Compound and organic light-emitting device containing the same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device including the same.

Description

[Technical Field]

[0001] The present specification relates to a compound and an organic light-emitting device including the same.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0083828 filed with the Korean Intellectual Property Office on July 7, 2022, and Korean Patent Application No. 10-2022-0160689 filed with the Korean Intellectual Property Office on November 25, 2022, the entire contents of which are incorporated herein by reference. [Background technology]

[0003] Generally, organic light-emitting refers to the conversion of electrical energy into light energy using organic materials. Organic light-emitting devices using organic light-emitting technology typically have a structure including an anode, a cathode, and an organic material layer between them. To enhance the efficiency and stability of the organic light-emitting device, the organic material layer often has a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this organic light-emitting device, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons combine, excitons are formed. Light is emitted when the excitons return to their ground state.

[0004] There is a continuing need to develop new materials for such organic light-emitting devices. Summary of the Invention [Problem to be solved by the invention]

[0005] The present specification aims to provide a compound and an organic light-emitting device including the compound. [Means for solving the problem]

[0006] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1: [Chemical formula 1] [ka] In the above Chemical Formula 1, R1 to R8 are the same or different and each independently represent hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Ar1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; L is a direct bond; or a substituted or unsubstituted arylene group; Q is any one of the substituents represented by the following chemical formulas 2-1 to 2-6: [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] [Chemical formula 2-5] [ka] [Chemical formula 2-6] [ka] In the above chemical formulas 2-1 to 2-6, X and Y are the same or different and each independently represent O; or S; R9~R 16 are the same or different, R9 to R16 any one of the following is linked to L in Chemical Formula 1; R9~R 16 the remaining groups not connected to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; halogen; a cyano group; a silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; In the formula 1, L is a direct bond, Q is the formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15 When any one of the groups is an unsubstituted phenyl group, the remaining group is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0007] Furthermore, according to one embodiment of the present invention, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite 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 contains the compound described above. [Effects of the Invention]

[0008] The compounds described herein can be used as materials for the organic layer of an organic light-emitting device. When an organic light-emitting device containing a compound according to at least one embodiment of the present invention is manufactured, an organic light-emitting device having low voltage, high efficiency, and / or long life characteristics can be obtained.

[0009] When the compound of the present invention is used in at least one layer of the hole transport layer, hole injection layer, electron transport layer, electron injection layer, and light emitting layer, the effect of lowering the driving voltage of the device, increasing the efficiency of the device, and / or increasing the lifespan of the device can be obtained.

[0010] In particular, when the compound of the present invention is used as a blue host in the light-emitting layer, the effects of lowering the driving voltage of the device, increasing the efficiency of the device, and / or increasing the lifespan of the device can be obtained. [Brief explanation of the drawings]

[0011] [Figure 1] 1 shows an example of an organic light-emitting device according to the present invention. [Figure 2] 1 shows an example of an organic light-emitting device according to the present invention. [Explanation of symbols]

[0012] 1. Circuit board 2 anode 3...organic layer 4 cathode 5. Hole injection layer 6. Hole transport layer 7. Emitting layer 8...electron transport layer DETAILED DESCRIPTION OF THE INVENTION

[0013] The present specification will be explained in more detail below.

[0014] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0015] In this specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.

[0016] Herein, the first electrode may be an anode and the second electrode may be a cathode, or the first electrode may be a cathode and the second electrode may be an anode.

[0017] In this specification, examples of the substituents are described below, but are not limited to these.

[0018] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0019] In this specification, unless otherwise defined, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium (-D); halogen; cyano (-CN); silyl; boron; amine; alkyl; alkenyl; alkynyl; alkoxy; cycloalkyl; aryl; and heterocyclic groups, or substituted with a substituent in which two or more of the above-exemplified substituents are linked, or no substituents are present. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, a biphenyl group may be interpreted as either an aryl group or a substituent in which two phenyl groups are linked.

[0020] Examples of the substituents used in this specification are described below, but the invention is not limited to these.

[0021] As used herein, examples of halogen (-X) include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0022] As used herein, a silyl group is —SiY a Y b Y c and the Y a , Y b , and Y cmay be substituted or unsubstituted with hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, etc. 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.

[0023] In this specification, the boron group may be substituted or unsubstituted with deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 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.

[0024] In this specification, the amine group may be selected from the group consisting of -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group, and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine group, an N-phenylterphenylamine group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group.

[0025] In this specification, the term "N-alkylarylamine group" refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.

[0026] As used herein, the term "N-arylheteroarylamine group" refers to an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group.

[0027] As used herein, the term "N-alkylheteroarylamine group" refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.

[0028] In this specification, the alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as the examples of the alkyl group described above. Specific examples of the alkylthioxy group include a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, and an octylthioxy group. Examples of the alkylsulfoxy group include, but are not limited to, a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, and a butylsulfoxy group.

[0029] 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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0030] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably ranges from 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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.

[0031] In this specification, the alkynyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably is 2 to 30. Specific examples include alkynyl groups such as ethynyl, propynyl, 2-methyl-2-propynyl, 2-butynyl, and 2-pentynyl, but are not limited to these.

[0032] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably has 1 to 40 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, and p-methylbenzyloxy.

[0033] The alkyl groups, alkoxy groups, and other alkyl moiety-containing substituents described herein include either straight-chain or branched-chain groups.

[0034] In this 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 another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0035] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, examples include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylene group, a chrysenyl group, and a fluorenyl group.

[0036] As used herein, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0037] When the fluorenyl group is substituted, [ka] (spirofluorenyl group) and [ka] (spirobifluorenyl group), [ka] (9,9-dimethylfluorenyl group) and [ka] The fluorenyl group may be a substituted fluorenyl group such as, but not limited to, a 9,9-diphenylfluorenyl group.

[0038] The aryl group may be substituted with an alkyl group to function as an arylalkyl group. The alkyl group may be selected from the examples given above.

[0039] In this specification, a heterocyclic group refers to a ring containing one or more heteroatoms that are not carbon atoms, and specifically, the heteroatoms may contain one or more atoms selected from the group consisting of O, N, and S. The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or fused aromatic and aliphatic ring, and may be selected from the examples of heteroaryl groups listed below.

[0040] In this specification, a heteroaryl group is an aryl group containing one or more heteroatoms selected from N, O, P, S, Si, and Se, and although the number of carbon atoms is not particularly limited, it is preferably 2 to 60. According to one embodiment, the number of carbon atoms in the heteroaryl group is 2 to 30. Examples of heteroaryl groups include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, and a carbazole group.

[0041] In this specification, the alkylene group has the same definition as the alkyl group described above, except that it is a divalent group.

[0042] In this specification, the alkenylene group has the same definition as the alkenyl group described above, except that it is a divalent group.

[0043] In this specification, the cycloalkylene group has the same definition as the cycloalkyl group described above, except that it is a divalent group.

[0044] In this specification, the cycloalkenylene group has the same definition as the cycloalkenyl group described above, except that it is a divalent group.

[0045] In this specification, the arylene group has the same definition as the aryl group, except that it is a divalent group.

[0046] In this specification, the heteroarylene group has the same definition as the heteroaryl group, except that it is a divalent group.

[0047] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1: [Chemical formula 1] [ka] In the above Chemical Formula 1, R1 to R8 are the same or different and each independently represent hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Ar1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; L is a direct bond; or a substituted or unsubstituted arylene group; Q is any one of the substituents represented by the following chemical formulas 2-1 to 2-6: [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] [Chemical formula 2-5] [ka] [Chemical formula 2-6] [ka] In the above chemical formulas 2-1 to 2-6, X and Y are the same or different and each independently represent O; or S; R9~R 16 any one of the following is linked to L in Chemical Formula 1; R9~R 16 the remaining groups not connected to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; halogen; a cyano group; a silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; In the formula 1, L is a direct bond, Q is the formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15 If any one of the groups is an unsubstituted phenyl group, the remaining groups are a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. In other words, in the above Chemical Formula 1, L is a direct bond, Q is the above Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15 If any one of them is an unsubstituted phenyl group, the remaining one must not be an unsubstituted phenyl group.

[0048] The compounds according to the above-described embodiments have stable forms in both oxidized and reduced states, and when excitons are formed, they are converted into light with high luminescence efficiency.

[0049] When the compound of the present invention is used in at least one layer of the hole transport layer, hole injection layer, electron transport layer, electron injection layer, and light emitting layer, the effect of lowering the driving voltage of the device, increasing the efficiency of the device, and / or increasing the lifespan of the device can be obtained.

[0050] In particular, when the compound of the present invention is used as a blue host in the light-emitting layer, the effects of lowering the driving voltage of the device, increasing the efficiency of the device, and / or increasing the lifespan of the device can be obtained.

[0051] According to one embodiment of the present specification, there is provided a compound in which R1 to R8 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0052] According to one embodiment of the present specification, there is provided a compound in which R1 to R8 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0053] According to one embodiment of the present specification, there is provided a compound in which R1 to R8 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0054] According to one embodiment of the present specification, there is provided a compound in which R1 to R8 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0055] According to one embodiment of the present specification, there is provided a compound wherein R1 to R8 are the same or different and each independently represent hydrogen or deuterium.

[0056] According to one embodiment of the present specification, there is provided a compound, wherein Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0057] According to one embodiment of the present specification, there is provided a compound, wherein Ar1 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0058] According to one embodiment of the present specification, there is provided a compound, wherein Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0059] According to one embodiment of the present specification, there is provided a compound wherein Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group, wherein the substituted or unsubstituted means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms, or the one or more adjacent substituents are bonded to each other to form a ring.

[0060] According to one embodiment of the present specification, there is provided a compound wherein Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group, wherein the substituted or unsubstituted means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 2 to 40 carbon atoms, or the one or more adjacent substituents are bonded to each other to form an aromatic hydrocarbon ring having 6 to 40 carbon atoms or an aromatic heterocycle having 2 to 40 carbon atoms.

[0061] According to one embodiment of the present specification, there is provided a compound wherein Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group, wherein the substituted or unsubstituted means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or the one or more adjacent substituents are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms or an aromatic heterocycle having 2 to 30 carbon atoms.

[0062] According to one embodiment of the present specification, there is provided a compound wherein Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group, wherein the substituted or unsubstituted means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 2 to 20 carbon atoms, or the one or more adjacent substituents are bonded to each other to form a phenyl ring, a naphthyl ring, a benzofuran ring, or a benzothiophene ring.

[0063] According to one embodiment of the present specification, there is provided a compound wherein L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0064] According to one embodiment of the present specification, there is provided a compound wherein L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0065] According to one embodiment of the present invention, there is provided a compound wherein L is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0066] According to one embodiment of the present invention, there is provided a compound wherein L is a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted naphthylene group.

[0067] According to one embodiment of the present invention, there is provided a compound wherein L is a direct bond; or an unsubstituted phenylene group.

[0068] According to one embodiment of the present specification, there is provided a compound wherein the chemical formula 2-1 is any one of the following chemical formulas 2-1-A to 2-1-D. [Chemical formula 2-1-A] [ka] [Chemical formula 2-1-B] [ka] [Chemical formula 2-1-C] [ka] [Chemical formula 2-1-D] [ka] In the chemical formulas 2-1-A to 2-1-D, R9~R 16 is the same as defined in the above chemical formulas 2-1 to 2-6.

[0069] According to one embodiment of the present specification, there is provided a compound wherein the chemical formula 2-2 is any one of the following chemical formulas 2-2-A to 2-2-D. [Chemical formula 2-2-A] [ka] [Chemical formula 2-2-B] [ka] [Chemical formula 2-2-C] [ka] [Chemical formula 2-2-D] [ka] In the chemical formulas 2-2-A to 2-2-D, R9~R 16 is the same as defined in the above chemical formulas 2-1 to 2-6.

[0070] According to one embodiment of the present specification, there is provided a compound wherein the chemical formula 2-3 is any one of the following chemical formulas 2-3-A to 2-3-D. [Chemical formula 2-3-A] [ka] [Chemical formula 2-3-B] [ka] [Chemical formula 2-3-C] [ka] [Chemical formula 2-3-D] [ka] In the above chemical formulas 2-3-A to 2-3-D, R9~R 16 is the same as defined in the above chemical formulas 2-1 to 2-6.

[0071] According to one embodiment of the present specification, there is provided a compound wherein the chemical formula 2-4 is any one of the following chemical formulas 2-4-A to 2-4-D. [Chemical formula 2-4-A] [ka] [Chemical formula 2-4-B] [ka] [Chemical formula 2-4-C] [ka] [Chemical formula 2-4-D] [ka] In the chemical formulas 2-4-A to 2-4-D, R9~R 16 is the same as defined in the above chemical formulas 2-1 to 2-6.

[0072] According to one embodiment of the present specification, there is provided a compound wherein the chemical formula 2-5 is any one of the following chemical formulas 2-5-A to 2-5-D. [Chemical formula 2-5-A] [ka] [Chemical formula 2-5-B] [ka] [Chemical formula 2-5-C] [ka] [Chemical formula 2-5-D] [ka] In the chemical formulas 2-5-A to 2-5-D, R9~R 16 is the same as defined in the above chemical formulas 2-1 to 2-6.

[0073] According to one embodiment of the present specification, there is provided a compound wherein the chemical formula 2-6 is any one of the following chemical formulas 2-6-A to 2-6-D. [Chemical formula 2-6-A] [ka] [Chemical formula 2-6-B] [ka] [Chemical formula 2-6-C] [ka] [Chemical formula 2-6-D] [ka] In the chemical formulas 2-6-A to 2-6-D, R9~R 16 is the same as defined in the above chemical formulas 2-1 to 2-6.

[0074] According to one embodiment of the present specification, in the chemical formula 1, L is a direct bond, Q is the chemical formula 2-2, X and Y are both O, and R9 to R 14 and R16 When any one of Ar and R is linked to L in Formula 1, 15 If one of Ar and R is an unsubstituted phenyl group, the remaining 15 the remaining group (one of which is not an unsubstituted phenyl group) is a substituted or unsubstituted aryl group having 10 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0075] According to one embodiment of the present specification, in the chemical formula 1, L is a direct bond, Q is the chemical formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15 When any one of the groups is an unsubstituted phenyl group, the remaining group is a substituted or unsubstituted aryl group having 10 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0076] According to one embodiment of the present specification, in the chemical formula 1, L is a direct bond, Q is the chemical formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15 is an unsubstituted phenyl group, the remaining is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and the "substituted or unsubstituted" means that the one or more substituents are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms, or that the one or more adjacent substituents may be bonded to each other to form a ring.

[0077] According to one embodiment of the present specification, in the chemical formula 1, L is a direct bond, Q is the chemical formula 2-2, X and Y are both O, and R9 to R 14 and R16 When any one of Ar and R is linked to L in Formula 1, 15 is an unsubstituted phenyl group, the remaining is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and the "substituted or unsubstituted" means that the substituted or unsubstituted group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 2 to 40 carbon atoms, or the one or more adjacent substituents may be bonded to each other to form an aromatic hydrocarbon ring having 6 to 40 carbon atoms or an aromatic heterocycle having 2 to 40 carbon atoms.

[0078] According to one embodiment of the present specification, in the chemical formula 1, L is a direct bond, Q is the chemical formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15 is an unsubstituted phenyl group, the remaining is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and the "substituted or unsubstituted" means that the substituted or unsubstituted group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or the one or more adjacent substituents may be bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms or an aromatic heterocycle having 2 to 30 carbon atoms.

[0079] According to one embodiment of the present specification, in the chemical formula 1, L is a direct bond, Q is the chemical formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar and R is linked to L in Formula 1, 15is an unsubstituted phenyl group, the remaining is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and the "substituted or unsubstituted" means that the one or more adjacent substituents are substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or the one or more adjacent substituents may be bonded to each other to form a phenyl ring, a naphthyl ring, a benzofuran ring, or a benzothiophene ring.

[0080] According to one embodiment of the present specification, the R9 to R 16 wherein the remaining groups not linked to L in Chemical Formula 1 are the same or different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0081] According to one embodiment of the present specification, the R9 to R 16 wherein the remaining groups not linked to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0082] According to one embodiment of the present specification, the R9 to R 16 wherein the remaining groups not linked to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0083] According to one embodiment of the present specification, the R9 to R 16wherein the remaining groups not linked to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0084] According to one embodiment of the present specification, the R9 to R 16 wherein the remaining groups not linked to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0085] According to one embodiment of the present specification, the R9 to R 16 wherein the remaining groups not connected to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group, wherein the "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms, or the one or more adjacent substituents are bonded to each other to form a ring.

[0086] According to one embodiment of the present specification, the R9 to R 16wherein the remaining groups not connected to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group, and the "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 2 to 40 carbon atoms, or the one or more adjacent substituents are bonded to each other to form an aromatic hydrocarbon ring having 6 to 40 carbon atoms or an aromatic heterocycle having 2 to 40 carbon atoms.

[0087] According to one embodiment of the present specification, the R9 to R 16 wherein the remaining groups not connected to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group, wherein the "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or the one or more adjacent substituents are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms or an aromatic heterocycle having 2 to 30 carbon atoms.

[0088] According to one embodiment of the present specification, the R9 to R 16wherein the remaining groups not connected to L in Chemical Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group, wherein the "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or the one or more adjacent substituents are bonded to each other to form a phenyl ring, a naphthyl ring, a benzofuran ring, or a benzothiophene ring.

[0089] According to one embodiment of the present specification, the Chemical Formula 1 may be represented by any one of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0090] According to one embodiment of the present specification, the Chemical Formula 1 may be represented by any one of the following compounds: [ka] [ka] [ka] [ka]

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[0091] Furthermore, when the compound of the present invention is used in at least one layer selected from the group consisting of a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and an emitting layer, the driving voltage of the device can be reduced or the efficiency of the device can be increased.

[0092] In particular, when the compound of the present invention is used as a blue host in the light-emitting layer, the driving voltage of the device can be reduced or the efficiency of the device can be increased.

[0093] The substituents of the compound of Chemical Formula 1 may be bonded by a method known in the art according to the following Reaction Scheme 1, and the type, position, or number of the substituents may be changed by a technique known in the art. Also, Q, L, and Ar1 referred to in the following Reaction Scheme 1 are the same as defined above. [Reaction Scheme 1] [ka]

[0094] Furthermore, in this specification, by introducing a heterocyclic group (Q) containing two O or S atoms into the anthracene core as described above, it is possible to synthesize a compound with unique properties. Specifically, by introducing into the core structure a substituent that is mainly used in materials for hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, etc., which are used in the manufacture of organic light-emitting devices, it is possible to synthesize a material that satisfies the requirements for each organic layer.

[0095] In particular, in this specification, by introducing a heterocyclic group, which is mainly used in materials for light-emitting layers used in the manufacture of organic light-emitting devices, into the anthracene core, it is possible to synthesize a material that satisfies the conditions required for the light-emitting layer.

[0096] In addition, in this specification, the core structure described above allows compounds with various energy band gaps to be synthesized, and the HOMO and LUMO energy levels of the compounds can also be adjusted by introducing various substituents into the core structure described above.

[0097] According to another embodiment of the present specification, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of the above-described embodiments.

[0098] The organic light-emitting device according to the above-described embodiment has a stable morphology in both an oxidized state and a reduced state, and uses a compound with high luminescence efficiency that converts excitons into light when they are formed, thereby achieving the effects of lowering the driving voltage of the device or increasing the efficiency of the device.

[0099] The organic light-emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers or light-emitting layers are formed using the above-mentioned compounds.

[0100] The compound may be formed in the organic material layer or the light-emitting layer by a solution coating method as well as a vacuum deposition method during fabrication of the organic light-emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0101] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include fewer or more organic material layers.

[0102] According to another embodiment of the present specification, in the organic light-emitting device, the organic layer may include one or more layers selected from a hole transport layer, a hole injection layer, an emission layer, an electron injection layer, and an electron transport layer, and the one or more layers may include a compound represented by Chemical Formula 1.

[0103] According to still another embodiment of the present specification, there is provided an organic light-emitting device, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0104] According to yet another embodiment of the present specification, there is provided an organic light-emitting device, wherein the light-emitting layer contains the compound as a blue host.

[0105] The organic light-emitting device according to the above-described embodiment has a stable morphology in both an oxidized state and a reduced state, and uses a compound with high luminescence efficiency that converts excitons into light when they are formed, thereby achieving the effects of lowering the driving voltage of the device or increasing the efficiency of the device.

[0106] In the organic light-emitting device of the present specification, the organic material layer includes an electron transport layer, and the electron transport layer includes the compound represented by Chemical Formula 1 above.

[0107] In the organic light-emitting device of the present specification, the organic material layer includes an electron injection layer, and the electron injection layer includes the compound represented by Chemical Formula 1 above.

[0108] In the organic light-emitting device of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1 above.

[0109] According to another embodiment, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a host of the light-emitting layer.

[0110] According to another embodiment, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a phosphorescent host of the light-emitting layer.

[0111] In another example, the organic material layer may include a light-emitting layer, which may include the compound represented by Chemical Formula 1 as a host of the light-emitting layer and may further include a dopant.

[0112] In another example, the organic material layer may include an emitting layer, which includes the compound represented by Chemical Formula 1 as a host of the emitting layer, and may further include a dopant. The content of the dopant may be 1 to 20 parts by weight, more preferably 1 to 5 parts by weight, based on 100 parts by weight of the host.

[0113] According to another embodiment, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a dopant for the light-emitting layer.

[0114] In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1 as a dopant of the light-emitting layer, and may further include a host.

[0115] In another embodiment, the organic layer includes an emitting layer, which contains the compound represented by Chemical Formula 1 as a dopant for the emitting layer, and which may contain a fluorescent host or a phosphorescent host, and may contain another organic compound, a metal, or a metal compound as a dopant.

[0116] In another example, the organic material layer includes an emitting layer, and the emitting layer includes the compound represented by Chemical Formula 1 as a blue host of the emitting layer, and may include a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.

[0117] In another example, the organic material layer includes an emitting layer, and the emitting layer includes the compound represented by Chemical Formula 1 as a dopant of the emitting layer, and includes a fluorescent host or a phosphorescent host, which may be used together with an iridium (Ir) dopant.

[0118] In the organic light emitting device of the present specification, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the compound represented by Chemical Formula 1 above.

[0119] In the organic light-emitting device of the present specification, the organic material layer may include an electron inhibiting layer, and the electron inhibiting layer may include a compound represented by Chemical Formula 1 above.

[0120] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer includes the compound of Chemical Formula 1 and a metal complex.

[0121] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer includes the compound of Chemical Formula 1 and lithium quinolate (LiQ).

[0122] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer may contain the compound of Chemical Formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.

[0123] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer may contain the compound of Chemical Formula 1 and the metal complex in a weight ratio of 1:5 to 5:1.

[0124] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer may contain the compound of Chemical Formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.

[0125] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer may contain the compound of Chemical Formula 1 and lithium quinolate in a weight ratio of 1:10 to 10:1.

[0126] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer may contain the compound of Chemical Formula 1 and lithium quinolate in a weight ratio of 1:5 to 5:1.

[0127] In the organic light emitting device of the present specification, the electron injection layer and / or the electron transport layer may contain the compound of Chemical Formula 1 and lithium quinolate in a weight ratio of 1:3 to 3:1.

[0128] (1) Anode / hole transport layer / light-emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (10) Anode / hole transport layer / electron inhibiting layer / light emitting layer / electron transport layer / cathode (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode (12) Anode / hole injection layer / hole transport layer / electron inhibiting layer / light emitting layer / electron transport layer / cathode (13) Anode / hole injection layer / hole transport layer / electron inhibiting layer / light emitting layer / electron transport layer / electron injection layer / cathode (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0129] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

[0130] 1 illustrates an example of the structure of an organic light-emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In this structure, the compound represented by Chemical Formula 1 may be contained in the organic material layer 3.

[0131] For example, an organic light emitting device according to the present invention can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, then forming an organic layer on the anode, the organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes (hole transport and hole injection layer), an emissive layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons (electron transport and electron injection layer), and then depositing a material usable as a cathode on the anode. Alternatively, an organic light emitting device can be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0132] The organic layer may have a multi-layer structure including, but not limited to, a hole injection layer, a hole transport layer, an emitting layer, and an electron transport layer, etc. Alternatively, the organic layer may have a single layer structure. The organic layer may be formed into fewer layers using various polymer materials by a solvent process, such as spin coating, dip coating, doctor blade, screen printing, inkjet printing, or thermal transfer, rather than a vapor deposition method.

[0133] The anode is an electrode that injects holes, and anode materials are generally preferred that have a high work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention 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 SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0134] The cathode is an electrode that injects electrons, and a cathode material is generally preferred that has a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode 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 LiO / Al.

[0135] The hole injection layer facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that facilitates the injection of holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, 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.

[0136] The thickness of the hole injection layer may be 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it is advantageous in that it can prevent a decrease in hole injection characteristics, and when it is 150 nm or less, it is advantageous in that it can prevent an increase in driving voltage due to an increase in hole mobility caused by a hole injection layer that is too thick.

[0137] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer prevents holes injected from the hole injection layer from passing through the light emitting layer and entering the electron injection layer, thereby improving the life and efficiency of the device. The electron blocking layer may be made of the compound of Formula 1 or a material known in the art.

[0138] The light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent or fluorescent material. The light-emitting material is 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. A material with high quantum efficiency for fluorescence or phosphorescence is preferred. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole, and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene groups, and rubrene.

[0139] Examples of the host material of the light-emitting layer include fused aromatic ring derivatives and heterocyclic ring-containing compounds. Specific examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocyclic ring-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0140] When the light-emitting layer emits red light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), or PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the light-emitting layer emits green light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the light-emitting layer emits blue light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyribenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, or a PPV-based polymer.

[0141] A hole-blocking layer may be provided between the electron-transporting layer and the light-emitting layer. The hole-blocking layer is a layer that blocks holes from reaching the cathode and may be generally formed under the same conditions as the hole-injecting layer. Specific examples of hole-blocking materials include, but are not limited to, triazine derivatives, phenanthroline derivatives, and BCP, and materials well known in the art may be used.

[0142] The electron transport layer can facilitate the transport of electrons. The electron transport material is a material that can smoothly receive electrons injected from the cathode and transfer them to the light-emitting layer, and is preferably a material with high electron mobility. Specific examples include, but are not limited to, 8-hydroxyquinoline Al complexes; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes.

[0143] The thickness of the electron transport layer may be 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it is advantageous in that it can prevent the electron transport properties from deteriorating, and when it is 50 nm or less, it is advantageous in that it can prevent the drive voltage from increasing due to the electron transport layer being too thick to improve electron mobility.

[0144] The electron injection layer can facilitate electron injection. The electron injection material is preferably a compound that has the ability to transport electrons, has an excellent electron injection effect from the cathode, has an excellent electron injection effect into the light-emitting layer or light-emitting material, prevents excitons generated from the light-emitting layer from migrating to the hole injection layer, and has excellent thin-film forming ability. Specific examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0145] Examples of the metal complex compounds include, but are not limited to, 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolate)gallium, bis(2-methyl-8-quinolinato)(1-naphtholate)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholate)gallium.

[0146] The organic light emitting device according to the present invention may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type, depending on the materials used. [Example]

[0147] Hereinafter, the present specification will be described in detail with reference to examples in order to specifically explain the present specification. However, the examples according to the present specification may be modified in various different forms, and the scope of the present application should not be construed as being limited to the examples described below. The examples of the present application are provided to more clearly explain the present specification to those skilled in the art.

[0148] <Production Example> Production of precursor of Q Manufacturing Example 1 [ka] 1) Preparation of chemical formula a-2 Under a nitrogen atmosphere, (5-chloro-2-hydroxyphenyl)boronic acid (100 g, 580.1 mmol) and 4-bromo-5-fluorobenzofuran (124.7 g, 580.1 mmol) were added to 2000 mL of THF and stirred at reflux. Potassium carbonate (320.7 g, 2320.6 mmol) was then dissolved in 962 mL of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (20.1 g, 17.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 106.7 g of compound a-2 (yield 70%, MS: [M+H] + = 264).

[0149] 2) Preparation of chemical formula a-1 Under a nitrogen atmosphere, a-2 (106.7 g, 406.2 mmol) was added to 2134 ml of DMAC and stirred under reflux. Potassium carbonate (168.4 g, 1218.7 mmol) was then added and stirred. After reacting for 1 hour, the mixture was cooled to room temperature and 2.5 L of water was poured into it to solidify, followed by filtration. This was then dissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 69 g of compound a-1 (yield 70%, MS: [M+H]+ = 244).

[0150] 3) Preparation of chemical formula a Under a nitrogen atmosphere, a-1 (69 g, 284.3 mmol) and bis(pinacolato)diboron (86.6 g, 341.2 mmol) were refluxed and stirred in 1,380 mL of 1,4-dioxane. Potassium acetate (41.9 g, 426.5 mmol) was then added and thoroughly stirred. After that, bis(dibenzylideneacetone)palladium(0) (4.9 g, 8.5 mmol) and tricyclohexylphosphine (4.8 g, 17.1 mmol) were added. The reaction was allowed to proceed for 7 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. The resulting mixture was dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 70.3 g of compound a (yield 74%, MS: [M+H] + = 335).

[0151] Manufacturing Example 2 [ka] 1) Preparation of chemical formula b Compound b was synthesized in the same manner as compound a, except that (4-chloro-2-hydroxyphenyl)boronic acid was used instead of (5-chloro-2-hydroxyphenyl)boronic acid.

[0152] Manufacturing Example 3 [ka] 1) Preparation of chemical formula c-2 Under a nitrogen atmosphere, 1-bromo-2-fluorobenzene (60 g, 342.9 mmol) and 6-chlorobenzofuran-5-ol (57.8 g, 342.9 mmol) were added to 1200 mL of DMAC and stirred under reflux. Potassium carbonate (142.2 g, 1028.6 mmol) was then added and stirred. After reacting for 1 hour, the mixture was cooled to room temperature and solidified by pouring in 2.5 L of water and filtering. This was then dissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 75.4 g of compound c-2 (yield 68%, MS: [M+H]+ = 325).

[0153] 2) Preparation of chemical formula c-1 Under a nitrogen atmosphere, c-2 (75.4 g, 233 mmol) was added to 754 mL of DMAC and stirred and refluxed. Then, DBU (212.9 g, 1398.2 mmol) and palladium(II) acetate (1.6 g, 7 mmol) were added. After reacting for 8 hours, the mixture was cooled to room temperature, solidified by pouring in 1.5 L of water, and filtered. The solid was dissolved again in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.3 g of compound c-1 (yield 43%, MS: [M+H]+ = 244).

[0154] 3) Preparation of chemical formula c Using c-1 instead of a-1, compound c of the chemical formula was synthesized in the same manner as in compound a of the chemical formula.

[0155] Manufacturing Example 4 [ka] 1) Preparation of chemical formula d-3 Compound d-3 was synthesized in the same manner as compound a-2, except that (2-hydroxyphenyl)boronic acid was used instead of (5-chloro-2-hydroxyphenyl)boronic acid and 5-bromo-6-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0156] 2) Preparation of chemical formula d-2 Using d-3 instead of a-2, chemical formula d-2 was synthesized in the same manner as in the preparation method of chemical formula a-1.

[0157] 3) Preparation of chemical formula d-1 Under a nitrogen atmosphere, d-2 (30 g, 144.1 mmol) was added to 600 mL of dichloromethane and stirred at -10°C. Bromine (25.3 g, 158.5 mmol) was then slowly added dropwise and stirred for 1 hour. After the reaction was complete, the mixture was extracted with chloroform, NaSO, and water. The organic layer was then distilled and redissolved in ethanol. The solution was added dropwise to 300 mL of an ethanol solution saturated with KOH at 10°C and refluxed for 2 hours. After the reaction was complete, the ethanol was distilled and extracted with ethyl acetate and brine. Anhydrous magnesium sulfate was added to the organic layer, which was then stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29 g of compound d-1 (yield 70%, MS: [M+H]+ = 288).

[0158] 4) Preparation of chemical formula d Using d-1 instead of a-1, compound d of the chemical formula was synthesized in the same manner as in compound a.

[0159] Manufacturing Example 5 [ka] 1) Preparation of chemical formula e Compound e was synthesized in the same manner as compound a, except that 5-bromo-6-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0160] Manufacturing Example 7 [ka] 1) Preparation of chemical formula f Compound f was synthesized in the same manner as compound a, except that (4-chloro-2-hydroxyphenyl)boronic acid was used instead of (5-chloro-2-hydroxyphenyl)boronic acid and 5-bromo-6-fluorobenzo[b]thiophene was used instead of 4-bromo-5-fluorobenzofuran.

[0161] Manufacturing Example 8 [ka] 1) Preparation of chemical formula g Compound g was synthesized in the same manner as in compound a, except that (3-chloro-2-hydroxyphenyl)boronic acid was used instead of (5-chloro-2-hydroxyphenyl)boronic acid and 6-bromo-7-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0162] Manufacturing Example 9 [ka] 1) Preparation of chemical formula H Chemical formula h was synthesized in the same manner as chemical formula c, except that 2-bromo-1-chloro-3-fluorobenzene was used instead of 1-bromo-2-fluorobenzene and 2,3-diphenylbenzofuran-7-ol was used instead of 6-chlorobenzofuran-5-ol.

[0163] Manufacturing Example 10 [ka] 1) Preparation of Chemical Formula i Compound I was synthesized in the same manner as compound C, except that 2-bromo-1-chloro-3-fluorobenzene was used instead of 1-bromo-2-fluorobenzene and 2-phenylbenzofuran-7-ol was used instead of 6-chlorobenzofuran-5-ol.

[0164] Manufacturing Example 11 [ka] 1) Preparation of Chemical Formula j Compound j was synthesized in the same manner as compound c, except that 2-bromobenzofuran-4-ol was used instead of 6-chlorobenzofuran-5-ol.

[0165] Manufacturing Example 12 [ka] 1) Preparation of chemical formula k Compound k was synthesized in the same manner as in compound a, except that (2-chloro-6-hydroxyphenyl)boronic acid was used instead of (5-chloro-2-hydroxyphenyl)boronic acid and 5-bromo-4-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0166] Manufacturing Example 13 [ka] 1) Preparation of Chemical Formula 1 Chemical formula l was synthesized in the same manner as in the preparation of chemical formula c, except that 7-chloro-4-fluorobenzofuran was used instead of 1-bromo-2-fluorobenzene and 2-bromophenol was used instead of 6-chlorobenzofuran-5-ol.

[0167] Manufacturing Example 14 [ka] 1) Preparation of chemical formula m Compound m was synthesized in the same manner as compound a, except that (3-chloro-2-hydroxyphenyl)boronic acid was used instead of (5-chloro-2-hydroxyphenyl)boronic acid and 6-bromo-5-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0168] Manufacturing Example 15 [ka] 1) Preparation of chemical formula n Compound n was synthesized in the same manner as compound a, except that 6-bromo-5-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0169] Manufacturing Example 16 [ka] 1) Preparation of chemical formula o-2 7-Chlorodibenzo[b,d]furan-1-ol (60 g, 274.4 mmol) and 2-bromo-1-phenylethan-1-one (54.6 g, 274.4 mmol) were added to 600 mL of acetone and stirred. Potassium carbonate (56.9 g, 411.6 mmol) was then added and stirred. After reacting for 9 hours, the mixture was distilled and extracted with chloroform and water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 66.5 g of compound o-2 (yield 72%, MS: [M+H]+ = 338).

[0170] 2) Preparation of chemical formula o-1 o-2 (66.5 g, 197.5 mmol) was added to 665 mL of chloroform and stirred. Then, phosphorus pentoxide (7.7 wt.% in methanesulfonic acid, Eaton's reagent, 112.1 g, 394.9 mmol) was added and stirred at 40 °C. After reacting for 7 hours, the mixture was cooled to room temperature and the organic layer was separated using chloroform, NaHCO3, and water. The organic layer was then washed twice with water and separated again. Anhydrous magnesium sulfate was added and the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound o-1 (yield 31%, MS: [M+H]+ = 320).

[0171] 3) Preparation of chemical formula o Using o-1 instead of a-1, the compound of the formula o was synthesized in the same manner as the compound of the formula a.

[0172] Manufacturing Example 17 [ka] 1) Preparation of chemical formula p-3 Compound p-3 was synthesized in the same manner as compound o-2, except that dibenzo[b,d]furan-1-ol was used instead of 7-chlorodibenzo[b,d]furan-1-ol.

[0173] 2) Preparation of chemical formula p-2 Compound p-2 of the chemical formula was synthesized in the same manner as in the preparation of compound o-1, except that compound p-3 was used instead of compound o-2.

[0174] 3) Preparation of chemical formula p-1 Under a nitrogen atmosphere, p-2 (30 g, 105.5 mmol) and N-bromosuccinimide (19.7 g, 110.8 mmol) were added to 600 mL of chloroform and stirred at room temperature. After 3 hours of reaction, the organic layer was separated using chloroform and water, and then anhydrous magnesium sulfate was added and stirred, followed by filtration. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.8 g of compound p-1 (yield 62%, MS: [M+H]+ = 364).

[0175] 4) Preparation of chemical formula p Compound p was synthesized in the same manner as compound a, except that compound p-1 was used instead of compound a-1.

[0176] Manufacturing Example 18 [ka] 1) Preparation of chemical formula q Compound q was synthesized in the same manner as compound o, except that 6-bromodibenzo[b,d]thiophen-1-ol was used instead of 7-chlorodibenzo[b,d]furan-1-ol and 2-bromo-1-(naphthalen-2-yl)ethan-1-one was used instead of 2-bromo-1-phenylethan-1-one.

[0177] Manufacturing Example 19 [ka] 1) Preparation of chemical formula r Compound r was synthesized in the same manner as compound o, except that dibenzo[b,d]furan-1-ol was used instead of 7-chlorodibenzo[b,d]furan-1-ol and 2-bromo-2-(4-chlorophenyl)-1-phenylethan-1-one was used instead of 2-bromo-1-phenylethan-1-one.

[0178] Manufacturing Example 20 [ka] 1) Preparation of chemical formula s Compound s was synthesized in the same manner as compound o, except that 4-chlorodibenzo[b,d]furan-1-ol was used instead of 7-chlorodibenzo[b,d]furan-1-ol and 2-bromo-1,2-diphenylethan-1-one was used instead of 2-bromo-1-phenylethan-1-one.

[0179] Manufacturing Example 21 [ka] 1) Preparation of chemical formula t Compound t was synthesized in the same manner as compound c, except that 2-bromo-4-chloro-1-fluorobenzene was used instead of 1-bromo-2-fluorobenzene and 2-phenylbenzofuran-6-ol was used instead of 6-chlorobenzofuran-5-ol.

[0180] <Synthesis Example> Synthesis of the compound represented by chemical formula 1 Synthesis Example 1 [ka] Under a nitrogen atmosphere, compound a (15 g, 44.9 mmol) and 9-bromo-10-phenylanthracene (15 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7 g of compound 1 (yield 34%, MS: [M+H]+ = 462).

[0181] Synthesis Example 2 [ka] Under a nitrogen atmosphere, compound b (15 g, 44.9 mmol) and 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene (18.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.8 g of compound 2 (49% yield, MS: [M+H]+ = 538).

[0182] Synthesis Example 3 [ka] Under a nitrogen atmosphere, compound c (15 g, 44.9 mmol) and 9-([1,1'-biphenyl]-2-yl)-10-bromoanthracene (18.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.9 g of compound 3 (yield 37%, MS: [M+H]+ = 538).

[0183] Synthesis Example 4 [ka] Under a nitrogen atmosphere, compound d (15 g, 44.9 mmol) and 2-(10-bromoanthracen-9-yl)dibenzo[b,d]furan (19 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 4 (50% yield, MS: [M+H]+ = 552).

[0184] Synthesis Example 5 [ka] Under a nitrogen atmosphere, compound e (15 g, 44.9 mmol) and 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene (18.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.6 g of compound 5 (40% yield, MS: [M+H]+ = 538).

[0185] Synthesis Example 6 [ka] Under a nitrogen atmosphere, compound f (15 g, 42.8 mmol) and 9-bromo-10-phenylanthracene (14.3 g, 42.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (23.7 g, 171.3 mmol) dissolved in 71 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.5 g, 1.3 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.8 g of compound 6 (48% yield, MS: [M+H]+ = 478).

[0186] Synthesis Example 7 [ka] Under a nitrogen atmosphere, compound g (15 g, 44.9 mmol) and 9-([1,1'-biphenyl]-2-yl)-10-bromoanthracene (18.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.4 g of compound 7 (39% yield, MS: [M+H]+ = 538).

[0187] Synthesis Example 8 [ka] Under a nitrogen atmosphere, compound h (15 g, 30.8 mmol) and 9-([1,1'-biphenyl]-2-yl)-10-bromoanthracene (12.6 g, 30.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (17 g, 123.4 mmol) dissolved in 51 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.4 g of compound 8 (35% yield, MS: [M+H]+ = 690).

[0188] Synthesis Example 9 [ka] Under a nitrogen atmosphere, compound i (15 g, 36.6 mmol) and 2-(10-bromoanthracen-9-yl)dibenzo[b,d]furan (15.5 g, 36.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.2 g, 146.2 mmol) dissolved in 61 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.4 g of compound 9 (41% yield, MS: [M+H]+ = 628).

[0189] Synthesis Example 10 [ka] Under a nitrogen atmosphere, compound i (15 g, 36.6 mmol) and 9-bromo-10-(phenyl-d5)anthracene-1,2,3,4,5,6,7,8-d8 (12.7 g, 36.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.2 g, 146.2 mmol) dissolved in 61 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 10 (yield 45%, MS: [M+H] + = 551).

[0190] Synthesis Example 11 [ka] Under a nitrogen atmosphere, compound j (15 g, 44.9 mmol) and 9-bromo-10-(naphthalen-2-yl)anthracene (17.2 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.7 g of compound 11 (yield 38%, MS: [M+H]+ = 512).

[0191] Synthesis Example 12 [ka] Under a nitrogen atmosphere, compound k (15 g, 44.9 mmol) and 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene (18.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.7 g of compound 12 (yield 36%, MS: [M+H]+ = 538).

[0192] Synthesis Example 13 [ka] Under a nitrogen atmosphere, compound l (15 g, 44.9 mmol) and 9-bromo-10-phenylanthracene-1,2,3,4,5,6,7,8-d8 (15.3 g, 44.9 mmol) were added to 300 mL of THF and stirred at reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.9 g of compound 13 (47% yield, MS: [M+H]+ = 470).

[0193] Synthesis Example 14 [ka] Under a nitrogen atmosphere, compound m (15 g, 44.9 mmol) and 2-(10-bromoanthracen-9-yl)dibenzo[b,d]furan (19 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 14 (50% yield, MS: [M+H]+ = 552).

[0194] Synthesis Example 15 [ka] Under a nitrogen atmosphere, compound n (15 g, 44.9 mmol) and 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene (18.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.8 g, 179.5 mmol) dissolved in 74 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.4 g of compound 15 (43% yield, MS: [M+H]+ = 538).

[0195] Synthesis Example 16 [ka] Under a nitrogen atmosphere, compound o (15 g, 36.6 mmol) and 9-bromo-10-phenylanthracene (12.2 g, 36.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.2 g, 146.2 mmol) dissolved in 61 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.4 g of compound 16 (43% yield, MS: [M+H]+ = 538).

[0196] Synthesis Example 17 [ka] Under a nitrogen atmosphere, compound p (15 g, 36.6 mmol) and 9-bromo-10-phenylanthracene (12.2 g, 36.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.2 g, 146.2 mmol) dissolved in 61 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 17 (yield 63%, MS: [M+H]+ = 538).

[0197] Synthesis Example 18 [ka] Under a nitrogen atmosphere, compound q (15 g, 31.5 mmol) and 9-bromo-10-phenylanthracene (10.5 g, 31.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (17.4 g, 125.9 mmol) dissolved in 52 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6 g of compound 18 (yield 61%, MS: [M+H]+ = 604).

[0198] Synthesis Example 19 [ka] Under a nitrogen atmosphere, compound r (15 g, 30.8 mmol) and 9-bromo-10-phenylanthracene (10.3 g, 30.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (17 g, 123.4 mmol) dissolved in 51 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.6 g of compound 19 (yield 51%, MS: [M+H]+ = 614).

[0199] Synthesis Example 20 [ka] Under a nitrogen atmosphere, compound s (15 g, 30.8 mmol) and 9-bromo-10-phenylanthracene (10.3 g, 30.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (17 g, 123.4 mmol) dissolved in 51 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.9 g of compound 20 (42% yield, MS: [M+H]+ = 614).

[0200] Synthesis Example 21 [ka] Under a nitrogen atmosphere, compound e (15 g, 44.9 mmol) and 9-bromo-10-phenylanthracene (15 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.6 g, 134.7 mmol) dissolved in 56 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.3 g of compound 21 (50% yield, MS: [M+H]+ = 461).

[0201] Synthesis Example 22 [ka] Under a nitrogen atmosphere, compound t (15 g, 36.6 mmol) and 9-bromo-10-(naphthalen-1-yl)anthracene (14 g, 36.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (15.2 g, 109.7 mmol) dissolved in 45 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 22 (yield 53%, MS: [M+H]+ = 587).

[0202] Synthesis Example 23 [ka] Under a nitrogen atmosphere, compound a (15 g, 44.9 mmol) and Int a (23 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.6 g, 134.7 mmol) dissolved in 56 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 23 (40% yield, MS: [M+H]+ = 641).

[0203] Synthesis Example 24 [ka] Under a nitrogen atmosphere, compound i (15 g, 36.6 mmol) and 9-(10-bromoanthracen-9-yl)naphtho[2,1-b]benzofuran (17.3 g, 36.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (15.2 g, 109.7 mmol) dissolved in 45 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 24 (44% yield, MS: [M+H]+ = 677).

[0204] Synthesis Example 25 [ka] Under a nitrogen atmosphere, compound m (15 g, 44.9 mmol) and Int m (23 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.6 g, 134.7 mmol) was then dissolved in 56 mL of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 6 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.1 g of compound 25 (49% yield, MS: [M+H]+ = 641).

[0205] Synthesis Example 26 [ka] Under a nitrogen atmosphere, compound f (15 g, 42.8 mmol) and Int f (22 g, 42.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (17.8 g, 128.5 mmol) was then dissolved in 53 mL of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.1 g of compound 26 (43% yield, MS: [M+H]+ = 657).

[0206] Synthesis Example 27 [ka] Under a nitrogen atmosphere, compound h (15 g, 30.8 mmol) and 1-(10-bromoanthracen-9-yl)naphtho[2,3-b]benzofuran (14.6 g, 30.8 mmol) were added to 300 mL of THF and stirred at reflux. Potassium carbonate (12.8 g, 92.5 mmol) dissolved in 38 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.2 g of compound 27 (44% yield, MS: [M+H]+ = 753).

[0207] Synthesis Example 28 [ka] Under a nitrogen atmosphere, compound i (15 g, 36.6 mmol) and 2-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8) naphtho[2,3-b]benzofuran (17.6 g, 36.6 mmol) were added to 300 mL of THF and stirred at reflux. Potassium carbonate (15.2 g, 109.7 mmol) dissolved in 45 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was then distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.8 g of compound 28 (yield 59%, MS: [M+H] + = 685).

[0208] Synthesis Example 29 [ka] Under a nitrogen atmosphere, compound n (15 g, 44.9 mmol) and Int n (23.4 g, 44.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.6 g, 134.7 mmol) was then dissolved in 56 mL of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.9 g of compound 29 (yield 58%, MS: [M+H]+ = 649).

[0209] Synthesis Example 30 [ka] Under a nitrogen atmosphere, compound q (15 g, 31.5 mmol) and 1-(10-bromoanthracen-9-yl)naphtho[2,3-b]benzofuran (14.9 g, 31.5 mmol) were added to 300 mL of THF and stirred at reflux. Potassium carbonate (13.1 g, 94.5 mmol) dissolved in 39 mL of water was then added. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. The mixture was then dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.5 g of compound 30 (45% yield, MS: [M+H]+ = 743).

[0210] <Example> Example 1 A glass substrate coated with a 150 nm thick indium tin oxide (ITO) thin film was placed in distilled water containing a detergent and ultrasonically cleaned. The detergent used was from Fischer Co., and the distilled water was filtered through a Millipore Co. filter. The ITO was washed for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water wash, the substrate was ultrasonically cleaned with a solvent consisting of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using nitrogen plasma for 5 minutes and then transferred to a vacuum evaporator. A hole injection layer (HIL) was formed on the prepared ITO transparent electrode by thermal vacuum deposition of the following HAT-CN compound to a thickness of 5 nm. Next, HTL1 was thermally vacuum deposited to a thickness of 100 nm, followed by thermal vacuum deposition of HTL2 to a thickness of 10 nm to form a hole transport layer. Next, Compound 1 as the host and BD-A as the dopant (weight ratio 95:5) were simultaneously vacuum-deposited to form a 20 nm thick light-emitting layer. Next, ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Next, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Next, aluminum was vacuum-deposited to a thickness of 100 nm to form a cathode, thereby fabricating an organic light-emitting device.

[0211] The structures of the compounds used in the examples are as follows: [ka]

[0212] Examples 1 to 30 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 in place of Compound 1 in the light emitting layer.

[0213] Comparative Examples 1 to 5 Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds shown in Table 1 below were used in the light-emitting layer instead of Compound 1. Compounds BH-A, BH-B, BH-C, BH-D, and BH-E used in Comparative Examples 1 to 5 in Table 1 below are as follows. [ka]

[0214] In the organic light-emitting devices manufactured in Examples 1 to 30 and Comparative Examples 1 to 5, the current was 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm. 2 The time (LT) required for the luminance to reach 95% of the initial luminance was measured at this current density, and the results are shown in Table 1 below.

[0215] [Table 1] [Table 1] [Table 2]

[0216] According to Table 1, the organic light-emitting devices of Examples 1 to 30 using the compound represented by Chemical Formula 1 of the present invention exhibited excellent properties in terms of efficiency, driving voltage, and / or stability. Specifically, Examples 1 to 30 exhibited lower voltage and / or higher efficiency properties than the organic light-emitting devices of Comparative Examples 1 to 5, and also exhibited longer lifespans than the organic light-emitting devices of Comparative Examples 1 to 5.

[0217] Furthermore, Examples 10, 13, 28, and 29 showed that deuterium substitution further improved the lifetime.

[0218] Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto and can be embodied in various modifications within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemical 319】 In the above Chemical Formula 1, R １ ~R ８ are the same or different and each independently represent hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; Ar １ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group containing O or S and having 2 to 30 carbon atoms, L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Q is any one of groups represented by the following chemical formula 2-1 and chemical formulas 2-3 to 2-6: [Chemical formula 2-1] 【Chem.320】 [Chemical formula 2-3] 【Chemistry 322】 [Chemical formula 2-4] 【Chemical 323】 [Chemical formula 2-5] 【Chemical 324】 [Chemical formula 2-6] 【Chemical 325】 In the chemical formula 2-1 and chemical formulas 2-3 to 2-6, X and Y are the same or different and each independently represent O or S; R ９ ~R １６ any one of the following is connected to L in Formula 1; R ９ ~R １６ The remaining groups not connected to L in Formula 1 may be the same or different and each independently represent hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

2. The R １ ~R ８ The compound of claim 1 , wherein: are the same or different from each other and are each independently hydrogen; or deuterium.

3. The Ar １ is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group, The compound according to claim 1, wherein the substituted or unsubstituted group means that the compound is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms, or the one or more adjacent substituents are bonded to each other to form a ring.

4. 2. The compound of claim 1, wherein L is a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted naphthylene group.

5. The compound according to claim 1, wherein the chemical formula 2-1 is any one of the following chemical formulas 2-1-A to 2-1-D: [Chemical formula 2-1-A] 【Chemistry 326】 [Chemical formula 2-1-B] 【Chemistry 327】 [Chemical formula 2-1-C] 【Chemical 328】 [Chemical formula 2-1-D] 【Chemistry 329】 In the chemical formulas 2-1-A to 2-1-D, R ９ ~R １６ is the same as defined in the above chemical formulas 2-1 to 2-6.

6. The compound according to claim 1, wherein the chemical formula 2-3 is any one of the following chemical formulas 2-3-A to 2-3-D: [Chemical formula 2-3-A] 【Chemistry 334】 [Chemical formula 2-3-B] 【Chemistry 335】 [Chemical formula 2-3-C] 【Chemistry 336】 [Chemical formula 2-3-D] 【Chemistry 337】 In the chemical formulas 2-3-A to 2-3-D, R ９ ~R １６ is the same as defined in the above chemical formulas 2-1 to 2-6.

7. The compound according to claim 1, wherein the chemical formula 2-4 is any one of the following chemical formulas 2-4-A to 2-4-D: [Chemical formula 2-4-A] 【Chemical 338】 [Chemical formula 2-4-B] 【Chemistry 339】 [Chemical formula 2-4-C] 【Chemistry 340】 [Chemical formula 2-4-D] 【Chemistry 341】 In the chemical formulas 2-4-A to 2-4-D, R ９ ~R １６ is the same as defined in the above chemical formulas 2-1 to 2-6.

8. The compound according to claim 1, wherein the chemical formula 2-5 is any one of the following chemical formulas 2-5-A to 2-5-D: [Chemical formula 2-5-A] 【Chemistry 342】 [Chemical formula 2-5-B] 【Transformation 343】 [Chemical formula 2-5-C] 【Transformation 344】 [Chemical formula 2-5-D] 【Chemistry 345】 In the chemical formulas 2-5-A to 2-5-D, R ９ ~R １６ is the same as defined in the above chemical formulas 2-1 to 2-6.

9. The compound according to claim 1, wherein the chemical formula 2-6 is any one of the following chemical formulas 2-6-A to 2-6-D: [Chemical formula 2-6-A] 【Transformation 346】 [Chemical formula 2-6-B] 【Transformation 347】 [Chemical formula 2-6-C] 【Transformation 348】 [Chemical formula 2-6-D] 【Chemistry 349】 In the chemical formulas 2-6-A to 2-6-D, R ９ ~R １６ is the same as defined in the above chemical formulas 2-1 to 2-6.

10. The R ９ ~R １６ the remaining groups not connected to L in Formula 1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group; The compound according to claim 1, wherein the substituted or unsubstituted group means that the compound is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms, or the one or more adjacent substituents are bonded to each other to form a ring.

11. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds: [Chemical 350] 【Chemistry 351】 【Chemistry 352】 【Chemistry 353】 【Chemistry 354】 【Chemical 355】 【Transformation 356】 【Chemistry 357】 【Chemical 358】 【Chemistry 359】 【Chemical 360】 【Chemical 361】 【Chemical 362】 【Chemical 363】 【Chemical 364】 【Chemical 365】 【Chemical 366】 【Chemical 367】 【Chemical 368】 【Chemical 369】 【Chemistry 370】 【Chemistry 371】 【Chemistry 372】 【Chemistry 373】 【Chemistry 374】 【Chemistry 375】 【Transformation 376】 【Chemical 377】 【Chemistry 378】 【Chemistry 379】 【Chemical 380】 【Chemistry 381】 【Chemistry 382】 【Chemistry 383】 【Chemical 384】 【Chem.385】 【Chemical 386】 【Chemistry 387】 【Chemical 388】 【Chem.389】 【Chemical 390】 【Chemistry 391】 【Chemistry 392】 【Chemistry 393】 【Chem. 394】 【Chemical 395】 【Chemistry 396】 【Chemistry 397】 【Chem.398】 【Chem.399】 【Chemical 400】 【Chemical 401】 【Chemical 402】 【Chemical 403】 【Chemical 404】 【Chemical 405】 【Chemical 406】 【Chemical 407】 【Chemical 408】 【Chemical 409】 【Chemical 410】 【Chemical 411】 【Chemical 412】 【Chemical 413】 【Chemical 414】 【Chemical 415】 【Chemical 416】 【Chemical 417】 【Chemical 418】 【Chemical 419】 【Chem.420】 【Chemistry 421】 【Chemistry 422】 【Chemistry 423】 【Chemistry 424】 【Chemical 425】 【Chemistry 426】 【Chemistry 427】 【Chemical 428】 【Chemistry 429】 【Chemistry 430】 【Chemistry 431】 【Chemistry 432】 【Chemistry 433】 【Chemistry 434】 【Chemical 435】 【Chemistry 436】 【Chemistry 437】 【Chemistry 438】 【Chemistry 439】 【Chemical 440】 【Chemistry 441】 【Chemistry 442】 【Chemistry 443】 【Chemistry 444】 【Chemistry 445】 【Chemistry 446】 【Chemistry 447】 【Chemistry 448】 【Chemistry 449】 [Chemical 450] 【Chemistry 451】 【Chemistry 452】 【Chemistry 453】 【Chemical 454】 【Chemistry 455】 【Chemistry 456】 【Chemistry 457】 【Chemistry 458】 【Chemistry 459】 【Chemical Formula 460】 【Chemistry 461】 【Chemistry 462】 【Chemical 463】 【Chemical 464】 【Chemical 465】 【Chemical 466】 【Chemistry 467】 【Chemical 468】 【Chemistry 469】 【Chemical 470】 【Chemistry 471】 【Chemistry 472】 【Chemistry 473】 【Chemistry 474】 【Chemistry 475】 【Chemistry 476】 【Chemistry 477】 【Chemistry 478】 【Chemistry 479】 【Chemical 480】 【Chemistry 481】 【Chemistry 482】 【Chemistry 483】 【Chem.484】 【Chemistry 485】 【Chemical 486】 【Chemistry 487】 【Chemical 488】 【Chemistry 489】 【Chemistry 490】 【Chemistry 491】 【Chemistry 492】 【Chemistry 493】 【Chem.494】 【Chemical 495】 【Chemistry 496】 【Chemistry 497】 【Chem.498】 【Chem.499】 [500] 【Chemical 501】 【Chemical 502】 【Chemical 503】 【Chemical 504】 【Chemical 505】 【Chemical 506】 【Chemical 507】 【Chemical 508】 【Chemical 509】 【Chemical 510】 【Chemical 511】 【Chemical 512】 【Chemical Formula 513】 【Chemical Formula 514】 【Chemical 515】 【Chemical 516】 【Chemical 517】 【Chemical 518】 【Chemical 519】 【Chemical 520】 【Chem.521】 【Chemical 522】 【Chemical 523】 【Chemical Formula 524】 【Chemical 525】 【Chemical 526】 【Chemical Formula 527】 【Chemical Formula 528】 【Chemical 529】 【Chemical 530】 【Chemistry 531】 【Chemical 532】 【Chemical 533】 【Chemistry 534】 【Chemical Formula 535】 【Chemical 536】 【Chemical 537】 【Chemical 538】 【Chemical Formula 539】 【Chemical 540】 【Chemistry 541】 【Chemistry 542】 【Chemistry 543】 【Chemical 544】 【Chemical 545】 【Chemical 546】 。

12. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite 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 11.

13. The organic light-emitting device according to claim 12 , wherein the organic layer comprises one or more of a hole transport layer, a hole injection layer, a light-emitting layer, an electron injection layer, and an electron transport layer, and the one or more layers comprise the compound.

14. the organic layer includes a light-emitting layer, The organic light-emitting device according to claim 13 , wherein the light-emitting layer comprises the compound.

15. The organic light-emitting device of claim 14 , wherein the light-emitting layer comprises the compound as a blue host.

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