Compounds and organic light emitting devices comprising the same

Abstract

The present specification provides a compound of Chemical Formula 1 and an organic light emitting device comprising 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 priority to Korean Patent Application No. 10-2020-0155403, filed on November 19, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein. BACKGROUND

[0003] Generally, an organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using an organic substance. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including an anode and a cathode and an organic layer between them. Here, in order to improve efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different substances, respectively, for example, can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when the excitons recombine to the ground state, light is emitted.

[0004] In order to improve the performance, lifespan, or efficiency of the organic light emitting device as described above, there is a continuous demand for development of new materials. SUMMARY

[0005] Technical Problem

[0006] The present specification relates to a compound and an organic light emitting device including the same.

[0007] Solution to Problem

[0008] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above Chemical Formula 1,

[0012] R1and R2are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group,

[0013] R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0014] a is an integer of 0 to 4, and when a is 2 or more, 2 or more of R3are the same as or different from each other,

[0015] b is an integer of 0 to 2, and when b is 2, R4are the same as or different from each other,

[0016] L1to L4are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0017] Ar3is a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0018] Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a group represented by the following Chemical Formula 2, and at least one of Ar1and Ar2is a group represented by the following Chemical Formula 2,

[0019] [Chemical Formula 2]

[0020]

[0021] In the above Chemical Formula 2,

[0022] R5is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0023] c is an integer of 0 to 3, and when c is 2 or more, 2 or more of R5are the same as or different from each other.

[0024] In addition, an embodiment of the present specification provides an organic light emitting device including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers include the compound.

[0025] Effects of the Invention

[0026] The compound described in the present specification can be used as a material for an organic layer of an organic light emitting device. In the production of an organic light emitting device containing the compound according to an embodiment of the present application, an organic light emitting device having excellent luminous efficiency, low driving voltage, high efficiency, and long lifetime can be obtained.

[0027] In particular, when the compound of the present application is used for a hole injection layer, a hole transport layer, or an electron blocking layer, the driving voltage of the device is reduced, and an effect of increasing the efficiency and lengthening the lifetime of the device can be obtained. BRIEF DESCRIPTION OF DRAWINGS

[0028] Fig. 1 An example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is shown.

[0029] Fig. 2 An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 is shown.

[0030] Fig. 3 An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, a hole blocking layer 10, a layer 11 which simultaneously performs electron transport and electron injection, and a cathode 4 is shown.

[0031] [SYMBOL EXPLANATION]

[0032] 1: Substrate

[0033] 2: Anode

[0034] 3: Light emitting layer

[0035] 4: Cathode

[0036] 5: Hole injection layer

[0037] 6: Hole transport layer

[0038] 7: Light emitting layer

[0039] 8: Electron transport layer

[0040] 9: Electron blocking layer

[0041] 10: Hole blocking layer

[0042] 11: Layer which simultaneously performs electron transport and electron injection DETAILED DESCRIPTION

[0043] Hereinafter, the present specification will be described in more detail.

[0044] The present specification provides a compound represented by the following Chemical Formula 1. The compound represented by the following Chemical Formula 1 can adjust the energy barrier with each organic layer by substituting an amine group at the 2nd position of fluorene, substituting at least one of Ar1 and Ar2 with a group represented by Chemical Formula 2, and having a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, etc. as a substituent at the 3rd position of fluorene, thereby adjusting the HOMO and LUMO energy levels of the compound.

[0045] In the present specification, when a certain part is referred to as being "on" another part, it can include the case where the certain part is directly on the other part and the case where another part is interposed therebetween.

[0046] In the present specification, when a certain part "comprises / comprises" a certain component, unless specifically described otherwise, it means that it can further include another component, rather than excluding another component.

[0047] In the present specification, the phrase "combination thereof" included in the expression of Markush form means a mixture or a combination of one or more selected from the components described in the expression of Markush form, and means to include one or more selected from the above components.

[0048] Hereinafter, the substituents of the present specification will be explained in detail, but are not limited thereto.

[0049] In the present specification, represents a site to be combined with another substituent or a bonding part.

[0050] In the present specification, the above-mentioned term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents can be the same as or different from each other.

[0051] In the present specification, the term "substituted or unsubstituted" means that it is substituted with one or more substituents selected from deuterium, a halogen group, a nitro group, a nitrile group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an arylalkyl group, an arylalkenyl group, an aryloxy group, a silyl group, an aryl group, and a heteroaryl group, or is substituted with a substituent formed by linking two or more substituents selected from the above-mentioned exemplary substituents, or is not substituted with any substituent.

[0052] In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0053] In the present specification, the above-mentioned alkyl group can be linear, branched, or cyclic, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 50. According to one embodiment, the number of carbon atoms of the above-mentioned alkyl group is from 1 to 40. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is from 1 to 10. As specific examples of the alkyl group, there are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, iso-hexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0054] In the present specification, the above-mentioned alkenyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 40. According to one embodiment, the number of carbon atoms of the above-mentioned alkenyl group is from 2 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is from 2 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is from 2 to 6. As specific examples, there are ethenyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butanedienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphen-1-yl)ethen-1-yl, stilbenyl, styryl, and the like, but are not limited thereto.

[0055] In the present specification, the above-mentioned cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having a number of carbon atoms of from 3 to 60, and according to one embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is from 3 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is from 3 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is from 3 to 6. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like, but are not limited thereto.

[0056] In the present specification, the above-mentioned alkoxy group can be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably from 1 to 40. Specifically, it can be methoxy group, ethoxy group, n-propoxy group, isopropoxy group, isopropyl-oxy group, n-butoxy group, isobutoxy group, t-butoxy group, sec-butoxy group, n-pentoxy group, neopentoxy group, isopentoxy group, n-hexyloxy group, 3,3-dimethylbutoxy group, 2-ethylbutoxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group, and the like, but is not limited thereto.

[0057] The alkyl group, alkoxy group, and substituents containing an alkyl moiety other than the above described in the present specification include both linear and branched forms.

[0058] In the present specification, the amine group can be selected from -NH2, monoalkylamine group, dialkylamine group, N-alkylarylamine group, monoarylamine group, diarylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, monoheteroarylamine group, and diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 30. As specific examples of the amine group, there are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthrylamine group, 9-methyl-anthrylamine group, diphenylamine group, ditolylamine group, N-tolylphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrylamine group, N-biphenylphenanthrylamine group, N-phenylfluorenylamine group, N-phenyltrisbiphenylamine group, N-phenanthrylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

[0059] In the present specification, the silyl group can be represented by the chemical formula of -SiY a Y b Y c , the above-mentioned Y a , Y b , and Y c each can be hydrogen, substituted or unsubstituted alkyl group, or substituted or unsubstituted aryl group. The above-mentioned silyl group specifically has trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyl dimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like, but is not limited thereto.

[0060] In the present specification, an aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and can be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group described above has 6 to 30 carbon atoms. According to one embodiment, the aryl group described above has 6 to 20 carbon atoms. As the monocyclic aryl group, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, or the like can be given, but is not limited thereto. As the polycyclic aryl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenyl group, a fluorenyl group, a triphenylenyl group, or the like can be given, but is not limited thereto.

[0061] In the present specification, the fluorenyl group described above can be substituted, and two substituents can be combined with each other to form a spiro structure.

[0062] In the case where the fluorenyl group described above is substituted, a fluorenyl group substituted with a spirofluorenyl group, and a spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group, or the like can be given, but is not limited thereto.

[0063] The aryl group described above can be substituted with an alkyl group to function as an arylalkyl group. The alkyl group described above can be selected from the examples described above.

[0064] In the present specification, a heteroaryl group is an aromatic ring group containing one or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms can contain one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group described above has 2 to 30 carbon atoms. The heteroaryl group can be monocyclic or polycyclic. As examples of the heteroaryl group, a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, a dioxazolyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, a quinolyl group, a quinazolyl group, a carbazolyl group, a benz oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a phenanthroline group, an iso azolyl group, a thiadiazolyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, or the like can be given, but is not limited thereto.

[0065] In the present specification, an arylene group refers to a group having two bonding sites on an aryl group, i.e., a divalent group. They can be applied to the description of the aryl group described above except that each is a divalent group.

[0066] In the present specification, heteroarylene means a group having two bonding sites, i.e., a divalent group, to a heteroaryl group. They can apply the above description of the heteroaryl group except that each is a divalent group.

[0067] In one embodiment of the present specification, R1and R2are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 40, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 40, a substituted or unsubstituted alkoxy group having a carbon atom number of 1 to 40, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60.

[0068] In one embodiment of the present specification, R1and R2are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 20, a substituted or unsubstituted alkoxy group having a carbon atom number of 1 to 20, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30.

[0069] In one embodiment of the present specification, R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30.

[0070] In one embodiment of the present specification, R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.

[0071] In one embodiment of the present specification, R1and R2are the same as or different from each other, and each is independently a methyl group or a phenyl group.

[0072] In one embodiment of the present specification, the compound represented by Chemical Formula 1 can be represented by Chemical Formula 1-1 or 1-2 below.

[0073] [Chemical Formula 1-1]

[0074]

[0075] [Chemical Formula 1-2]

[0076]

[0077] In Chemical Formula 1-1 or Chemical Formula 1-2 above,

[0078] R3, R4, Ar1to Ar3, L1to L4, a, and b are the same as the definitions in Chemical Formula 1 above,

[0079] R6and R7are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group,

[0080] R8and R9are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0081] d and e are integers of 0 to 5, and when d and e are 2 or more, two or more of R8and R9are the same as or different from each other.

[0082] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group.

[0083] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0084] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having a carbon number of 1 to 50.

[0085] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having a carbon number of 1 to 20.

[0086] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen, or an alkyl group having a carbon number of 1 to 10.

[0087] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen or a methyl group.

[0088] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen or a methyl group.

[0089] In one embodiment of the present specification, R6and R7are the same as or different from each other, and each independently hydrogen or a methyl group.

[0090] In one embodiment of the present specification, R8and R9are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having a carbon number of 1 to 40, a substituted or unsubstituted alkenyl group having a carbon number of 2 to 40, a substituted or unsubstituted aryl group having a carbon number of 6 to 60, or a substituted or unsubstituted heteroaryl group having a carbon number of 2 to 60.

[0091] In one embodiment of the present specification, the above R8and R9are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30.

[0092] In one embodiment of the present specification, the above R8and R9are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30.

[0093] In one embodiment of the present specification, the above R8and R9are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30.

[0094] In one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 40, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 40, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60.

[0095] In one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0096] In one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0097] In one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0098] In one embodiment of the present specification, the above a is an integer of 0 to 4, and when the above a is 2 or more, 2 or more R3are the same as or different from each other, respectively.

[0099] In one embodiment of the present specification, the above R3is hydrogen, and the above a is 4.

[0100] In one embodiment of the present specification, the above b is an integer of 0 to 2, and when the above b is 2, 2 R4are the same as or different from each other, respectively.

[0101] In one embodiment of the present specification, the above R4is hydrogen, and the above b is 2.

[0102] In one embodiment of the present specification, the above L1to L4are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having a carbon atom number of 6 to 60.

[0103] In one embodiment of the present specification, the aforementioned L1to L4are the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0104] In one embodiment of the present specification, the aforementioned L1is a direct bond, or a substituted or unsubstituted phenylene group.

[0105] In one embodiment of the present specification, the aforementioned L1is a direct bond or a phenylene group.

[0106] In one embodiment of the present specification, the aforementioned L1is a direct bond.

[0107] In one embodiment of the present specification, the aforementioned L2to L4are the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0108] In one embodiment of the present specification, the aforementioned L2to L4are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted fluorenylene group.

[0109] In one embodiment of the present specification, the aforementioned L2to L4are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0110] In one embodiment of the present specification, the aforementioned L2to L4are the same as or different from each other, and each is independently a direct bond, a phenylene group, or a biphenylene group.

[0111] In one embodiment of the present specification, the aforementioned Ar3is a substituted or unsubstituted amine group having 1 to 30 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.

[0112] In one embodiment of the present specification, the aforementioned Ar3is a substituted or unsubstituted diarylamine group, 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.

[0113] In one embodiment of the present specification, the aforementioned Ar3is a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0114] In one embodiment of the present specification, the above-described Ar3 is a diphenylamine group, a phenyl group substituted with or without a butyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0115] In one embodiment of the present specification, the above-described Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 40, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 40, a substituted or unsubstituted cycloalkyl group having a carbon atom number of 3 to 60, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60, or a group represented by the above-described Chemical Formula 2, at least one of the above-described Ar1 and Ar2 being the group represented by the above-described Chemical Formula 2.

[0116] In one embodiment of the present specification, the above-described Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 20, a substituted or unsubstituted cycloalkyl group having a carbon atom number of 3 to 30, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30, or a group represented by the above-described Chemical Formula 2, at least one of the above-described Ar1 and Ar2 being the group represented by the above-described Chemical Formula 2.

[0117] In one embodiment of the present specification, the above-described Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 20, a substituted or unsubstituted cycloalkyl group having a carbon atom number of 3 to 30, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30, or a group represented by the above-described Chemical Formula 2, at least one of the above-described Ar1 and Ar2 being the group represented by the above-described Chemical Formula 2.

[0118] In one embodiment of the present specification, the above-described Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 20, a substituted or unsubstituted cycloalkyl group having a carbon atom number of 3 to 30, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30, or a group represented by the above-described Chemical Formula 2, at least one of the above-described Ar1 and Ar2 being the group represented by the above-described Chemical Formula 2.

[0119] In an embodiment of the present specification, the above R5is hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.

[0120] In an embodiment of the present specification, the above R5is hydrogen or deuterium.

[0121] In an embodiment of the present specification, the above R5is hydrogen.

[0122] In an embodiment of the present specification, the above R5is hydrogen, and the above c is 3.

[0123] In an embodiment of the present specification, the above compound of Chemical Formula 1 can be represented by any one of the following compounds.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The compound of Chemical Formula 1 of the present specification can be manufactured to have a core structure as in the following reaction formula. The kind, position, or number of substituents can be changed according to techniques known in the art.

[0171] <Reaction Formula 1>

[0172]

[0173] <Reaction Formula 2>

[0174]

[0175] In the above Reaction Formulas 1 and 2, R1 to R5, Ar1 to Ar3, L1 to L4, a, b, c, and d have the same definitions as those in Chemical Formulas 1 and 2 described above.

[0176] In the above Reaction Formulas 1 and 2, X and Y can be halogen groups such as Cl, Br, and I.

[0177] In the present specification, by introducing various substituents into the core structure as described above, compounds having various energy band gaps can be synthesized. In addition, in the present application, by introducing various substituents into the core structure of the structure as described above, the HOMO and LUMO energy levels of the compound can also be adjusted.

[0178] In addition, by introducing various substituents into the core structure of the structure as described above, compounds having inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in a hole injection layer material, a hole transport material, an electron suppression material, a light emitting layer material, and an electron transport layer material used in the manufacture of an organic light emitting device into the above core structure, a material satisfying the required conditions in each organic layer can be synthesized.

[0179] In addition, the organic light emitting device according to the present specification is characterized by comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers comprising the compound represented by Chemical Formula 1 mentioned above.

[0180] The organic light emitting device of the present specification forms one or more organic layers using the above compound, and can be manufactured using the manufacturing method and materials of a general organic light emitting device, except for this.

[0181] The above compound can be used not only in a vacuum evaporation method but also in a solution coating method to form an organic layer in the production of an organic light emitting device. Here, the solution coating method refers to a spin coating method, a dip coating method, an inkjet printing method, a screen printing method, a spray method, a roll coating method, and the like, but is not limited thereto.

[0182] The organic layer of the organic light emitting device of the present specification can be formed of a single layer structure or a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present specification can have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron blocking layer, a light emitting layer, an electron transport layer, and an electron injection layer, a layer that simultaneously performs electron transport and electron injection, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller or larger number of organic layers.

[0183] In the organic light emitting device of the present specification, the above organic layer can include an electron transport layer or an electron injection layer, and the above electron transport layer or electron injection layer can include the above-mentioned compound.

[0184] In the organic light emitting device of the present specification, the above organic layer can include a hole injection layer or a hole transport layer, and the above hole injection layer or hole transport layer can include the above-mentioned compound.

[0185] In the organic light emitting device of the present specification, the above organic layer includes a light emitting layer, and the above light emitting layer includes the above-mentioned compound.

[0186] According to another embodiment, the above organic layer includes a light emitting layer, and the above light emitting layer can include the above-mentioned compound as a dopant of the light emitting layer.

[0187] In another embodiment, the above organic layer includes a light emitting layer, and the above light emitting layer includes the above-mentioned compound as a dopant of the light emitting layer, and can include a host.

[0188] In another embodiment, the above organic layer includes a light emitting layer, and the above light emitting layer includes the above-mentioned compound as a dopant of the light emitting layer, and includes a fluorescent host or a phosphorescent host, and can include another organic compound, a metal, or a metal compound as a dopant.

[0189] As another example, the above organic layer includes a light emitting layer, and the above light emitting layer includes the above-mentioned compound as a dopant of the light emitting layer, and includes a fluorescent host or a phosphorescent host, and can be used together with an iridium (Ir) dopant.

[0190] According to another embodiment, the above organic layer includes a light emitting layer, and the above light emitting layer can include the above-mentioned compound as a host of the light emitting layer.

[0191] As another example, the organic layer described above includes a light-emitting layer, and the light-emitting layer contains the compound described above as a host of the light-emitting layer, and can further contain a dopant.

[0192] In the organic light-emitting device of the present specification, the organic layer described above includes an electron-blocking layer, and the electron-blocking layer can contain the compound described above.

[0193] In an embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0194] According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0195] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited thereto.

[0196] (1) anode / hole-transporting layer / light-emitting layer / cathode

[0197] (2) anode / hole-injecting layer / hole-transporting layer / light-emitting layer / cathode

[0198] (3) anode / hole-transporting layer / light-emitting layer / electron-transporting layer / cathode

[0199] (4) anode / hole-transporting layer / light-emitting layer / electron-transporting layer / electron-injecting layer / cathode

[0200] (5) anode / hole-injecting layer / hole-transporting layer / light-emitting layer / electron-transporting layer / cathode

[0201] (6) anode / hole-injecting layer / hole-transporting layer / light-emitting layer / electron-transporting layer / electron-injecting layer / cathode

[0202] (7) anode / hole-transporting layer / electron-blocking layer / light-emitting layer / electron-transporting layer / cathode

[0203] (8) anode / hole-transporting layer / electron-blocking layer / light-emitting layer / electron-transporting layer / electron-injecting layer / cathode

[0204] (9) anode / hole-injecting layer / hole-transporting layer / electron-blocking layer / light-emitting layer / electron-transporting layer / cathode

[0205] (10) anode / hole-injecting layer / hole-transporting layer / electron-blocking layer / light-emitting layer / electron-transporting layer / electron-injecting layer / cathode

[0206] (11) anode / hole-transporting layer / light-emitting layer / hole-blocking layer / electron-transporting layer / cathode

[0207] (12) anode / hole-transporting layer / light-emitting layer / hole-blocking layer / electron-transporting layer / electron-injecting layer / cathode

[0208] (13) anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0209] (14) anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0210] (15) anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / layer simultaneously functioning as electron transport and electron injection / cathode

[0211] The structure of the organic light-emitting device of the present specification can have a structure as shown in Figs. 1 to 3 but is not limited thereto.

[0212] Fig. 1 A structure of an organic light-emitting device in which an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1 is exemplified in the present specification. In the structure as described above, the above compound can be contained in the above light-emitting layer 3.

[0213] Fig. 2 A structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1 is exemplified in the present specification. In the structure as described above, the above compound can be contained in the above hole injection layer 5, hole transport layer 6, light-emitting layer 7, or electron transport layer 8.

[0214] Fig. 3 A structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, a hole blocking layer 10, a layer simultaneously functioning as electron transport and electron injection 11, and a cathode 4 are sequentially stacked on a substrate 1 is exemplified in the present specification. In the structure as described above, the above compound can be contained in the above hole transport layer 6 or electron blocking layer 9.

[0215] For example, the organic light-emitting device according to the present specification can be manufactured by forming an anode by evaporating a metal or a metal oxide having conductivity or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, a hole blocking layer, and a layer simultaneously functioning as electron transport and electron injection on the anode, and thereafter evaporating a substance usable as a cathode on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0216] The organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a hole blocking layer, a layer that simultaneously performs electron injection and electron transport, an emission layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs hole injection and hole transport, and the like, but is not limited thereto, and can be a single layer structure. In addition, the organic layer can be formed in a smaller number of layers using various polymer materials and by a solvent process other than an evaporation method, such as a spin coating method, a dip coating method, a doctor blade method, a screen printing method, an inkjet printing method, or a thermal transfer method.

[0217] The anode is an electrode that injects holes, and as an anode material, a material having a large work function is generally preferred in order to smoothly inject holes into the organic layer. As specific examples of the anode material that can be used in the present application, there are metals such as vanadium, chromium, copper, zinc, gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.

[0218] The cathode is an electrode that injects electrons, and as a cathode material, a material having a small work function is generally preferred in order to easily inject electrons into the organic layer. As specific examples of the cathode material, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0219] The hole injection layer is a layer that functions to smoothly inject holes from the anode to the emission layer, and the hole injection material is a material that can receive holes from the anode well at a low voltage, and preferably 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 layer. As specific examples of the hole injection material, there are metal porphyrine, oligothiophene, arylamine-based organic material, hexacene hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0220] The hole-transporting layer described above can function to smoothly transport holes. The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer them to the light-emitting layer, and a substance having a large mobility of holes is suitable. As specific examples, there are arylamine-based organic compounds, electrically conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but the present application is not limited thereto.

[0221] The electron-blocking layer described above is a layer that is formed on the hole-transporting layer, is preferably provided in contact with the light-emitting layer, and functions to improve the efficiency of the organic light-emitting device by adjusting the mobility of holes, preventing the excessive transfer of electrons, and increasing the probability of combination between holes and electrons. The electron-blocking layer contains an electron-blocking substance, and as examples of such an electron-blocking substance, a compound represented by Chemical Formula 1 described above, or an arylamine-based organic compound, etc. can be used, but the present application is not limited thereto.

[0222] The light-emitting layer described above can emit red, green, or blue light, and can be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having a high quantum efficiency for fluorescence or phosphorescence. When the organic light-emitting device includes another light-emitting layer in addition to the light-emitting layer containing the compound represented by Chemical Formula 1 described above, the other light-emitting layer can emit red, green, or blue light, and can be formed of a phosphorescent substance or a fluorescent substance. As specific examples, there are 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benz azoles, benzothiazoles, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but the present application is not limited thereto.

[0223] As the host material of the light-emitting layer, there are aromatic condensed ring derivatives or heterocycle-containing compounds, etc. Specifically, as the aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocycle-containing compounds, there are carbazole derivatives, diphenylfuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but the present application is not limited thereto.

[0224] ​A hole-blocking layer can be provided between the above-described electron-transporting layer and the light-emitting layer, and the hole-blocking layer is a layer that prevents holes from reaching the cathode, and can be formed using the same conditions as the hole-injecting layer. Specifically, as a hole-blocking substance, there are triazine derivatives, phenanthroline derivatives, and the like, but the application is not limited thereto, and a material known in the art can be used.

[0225] The above-described electron-transporting layer can function to smoothly transport electrons. The electron-transporting substance is a substance that can receive electrons from the cathode and transfer them to the light-emitting layer, and a substance having a large mobility of electrons is suitable. As specific examples, there are 8-hydroxyquinoline Al complexes, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, and the like, but the application is not limited thereto.

[0226] The above-described electron-injecting layer can function to smoothly inject electrons. As an electron-injecting substance, a compound having the ability to transport electrons, having the effect of injecting electrons from the cathode, having an excellent electron-injecting effect on the light-emitting layer or the light-emitting material, preventing the migration of excitons generated in the light-emitting layer to the hole-injecting layer, and having excellent film-forming ability is preferred. Specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but the application is not limited thereto.

[0227] As the above-described metal complex compound, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinoline) chloride, gallium bis(2-methyl-8-quinoline)(o-cresol), aluminum bis(2-methyl-8-quinoline)(o-naphthol), gallium bis(2-methyl-8-quinoline)(2-naphthol), and the like, but the application is not limited thereto.

[0228] The organic light-emitting device according to the present application can be a top emission type, a bottom emission type, or a bidirectional emission type, depending on the material used.

[0229] Hereinafter, in order to specifically describe the present specification, experimental examples will be cited to explain in detail. However, the embodiments according to the present specification can be variously modified, and are not construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.

[0230] Mode for carrying out the invention

[0231] <synthesis example>

[0232] Synthesis Example 1. Synthesis of Compound 1

[0233] Step 1) Synthesis of Compound 1-A

[0234]

[0235] After adding toluene (400 ml) to 9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (50.0 g, 175.20 mmol), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (46.81 g, 175.20 mmol), and sodium tert-butoxide (NaOtBu, 23.57 g, 245.28 mmol), it was stirred for 10 minutes with heating. After adding 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride (Pd(dppf)Cl2, 0.64 g, 0.88 mmol) dissolved in toluene (30 ml) to the above mixture, it was stirred for 1 hour with heating. After the reaction was completed and filtered, it was subjected to layer separation with chloroform and water. After removing the solvent, it was recrystallized with ethyl acetate, thereby obtaining the above compound 1-A (64.0 g, yield 77.44%).

[0236] Step 2) Synthesis of Compound 1

[0237]

[0238] After adding toluene (200 ml) to the compound 1-A (20.0 g, 42.40 mmol) obtained in Step 1 of the above synthesis example 1, 4-bromo-1,1'-biphenyl (10.08 g, 43.25 mmol), and sodium tert-butoxide (5.70 g, 59.36 mmol), it was stirred for 10 minutes with heating. After adding bis(tri-tert-butylphosphine)palladium (BTP, 0.11 g, 0.21 mmol) dissolved in toluene (20 ml) to the above mixture, it was stirred for 1 hour with heating. After the reaction was completed and filtered, it was subjected to layer separation with toluene and water. After removing the solvent, it was recrystallized with ethyl acetate, thereby obtaining the above compound 1 (20.5 g, yield 77.50%). + = 624)

[0239] Synthesis Example 2. Synthesis of Compound 2

[0240]

[0241] Using compound 1-A (20.0 g, 42.40 mmol) obtained in step 1 of the above synthetic example 1 and 1-(4-bromophenyl)naphthalen-2-ol (12.25 g, 43.25 mmol), the above compound 2 (22.0 g, yield 76.99%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 674)

[0242] Synthetic example 3. Synthesis of compound 3

[0243]

[0244] Using compound 1-A (20.0 g, 42.40 mmol) obtained in step 1 of the above synthetic example 1 and 2-bromo-9,9-dimethyl-9H-fluorene (11.81 g, 43.25 mmol), the above compound 3 (21.5 g, yield 76.37%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 664)

[0245] Synthetic example 4. Synthesis of compound 4

[0246]

[0247] Using compound 1-A (20.0 g, 42.40 mmol) obtained in step 1 of the above synthetic example 1 and 4-bromodibenzo[b,d]furan (10.69 g, 43.25 mmol), the above compound 4 (20.8 g, yield 76.91%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 638)

[0248] Synthetic example 5. Synthesis of compound 5

[0249]

[0250] Using N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (20.0 g, 45.70 mmol) and 6-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (13.93 g, 46.62 mmol), the above compound 5 (25.2 g, yield 78.78%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 700)

[0251] Synthetic example 6. Synthesis of compound 6

[0252] Step 1) Synthesis of compound 6-A

[0253]

[0254] Using 3-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 138.32 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (36.96 g, 138.32 mmol), the above compound 6-A (59.5 g, yield 78.53%) was obtained by the same method as that of Step 1 of the above Synthesis Example 1.

[0255] Step 2) Synthesis of compound 6

[0256]

[0257] Using the compound 6-A (20.0 g, 36.51 mmol) obtained in Step 1 of the above Synthesis Example 6 and 4-bromo-1,1'-biphenyl (8.68 g, 37.24 mmol), the above compound 6 (20.0 g, yield 78.26%) was obtained by the same method as that of Step 2 of the above Synthesis Example 1. (MS [M+H] + = 700)

[0258] Synthesis Example 7. Synthesis of compound 7

[0259] Step 1) Synthesis of compound 7-A

[0260]

[0261] Using 3-(dibenzo[b,d]furan-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 133.17 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (35.58 g, 133.17 mmol), the above compound 7-A (58.0 g, yield 77.53%) was obtained by the same method as that of Step 1 of the above Synthesis Example 1.

[0262] Step 2) Synthesis of compound 7

[0263]

[0264] Using the compound 7-A (20.0 g, 35.60 mmol) obtained in Step 1 of the above Synthesis Example 7 and 4-bromo-1,1'-biphenyl (8.47 g, 36.31 mmol), the above compound 7 (19.8 g, yield 77.90%) was obtained by the same method as that of Step 2 of the above Synthesis Example 1. (MS [M+H] + = 714)

[0265] Synthesis of compound 8

[0266] Step 1) Synthesis of compound 8-A

[0267]

[0268] Using 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 110.47 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (29.52 g, 110.47 mmol), the above compound 8-A (56.0 g, yield 79.34%) was obtained by the same method as step 1 of the above synthesis example 1.

[0269] Step 2) Synthesis of compound 8

[0270]

[0271] Using the compound 8-A (20.0 g, 31.30 mmol) obtained in step 1 of the above synthesis example 8 and 4-bromo-1,1'-biphenyl (7.44 g, 31.93 mmol), the above compound 8 (19.5 g, yield 78.85%) was obtained by the same method as step 2 of the above synthesis example 1.(MS [M+H] + = 791)

[0272] Synthesis of compound 9

[0273]

[0274] After adding sodium tert-butoxide (14.14 g, 147.17 mmol) to 9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (15.0 g, 52.56 mmol), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (28.79 g, 107.75 mmol) and xylene (200 ml), it was heated and stirred for 10 minutes. After adding bis(tri-tert-butylphosphine)palladium (0.21 g, 0.42 mmol) dissolved in xylene (20 ml) to the above mixture, it was heated and stirred for 1 hour. After the reaction was completed and filtered, it was subjected to layer separation with toluene and water. After removing the solvent, it was recrystallized with ethyl acetate, thereby obtaining the above compound 9 (27.0 g, yield 78.07%).(MS [M+H] + = 658)

[0275] Synthesis of compound 10

[0276]

[0277] Using 9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (15.0 g, 52.56 mmol) and 6-(4- chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (32.20 g, 107.75 mmol), the above compound 10 (33.0 g, yield 77.50%) was obtained by the same method as Synthetic Example 9 described above. (MS [M+H] + = 810)

[0278] Synthetic Example 11. Synthesis of Compound 11

[0279]

[0280] Using 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (15.0 g, 33.14 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (18.15 g, 67.94 mmol), the above compound 11 (21.5 g, yield 78.62%) was obtained by the same method as Synthetic Example 9 described above. (MS [M+H] + = 825)

[0281] Synthetic Example 12. Synthesis of Compound 12

[0282]

[0283] Using 3-(4-(9H-carbazol-9-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (15.0 g, 33.32 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (18.25 g, 68.30 mmol), the above compound 12 (21.0 g, yield 76.56%) was obtained by the same method as Synthetic Example 9 described above. (MS [M+H] + = 823)

[0284] Synthetic Example 13. Synthesis of Compound 13

[0285]

[0286] Using N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (20.0 g, 45.70 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (12.46 g, 46.62 mmol), the above compound 13 (22.0 g, yield 77.16%) was obtained by the same method as Step 2 of Synthetic Example 1 described above. (MS [M+H] + = 624)

[0287] Synthesis of compound 14

[0288] Step 1) Synthesis of compound 14-A

[0289]

[0290] Using 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 110.47 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (29.52 g, 110.47 mmol), the above compound 14-A (55.0 g, yield 77.93%) was obtained by the same method as step 1 of the above synthesis example 1.

[0291] Step 2) Synthesis of compound 14

[0292]

[0293] Using the compound 14-A (20.0 g, 31.30 mmol) obtained in step 1 of the above synthesis example 14 and 4-bromo-1,1'-biphenyl (7.44 g, 31.93 mmol), the above compound 14 (19.0 g, yield 76.73%) was obtained by the same method as step 2 of the above synthesis example 1. (MS [M+H] + = 791)

[0294] Synthesis of compound 15

[0295]

[0296] Using 9,9-dimethyl-3-phenyl-9H-fluoren-2-amine (15.0 g, 52.56 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (28.79 g, 107.75 mmol), the above compound 15 (26.5 g, yield 76.63%) was obtained by the same method as the above synthesis example 9. (MS [M+H] + = 658)

[0297] Synthesis of compound 16

[0298]

[0299] The above compound 16 (21.0 g, yield 76.79%) was obtained by the same method as synthetic example 9 described above, using 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (15.0 g, 33.14 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (18.15 g, 67.94 mmol). + = 825)

[0300] Synthesis example 17. Synthesis of compound 17

[0301] Step 1) Synthesis of compound 17-A

[0302]

[0303] The above compound 17-A (58.0 g, yield 79.73%) was obtained by the same method as step 1 of synthetic example 1 described above, using 3,9,9-triphenyl-9H-fluoren-2-amine (50.0 g, 122.09 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (32.62 g, 122.09 mmol).

[0304] Step 2) Synthesis of compound 17

[0305]

[0306] The above compound 17 (20.0 g, yield 79.65%) was obtained by the same method as step 2 of synthetic example 1 described above, using the compound 17-A (20.0 g, 33.57 mmol) obtained in step 1 of synthetic example 17 described above and 4-bromo-1,1'-biphenyl (7.98 g, 34.24 mmol).(MS [M+H] + = 748)

[0307] Synthesis example 18. Synthesis of compound 18

[0308]

[0309] The above compound 18 (20.8 g, yield 77.64%) was obtained by the same method as step 2 of synthetic example 1 described above, using the compound 17-A (20.0 g, 33.57 mmol) obtained in step 1 of synthetic example 17 described above and 1-(4-bromophenyl)naphthalene (9.70 g, 34.24 mmol).(MS [M+H] + = 798)

[0310] Synthesis example 19. Synthesis of compound 19

[0311]

[0312] Using compound 17-A (20.0 g, 33.57 mmol) obtained in step 1 of the above synthetic example 17 and 2-bromo-9,9-dimethyl-9H-fluorene (9.35 g, 34.24 mmol), the above compound 19 (20.2 g, yield 76.35%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 788)

[0313] Synthetic example 20. Synthesis of compound 20

[0314]

[0315] Using compound 17-A (20.0 g, 33.57 mmol) obtained in step 1 of the above synthetic example 17 and 4-bromodibenzo[b,d]furan (8.46 g, 34.24 mmol), the above compound 20 (19.8 g, yield 77.40%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 762)

[0316] Synthetic example 21. Synthesis of compound 21

[0317]

[0318] Using N-([1,1'-biphenyl]-4-yl)-3,9,9-triphenyl-9H-fluoren-2-amine (20.0 g, 35.60 mmol) and 6-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10.85 g, 36.32 mmol), the above compound 21 (23.0 g, yield 78.89%) was obtained by the same method as that of step 2 of the above synthetic example 1. (MS [M+H] + = 824)

[0319] Synthetic example 22. Synthesis of compound 22

[0320] Step 1) Synthesis of compound 22-A

[0321]

[0322] Using 3,9,9-triphenyl-9H-fluoren-2-amine (50.0 g, 122.09 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (33.35 g, 122.09 mmol), the above compound 22-A (58.0 g, yield 78.94%) was obtained by the same method as that of step 1 of the above synthetic example 1.

[0323] Step 2) Synthesis of compound 22

[0324]

[0325] Using compound 22-A (20.0 g, 33.23 mmol) obtained in step 1 of the above synthetic example 22 and 6-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10.13 g, 33.90 mmol), the above compound 22 (22.0 g, yield 76.61%) was obtained by the same method as step 2 of the above synthetic example 1. (MS [M+H] + = 864)

[0326] Synthetic example 23. Synthesis of compound 23

[0327] Step 1) Synthesis of compound 23-A

[0328]

[0329] Using 3-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-9H-fluoren-2-amine (50.0 g, 102.96 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (27.51 g, 102.96 mmol), the above compound 23-A (54.0 g, yield 78.06%) was obtained by the same method as step 1 of the above synthetic example 1.

[0330] Step 2) Synthesis of compound 23

[0331]

[0332] Using compound 23-A (20.0 g, 29.77 mmol) obtained in step 1 of the above synthetic example 23 and 4-bromo-1,1'-biphenyl (7.08 g, 30.36 mmol), the above compound 23 (19.0 g, yield 77.44%) was obtained by the same method as step 2 of the above synthetic example 1. (MS [M+H] + = 824)

[0333] Synthetic example 24. Synthesis of compound 24

[0334] Step 1) Synthesis of compound 24-A

[0335]

[0336] Using 3-(dibenzo[b,d]furan-4-yl)-9,9-diphenyl-9H-fluoren-2-amine (50.0 g, 100.08 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (26.74 g, 100.08 mmol), the above compound 24-A (54.0 g, yield 78.66%) was obtained by the same method as step 1 of the above synthesis example 1.

[0337] Step 2) Synthesis of compound 24

[0338]

[0339] Using the compound 24-A (20.0 g, 29.16 mmol) obtained in step 1 of the above synthesis example 24 and 4-bromo-1,1'-biphenyl (6.93 g, 29.74 mmol), the above compound 24 (19.5 g, yield 79.79%) was obtained by the same method as step 2 of the above synthesis example 1. (MS [M+H] + = 838)

[0340] Synthesis example 25. Synthesis of compound 25

[0341] Step 1) Synthesis of compound 25-A

[0342]

[0343] Using 3-(4-(diphenylamino)phenyl)-9,9-diphenyl-9H-fluoren-2-amine (50.0 g, 86.69 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (23.17 g, 86.69 mmol), the above compound 25-A (52.0 g, yield 78.61%) was obtained by the same method as step 1 of the above synthesis example 1.

[0344] Step 2) Synthesis of compound 25

[0345]

[0346] Using the compound 25-A (20.0 g, 26.21 mmol) obtained in step 1 of the above synthesis example 25 and 4-bromo-1,1'-biphenyl (6.23 g, 26.74 mmol), the above compound 25 (19.0 g, yield 79.20%) was obtained by the same method as step 2 of the above synthesis example 1. (MS [M+H] + = 915)

[0347] Synthesis example 26. Synthesis of compound 26

[0348]

[0349] Using 3,9,9-triphenyl-9H-fluoren-2-amine (15.0 g, 36.63 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.06 g, 75.09 mmol), the above compound 26 (22.0 g, yield 76.79%) was obtained by the same method as Synthetic Example 9 described above. (MS [M+H] + = 782)

[0350] Synthesis Example 27. Synthesis of compound 27

[0351]

[0352] Using 3-(4-(diphenylamino)phenyl)-9,9-diphenyl-9H-fluoren-2-amine (15.0 g, 26.01 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (14.25 g, 53.32 mmol), the above compound 27 (19.8 g, yield 80.19%) was obtained by the same method as Synthetic Example 9 described above. (MS [M+H] + = 949)

[0353] Synthesis Example 28. Synthesis of compound 28

[0354]

[0355] Using N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-3-phenyl-9H-fluoren-2-amine (20.0 g, 35.60 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.70 g, 36.32 mmol), the above compound 28 (20.5 g, yield 76.98%) was obtained by the same method as Step 2 of Synthetic Example 1 described above. (MS [M+H] + = 748)

[0356] Synthesis Example 29. Synthesis of compound 29

[0357]

[0358] Using the compound 22-A (20.0 g, 33.23 mmol) obtained in Step 1 of Synthetic Example 22 described above and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.06 g, 33.90 mmol), the above compound 29 (20.5 g, yield 78.28%) was obtained by the same method as Step 2 of Synthetic Example 1 described above. (MS [M+H] + = 788)

[0359] Synthesis Example 30. Synthesis of Compound 30

[0360]

[0361] Using 3,9,9-triphenyl-9H-fluoren-2-amine (15.0 g, 36.63 mmol) and 5-bromo- 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.06 g, 75.09 mmol), the above compound 30 (22.0 g, yield 76.79%) was obtained by the same method as the above synthesis example 9. (MS [M+H] + = 782)

[0362] Synthesis Example 31. Synthesis of Compound 31

[0363]

[0364] Using 3,9,9-triphenyl-9H-fluoren-2-amine (15.0 g, 36.63 mmol) and 5-bromo- 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.06 g, 75.09 mmol), the above compound 30 (22.0 g, yield 76.79%) was obtained by the same method as the above synthesis example 9. (MS [M+H] + = 949)

[0365] <Experimental Example>

[0366] Experimental Example 1-1.

[0367] ITO (Indium Tin Oxide) was coated on a glass substrate in a thickness of 1500 A to form a thin film, and the substrate was washed with distilled water in which a detergent was dissolved, using ultrasonic waves. At this time, the detergent was a product of Fischer Co., and the distilled water was distilled water filtered twice using a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, the washing was repeated twice with distilled water for 10 minutes using ultrasonic waves. After the washing with distilled water was completed, the substrate was washed with solvents of isopropyl alcohol, acetone, and methanol using ultrasonic waves, and dried, and then transferred to a plasma cleaning machine. Further, the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporation machine. On the ITO transparent electrode thus prepared, a compound represented by the following chemical formula HAT was coated in a thickness of 100 A to form a thin film.

[0368] ​a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm. a thickness of 10 nm. Next, as a hole injection layer, Compound 1 manufactured in the above Synthesis Example 1 was vacuum-deposited to a thickness of 10 nm. Next, as a hole transport layer, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 10 nm.

[0369]

[0370] Experimental Examples 1-2 to 1-20 and Comparative Experimental Examples 1-1 to 1-4.

[0371] In the above Experimental Example 1-1, the compounds described in the following Table 1 were used instead of Compound 1, and otherwise, the organic light emitting devices of Experimental Examples 1-2 to 1-20 and Comparative Experimental Examples 1-1 to 1-4 were produced by the same method as in Experimental Example 1-1. The voltage, efficiency, color coordinates and lifetime of the organic light emitting devices produced in Experimental Examples 1-2 to 1-20 and Comparative Experimental Examples 1-1 to 1-4 were measured when a current of 10 mA / cm 2 was applied, and the results are shown in the following Table 1. On the other hand, T95 indicates the time required for the luminance to decrease to 95% from the initial luminance (6000 nits) at a current density of 10 mA / cm 2

[0372] [Table 1]

[0373]

[0374]

[0375] As shown in the above Table 1, it was confirmed that the electron blocking ability of the compounds of the present application is excellent, and the organic light emitting devices using the same as an electron blocking layer showed significant effects in driving voltage, efficiency and lifetime. ​

[0376] In particular, with respect to the effects, it was confirmed that the following cases were not good in terms of the lifetime: a case where the binding position of Ar3 is bound to a position other than the 3rd position of fluorene of the present application, a case where Ar1 or Ar2 is represented by the above-described Chemical Formula 2 and Ar3 is hydrogen, a case where both Ar1 and Ar2 are not a group of Chemical Formula 2, and a case where the binding position of the amine group to fluorene is different.

[0377] Experimental Examples 2-1 to 2-24 and Comparative Experimental Examples 2-1 to 2-4.

[0378] In Experimental Example 1-1 described above, the organic light emitting device of Experimental Examples 2-1 to 2-24 and Comparative Experimental Examples 2-1 to 2-4 was produced in the same manner as Experimental Example 1-1 described above, except that a compound represented by the above-described Chemical Formula EB1 was used instead of Compound 1 as the electron blocking layer, and the compounds described in Table 2 below were used instead of the compound represented by the above-described Chemical Formula HT1 as the hole transport layer. When a current of 10 mA / cm2was applied to the organic light emitting device produced in Experimental Examples 2-1 to 2-24 and Comparative Experimental Examples 2-1 to 2-4, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. On the other hand, T95 indicates the time required for the luminance to decrease to 95% from the initial luminance (6000 nit). 2

[0379] [Table 2]

[0380]

[0381]

[0382]

[0383] As shown in Table 2 described above, it was confirmed that the hole transport ability of the compound of the present application is excellent, and the organic light emitting device in which it is used as the hole transport layer shows a significant effect in terms of the driving voltage, efficiency, and lifetime.​

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, R1 and R2 may be the same as or different from each other, and each can be either methyl or phenyl. R3 and R4 are both hydrogen atoms. a = 4 b is 2. L1 is a direct bond. L2 to L4 may be the same as or different from each other, and each can be directly bonded or benzene independently. Ar3 can be phenyl, diphenylamino, dibenzofuranyl, or carbazoleyl. Ar1 and Ar2 may be the same as or different from each other, and each is independently a phenyl, biphenyl, naphthyl, 9,9'-dimethylfluorenyl, dibenzofuranyl, or a group represented by the following chemical formula 2, wherein at least one of Ar1 and Ar2 is a group represented by the following chemical formula 2. Chemical formula 2 In the chemical formula 2, R5 is hydrogen. c is 3.

2. The compound according to claim 1, wherein, The compound represented by chemical formula 1 is any one of the following compounds:

3. An organic light-emitting device, comprising: The first electrode, the second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound according to any one of claims 1 to 2.

4. The organic light-emitting device according to claim 3, wherein, The organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, hole transport layer, or electron blocking layer contains the compound.

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