following structure, but is not limited thereto. [ka]

[0018] In this specification, specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group, but are not limited to these.

[0019] In this specification, specific examples of the boron group include a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group, but are not limited to these.

[0020] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0021] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, 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, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-methylpentyl, 4-methyl-2-pentyl, 5,6-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 1,5-dimethylbutyl, 1,6-dimethylbutyl, 1,7-dimethylbutyl, 1,8-dimethylbutyl, 1,9-dimethylbutyl, 1,9-dimethylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl ...5-dimethylbutyl, 1,6-dimethylbutyl, 1,7-dimethylbutyl, 1,8-dimethylbutyl, 1,9-dimethylbutyl, 1,9-dimethylbutyl, 1,9-dimethylbutyl, 1,1-dimethylpropyl, 1, Examples of aryl groups include, but are not limited to, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, and 2,2-dimethylheptyl.

[0022] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited thereto.

[0023] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl, but are not limited thereto.

[0024] 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 having aromaticity. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, etc.

[0025] In this specification, heteroaryl refers to heteroaryl containing one or more of O, N, Si and S as a hetero element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of heteroaryl include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

[0026] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group. In this specification, the above-mentioned explanation regarding the heteroaryl is applicable to the heteroaryl in the heteroarylamine. In this specification, the above-mentioned explanation regarding the alkenyl group is applicable to the alkenyl group in the aralkenyl group. In this specification, the above-mentioned explanation regarding the aryl group is applicable to the arylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the heteroaryl is applicable to the heteroarylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the aryl group or the cycloalkyl group is applicable to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the above-mentioned explanation regarding the heteroaryl is applicable to the heterocycle, except that it is not a monovalent group but is formed by bonding two substituents.

[0027] (compound) Meanwhile, the present invention provides a compound represented by Formula 1.

[0028] Specifically, the compound represented by Chemical Formula 1 has a structure in which the benzene ring is substituted with carbazol-9-yl at position 1, triazinyl at position 3, and aryl at position 5. The compound may also have a structure in which the carbon at position 8 of the dibenzofuran / dibenzothiophene is unsubstituted or substituted with an aryl substituted with deuterium.

[0029] In particular, the compound has a structure in which the carbazol-9-yl substituent is substituted with one or more deuterium or deuterium-substituted phenyl, and the 2nd, 4th, and 6th carbons of the benzene ring are not substituted with deuterium, and such a compound may have increased intramolecular electronic stability compared to a compound that does not have deuterium in the molecule and a compound in which at least one of the 2nd, 4th, and 6th carbons of the benzene ring is substituted with deuterium. In addition, since the compound has a carbazol-9-yl structure substituted with deuterium or deuterium-substituted phenyl, the bond energy of the CD bond is greater than that of the C-H bond, and therefore the compound has stronger intramolecular bond energy compared to a compound that does not have deuterium, thereby improving material stability.

[0030] Therefore, the organic light emitting device using the compound not only exhibits a low driving voltage but also has improved life characteristics.

[0031] In one embodiment, L can be a single bond; an arylene having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or a heteroarylene having 2 to 20 carbon atoms which is unsubstituted or substituted with deuterium and contains one of the heteroatoms O and S.

[0032] Specifically, L can be a single bond, phenylene, biphenyldiyl, naphthylene, or dibenzofuranylene, dibenzothiophenylene.

[0033] For example, L is a single bond or any one selected from the group consisting of: [ka]

[0034] In one embodiment, L1 and L2 can each independently be a single bond, or an unsubstituted or deuterium-substituted arylene having 6 to 20 carbon atoms.

[0035] Specifically, L1 and L2 may each independently be a single bond or phenylene. In other words, L1 and L2 may each independently be a single bond, 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0036] For example, L1 and L2 are all single bonds; or One of L1 and L2 is a single bond, and the remaining one can be 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0037] In this case, L1 and L2 may be the same as each other, or L1 and L2 may be different.

[0038] In one embodiment, Ar1 and Ar2 are each independently an aryl having 6 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms; or a heteroaryl having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms and contains one or more heteroatoms selected from N, O, and S.

[0039] Specifically, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;

[0040] wherein Ar1 and Ar2 can be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl and phenyl.

[0041] Specifically, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;

[0042] wherein Ar1 and Ar2 can be unsubstituted or substituted with 1 to 5 substituents selected from the group consisting of deuterium, methyl and phenyl.

[0043] More specifically, Ar1 and Ar2 can each independently be phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl.

[0044] For example, Ar1 and Ar2 can each independently be any one selected from the group consisting of, but not limited to, the following: [ka]

[0045] In this case, Ar1 and Ar2 may be the same as each other, or Ar1 and Ar2 may be different.

[0046] In one embodiment, at least one of Ar1 and Ar2 may be an unsubstituted or deuterium-substituted aryl having 6 to 12 carbon atoms.

[0047] For example, at least one of Ar1 and Ar2 is [ka] , [ka] , [ka] or [ka] It could be.

[0048] In one embodiment, when L is not a single bond, Ar1 and Ar2 can all be phenyl.

[0049] More specifically, L is a single bond and Ar1 and Ar2 are each independently phenyl, phenyl substituted with five deuteriums, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl; or

[0050] L may be an arylene having 6 to 20 carbon atoms or a heteroarylene having 2 to 20 carbon atoms containing one heteroatom selected from O and S, and Ar1 and Ar2 may all be phenyl.

[0051] In one embodiment, L' may be a single bond or an unsubstituted or deuterium-substituted arylene having 6 to 20 carbon atoms.

[0052] Specifically, L' can be a single bond or phenylene. In other words, L' can be a single bond, 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0053] In one embodiment, Q may be unsubstituted or aryl having 6 to 24 carbon atoms substituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms.

[0054] Specifically, Q is phenyl, biphenylyl, naphthyl, phenanthryl, triphenylenyl, benzophenanthryl, or 9,9-dimethylfluorenyl;

[0055] Here, Q can be unsubstituted or substituted with deuterium.

[0056] Alternatively, where Q is unsubstituted or substituted with one or more deuterium atoms, more specifically, Q is unsubstituted or all carbons in the molecule are substituted with deuterium.

[0057] For example, Q can be any one selected from the group consisting of, but not limited to, the following: [ka]

[0058] Also, in one embodiment, R can be deuterium or phenyl substituted with 1 to 5 deuterium.

[0059] For example, R is deuterium, or [ka] It could be.

[0060] In this case, n means the number of R, and when n is 2 or more, two or more R are the same or different from each other. For example, n can be 1, 2, 3, 4, 5, 6, 7, or 8.

[0061] In addition, [ka] can be any one selected from the group consisting of: [ka]

[0062] The compound is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] In the above Chemical Formulas 1-1 to 1-3, D is deuterium, m is 1, 2, 3, 4, 5 or 7; L, L1, L2, Ar1, Ar2, L' and Q are as defined in Chemical Formula 1 above.

[0063] Meanwhile, representative examples of the compound represented by Chemical Formula 1 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0064] Meanwhile, the compound represented by Chemical Formula 1 can be prepared, for example, by the following reaction scheme 1: [Reaction Scheme 1] [ka]

[0065] In the above reaction scheme 1, X is a halogen, preferably bromine or chlorine, and the remaining substituents are as defined above.

[0066] Specifically, the compound represented by the formula 1 can be prepared by Suzuki-coupling reaction of reactants A1 and A2. At this time, the Suzuki-coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the reaction can be changed according to those known in the art. The preparation method is further embodied in the preparation examples described below.

[0067] (Organic light-emitting device) Meanwhile, the present invention provides an organic light emitting device including a compound represented by Chemical Formula 1. As an example, the present invention provides an organic light emitting device including a first electrode, a second electrode facing the first electrode, and one or more organic material layers between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1.

[0068] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0069] In one embodiment, the organic layer may include a light-emitting layer, and in this case, the organic layer including the compound may be the light-emitting layer.

[0070] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer, and in this case, the organic layer including the compound may be an emitting layer or an electron transport layer.

[0071] In yet another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, an electron transport layer, and an electron injection layer, and in this case, the organic layer including the compound may be an emitting layer or an electron transport layer.

[0072] In yet another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and in this case, the organic layer including the compound may be an emitting layer or an electron transport layer.

[0073] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including, in addition to the light-emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited thereto, and may include fewer or more organic layers.

[0074] In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate, with the first electrode being a positive electrode and the second electrode being a negative electrode. In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (inverted type) in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate, with the first electrode being a negative electrode and the second electrode being a positive electrode. For example, the structure of an organic light emitting device according to an embodiment of the present invention is shown in FIG. 1 and FIG. 2.

[0075] 1 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer.

[0076] 2 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, an emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be contained in the emitting layer.

[0077] 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.

[0078] 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, an emission layer, and an electron transport layer may be formed thereon, and a material 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.

[0079] In addition, the compound represented by Formula 1 may be formed in 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.

[0080] 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). However, the manufacturing method is not limited to this.

[0081] 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.

[0082] The positive electrode material is preferably a material having a large work function so that holes can be easily injected into the organic layer. Specific examples of the positive electrode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SNO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0083] The negative electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0084] In addition, the hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect from the positive electrode, has an excellent hole injection effect on the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. 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 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.

[0085] The hole transport layer receives holes from the hole injection layer and transports them to the light emitting layer, and the hole transport material is preferably 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. The hole transport material may be, but is not limited to, an arylamine-based organic material, a conductive polymer, or a block copolymer having both a conjugated portion and a non-conjugated portion.

[0086] The electron blocking layer is formed on the hole transport layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by controlling hole mobility and preventing excessive movement of electrons to increase the probability of hole-electron binding. The electron blocking layer includes an electron blocking material, and examples of the electron blocking material include, but are not limited to, arylamine-based organic materials.

[0087] The light-emitting layer may include a host material and a dopant material. The dopant material may be a compound represented by Chemical Formula 1. The host material may further include a fused aromatic ring derivative or a heterocyclic ring-containing compound in addition to the compound represented by Chemical Formula 1. 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 heterocyclic ring-containing compound may be a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc., but is not limited thereto.

[0088] In one embodiment, the light emitting layer may further include a compound represented by the following Chemical Formula 2 in addition to the compound represented by Chemical Formula 1: [Chemical formula 2] [ka] In the above Chemical Formula 2, Ar'1 and Ar'2 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 one or more heteroatoms selected from N, O and S; R'1 and R'2 are each independently hydrogen; deuterium; alkyl having 1 to 60 carbon atoms; aryl having 6 to 60 carbon atoms; or heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from N, O, and S; Each of r and s independently represents an integer of 0 to 7. When the organic light emitting device further includes the compound represented by Chemical Formula 2, which can efficiently transfer holes to a dopant material as a host material in the light emitting layer, together with the compound represented by Chemical Formula 1, which has excellent electron transport ability, the recombination probability of holes and electrons in the light emitting layer is increased, thereby improving the efficiency and lifespan of the organic light emitting device.

[0089] According to one embodiment, the compound represented by Formula 2 is represented by the following Formula 2': [Chemical formula 2'] [ka] In the above Chemical Formula 2', Ar'1, Ar'2, R'1, R'2, r and s are as defined in Chemical Formula 2 above.

[0090] In addition, in the above Chemical Formula 2, Ar'1 and Ar'2 are each independently an aryl having 6 to 20 carbon atoms, or a heteroaryl having 2 to 20 carbon atoms containing one heteroatom selected from N, O, and S; Here, Ar'1 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl having 6 to 20 carbon atoms.

[0091] For example, Ar'1 and Ar'2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl; Here, Ar'1 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl having 6 to 20 carbon atoms.

[0092] In this case, at least one of Ar'1 and Ar'2 can be phenyl or biphenylyl.

[0093] In addition, in the above Chemical Formula 2, R'1 and R'2 may each independently be hydrogen, deuterium, or an aryl having 6 to 20 carbon atoms.

[0094] For example, R'1 and R'2 can each independently be, but are not limited to, hydrogen, deuterium, or phenyl.

[0095] Furthermore, r and s, which indicate the numbers of R'1 and R'2, respectively, are each independently 0, 1, 2, 3, 4, 5, 6, or 7.

[0096] More specifically, r and s are each independently 0, 1 or 7.

[0097] For example, r+s is 0 or 1.

[0098] Representative examples of the compound represented by Chemical Formula 2 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0099] The two host materials, the compound represented by Formula 1 and the compound represented by Formula 2, are contained in the light emitting layer in a weight ratio of 10:90 to 90:10, for example, a weight ratio of 50:50.

[0100] In addition, the dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the dopant material includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0101] The hole blocking layer is formed on the light emitting layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by controlling the electron mobility, preventing excessive movement of holes, and increasing the probability of hole-electron binding. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include compounds having an electron withdrawing group introduced therein, such as azine derivatives including triazine, triazole derivatives, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives, but are not limited thereto.

[0102] The electron transport layer is a layer that transports electrons received from the electron injection layer to the light emitting layer, and is formed on the light emitting layer or the hole blocking layer. The electron transport layer includes an electron transport material, and the electron transport material is preferably a material with high mobility for electrons. Specific examples of the electron transport material include, but are not limited to, 8-hydroxyquinoline Al complex; complex containing Alq3; organic radical compound; hydroxyflavone-metal complex; triazine derivative; and the like. Alternatively, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives can be used together with the electron transport material.

[0103] The electron injection layer, which serves to inject electrons from the electrode, is formed on the electron transport layer. Examples of the electron injection material contained in the electron injection layer include, but are not limited to, LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0104] Here, 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-hydroxyquinolinato) chlorogallium, bis(2-methyl-8-hydroxyquinolinato) (o-cresolate) gallium, bis(2-methyl-8-hydroxyquinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-hydroxyquinolinato) (2-naphtholato) gallium.

[0105] The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a dual emission device, and in particular may be a bottom emission device which is required to have a relatively high light emitting efficiency.

[0106] In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

[0107] Hereinafter, the compound represented by Formula 1 and the preparation of an organic light-emitting device including the same will be described in detail with reference to examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto.

[0108] Preparation Example 1: Preparation of Compound A-3 1) Preparation of Compound A-1 [ka]

[0109] Bromobenzene (100g, 641.2mmol) and (3-chloro-5-fluorophenyl)boronic acid (111.6g, 641.2mmol) were added to 2000mL of tetrahydrofuran under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (265.9g, 1923.6mmol) was dissolved in 266mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (22.2g, 19.2mmol) was added. After reacting for 1 hour, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 2642mL of chloroform and dissolved, washed twice with water, and then 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 with chloroform and ethyl acetate to obtain a gray solid compound A-1 (80.6g, 61%, MS: [M+H] + =207) was manufactured.

[0110] 2) Preparation of Compound A-2 [ka]

[0111] Under a nitrogen atmosphere, A-1 (100 g, 485.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (84 g, 485.4 mmol) were added to 2000 mL of xylene and stirred and refluxed. Then, sodium tert-butoxide (140 g, 1456.1 mmol) was added and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium (7.4 g, 14.6 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 5229 mL of chloroform and 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 purified using chloroform and ethyl acetate on a silica column to obtain white solid compound A-2 (111.6 g, 64%, MS: [M+H] + =360.1) was produced.

[0112] 3) Preparation of Compound A-3 [ka]

[0113] A-2 (50 g, 139.2 mmol) and bis(pinacolato)diboron (38.9 g, 153.1 mmol) were added to 1,4-dioxane in 1000 mL under nitrogen atmosphere and stirred and refluxed. Then, potassium acetate (40.1 g, 417.7 mmol) was added and thoroughly stirred, and dibenzylideneacetonepalladium (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 628 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethanol to obtain a gray solid compound A-3 (51.5 g, 82%, MS: [M+H] + =452.3) was produced.

[0114] Preparation Example 2: Preparation of Compound B-3 1) Preparation of Compound B-1 [ka]

[0115] Under a nitrogen atmosphere, 1-bromobenzene-2,3,4,5,6-d5 (100g, 621.2mmol) and (3-chloro-5-fluorophenyl)boronic acid (108.1g, 621.2mmol) were added to 2000mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (257.6g, 1863.5mmol) was dissolved in 258mL of water and added, stirred thoroughly, and then tetrakistriphenyl-phosphinopalladium (21.5g, 18.6mmol) was added. After reacting for 1 hour, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 2622mL of chloroform and dissolved, washed twice with water, separated the organic layer, added anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a gray solid compound B-1 (80 g, 61%, MS: [M+H] + =212.1) was produced.

[0116] 2) Preparation of Compound B-2 [ka]

[0117] Under a nitrogen atmosphere, B-1 (100 g, 473.8 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (82 g, 473.8 mmol) were added to 2000 mL of xylene and stirred and refluxed. Then, sodium tert-butoxide (136.6 g, 1421.4 mmol) was added and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium (7.3 g, 14.2 mmol) 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 5176 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica column with chloroform and ethyl acetate to obtain white solid compound B-2 (103.5 g, 60%, MS: [M+H] + =365.2) was produced.

[0118] 3) Preparation of Compound B-3 [ka]

[0119] B-2 (50 g, 137.3 mmol) and bis(pinacolato)diboron (38.4 g, 151 mmol) were added to 1,4-dioxane in a nitrogen atmosphere and stirred and refluxed. Then, potassium acetate (39.6 g, 411.9 mmol) was added and thoroughly stirred, and dibenzylideneacetonepalladium (2.4 g, 4.1 mmol) and tricyclohexylphosphine (2.3 g, 8.2 mmol) were added. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 626 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethanol to obtain a gray solid compound B-3 (32 g, 51%, MS: [M+H] + =457.3) was produced.

[0120] Preparation Example 3: Preparation of Compound C-3 1) Preparation of Compound C-2 [ka]

[0121] Under a nitrogen atmosphere, B-1 (100 g, 473.8 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (83 g, 473.8 mmol) were added to 2000 mL of xylene and stirred and refluxed. Then, sodium tert-butoxide (136.6 g, 1421.4 mmol) was added and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium (7.3 g, 14.2 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 5205 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica column with chloroform and ethyl acetate to obtain white solid compound C-2 (131.9 g, 76%, MS: [M+H] + =367.2) was produced.

[0122] 2) Preparation of Compound C-3 [ka]

[0123] Under a nitrogen atmosphere, C-2 (50 g, 137.3 mmol) and bis(pinacolato)diboron (38.4 g, 151 mmol) were added to 1,4-dioxane in 1000 mL and stirred and refluxed. Then, potassium acetate (39.6 g, 411.9 mmol) was added and thoroughly stirred, and dibenzylideneacetonepalladium (2.4 g, 4.1 mmol) and tricyclohexylphosphine (2.3 g, 8.2 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 626 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethanol to obtain a gray solid compound C-3 (48.9 g, 78%, MS: [M+H] + =457.3) was produced.

[0124] Production Example 4: Production of Compound D-3 1) Preparation of Compound D-1 [ka]

[0125] Under a nitrogen atmosphere, 2-chloro-4,6-diphenyl-1,3,5-triazine (100 g, 200.3 mmol) and (3-chloro-5-fluorophenyl)boronic acid (68.7 g, 200.3 mmol) were added to 2000 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (83.1 g, 601 mmol) was dissolved in 83 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (6.9 g, 6 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 1447 mL 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 with chloroform and ethyl acetate to obtain a gray solid compound D-1 (41.2 g, 57%, MS: [M+H] + =362.1) was produced.

[0126] 2) Preparation of Compound D-2 [ka]

[0127] Under a nitrogen atmosphere, D-1 (30 g, 83.1 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.4 g, 83.1 mmol) were added to 600 mL of dimethylformamide and stirred and refluxed. Then, tripotassium phosphate (52.9 g, 249.3 mmol) was added and thoroughly stirred, and after reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 427 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica column with chloroform and ethyl acetate to obtain yellow solid compound D-2 (25.6 g, 60%, MS: [M+H] + =515.2) was produced.

[0128] 3) Preparation of Compound D-3 [ka]

[0129] Under a nitrogen atmosphere, D-2 (50 g, 97.2 mmol) and bis(pinacolato)diboron (27.2 g, 107 mmol) were added to 1,4-dioxane in 1000 mL and stirred and refluxed. Then, potassium acetate (28 g, 291.7 mmol) was added and thoroughly stirred, and dibenzylideneacetonepalladium (1.7 g, 2.9 mmol) and tricyclohexylphosphine (1.6 g, 5.8 mmol) were added. After reacting for 7 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 590 mL of chloroform and dissolved, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethanol to obtain a gray solid compound D-3 (35.4 g, 60%, MS: [M+H] + =607.3) was produced.

[0130] Synthesis Example 1: Preparation of Compound 1 [ka]

[0131] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.8 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1233 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 1 (19.2 g, 78%, MS: [M+H] + =557.3) was produced.

[0132] Synthesis Example 2: Preparation of Compound 2 [ka]

[0133] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.2 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1401 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 2 (17.1 g, 61%, MS: [M+H] + =633.3).

[0134] Synthesis Example 3: Preparation of Compound 3 [ka]

[0135] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-([1,1'-biphenyl]- 4 -yl)-3-chloro-6-phenyl-1,3,5-triazine (15.2 g, 44.3 mmol) was added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1401 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 3 (15.7 g, 56%, MS: [M+H] + =633.3).

[0136] Synthesis Example 4: Preparation of Compound 4 [ka]

[0137] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (15.8 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1432 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 4 (14.9 g, 52%, MS: [M+H] + =647.3) was produced.

[0138] Synthesis Example 5: Preparation of Compound 5 [ka]

[0139] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (16.5 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1468 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 5 (21.1 g, 72%, MS: [M+H] + =663.2) was produced.

[0140] Synthesis Example 6: Preparation of Compound 6 [ka]

[0141] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (14.1 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1344 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 6 (19.1 g, 71%, MS: [M+H] + =607.3) was produced.

[0142] Synthesis Example 7: Preparation of Compound 7 [ka]

[0143] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.4 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1512 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 7 (23.6 g, 78%, MS: [M+H] + =683.3) was produced.

[0144] Synthesis Example 8: Preparation of Compound 8 [ka]

[0145] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro- 4 -(dibenzo[b,d]furan- 3(-yl)-6-phenyl-1,3,5-triazine (15.8 g, 44.3 mmol) was added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1432 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 8 (18.9 g, 66%, MS: [M+H] + =647.3) was produced.

[0146] Synthesis Example 9: Preparation of Compound 9 [ka]

[0147] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (17.2 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1401 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 9 (15.4 g, 55%, MS: [M+H] + =633.3).

[0148] Synthesis Example 10: Preparation of Compound 10 [ka]

[0149] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (12.3 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) 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 1244 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 10 (15.7 g, 63%, MS: [M+H] + =562.3) was produced.

[0150] Synthesis Example 11: Preparation of Compound 11 [ka]

[0151] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.7 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1230 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 11 (18.2 g, 74%, MS: [M+H] + =562.3) was produced.

[0152] Synthesis Example 12: Preparation of Compound 12 [ka]

[0153] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1397 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 12 (15.4 g, 55%, MS: [M+H] + =638.3) was produced.

[0154] Synthesis Example 13: Preparation of Compound 13 [ka]

[0155] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (15 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1397 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 13 (14.8 g, 53%, MS: [M+H] + =638.3) was produced.

[0156] Synthesis Example 14: Preparation of Compound 14 [ka]

[0157] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (15.7 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) 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 1427 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 14 (22.3 g, 78%, MS: [M+H] + =652.3) was produced.

[0158] Synthesis Example 15: Preparation of Compound 15 [ka]

[0159] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (16.4 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) 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 1462 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 15 (17.8 g, 61%, MS: [M+H] + =668.2) was produced.

[0160] Synthesis Example 16: Preparation of Compound 16 [ka]

[0161] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (13.9 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1340 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 16 (13.9 g, 52%, MS: [M+H] + =612.3) was produced.

[0162] Synthesis Example 17: Preparation of Compound 17 [ka]

[0163] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.2 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1506 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 17 (16.3 g, 54%, MS: [M+H] + =688.3) was produced.

[0164] Synthesis Example 18: Preparation of Compound 18 [ka]

[0165] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-chloro- 4 -(dibenzo[b,d]furan- 3 (-yl)-6-phenyl-1,3,5-triazine (15.7 g, 43.8 mmol) was added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1427 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 18 (15.1 g, 53%, MS: [M+H]+ =652.3) was produced.

[0166] Synthesis Example 19: Preparation of Compound 19 [ka]

[0167] Under a nitrogen atmosphere, B-3 (20 g, 43.8 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (17 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1408 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 19 (22.5 g, 80%, MS: [M+H] + =643.3) was produced.

[0168] Synthesis Example 20: Preparation of Compound 20 [ka]

[0169] Under a nitrogen atmosphere, B-3 (100g, 219.2mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (78g, 219.2mmol) were added to 2000mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (90.9g, 657.5mmol) was dissolved in 91mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (7.6g, 6.6mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 2850mL of chloroform and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a gray solid compound Compound 20 (102.6 g, 72%, MS: [M+H] + =651.3) was produced.

[0170] Synthesis Example 21: Preparation of Compound 21 [ka]

[0171] Under a nitrogen atmosphere, C-3 (20 g, 43.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.7 g, 43.6 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1229 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 21 (13 g, 53%, MS: [M+H] + =564.3) was produced.

[0172] Synthesis Example 22: Preparation of Compound 22 [ka]

[0173] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 4-bromo-1,1'-biphenyl (7.6 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) 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 1040 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 22 (13.3 g, 64%, MS: [M+H] + =633.3).

[0174] Synthesis Example 23: Preparation of Compound 23 [ka]

[0175] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 3-bromo-1,1'-biphenyl (7.6 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1040 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 23 (16.2 g, 78%, MS: [M+H] + =633.3).

[0176] Synthesis Example 24: Preparation of Compound 24 [ka]

[0177] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 2-bromonaphthalene (6.8 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 997 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 24 (13 g, 65%, MS: [M+H] + =607.3) was produced.

[0178] Synthesis Example 25: Preparation of Compound 25 [ka]

[0179] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 9-bromophenanthrene (8.4 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1079 mL of chloroform and 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 with chloroform and ethyl acetate to obtain a white solid compound Compound 25 (13.6 g, 63%, MS: [M+H] + =657.3) was produced.

[0180] Synthesis Example 26: Preparation of Compound 26 [ka]

[0181] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 2-(4-bromophenyl)naphthalene (9.3 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1122 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 26 (15 g, 67%, MS: [M+H] + =683.3) was produced.

[0182] Synthesis Example 27: Preparation of Compound 27 [ka]

[0183] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 2-bromotriphenylene (11.7 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) 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 1161 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 27 (16.7 g, 72%, MS: [M+H] + =707.3).

[0184] Synthesis Example 28: Preparation of Compound 28 [ka]

[0185] Under a nitrogen atmosphere, D-3 (20 g, 32.9 mmol) and 4-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 (7.8 g, 32.9 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (13.6 g, 98.6 mmol) was dissolved in 14 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.1 g, 1 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1048 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound Compound 28 (11.1 g, 53%, MS: [M+H] + =638.3) was produced.

[0186] Synthesis Example 29: Preparation of Compound 29 [ka]

[0187] Under a nitrogen atmosphere, A-3 (20 g, 44.3 mmol) and 2-(8-bromodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine (21.1 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (18.4 g, 133 mmol) was dissolved in 18 mL of water and added, and the mixture was thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1601 mL of chloroform and washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a yellow solid compound Compound 29 (23.4 g, 73%, MS: [M+H] + =723.3) was produced.

[0188] Example 1: Fabrication of an organic light-emitting device A glass substrate coated with a 1,300 Å-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water with a 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, and then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent 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.

[0189] On the ITO transparent electrode thus prepared, the following HI-1 compound was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, the following HT-1 compound was thermally vacuum deposited to a thickness of 250 Å to form a hole transport layer, and the following HT-2 compound was vacuum deposited to a thickness of 50 Å on the HT-1 deposition film to form an electron blocking layer.

[0190] On the HT-2 deposition film, Compound 1 prepared in Synthesis Example 1, the following YGH-1 compound, and phosphorescent dopant YGD-1 were co-deposited in a weight ratio of 44:44:12 to form a 400 Å-thick light-emitting layer.

[0191] On the light-emitting layer, the following ET-1 compound was vacuum-deposited to a thickness of 250 Å to form an electron transport layer, and on the electron transport layer, the following ET-2 compound and LiF were vacuum-deposited in a weight ratio of 8:2 to form an electron injection layer to a thickness of 100 Å. On the electron injection layer, aluminum was vacuum-deposited to a thickness of 1000 Å to form a negative electrode. [ka]

[0192] During the above process, the deposition rate of the organic material was kept at 0.4-0.7 Å / sec, and the deposition rate of aluminum was kept at 2 Å / sec. The vacuum degree during deposition was 1×10 -7 ~5×10 -8 torr was maintained.

[0193] Examples 2 to 29 An organic light emitting device was prepared in the same manner as in Example 1, except that a compound shown in Table 1 below was used instead of Compound 1 in Synthesis Example 1 as one of the host materials of the emission layer.

[0194] At this time, the structures of the compounds used in Examples 1 to 29 are summarized as follows. [ka] [ka] [ka]

[0195] Comparative Examples 1 to 4 Organic light emitting devices were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 in Synthesis Example 1 as one of the host materials in the light emitting layer. At this time, the compounds CE1 to CE4 in Table 1 below are as follows. [ka]

[0196] Experimental example 1: Evaluation of element characteristics The organic light emitting devices manufactured in the examples and comparative examples were each supplied with 10 mA / cm 2 The voltage and efficiency were measured at a current density of 50mA / cm 2 The results are shown in Table 1. Here, LT95 means the time until the initial luminance decreases to 95%. [Table 1] JPEG0007608699000094.jpg214146

[0197] As shown in Table 1, the organic light emitting device of the Example using the compound represented by Chemical Formula 1 as the host material of the light emitting layer exhibited significantly improved life characteristics without a decrease in efficiency, compared to the organic light emitting device of the Comparative Example using a compound having a different structure. Therefore, considering that the luminous efficiency and life characteristics of an organic light emitting device generally have a trade-off relationship, it was confirmed that the compound of the present invention improves the characteristics of the organic light emitting device compared to the comparative compound. [Explanation of symbols]

[0198] 1 Board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7 Electron blocking layer 8 Electron transport layer 9 Electron injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 1】 In the above Chemical Formula 1, L is a single bond; an unsubstituted or deuterium-substituted arylene having 6 to 20 carbon atoms; or an unsubstituted or deuterium-substituted heteroarylene having 2 to 20 carbon atoms and containing one heteroatom selected from O and S; L 1 and L 2 each independently represent a single bond or an unsubstituted or deuterium-substituted arylene having 6 to 20 carbon atoms; Ar １ and Ar ２ 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 one or more heteroatoms selected from N, O and S; L' is a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Q is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; R is deuterium; or phenyl substituted with deuterium; n is an integer from 1 to 8.

2. 2. The compound of claim 1, wherein L is a single bond, phenylene, biphenyldiyl, naphthylene, dibenzofuranylene, dibenzothiophenylene.

3. L １ and L ２ The compound of claim 1 , wherein each is independently a single bond or phenylene.

4. Ar １ and Ar ２ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; Here, Ar １ and Ar ２ 2. The compound of claim 1, wherein is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl and phenyl.

5. Ar １ and Ar ２ is independently any one selected from the group consisting of: 【Chemistry 2】 。

6. Ar １ and Ar ２ The compound according to claim 1, wherein at least one of is an unsubstituted or deuterium-substituted aryl having 6 to 12 carbon atoms.

7. L is a single bond, and Ar １ and Ar ２ are each independently phenyl, phenyl substituted with five deuterons, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl; or L is an arylene having 6 to 20 carbon atoms or a heteroarylene having 2 to 20 carbon atoms containing one heteroatom selected from O and S, and Ar １ and Ar ２ The compound of claim 1 , wherein all are phenyl.

8. 2. The compound of claim 1, wherein L' is a single bond or phenylene.

9. Q is phenyl, biphenylyl, naphthyl, phenanthryl, triphenylenyl, benzophenanthryl, or 9,9-dimethylfluorenyl; 2. The compound of claim 1 , wherein Q is unsubstituted or substituted with deuterium.

10. The compound of claim 9, wherein Q is any one selected from the group consisting of: 【Chemistry 3】 。

11. R is deuterium, or 【Chemistry 4】 2. The compound of claim 1 ,

12. The above 【Chemistry 5】 is any one selected from the group consisting of: 【Chemistry 6】 。

13. The compound according to claim 1, which is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] 【Chemistry 7】 [Chemical formula 1-2] 【Chemistry 8】 [Chemical formula 1-3] 【Chemistry 9】 In the above Chemical Formulas 1-1 to 1-3, D is deuterium; m is 1, 2, 3, 4, 5 or 7; L, L １ , L ２ , Ar １ , Ar ２ , L′ and Q are as defined in claim 1.

14. The compound according to claim 1, which is any one selected from the group consisting of the following compounds: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 。

15. 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 comprises the compound according to any one of claims 1 to 14.

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

17. The organic light-emitting device according to claim 16, wherein the light-emitting layer further comprises a compound represented by the following Chemical Formula 2: [Chemical formula 2] 【Chemical 27】 In the above Chemical Formula 2, Ar' １ and Ar' ２ 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 one or more heteroatoms selected from N, O and S; R' １ and R' ２ are each independently hydrogen; deuterium; alkyl having 1 to 60 carbon atoms; aryl having 6 to 60 carbon atoms; or heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from N, O and S; Each of r and s is independently an integer of 0 to 7.

18. The organic light-emitting device according to claim 17, wherein the compound represented by Chemical Formula 2 is any one selected from the group consisting of the following compounds: 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 。

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