Compound and organic light-emitting device including 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 phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons combine, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[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] An object of the present specification is to provide a compound and an organic light-emitting device including the same. [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 represents 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 represents 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 Ar1 and R 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] 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. Effect 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 the compound of at least one embodiment of the embodiments presented herein 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, the hole injection layer, the electron transport layer, the electron injection layer, and the light emitting layer, it is possible to obtain the effects of lowering the driving voltage of the device, increasing the efficiency of the device, and / or increasing the life of the device.

[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 description of the drawings]

[0011] [Figure 1] 1 shows an example of an organic light-emitting device according to the present invention. [Diagram 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 PREFERRED EMBODIMENTS

[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 specifically stated to the contrary.

[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 that the group is substituted with one or more substituents selected from the group consisting of deuterium (-D); halogen group; cyano group (-CN); silyl group; boron group; amine group; alkyl group; alkenyl group; alkynyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclic group, or is substituted with a substituent in which two or more of the above-mentioned exemplified substituents are linked, or has no substituents. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be interpreted as an aryl group, or as a substituent in which two phenyl groups are linked.

[0020] Examples of the substituents in the present specification will be 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 wherein 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 the present 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, a phenyl boron group, and the like.

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

[0025] As used herein, an 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, an 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 group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the above-mentioned alkyl group.Specifically, the alkylthioxy group includes methylthioxy group, ethylthioxy group, tert-butylthioxy group, hexylthioxy group, and octylthioxy group, and the alkylsulfoxy group includes, but is not limited to, methylsulfoxy group, ethylsulfoxy group, propylsulfoxy group, and 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 is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, and 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 is preferably 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 of the alkoxy group is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 40. Specific examples of the alkoxy group 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 substituents containing alkyl moieties described herein include either straight or branched chain groups.

[0034] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to 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 the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, there are exemplified, but not limited to, a phenyl group, a biphenyl group, and a terphenyl group. As the polycyclic aryl group, there are exemplified, but 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, a fluorenyl group may be optionally 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 act as an arylalkyl group. The alkyl group may be selected from the examples given above.

[0039] In this specification, a heterocyclic group is a ring containing one or more non-carbon atoms, heteroatoms, 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 a monocyclic or polycyclic ring, an aromatic, aliphatic, or aromatic and aliphatic fused ring, and may be selected from the examples of heteroaryl groups below.

[0040] In the present specification, a heteroaryl group is an aryl group containing one or more of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of 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 is defined in the same way as the alkyl group described above, except that the alkylene group is a divalent group.

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

[0043] In this specification, the cycloalkylene group is defined in the same way as the above cycloalkyl group, except that it is a divalent group.

[0044] In this specification, the cycloalkenylene group is defined in the same way as the above cycloalkenyl group, except that it is a divalent group.

[0045] In this specification, the arylene group is defined in the same manner as the aryl group, except that the arylene group is a divalent group.

[0046] In this specification, the heteroarylene group is defined in the same manner 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 represents 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 represents 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 Ar1 and R 15 If any one of the above is an unsubstituted phenyl group, the remaining 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. 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 Ar1 and R 15 If any one of them is an unsubstituted phenyl group, the remaining one cannot be an unsubstituted phenyl group.

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

[0049] When the compound of the present invention is used in at least one layer of the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer, and the light emitting layer, it is possible to obtain the effects of lowering the driving voltage of the device, increasing the efficiency of the device, and / or increasing the life of the device.

[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, wherein 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, wherein 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, wherein 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, wherein 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, 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 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, and the substituted or unsubstituted group 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, and the substituted or unsubstituted group 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, compounds are provided 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, compounds are provided 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 above 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 above 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 above 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 above 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 above 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 above-mentioned Chemical Formula 1, L is a direct bond, Q is the above-mentioned Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R16 When any one of Ar1 and R 15 If any one of Ar1 and R 15 the remaining (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 above-mentioned Chemical Formula 1, L is a direct bond, Q is the above-mentioned Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar1 and R 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 above-mentioned Chemical Formula 1, L is a direct bond, Q is the above-mentioned Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar1 and R 15 If any one of the above 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 group 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 may be bonded to each other to form a ring.

[0077] According to one embodiment of the present specification, in the above-mentioned Chemical Formula 1, L is a direct bond, Q is the above-mentioned Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R16 When any one of Ar1 and R 15 If any one of the above 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 group 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 above-mentioned Chemical Formula 1, L is a direct bond, Q is the above-mentioned Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar1 and R 15 If any one of the above 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 group 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 above-mentioned Chemical Formula 1, L is a direct bond, Q is the above-mentioned Chemical Formula 2-2, X and Y are both O, and R9 to R 14 and R 16 When any one of Ar1 and R 15If any one of the above 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 group 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 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 are each independently 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 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 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 16the 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 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 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 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, where 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 16the remaining groups not linked to L in Chemical Formula 1 are the same or different from one another 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, where 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 the remaining groups not linked to L in Chemical Formula 1 are the same or different from one another 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, where 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 16the remaining groups not linked to L in Chemical Formula 1 are the same or different from one another 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, where 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 formula 1 may be represented by any one of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0090] The compounds according to the above-described embodiments have stable forms in both oxidized and reduced states, and have high luminescence efficiency in converting excitons into light when they are formed.

[0091] In addition, when the compound of the present invention is used in at least one layer of the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer, and the light 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 lowered 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] In addition, in the present specification, a compound having unique properties can be synthesized by introducing a heterocyclic group (Q) containing two O or S into the anthracene core as described above. Specifically, by introducing into the core structure a substituent that is mainly used in a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, and the like used in the manufacture of an organic light emitting device, a material that satisfies the conditions required for each organic layer can be synthesized.

[0095] In particular, in the present 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 the present specification, the above-mentioned core structure allows the synthesis of compounds having various energy band gaps. In addition, in the present invention, the HOMO and LUMO energy levels of the compounds can be adjusted by introducing various substituents into the above-mentioned core structure.

[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 layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of the above-mentioned embodiments.

[0098] The organic light-emitting device according to the above-described embodiment has a stable form 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 effect 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 manufacturing method and material for an organic light-emitting device, except that one or more organic layers or light-emitting layers are formed using the above-mentioned compounds.

[0100] In manufacturing an organic light emitting device, the compound may be formed in an organic layer or an emission layer by a solution coating method as well as a vacuum deposition method, 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 layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers or a larger number of organic 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, in which the organic 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 form 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 effect 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 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 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 layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1 above.

[0109] According to one 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 one 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] As another example, the organic 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] As 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. 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 one 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, which includes the compound represented by Chemical Formula 1 as a dopant for 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 contains 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 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 be used together with an iridium (Ir) dopant.

[0117] In another example, the organic 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 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 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 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 Formula 1 and a 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 Formula 1 and a 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 Formula 1 and a 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 inhibiting 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 inhibition 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 inhibition layer / light emitting layer / hole inhibition layer / electron injection and transport layer / cathode

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

[0130] 1 illustrates a structure of an organic light-emitting device in which an anode 2, an organic 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 included in the organic layer 3.

[0131] For example, the organic light emitting device according to the present invention may be fabricated by depositing a metal or 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, forming an 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), a light emitting 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 organic layer. In addition to this method, an organic light emitting device may 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, a light emitting layer, and an electron transport layer, etc. Also, the organic layer may be manufactured into a smaller number of layers using various polymer materials by a solvent process, such as spin coating, dip coating, doctor blade, screen printing, inkjet printing, or thermal transfer, instead of a deposition method.

[0133] The anode is an electrode that injects holes, and the anode material is preferably a material with a large work function so that holes can be easily injected 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 SnO2: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 the cathode material is preferably a material with a small work function so that electrons can be easily injected 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 materials with a multilayer structure such as LiF / Al or LiO2 / Al.

[0135] The hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that smoothly receives the injection of holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[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 the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, it is advantageous in that the thickness of the hole injection layer is too thick to improve the mobility of holes, and it is advantageous in that the driving voltage can be prevented from increasing.

[0137] An electron inhibiting layer may be provided between the hole transport layer and the light emitting layer. The electron inhibiting layer is a layer that 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, and may be made of the compound of Chemical 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, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene groups, rubrene, and the like.

[0139] The host material of the light-emitting layer may be a condensed aromatic ring derivative or a heterocyclic ring-containing compound, etc. Specifically, the condensed aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocyclic ring-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc.

[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 substance such as (4,6-F2ppy)2Irpic, or a fluorescent substance such as spiro-DPVBi, spiro-6P, distyrubenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, or a PPV-based polymer.

[0141] A hole-blocking layer may be provided between the electron transport layer and the light-emitting layer, and 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-injection layer.Specific examples of hole-blocking materials include, but are not limited to, triazine derivatives, phenanthroline derivatives, BCP, etc., 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 that has high mobility for electrons. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex, 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, there is an advantage that the deterioration of the electron transport properties can be prevented, and when the thickness is 50 nm or less, there is an advantage that the increase in driving voltage due to the electron transport layer being too thick to improve the mobility of electrons can be prevented.

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

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

[0146] The organic light emitting device according to the present invention may be of the top emission type, bottom emission type or double emitting type depending on the materials used. EXAMPLES

[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 interpreted 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 having average knowledge 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 (100g, 580.1mmol) and 4-bromo-5-fluorobenzofuran (124.7g, 580.1mmol) were added to 2000ml of THF and stirred and refluxed. Then, potassium carbonate (320.7g, 2320.6mmol) was dissolved in 962ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (20.1g, 17.4mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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. Then, potassium carbonate (168.4 g, 1218.7 mmol) was added and stirred. After reacting for 1 hour, it was cooled to room temperature, and 2.5 L of water was poured in to solidify and then filtered. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 1,4-dioxane 1380 ml. Then, potassium acetate (41.9 g, 426.5 mmol) was added and thoroughly stirred, after which bis(dibenzylideneacetone)palladium(0) (4.9 g, 8.5 mmol) and tricyclohexylphosphine (4.8 g, 17.1 mmol) were added. The mixture was reacted for 7 hours, cooled to room temperature, and the organic layer was separated using chloroform and water, and then the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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] Production Example 3 [ka] 1) Preparation of chemical formula c-2 Under a nitrogen atmosphere, 1-bromo-2-fluorobenzene (60g, 342.9mmol) and 6-chlorobenzofuran-5-ol (57.8g, 342.9mmol) were added to 1200ml of DMAC and refluxed and stirred. Then, potassium carbonate (142.2g, 1028.6mmol) was added and stirred. After reacting for 1 hour, it was cooled to room temperature, solidified by pouring in 2.5L of water, and filtered. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 75.4g 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, it was cooled to room temperature, and 1.5 L of water was poured in to solidify and then filtered. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 Compound c was synthesized in the same manner as compound a, except that compound c-1 was used instead of compound a-1.

[0155] Production 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 of chemical formula a-1.

[0157] 3) Preparation of chemical formula d-1 In a nitrogen atmosphere, d-2 (30 g, 144.1 mmol) was added to 600 ml of dichloromethane and stirred at -10°C. Then, bromine (25.3 g, 158.5 mmol) was gradually added dropwise and stirred for 1 hour. After the reaction was completed, the organic layer was distilled after extraction with chloroform, Na2S2O3, and water, and then dissolved in ethanol again. The organic layer was added dropwise to 300 ml of ethanol solution saturated with KOH at 10°C, and then refluxed for 2 hours to react. After completion, the ethanol was distilled and extracted with ethyl acetate and brine, anhydrous magnesium sulfate was added to the organic layer, stirred, filtered, and 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 Compound d was synthesized in the same manner as compound a, except that compound d-1 was used instead of compound a-1.

[0159] Production 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] Production Example 7 [ka] 1) Preparation of chemical formula f Chemical formula f was synthesized in the same manner as the preparation method of chemical formula 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] Production Example 8 [ka] 1) Preparation of chemical formula g Compound g 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-7-fluorobenzofuran was used instead of 4-bromo-5-fluorobenzofuran.

[0162] Production Example 9 [ka] 1) Preparation of chemical formula H Chemical formula H was synthesized in the same manner as in the preparation of 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 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 Chemical formula k was synthesized in the same manner as the preparation method of chemical formula 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 I 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 (60g, 274.4mmol) and 2-bromo-1-phenylethan-1-one (54.6g, 274.4mmol) were added to 600ml of acetone and stirred. Then, potassium carbonate (56.9g, 411.6mmol) was added and stirred. After reacting for 9 hours, the mixture was distilled and extracted with chloroform and water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 66.5g of compound o-2 (yield 72%, MS: [M+H]+=338).

[0170] 2) Preparation of chemical formula o-1 o-2 (66.5g, 197.5mmol) was added to 665ml of chloroform and stirred. Then, phosphorus pentoxide, 7.7wt.% in methanesulfonic acid (Eaton's reagent, 112.1g, 394.9mmol) was added and stirred at 40℃. After reacting for 7 hours, it was cooled to room temperature, and the organic layer was separated using chloroform, NaHCO3, and water, washed twice with water, and the organic layer was separated again, 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 19.5g of compound o-1 (yield 31%, MS: [M+H]+=320).

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

[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 Using p-3 instead of o-2, p-2 was synthesized in the same manner as in the preparation of o-1.

[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 reacting for 3 hours, the organic layer was separated using chloroform and water, and then anhydrous magnesium sulfate was added and stirred, followed by filtration, and 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 a similar manner to 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 a similar manner to 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 a similar manner to 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 Chemical formula t was synthesized in the same manner as in the preparation of chemical formula 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, then filtered, and 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] In 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.8 g of compound 2 (yield 49%, 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 4 (yield 50%, 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.6 g of compound 5 (yield 40%, 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 and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.5 g, 1.3 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.8 g of compound 6 (yield 48%, 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.4 g of compound 7 (yield 39%, 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 and refluxed. Then, potassium carbonate (17 g, 123.4 mmol) was dissolved in 51 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.4 g of compound 8 (yield 35%, 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 and refluxed. Then, potassium carbonate (20.2 g, 146.2 mmol) was dissolved in 61 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.4 g of compound 9 (yield 41%, MS: [M+H]+=628).

[0189] Synthesis Example 10 [ka] In 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 and refluxed. Then, potassium carbonate (20.2 g, 146.2 mmol) was dissolved in 61 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 10 (yield 45%, MS: [M+H]+=551).

[0190] Synthesis Example 11 [ka] In 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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] In 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, then filtered, and 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 (yield 47%, 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 14 (yield 50%, 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 and refluxed. Then, potassium carbonate (24.8 g, 179.5 mmol) was dissolved in 74 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.3 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.4 g of compound 15 (yield 43%, 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 and refluxed. Then, potassium carbonate (20.2 g, 146.2 mmol) was dissolved in 61 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.4 g of compound 16 (yield 43%, 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 and refluxed. Then, potassium carbonate (20.2 g, 146.2 mmol) was dissolved in 61 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (17.4 g, 125.9 mmol) was dissolved in 52 mL of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (17 g, 123.4 mmol) was dissolved in 51 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (17 g, 123.4 mmol) was dissolved in 51 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.9 g of compound 20 (yield 42%, 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 and refluxed. Then, potassium carbonate (18.6 g, 134.7 mmol) was dissolved in 56 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.3 g of compound 21 (yield 50%, MS: [M+H]+ = 461).

[0201] Synthesis Example 22 [ka] Under a nitrogen atmosphere, compound t (15 g, 36.6 mmol) and 9-bromo-10-(naphthalene-1-yl)anthracene (14 g, 36.6 mmol) were added to 300 ml of THF and stirred and refluxed. Then, potassium carbonate (15.2 g, 109.7 mmol) was dissolved in 45 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (18.6 g, 134.7 mmol) was dissolved in 56 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 23 (yield 40%, 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 and refluxed. Then, potassium carbonate (15.2 g, 109.7 mmol) was dissolved in 45 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 24 (yield 44%, MS: [M+H]+=677).

[0204] Synthesis Example 25 [ka] Compound m (15 g, 44.9 mmol) and Int m (23 g, 44.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.6 g, 134.7 mmol) was dissolved in 56 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 6 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.1 g of compound 25 (yield 49%, 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 and refluxed. Then, potassium carbonate (17.8 g, 128.5 mmol) was dissolved in 53 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.1 g of compound 26 (yield 43%, 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 and refluxed. Then, potassium carbonate (12.8 g, 92.5 mmol) was dissolved in 38 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.2 g of compound 27 (yield 44%, MS: [M+H]+=753).

[0207] Synthesis Example 28 [ka] In 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 and refluxed. Then, potassium carbonate (15.2 g, 109.7 mmol) was dissolved in 45 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic layer and aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (18.6 g, 134.7 mmol) was dissolved in 56 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was 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 and refluxed. Then, potassium carbonate (13.1 g, 94.5 mmol) was dissolved in 39 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.5 g of compound 30 (yield 45%, MS: [M+H]+=743).

[0210] <Example> Example 1 A glass substrate coated with a 150 nm-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent dissolved therein and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was distilled water that had been filtered a second time with a Millipore Co. filter. The ITO was washed for 30 minutes, and then ultrasonically washed twice with distilled water for 10 minutes. After the distilled water washing was completed, the substrate was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was also washed for 5 minutes using nitrogen plasma, and then transferred to a vacuum evaporator. The following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm on the ITO transparent electrode thus prepared to form a hole injection layer. Next, HTL1 was thermally vacuum deposited to a thickness of 100 nm, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer. Next, the 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 manufacturing 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 compound shown in Table 1 below was used in place of Compound 1 in the light emitting layer.

[0213] Comparative Examples 1 to 5 An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used as the light-emitting layer instead of Compound 1 in Example 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, 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 lifetime properties than the organic light-emitting devices of Comparative Examples 1 to 5.

[0217] Moreover, the above-mentioned Examples 10, 13, 28, and 29 showed that the lifetime was further improved by deuterium substitution.

[0218] Although the preferred embodiment of the present invention has 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 belong to 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; a 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; 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 groups represented by the following chemical formulas 2-1 to 2-6: [Chemical formula 2-1] 【Chemistry 320】 [Chemical formula 2-2] 【Chemistry 321】 [Chemical formula 2-3] 【Chemistry 322】 [Chemical formula 2-4] 【Chemistry 323】 [Chemical formula 2-5] 【Chemical 324】 [Chemical formula 2-6] 【Chemistry 325】 In the above Chemical Formulas 2-1 to 2-6, X and Y are the same or different and each independently represents O; or S; R ９ ~R １６ is linked to L in Formula 1; 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; halogen; cyano group; silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group; wherein, in Formula 1, L is a direct bond, Q is Formula 2-2, X and Y are both O, and R ９ ~R １４ and R １６ When any one of the following is linked to L in Formula 1, Ar １ and R 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.

2. The R １ ~R ８ 4. The compound of claim 1, wherein: are the same or different and each independently is hydrogen; or deuterium.

3. The Ar １ The compound according to claim 1, wherein 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.

4. 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 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.

5. The compound according to claim 1, wherein L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

6. 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.

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

8. The compound according to claim 1, wherein the formula 2-2 is any one of the following formulas 2-2-A to 2-2-D: [Chemical formula 2-2-A] 【Chemistry 330】 [Chemical formula 2-2-B] 【Chemistry 331】 [Chemical formula 2-2-C] 【Chemical 332】 [Chemical formula 2-2-D] 【Chemical 333】 In the above chemical formulas 2-2-A to 2-2-D, R ９ ~R １６ is the same as defined in Chemical Formulas 2-1 to 2-6.

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

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

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

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

13. In the formula 1, L is a direct bond, Q is the formula 2-2, X and Y are both O, and R ９ ~R １４ and R １６ When any one of the following is linked to L in Formula 1, Ar １ and R 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; The compound according to claim 1, wherein the substituted or unsubstituted 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.

14. The R ９ ~R １６ The remaining groups not linked to L in Chemical Formula 1 are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

15. 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; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group; The compound according to claim 14, wherein the substituted or unsubstituted 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.

16. The compound according to claim 1 , wherein the formula 1 is represented by any one of the following compounds: 【Chemistry 350】 【Chemistry 351】 【Chemistry 352】 【Chemical 353】 【Chemical 354】 【Chemistry 355】 【Chemical Formula 356】 【Chemical 357】 【Chemical 358】 【Chemical 359】 【Hua360】 【Chemistry 361】 【Chemical 362】 【Chemistry 363】 【Hua364】 【Chemistry 365】 【Chemistry 366】 【Chemical 367】 【Chemistry 368】 【Chemical 369】 【Hua370】 【Chemical 371】 【Chemical 372】 【Chemical 373】 【Chemical 374】 【Chemical 375】 【Chemical 376】 【Chemical 377】 【Chemical 378】 【Chemical 379】 【Hua380】 【Chemistry 381】 【Chemical 382】 【Chemical 383】 【Chemical 384】 【Chemistry 385】 【Chemistry 386】 【Chemical 387】 【Chemistry 388】 【Chemical 389】 【Chemical 390】 【Chemical 391】 【Chemical 392】 【Chemical 393】 【Chemical 394】 【Chemical 395】 【Chemical 396】 【Chemical 397】 【Chemical 398】 【Chemical 399】 【Chemical 400】 【Chemistry 401】 【Chemistry 402】 【Chemistry 403】 【Chemistry 404】 【Chemistry 405】 【Chemistry 406】 【Chemistry 407】 【Chemistry 408】 【Chemistry 409】 【Chemistry 410】 【Chemistry 411】 【Chemistry 412】 【Chemistry 413】 【Chemistry 414】 【Chemistry 415】 【Chemistry 416】 【Chemistry 417】 【Chemistry 418】 【Chemistry 419】 【Chemistry 420】 【Chemistry 421】 【Chemistry 422】 【Chemistry 423】 【Chemistry 424】 【Chemistry 425】 【Chemistry 426】 【Chemistry 427】 【Chemistry 428】 【Chemistry 429】 【Chemistry 430】 【Chemistry 431】 【Chemistry 432】 【Chemistry 433】 【Chemical 434】 【Chemistry 435】 【Chemistry 436】 【Chemistry 437】 【Chemistry 438】 【Chemistry 439】 【Chemistry 440】 【Chemistry 441】 【Chemical 442】 【Chemical 443】 【Chemical 444】 【Chemistry 445】 【Chemical 446】 【Chemical 447】 【Chemistry 448】 【Chemical 449】 【Chemical 450】 【Chemistry 451】 【Chemistry 452】 【Chemistry 453】 【Chemistry 454】 【Chemistry 455】 【Chemistry 456】 【Chemistry 457】 【Chemistry 458】 【Chemistry 459】 【Chemistry 460】 【Chemistry 461】 【Chemistry 462】 【Chemistry 463】 【Chemistry 464】 【Chemistry 465】 【Chemistry 466】 【Chemistry 467】 【Chemistry 468】 【Chemistry 469】 【Chemistry 470】 【Chemistry 471】 【Chemistry 472】 【Chemistry 473】 【Chemical 474】 【Chemistry 475】 【Chemistry 476】 【Chemistry 477】 【Chemistry 478】 【Chemical 479】 【Chemistry 480】 【Chemistry 481】 【Chemistry 482】 【Chemistry 483】 【Chemistry 484】 【Chemistry 485】 【Chemistry 486】 【Chemistry 487】 【Chemistry 488】 【Chemistry 489】 【Chemistry 490】 【Chemistry 491】 【Chemistry 492】 【Chemistry 493】 【Chemistry 494】 【Chemistry 495】 【Chemistry 496】 【Chemistry 497】 【Chemistry 498】 【Chemistry 499】 【Chemical 500】 【Chemistry 501】 【Chemistry 502】 【Chemistry 503】 【Chemistry 504】 【Chemistry 505】 【Chemistry 506】 【Chemistry 507】 【Chemistry 508】 【Chemistry 509】 【Chemistry 510】 【Chemistry 511】 【Chemistry 512】 【Chemistry 513】 【Chemistry 514】 【Chemistry 515】 【Chemistry 516】 【Chemistry 517】 【Chemistry 518】 【Chemistry 519】 【Chemistry 520】 【Chemistry 521】 【Chemistry 522】 【Chemistry 523】 【Chemistry 524】 【Chemistry 525】 【Chemistry 526】 【Chemistry 527】 【Chemistry 528】 【Chemistry 529】 【Chemistry 530】 【Chemistry 531】 【Chemistry 532】 【Chemistry 533】 【Chemical 534】 【Chemistry 535】 【Chemistry 536】 【Chemistry 537】 【Chemistry 538】 【Chemistry 539】 【Chemistry 540】 【Chemistry 541】 【Chemical Formula 542】 【Chemistry 543】 【Chemical 544】 【Chemistry 545】 【Chemical 546】 【Chemical 547】 【Chemistry 548】 【Chemical 549】 【Chemistry 550】 【Chemistry 551】 【Chemistry 552】 【Chemistry 553】 【Chemical 554】 【Chemistry 555】 【Chemistry 556】 【Chemistry 557】 【Chemistry 558】 【Chemical 559】 【Chemistry 560】 【Chemistry 561】 【Chemical 562】 【Chemistry 563】 【Chemistry 564】 【Chemistry 565】 【Chemistry 566】 【Chemistry 567】 【Chemistry 568】 【Chemical 569】 【Chemistry 570】 【Chemistry 571】 【Chemistry 572】 。

17. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 16.

18. The organic light-emitting device according to claim 17 , 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.

19. the organic layer includes a light-emitting layer, The organic light-emitting device according to claim 18 , wherein the light-emitting layer comprises the compound.

20. The organic light-emitting device of claim 19 , wherein the light-emitting layer comprises the compound as a blue host.

Images