Amine-based 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] This application claims priority to Korean Patent Application No. 10-2021-0017522, filed on February 8, 2021, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein.

[0002] The present specification relates to an amine-based compound and an organic light emitting device including the same. BACKGROUND

[0003] An organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. If a voltage is applied to the organic light emitting device of such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then quench and emit light. The organic thin film can be composed of a single layer or multiple layers, as necessary.

[0004] As a substance used in an organic light emitting device, a pure organic substance or a coordination compound in which an organic substance forms a complex with a metal occupies the majority, and can be classified into a hole injection substance, a hole transport substance, a light emitting substance, an electron transport substance, an electron injection substance, and the like, depending on the use. Here, as a hole injection substance or a hole transport substance, an organic substance having p-type properties, i.e., an organic substance that is easily oxidized and has an electrochemically stable state when oxidized, is mainly used. On the other hand, as an electron injection substance or an electron transport substance, an organic substance having n-type properties, i.e., an organic substance that is easily reduced and has an electrochemically stable state when reduced, is mainly used. As a light emitting layer substance, a substance having both p-type properties and n-type properties, i.e., a substance having a stable form in both oxidized and reduced states, is preferred, and a substance in which excitons generated by recombination of holes and electrons in a light emitting layer are converted into light with high efficiency is preferred.

[0005] In order to improve the performance, lifespan, or efficiency of an organic light emitting device, there is a continuous demand for the development of materials for an organic thin film.

[0006] PRIOR ART DOCUMENT

[0007] PATENT DOCUMENT

[0008] Korean Patent Publication No. 10-2017-091712 SUMMARY

[0009] TECHNICAL PROBLEM

[0010] The present specification provides a compound and an organic light emitting device including the same.

[0011] SOLUTION TO PROBLEM

[0012] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In the above Chemical Formula 1,

[0016] R1and R2are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a silyl group, or a substituted or unsubstituted alkyl group, or combine with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring,

[0017] L1and L2are the same as or different from each other, and each independently a substituted or unsubstituted arylene group,

[0018] L3to L6are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0019] Ar1to Ar4are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0020] R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0021] n1is an integer of 0 to 4, and when n1is 2 or more, 2 or more R3are the same as or different from each other, n2is an integer of 0 to 2, and when n2is 2, 2 R4are the same as or different from each other.

[0022] Another embodiment of the present specification provides an organic light emitting device, 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, wherein one or more of the organic layers comprise the compound.

[0023] Effects of the Invention

[0024] The compound described in the present specification can be used as a material for an organic layer of an organic light emitting device. When the compound according to one embodiment of the present invention is applied to an organic light emitting device, the electron injection and movement of the device are improved, and the hole inhibition ability is excellent, so that an organic light emitting device having excellent luminous efficiency, low driving voltage, high efficiency, and long lifespan can be obtained. BRIEF DESCRIPTION OF DRAWINGS

[0025] Figures 1 to 3 FIG. 1 illustrates an organic light emitting device according to one embodiment of the present specification. DETAILED DESCRIPTION

[0026] Hereinafter, the present specification will be described in more detail.

[0027] The present specification provides a compound represented by the above Chemical Formula 1.

[0028] The compound represented by the above Chemical Formula 1 can effectively adjust the energy barrier with an organic layer by substituting the amine group having a linking group such as L1 or L2 at the 2nd carbon and 3rd carbon positions of the Fluorene core structure, and the respective amine groups do not reduce the functions of each other, while adjusting the HOMO and LUMO energy levels of the compound represented by the above Chemical Formula 1.

[0029] In the present specification, when a certain part is referred to as "including / including" a certain component, it means that other components can be further included unless otherwise specifically stated, rather than excluding other components.

[0030] In the present specification, examples of substituents are described below, but are not limited thereto.

[0031] The term "substituted" above 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 or different.

[0032] In the present specification, the term "substituted or unsubstituted" means that it is substituted with one or two or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, an amine group, a silyl group, a boron group, an alkoxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or is substituted with a substituent in which two or more of the above-mentioned substituents are linked, or is not substituted with any substituent. For example, the "substituent in which two or more are linked" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent in which two phenyl groups are linked.

[0033] In the present specification, the term "substituted or unsubstituted" means that it is substituted with one or two or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, an amine group having 1 to 60 carbon atoms, a silyl group having 1 to 30 carbon atoms, a boron group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heterocyclic group having 1 to 60 carbon atoms, or is substituted with a substituent in which two or more of the above-mentioned substituents are linked, or is not substituted with any substituent.

[0034] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from arylamine groups having 6 to 60 carbon atoms, aryl groups having 6 to 60 carbon atoms, and heterocyclic groups having 1 to 60 carbon atoms, or substituted with substituents connected to each other by two or more of the above-mentioned exemplified substituents, or not having any substituents.

[0035] In the present specification, the halogen group can be fluorine, chlorine, bromine, or iodine.

[0036] In the present specification, the above-mentioned alkyl group can be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. As specific examples, 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, and the like, but are not limited thereto.

[0037] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

[0038] In the present specification, the above-mentioned alkoxy group can be straight chain or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto.

[0039] In the present specification, the amine group can be selected from -NH2, alkylamine groups, N-alkyl arylamine groups, arylamine groups, N-aryl heteroarylamine groups, N-alkyl heteroarylamine groups, and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30. As specific examples of the amine group, there are methylamine groups, dimethylamine groups, ethylamine groups, diethylamine groups, phenylamine groups, naphthylamine groups, biphenylamine groups, anthrylamine groups, 9-methyl-anthrylamine groups, diphenylamine groups, N-phenyl naphthylamine groups, ditolylamine groups, N-phenyl tolylamine groups, triphenyleneamine groups, N-phenyl biphenylamine groups, N-phenyl naphthylamine groups, N-biphenyl naphthylamine groups, N-naphthyl fluoreneamine groups, N-phenyl phenanthreneamine groups, N-biphenyl phenanthreneamine groups, N-phenyl fluoreneamine groups, N-phenyl triphenyleneamine groups, N-phenanthrene fluoreneamine groups, N-biphenyl fluoreneamine groups, and the like, but are not limited thereto.

[0040] In the present specification, an N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group.

[0041] In the present specification, an N-aryl heteroaryl amine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on the N of the amine group.

[0042] In the present specification, an N-alkyl heteroaryl amine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group.

[0043] In the present specification, the alkyl group in the alkyl amine group, the N-aryl alkyl amine group, and the N-alkyl heteroaryl amine group is the same as the exemplification of the alkyl group described above.

[0044] In the present specification, as examples of the heteroaryl amine group, there are a substituted or unsubstituted mono-heteroaryl amine group, or a substituted or unsubstituted di-heteroaryl amine group. The heteroaryl amine group containing two or more of the above-described heteroaryl groups can contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or can contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the above-described heteroaryl amine group can be selected from the exemplification of the heteroaryl group described later.

[0045] In the present specification, the exemplification of the heteroaryl group in the N-aryl heteroaryl amine group and the N-alkyl heteroaryl amine group is the same as the exemplification of the heteroaryl group described later.

[0046] In the present specification, the silyl group can be an alkylsilyl group or an arylsilyl group, and further can be a trialkylsilyl group or a triarylsilyl group. The number of carbon atoms of the above-described silyl group is not particularly limited, but is preferably 1 to 30, the number of carbon atoms of the alkylsilyl group is 1 to 30, and the number of carbon atoms of the arylsilyl group can be 6 to 30. Specifically, there are a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyl dimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but not limited thereto.

[0047] In the present specification, the boron group can be -BR 100 R 101 , the above-described R 100 and R 101 are the same or different, each independently can be selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted cycloalkyl group having a carbon atom number of 3 to 30, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 30, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0048] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having a carbon atom number of 6 to 60, for example, an aryl group having a carbon atom number of 6 to 30, and the above-described aryl group can be monocyclic or polycyclic.

[0049] When the above-described aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably from 6 to 60. Specifically, the monocyclic aryl group can be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

[0050] When the above-described aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably from 10 to 60. Specifically, the polycyclic aryl group can be a naphthyl group, a fluorenyl group, a fluoranthene group, or the like, but is not limited thereto.

[0051] In the present specification, the 9th carbon of the above-described fluorenyl group can be substituted, and the two substituents bound to the 9th carbon can be combined with each other to form a ring.

[0052] In the case where the above-described fluorenyl group is substituted, it can be or the like, but is not limited thereto.

[0053] The above-described arylene group, in addition to being divalent, can refer to the description of the above-described aryl group.

[0054] In the present specification, the heterocyclic group contains one or more non-carbon atoms, i.e., hetero elements, and specifically, the above-described hetero elements can contain one or more atoms selected from O, N, S, P, and the like. The number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably from 1 to 60, and further preferably from 2 to 60. The above-described heterocyclic group can be a monocyclic or polycyclic ring. The above-described heterocyclic group can be an aromatic ring, an aliphatic ring, and a fused ring thereof. As examples of the above-described heterocyclic group, there are 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 bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazyl group, a pyrazinyl group, a quinolyl group, a quinazolyl group, a quinoxalyl group, a phtalazyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benz oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthroline, an iso oxazolyl group, a thiodiazolyl group, a phenothiazyl group, and a dibenzofuranyl group, or the like, but is not limited thereto.

[0055] The above-described heteroaryl group refers to a monovalent aromatic heterocyclic group, and the heteroarylene group refers to a divalent aromatic heterocyclic group. The above-described heteroaryl group and the heteroarylene group, in addition to being aromatic, can refer to the description of the above-described heterocyclic group.

[0056] In the present specification, the aliphatic hydrocarbon ring refers to a ring that is not aromatic and is composed only of carbon and hydrogen atoms.

[0057] In the present specification, a saturated aliphatic hydrocarbon ring means that all carbons constituting the aliphatic hydrocarbon ring are saturated carbons. The number of carbon atoms of the above-mentioned saturated aliphatic hydrocarbon ring is 3 to 10, further can be 3 to 6, and as examples of the saturated aliphatic hydrocarbon ring, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and the like can be mentioned, but are not limited thereto.

[0058] In one embodiment of the present specification, the above-mentioned R1and R2are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a silyl group, or a substituted or unsubstituted alkyl group, or are combined with each other to form a substituted or unsubstituted saturated aliphatic ring.

[0059] According to another embodiment, the above-mentioned R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group, or are combined with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring.

[0060] In another embodiment, the above-mentioned R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or are combined with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

[0061] In another embodiment, the above-mentioned R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or are combined with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

[0062] In another embodiment, the above-mentioned R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or are combined with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring having 3 to 10 carbon atoms.

[0063] In another embodiment, the above-mentioned R1and R2are the same as or different from each other, and each is independently a substituted or unsubstituted methyl group, or are combined with each other to form a substituted or unsubstituted cyclopentane or a substituted or unsubstituted cyclohexane.

[0064] In another embodiment, the above-mentioned R1and R2are methyl groups, or are combined with each other to form a cyclopentane or a cyclohexane.

[0065] In another embodiment, the above-mentioned R1and R2are methyl groups.

[0066] In another embodiment, the above-mentioned R1and R2are combined with each other to form a cyclopentane.

[0067] In another embodiment, the above-mentioned R1and R2are combined with each other to form a cyclohexane.

[0068] According to one embodiment of the present specification, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.

[0069] [Chemical Formula 2]

[0070]

[0071] [Chemical Formula 3]

[0072]

[0073] In the above Chemical Formulas 2 and 3,

[0074] L1to L6, Ar1to Ar4, R3, R4, n1, and n2are the same as those in Chemical Formula 1,

[0075] R11and R12are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a silyl group, or a substituted or unsubstituted alkyl group,

[0076] R5is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0077] n3is an integer of 0 to 16, and when n3 is 2 or more, 2 or more R5s are the same as or different from each other,

[0078] m1is an integer of 0 to 5, and when m1 is 2 or more, 2 or more structures within the parentheses are the same as or different from each other.

[0079] In an embodiment of the present specification, the above Chemical Formula 3 is represented by the following Chemical Formula 3-1 or 3-2.

[0080] [Chemical Formula 3-1]

[0081]

[0082] [Chemical Formula 3-2]

[0083]

[0084] In the above Chemical Formulas 3-1 and 3-2,

[0085] L1to L6, Ar1to Ar4, R3to R5, n1to n3are the same as those in Chemical Formula 3,

[0086] R6is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0087] n4is an integer of 0 to 8, and when n4 is 2 or more, 2 or more R5s are the same as or different from each other,

[0088] n5 is an integer of 0 to 10, and when n5 is 2 or more, 2 or more of R6are the same as or different from each other.

[0089] According to one embodiment of the present specification, the above R11and R12are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a silyl group, or a substituted or unsubstituted alkyl group having a carbon number of 1 to 10.

[0090] In another embodiment, the above R11and R12are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having a carbon number of 1 to 10.

[0091] According to another embodiment, the above R11and R12are the same as or different from each other, and each is independently a substituted or unsubstituted methyl group.

[0092] According to another embodiment, the above R11and R12are methyl groups.

[0093] According to one embodiment of the present specification, the above R5is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0094] In one embodiment of the present specification, the above R5is hydrogen.

[0095] In one embodiment of the present specification, the above n3is an integer of 0 to 16, and when n3is 2 or more, 2 or more of R5are the same as or different from each other.

[0096] In one embodiment of the present specification, the above m1is an integer of 0 to 5, and when m1is 2 or more, 2 or more of the structures within the parentheses are the same as or different from each other.

[0097] According to one embodiment of the present specification, the above m1is 1.

[0098] According to one embodiment of the present specification, the above m1is 2.

[0099] According to one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group.

[0100] According to another embodiment, the above L1and L2are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having a carbon number of 6 to 60.

[0101] According to another embodiment, the above L1and L2are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having a carbon number of 6 to 30.

[0102] According to another embodiment, the aforementioned L1and L2are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0103] According to another embodiment, the aforementioned L1and L2are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0104] In another embodiment, the aforementioned L1and L2are the same as or different from each other, and each is independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0105] According to another embodiment, the aforementioned L1and L2are the same as or different from each other, and each is independently a phenylene group or a naphthylene group.

[0106] According to another embodiment, the aforementioned L1and L2are a phenylene group.

[0107] According to another embodiment, the aforementioned L1and L2are a naphthylene group.

[0108] According to another embodiment, one of the aforementioned L1and L2is a phenylene group, and the other is a naphthylene group.

[0109] In one embodiment of the present specification, the aforementioned L3to L6are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0110] In another embodiment, the aforementioned L3to L6are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0111] According to another embodiment, the aforementioned L3to L6are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0112] In another embodiment, the aforementioned L3to L6are the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted phenylene group.

[0113] In another embodiment, the aforementioned L3to L6are the same as or different from each other, and each is independently a direct bond or a phenylene group.

[0114] In one embodiment of the present specification, the aforementioned Ar1to Ar4are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0115] According to another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, or a substituted or unsubstituted heterocyclic group having a carbon atom number of 2 to 60.

[0116] According to another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heterocyclic group having a carbon atom number of 2 to 30.

[0117] In another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60 substituted or unsubstituted with an alkyl group having a carbon atom number of 1 to 20, or a substituted or unsubstituted heterocyclic group having a carbon atom number of 2 to 60 substituted or unsubstituted with an alkyl group having a carbon atom number of 1 to 20.

[0118] In another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30 substituted or unsubstituted with an alkyl group having a carbon atom number of 1 to 10, or a substituted or unsubstituted heterocyclic group having a carbon atom number of 2 to 30 substituted or unsubstituted with an alkyl group having a carbon atom number of 1 to 10.

[0119] According to another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently 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, or a substituted or unsubstituted dibenzothiophenyl group.

[0120] According to another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently 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, or a substituted or unsubstituted dibenzothiophenyl group.

[0121] According to another embodiment, the aforementioned Ar1to Ar4are the same as or different from each other, and each independently 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, or a substituted or unsubstituted dibenzothiophenyl group.

[0122] According to an embodiment of the present specification, the aforementioned R3and R4are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0123] In another embodiment, each of R3and R4is hydrogen.

[0124] In one embodiment of the present specification, the above-described Chemical Formula 1 is selected from the following compounds.

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] The compound of Chemical Formula 1 according to one embodiment of the present specification can manufacture a core structure as shown in Reaction Formula 1 below. The kind, position, or number of substituents can be changed according to the techniques known in the art.

[0134] <Reaction Formula 1>

[0135]

[0136] <Reaction Formula 2>

[0137]

[0138] In the above-described Reaction Formulas 1 and 2, the definition of the substituents can apply to the above-described description.

[0139] In the above-described Reaction Formulas 1 and 2, X1and X2may be a halogen group, and the above-described halogen group can be Cl, Br, or I.

[0140] The synthesis process of the compound having a specific substituent bound at a specific position is exemplified in the above-described Reaction Formulas 1 and 2, but a compound corresponding to the range of the above-described Chemical Formula 1 can be synthesized using the starting material, intermediate material, etc. known in the art and by the synthesis method known in the art.

[0141] In the present specification, by introducing various substituents in the core structure of the compound represented by the above Chemical Formula 1, a compound having various energy band gaps can be synthesized. Further, in the present specification, by introducing various substituents in the core structure of the structure as described above, the HOMO and LUMO energy levels of the compound can also be adjusted.

[0142] In addition, the present specification provides an organic light emitting device including the above-mentioned compound.

[0143] One 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, one or more of the organic layers including a compound represented by the above Chemical Formula 1.

[0144] The organic light emitting device of the present specification forms one or more organic layers using the above-mentioned compound, and can be manufactured using the manufacturing method and materials of a general organic light emitting device, except for this.

[0145] The organic layer of the organic light emitting device of the present specification can be formed of a single layer structure, or can be formed of a multi-layer structure in which two or more organic layers are stacked. For example, the organic layer can include a hole injection layer, a hole transport layer, a layer performing both hole transport and hole injection, an electron inhibition layer, a light emitting layer, an electron injection layer, an electron transport layer, a layer performing both electron transport and electron injection, a hole inhibition layer, and the like. However, the structure of the organic layer included in the organic light emitting device is not limited thereto, and can include a smaller or larger number of organic layers.

[0146] In one embodiment of the present specification, the organic layer includes one or more of a hole injection layer, a hole transport layer, and an electron inhibition layer, and one or more of the hole injection layer, the hole transport layer, and the electron inhibition layer include the above-mentioned compound.

[0147] In one embodiment of the present specification, the organic layer includes one or more of an electron injection layer, an electron transport layer, and a hole inhibition layer, and one or more of the electron injection layer, the electron transport layer, and the hole inhibition layer include the compound of the above Chemical Formula 1.

[0148] In one embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of the above Chemical Formula 1.

[0149] In one embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of the above Chemical Formula 1 as a host of the light emitting layer.

[0150] In an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of Chemical Formula 1 as a host of the light emitting layer.

[0151] In an embodiment of the present specification, the organic layer includes an electron transport layer, and the electron transport layer includes the compound of Chemical Formula 1.

[0152] In an embodiment of the present specification, the organic layer includes a hole transport layer, and the hole transport layer includes the compound of Chemical Formula 1.

[0153] In an embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, an electron transport layer, a light emitting layer, a hole transport layer, and a layer simultaneously performing electron injection and transport.

[0154] The layer simultaneously performing electron injection and transport can mean an electron injection and transport layer.

[0155] According to an embodiment of the present specification, the organic layer includes a light emitting layer, a hole transport layer, and an electron transport layer, and the hole transport layer can include the compound of Chemical Formula 1. At this time, the material of the electron transport layer can be a fluorene-based compound. The fluorene-based compound can be specifically a fluorene-based compound substituted with an arylamine, and more specifically a fluorene-based compound substituted with an arylamine and a dibenzofuranyl substituted with an arylamine. The organic layer can further include a hole injection layer.

[0156] According to another embodiment, the organic layer includes a light emitting layer, a hole transport layer, and an electron transport layer, and the electron transport layer can include the compound of Chemical Formula 1. At this time, the material of the hole transport layer can be an arylamine-based compound. The arylamine-based compound can be specifically an arylamine-based compound including an N-phenylcarbazolyl. The organic layer can further include a hole injection layer.

[0157] In an embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0158] According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0159] In another embodiment, the organic light emitting device can be an organic light emitting device of a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0160] In another embodiment, the organic light emitting device can be an organic light emitting device of an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0161] In addition, the organic light emitting device of the present specification can have a stacked structure as shown below, but is not particularly limited thereto.

[0162] (1) anode / hole transport layer / light emitting layer / cathode

[0163] (2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

[0164] (3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

[0165] (4) anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0166] (5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0167] (6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0168] (7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0169] (8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0170] (9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0171] (10) anode / hole transport layer / electron inhibition layer / light emitting layer / electron transport layer / cathode

[0172] (11) anode / hole transport layer / electron inhibition layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0173] (12) anode / hole injection layer / hole transport layer / electron inhibition layer / light emitting layer / electron transport layer / cathode

[0174] (13) anode / hole injection layer / hole transport layer / electron inhibition layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0175] (14) anode / hole transport layer / light emitting layer / hole inhibition layer / electron transport layer / cathode

[0176] (15) anode / hole transport layer / light emitting layer / hole inhibition layer / electron transport layer / electron injection layer / cathode

[0177] (16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0178] (17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0179] (18) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0180] The structure of the organic light emitting device of the present application can have a structure as shown in Figures 1 to 3 but is not limited thereto.

[0181] Figure 1 An example of a structure of an organic light emitting device in which an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked on a substrate 1 is illustrated. In the structure as illustrated above, the compound of the above chemical formula 1 can be contained in the above light emitting layer 6.

[0182] Figure 2 An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 is illustrated. In the structure as illustrated above, the compound of the above chemical formula 1 is contained in the above hole transport layer 4 or electron blocking layer 5.

[0183] Figure 3 An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 11, and a cathode 10 is illustrated. In the structure as illustrated above, the compound of the above chemical formula 1 is contained in the above hole transport layer 4 or electron blocking layer 5.

[0184] For example, the organic light emitting device of the present application 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, an electron transport layer, an electron injection layer, and the like 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.

[0185] The organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs electron injection and electron transport, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron injection and electron transport, a hole suppression layer, 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.

[0186] 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, or 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.

[0187] 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, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0188] The hole injection layer is a layer that functions to smoothly inject holes from the anode to the light-emitting layer, and the hole injection material is a material that can receive holes from the anode well at a low voltage, and preferably has a HOMO (highest occupied molecular orbital) 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, hexacarbonitrile 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.

[0189] The hole-transporting layer described above can function to smoothly transport holes. The hole-transporting substance is a substance that receives holes from the anode or the hole-injecting layer and transfers them to the light-emitting layer, and a substance having a large mobility of holes is suitable. Specific examples include arylamine-based organic compounds, electrically conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but are not limited thereto.

[0190] An electron-suppressing layer can be provided between the hole-transporting layer and the light-emitting layer described above. The electron-suppressing layer described above can use the compound described above or a material known in the technical field.

[0191] 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 described above is a substance that receives holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and emits light in the visible region by combining them, and is preferably a substance having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzofuran-based compounds; benzothiazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; rubrene; and the like, but are not limited thereto. 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 described above is a substance that receives holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and emits light in the visible region by combining them, and is preferably a substance having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzofuran-based compounds; benzothiazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; rubrene; and the like, but are not limited thereto.

[0192] In one embodiment of the present specification, the light-emitting layer described above contains the compound described above as a host, and can contain an additional host in addition to the compound described above.

[0193] As the additional host material described above, there are aromatic condensed ring derivatives or heterocycle-containing compounds, and the like. Specifically, as the aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and as the heterocycle-containing compounds, there are carbazole derivatives, diphenylfuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. As the additional host material described above, there are aromatic condensed ring derivatives or heterocycle-containing compounds, and the like. Specifically, as the aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and as the heterocycle-containing compounds, there are carbazole derivatives, diphenylfuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0194] As the above light-emitting dopant, phosphorescent substances such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum), and the like, or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino) aluminum), and the like, but not limited thereto. When the light-emitting layer emits green light, as the light-emitting dopant, phosphorescent substances such as Ir(ppy)3 (fac tris(2-phenylpyridine) iridium), and the like, or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino) aluminum), and the like, but not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, phosphorescent substances such as (4,6-F2ppy)2Irpic, and the like, or fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), DSB (diphenylstyrylbenzene), DSA (diphenylstyrylarylene), PFO-based polymers, PPV-based polymers, and the like, but not limited thereto.

[0195] In one embodiment of the present specification, a hole-blocking layer can be provided between the above-described electron-transporting layer and the light-emitting layer, and the hole-blocking layer can use a material known in the technical field.

[0196] 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 an Al complex of 8-hydroxyquinoline, a complex including Alq3, an organic radical compound, a hydroxyflavone-metal complex, and the like, but not limited thereto.

[0197] The above-described electron-injecting layer can function to smoothly inject electrons. As the electron-injecting substance, a compound having an ability to transport electrons, having an effect of injecting electrons from the cathode, having an excellent electron-injecting effect to 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 an excellent film formation ability is preferred. Specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, thiepin dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

[0198] As the metal complex compound, there are lithium 8-hydroxyquinoline, zinc bis(8-hydroxyquinoline), copper bis(8-hydroxyquinoline), manganese bis(8-hydroxyquinoline), aluminum tris(8-hydroxyquinoline), aluminum tris(2-methyl-8-hydroxyquinoline), gallium tris(8-hydroxyquinoline), 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) (1-naphthol), gallium bis(2-methyl-8-quinoline) (2-naphthol), and the like, but are not limited thereto.

[0199] 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 materials used.

[0200] Embodiment of the Invention

[0201] Hereinafter, the present specification will be described in detail, and embodiments will be described in detail. However, the embodiments according to the present specification can be variously modified, and are not construed as limiting the scope of the present application to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.

[0202] <Synthesis Example>

[0203] Synthesis Example 1. Synthesis of Compound 1

[0204] Step 1) Synthesis of Compound 1-A

[0205]

[0206] ​After adding acetonitrile (1700 ml) to 3-bromo-9,9-dimethyl-9H-fluoren-2-amine (50.00 g, 173.50 mmol), hydrogen bromide (HBr) (49.13 g, 607.25 mmol) was added and stirred at 0°C for 10 minutes. After slowly adding an aqueous solution of sodium nitrite (NaNO2) (15.56 g, 222.55 mmol) (45 ml) to the above mixture at 0°C, copper bromide (CuBr2) (42.63 g, 190.85 mmol) was added. After stirring the above mixture at 0°C for 20 minutes, the temperature was raised to 60°C and heated and stirred for 1 hour. After the reaction was completed, the solid was filtered after being inversely added dropwise in water. The above solid was dissolved in chloroform and separated into layers with water. After removing the solvent, recrystallization was performed with ethanol, thereby obtaining compound 1-A (46.0 g, yield 75.31%).

[0207] Step 2) Synthesis of compound 1

[0208]

[0209] After adding tetrahydrofuran (THF) (200 ml) to 1-A (20.00 g, 56.81 mmol) and (4-(diphenylamino)phenyl)boronic acid (34.49 g, 119.29 mmol) obtained in step 1 of the above synthesis example 1, heating and stirring were performed. After adding an aqueous solution of potassium carbonate (39.26 g, 284.05 mmol) (100 ml) to the above mixture, heating and stirring were performed for 5 minutes. After slowly adding bis(tri-tert-butylphosphine)palladium (0.15 g, 0.28 mmol) dissolved in tetrahydrofuran (THF) (20 ml) to the above mixture, heating and stirring were performed for 1 hour. After the reaction was completed and filtered, separation into layers was performed with toluene and water. After removing the solvent, recrystallization was performed with ethyl acetate, thereby obtaining compound 1 (30.0 g, yield 77.56%). + = 681)

[0210] Synthesis example 2. Synthesis of compound 2

[0211] Step 1) Synthesis of compound 2-A

[0212]

[0213] Compound 2-A (45.0 g, yield 78.87%) was obtained by the same method as in step 1 of the above synthesis example 1 using 3-(4-(diphenylamino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 110.47 mmol).

[0214] Step 2) Synthesis of compound 2

[0215]

[0216] To 2-A (20.00 g, 38.72 mmol) obtained in Step 1 of the above Synthesis Example 2 and (4-([l,l'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (14.85 g, 40.66 mmol) was added tetrahydrofuran (THF) (100 ml) and heated and stirred. To the above mixture was added an aqueous solution of potassium carbonate (16.05 g, 116.16 mmol) (50 ml) and heated and stirred for 5 minutes. To the above mixture was slowly added bis(tri-tert-butylphosphine)palladium (0.06 g, 0.12 mmol) dissolved in tetrahydrofuran (THF) (10 ml) and heated and stirred for 1 hour. After completion of the reaction and filtration, the layer was separated with toluene and water. After removal of the solvent, recrystallization was performed with ethyl acetate to obtain Compound 2 (23.5 g, yield 80.18 %). (MS [M+H] + = 757)

[0217] Synthesis Example 3. Synthesis of Compound 3

[0218]

[0219] Using Compound 2-A (20.0 g, 38.72 mmol) obtained in Step 1 of the above Synthesis Example 2 and (4-(di([l,l'-biphenyl]-4-yl)amino)phenyl)boronic acid (17.94 g, 40.66 mmol), the above Compound 3 (25.5 g, yield 79.05 %) was obtained by the same method as in Step 2 of the above Synthesis Example 2. (MS [M+H] + = 833)

[0220] Synthesis Example 4. Synthesis of Compound 4

[0221]

[0222] Using Compound 2-A (20.0 g, 38.72 mmol) obtained in Step 1 of the above Synthesis Example 2 and (4-(naphthalen-l-yl(phenyl)amino)phenyl)boronic acid (13.79 g, 40.66 mmol), the above Compound 4 (22.0 g, yield 77.73 %) was obtained by the same method as in Step 2 of the above Synthesis Example 2. (MS [M+H] + = 731)

[0223] Synthesis Example 5. Synthesis of Compound 5

[0224]

[0225] Using compound 2-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthetic example 2 and (4-(naphthalen-2-yl(phenyl)amino)phenyl)boronic acid (13.79 g, 40.66 mmol), the above compound 5 (21.5 g, yield 75.96%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 731)

[0226] Synthetic example 6. Synthesis of compound 6

[0227]

[0228] Using compound 2-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthetic example 2 and (4-(naphthalen-2-yl(phenyl)amino)phenyl)boronic acid (13.79 g, 40.66 mmol), the above compound 5 (21.5 g, yield 75.96%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 797)

[0229] Synthetic example 7. Synthesis of compound 7

[0230]

[0231] Using compound 2-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthetic example 2 and (4-(naphthalen-2-yl(phenyl)amino)phenyl)boronic acid (13.79 g, 40.66 mmol), the above compound 5 (21.5 g, yield 75.96%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 731)

[0232] Synthetic example 8. Synthesis of compound 8

[0233]

[0234] Using compound 2-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthetic example 2 and (4-(naphthalen-2-yl(phenyl)amino)phenyl)boronic acid (13.79 g, 40.66 mmol), the above compound 5 (21.5 g, yield 75.96%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 731)

[0235] Synthetic example 9. Synthesis of compound 9

[0236]

[0237] Using compound 2-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthetic example 2 and (4-(dibenzo[b,d]thiophen-4-yl(phenyl)amino)phenyl)boronic acid (16.07 g, 40.66 mmol), the above compound 10 (23.5 g, yield 77.11%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 771)

[0238] Synthetic example 10. Synthesis of compound 10

[0239]

[0240] Using compound 2-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthetic example 2 and (4-(dibenzo[b,d]thiophen-4-yl(phenyl)amino)phenyl)boronic acid (16.07 g, 40.66 mmol), the above compound 10 (23.5 g, yield 77.11%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 787)

[0241] Synthetic example 11. Synthesis of compound 11

[0242] Step 1) Synthesis of compound 11-A

[0243]

[0244] Using 3-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 82.67 mmol), the above compound 11-A (45.0 g, yield 81.40%) was obtained by the same method as that of step 1 of the above synthetic example 1.

[0245] Step 2) Synthesis of compound 11

[0246]

[0247] Using compound 11-A (20.0 g, 29.91 mmol) obtained in step 1 of the above synthetic example 11 and (4-(diphenylamino)phenyl)boronic acid (9.08 g, 31.41 mmol), the above compound 11 (19.5 g, yield 78.26%) was obtained by the same method as that of step 2 of the above synthetic example 2. (MS [M+H] + = 833)

[0248] Synthetic example 12. Synthesis of compound 12

[0249]

[0250] Using compound 1-A (20.0 g, 56.81 mmol) obtained in step 1 of the above synthetic example 1 and (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (43.57 g, 119.29 mmol), the above compound 12 (37.0 g, yield 78.18%) was obtained by the same method as step 2 of the above synthetic example 1. (MS [M+H] + = 833)

[0251] Synthesis example 13. Synthesis of compound 13

[0252]

[0253] Using compound 1-A (20.0 g, 56.81 mmol) obtained in step 1 of the above synthetic example 1 and (4-(naphthalen-1-yl(phenyl)amino)phenyl)boronic acid (40.46 g, 119.29 mmol), the above compound 13 (34.5 g, yield 77.76%) was obtained by the same method as step 2 of the above synthetic example 1. (MS [M+H] + = 781)

[0254] Synthesis example 14. Synthesis of compound 14

[0255]

[0256] Using compound 1-A (20.0 g, 56.81 mmol) obtained in step 1 of the above synthetic example 1 and (4-(diphenylamino)naphthalen-1-yl)boronic acid (40.46 g, 119.29 mmol), the above compound 14 (34.0 g, yield 76.63%) was obtained by the same method as step 2 of the above synthetic example 1. (MS [M+H] + = 781)

[0257] Synthesis example 15. Synthesis of compound 15

[0258]

[0259] Using compound 1-A (20.0 g, 56.81 mmol) obtained in step 1 of the above synthetic example 1 and (3-(diphenylamino)phenyl)boronic acid (34.49 g, 119.29 mmol), the above compound 15 (30.0 g, yield 77.56%) was obtained by the same method as step 2 of the above synthetic example 1. (MS [M+H] + = 681)

[0260] Synthesis of compound 16

[0261] Step 1) Synthesis of compound 16-A

[0262]

[0263] Using 3-(3-(diphenylamino)phenyl)-9,9-dimethyl-9H-fluoren-2-amine (50.0 g, 110.47 mmol), the above compound 16-A (44.0 g, yield 77.12%) was obtained by the same method as step 1 of the above synthesis example 1.

[0264] Step 2) Synthesis of compound 16

[0265]

[0266] Using the compound 16-A (20.0 g, 38.72 mmol) obtained in step 1 of the above synthesis example 16 and (4-(diphenylamino)phenyl)boronic acid (11.76 g, 40.66 mmol), the above compound 16 (20.0 g, yield 75.86%) was obtained by the same method as step 2 of the above synthesis example 2. (MS [M+H] + = 681)

[0267] Synthesis of compound 17

[0268] Step 1) Synthesis of compound 17-A

[0269]

[0270] Using 3'-bromospiro[cyclopentane-1,9'-fluoren]-2'-amine (50.00 g, 159.12 mmol), the above compound 17-A (47.0 g, yield 78.12%) was obtained by the same method as step 1 of the above synthesis example 1.

[0271] Step 2) Synthesis of compound 17

[0272]

[0273] Using the compound 17-A (20.0 g, 52.89 mmol) obtained in step 1 of the above synthesis example 17 and (4-(diphenylamino)phenyl)boronic acid (32.12 g, 111.08 mmol), the above compound 17 (29.5 g, yield 78.90%) was obtained by the same method as step 2 of the above synthesis example 1. (MS [M+H] + = 707)

[0274] Synthesis example 18. Synthesis of compound 18

[0275] Step 1) Synthesis of compound 18-A

[0276]

[0277] Using 3'-(4-(diphenylamino)phenyl)spiro[cyclopentane-l,9'-fluorene]-2'-amine (50.0 g, 104.46 mmol), the above compound 18-A (45.0 g, yield 79.40%) was obtained by the same method as step 1 of the above synthesis example 1.

[0278] Step 2) Synthesis of compound 18

[0279]

[0280] Using the compound 18-A (20.0 g, 36.87 mmol) obtained in step 1 of the above synthesis example 18 and (4-([l,l'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (14.14 g, 38.71 mmol), the above compound 18 (22.5 g, yield 77.93%) was obtained by the same method as step 2 of the above synthesis example 2. (MS [M+H] + = 783)

[0281] Synthesis example 19. Synthesis of compound 19

[0282] Step 1) Synthesis of compound 19-A

[0283]

[0284] Using 3'-bromospiro[cyclohexane-l,9'-fluorene]-2'-amine (50.00 g, 152.32 mmol), the above compound 19-A (46.0 g, yield 77.01%) was obtained by the same method as step 1 of the above synthesis example 1.

[0285] Step 2) Synthesis of compound 19

[0286]

[0287] Using the compound 19-A (20.0 g, 51.00 mmol) obtained in step 1 of the above synthesis example 19 and (4-(diphenylamino)phenyl)boronic acid (30.97 g, 107.11 mmol), the above compound 19 (29.0 g, yield 78.87%) was obtained by the same method as step 2 of the above synthesis example 1. (MS [M+H] + = 721)

[0288] Synthesis Example 20. Synthesis of Compound 20

[0289] Step 1) Synthesis of compound 20-A

[0290]

[0291] Compound 20-A (45.0 g, yield 79.67%) was obtained by using 3'-(4-(diphenylamino)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-amine (50.0 g, 101.49 mmol) in the same manner as step 1 of Synthesis Example 1 above.

[0292] Step 2) Synthesis of Compound 20

[0293]

[0294] Using compound 20-A (20.0 g, 35.94 mmol) obtained in step 1 of Synthesis Example 20 above and (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (13.78 g, 37.73 mmol), compound 20 (22.0 g, yield 76.80%) was obtained by the same method as in step 2 of Synthesis Example 2 above. (MS[M+H) + =797)

[0295] <Examples and Comparative Examples>

[0296] Example 1-1

[0297] ITO (Indium Tin Oxide) A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0298] On the ITO transparent electrode prepared in this way, a compound represented by the chemical formula HAT will be applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole injection layer, a compound represented by the chemical formula HT1 is used as a hole transport layer. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm. The compound 1 produced in the above Synthesis Example 1 was vacuum- deposited at a thickness of 20 nm as an electron-inhibiting layer. Next, as a light-emitting layer, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD were vacuum-deposited at a weight ratio of 25: 1 and at a thickness of 30 nm.

[0299]

[0300] Examples 1-2 to 1-18 and Comparative Examples 1-1 to 1-5

[0301] In the above Example 1-1, the compounds described in the following Table 1 were used instead of the compound 1, and otherwise, the organic light-emitting devices of Examples 1-2 to 1-18 and Comparative Examples 1-1 to 1-5 were produced by the same method as in the above Example 1-1. The voltage, efficiency, color coordinates and lifetime were measured when a current of 10 mA / cm 2

[0302] [Table 1]

[0303]

[0304]

[0305]

[0306] The compound of the present application is the above Chemical Formula 1 in which L1and L2are substituted or unsubstituted arylene, and, on the contrary, EB1of Comparative Example 1-1 is dibenzofuranyl in which the substituent corresponding to L1of the above Chemical Formula 1 is divalent, and EB2of Comparative Example 1-2 is a single bond in which the substituents corresponding to L1and L2of the above Chemical Formula 1 are divalent.

[0307] ​The compound of the present application is the compound of the above Chemical Formula 1 in which R1 and R2 are substituted or unsubstituted alkyl, or R1 and R2 are combined with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring, except that EB3 of Comparative Example 1-3 is a substituted group corresponding to R1 and R2 of the above Chemical Formula 1, which is a phenyl group, and EB4 of Comparative Example 1-4 is a substituted group corresponding to R1 and R2 of the above Chemical Formula 1, which is combined with each other to form a fluorene group.

[0308] The compound of the present application is the compound of the above Chemical Formula 1 in which L1 or L2 is a substituted group attached to the 2nd and 3rd carbon positions of the fluorene core structure, except that EB5 of Comparative Example 1-5 is a substituted group attached to the 2nd and 4th carbon positions of the fluorene core structure.

[0309] From the difference in the constitution of the above examples and comparative examples, it can be confirmed that the effects shown in the above Table 1 are different. That is, it is confirmed that the electron-inhibiting ability of the compound of the present application is excellent compared to the comparative examples, and the organic light emitting device using the same as an electron-inhibiting layer shows a significant effect in driving voltage, efficiency, and lifespan.

[0310] Examples 2-1 to 2-20 and Comparative Examples 1-1, 2-1 to 2-5

[0311] In the above Example 1-1, the compound represented by the above Chemical Formula EB1 was used instead of Compound 1 as an electron-inhibiting layer, and the compounds described in the following Table 2 were used instead of the compound represented by the above Chemical Formula HT1 as a hole-transporting layer, and otherwise, the organic light emitting devices of Examples 2-1 to 2-20 and Comparative Examples 2-1 to 2-5 were manufactured by the same method as in the above Example 1-1. When a current of 10 mA / cm2was applied to the organic light emitting devices manufactured in the examples and comparative examples, the voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in the following Table 2. On the other hand, T95 indicates the time required for the luminance to decrease to 95% from the initial luminance (6000 nit). 2

[0312] [Table 2]

[0313]

[0314]

[0315]

[0316] The compound of the present application is the compound of the above Chemical Formula 1 in which L1 and L2 are substituted or unsubstituted arylene, except that HT2 of Comparative Example 2-1 is a substituted group corresponding to L1 of the above Chemical Formula 1, which is a diphenylbenzofuranyl group having a valence of 2, and HT3 of Comparative Example 2-2 is a substituted group corresponding to L1 and L2 of the above Chemical Formula 1, which is a single bond. ​

[0317] The compound of the present application is the compound of the above Chemical Formula 1 in which R1and R2are substituted or unsubstituted alkyl, or R1and R2are combined with each other to form a substituted or unsubstituted saturated aliphatic hydrocarbon ring, with the exception that HT4of Comparative Example 2-3 is phenyl as a substituent corresponding to R1and R2of the above Chemical Formula 1, and HT5of Comparative Example 2-4 is fluorenyl in which substituents corresponding to R1and R2of the above Chemical Formula 1 are combined with each other.

[0318] The compound of the present application is the compound of the above Chemical Formula 1 in which L1or L2is a substituent attached to the 2ndand 3rdcarbon positions of the fluorene nucleus structure, with the exception that HT6of Comparative Example 2-5 is a substituent attached to the 2ndand 4thcarbon positions of the fluorene nucleus structure.

[0319] The difference in the effect as shown in Table 2 above can be confirmed from the difference in the constitution of the examples and the comparative examples. That is, it is confirmed that the hole transportability of the compound of the present application is excellent compared to the comparative examples, and the organic light emitting device using the same as a hole transport layer shows a significant effect in driving voltage, efficiency, and lifespan.

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 or different from each other, each being a methyl group independently, or they may combine to form cyclopentane or cyclohexane. L1 and L2 may be the same as or different from each other, and each is independently either phenylene or naphthylene. L3 to L6 may be the same as or different from each other, and each can be directly bonded or phenylene independently. Ar1 to Ar4 may be the same as or different from each other, and each is independently a phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, or dibenzothiopheneyl group, substituted or unsubstituted with tert-butyl. R3 and R4 are both hydrogen atoms. n1 is 4. n2 is 2.

2. The compound according to claim 1, wherein, The chemical formula 1 is either chemical formula 2 or 3 as follows: [Chemical Formula 2] [Chemical Formula 3] In the chemical formulas 2 and 3, The definitions of L1 to L6, Ar1 to Ar4, R3, R4, n1, and n2 are the same as those in chemical formula 1. R11 and R12 are each methyl groups. R5 is hydrogen. n3 is 4 or 5. m1 is an integer of 1 or 2. When m1 is 2, the two structures inside the parentheses are identical.

3. The compound according to claim 1, wherein, Chemical Formula 1 is selected from the following compounds:

4. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound according to any one of claims 1 to 3.

5. The organic light-emitting device according to claim 4, wherein, The organic layer includes one or more of a hole injection layer, a hole transport layer, and an electron suppression layer, and one or more of the hole injection layer, hole transport layer, and electron suppression layer contains the compound.

6. The organic light-emitting device according to claim 4, wherein, The organic layer includes one or more of an electron injection layer, an electron transport layer, and a hole suppression layer, and one or more of the electron injection layer, electron transport layer, and hole suppression layer contains the compound.

7. The organic light-emitting device according to claim 4, wherein, The organic layer includes an electron suppression layer, which contains the compound.

8. The organic light-emitting device according to claim 4, wherein, The organic layer includes a hole transport layer, and the hole transport layer contains the compound.

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